CN105218425A - A kind of synthetic method of 3,5-dimethoxy pyrroles-2-formic acid - Google Patents
A kind of synthetic method of 3,5-dimethoxy pyrroles-2-formic acid Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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Abstract
The invention discloses a kind of synthetic method of 3,5-dimethoxy pyrroles-2-formic acid, belong to the field of chemical synthesis.The present invention first ethyl acetate, acetone and anhydrous diethyl ether are raw material, add sodium Metal 99.5 and generate 3-oxo-2-amylene-2-sodium alkoxide, diethyl aminomalonate is added again afterwards under the condition of Glacial acetic acid, argon gas, 3 are obtained through operations such as backflow, suction filtrations, 5-dimethyl pyrrole-2-ethyl formate, with KF under given conditions to methyl replace 3,5-difluoro pyrroles-2-ethyl formate, again by fluorine-based under the condition such as NaS and etherifying reagent 3,5-dimethoxy pyrroles-2-ethyl formate, finally be hydrolyzed and can obtain 3,5-dimethoxy pyrroles-2-formic acid.
Description
Technical field
The invention discloses a kind of synthetic method of 3,5-dimethoxy pyrroles-2-formic acid, belong to the field of chemical synthesis.
Background technology
Pyrroles and methyl substituted homologue thereof are present in Dippel's oil.Colourless liquid.Boiling point 130 ~ 131 DEG C, relative density 0.9691(20/4 DEG C).Be slightly soluble in water, be soluble in the organic solvent such as ethanol, ether.Pyrroles just can blackening under the effect of micro amount of oxygen; Pine flakes reaction provides redness; Under hydrochloric acid effect, to become pyrroles red in polymerization; Generally unstable to oxygenant.Can there is substitution reaction in it, mainly replace on 2 or 5.15 DEG C time, pyrroles is with nitric acid nitrating in diacetyl oxide, and obtain 2-nitro-pyrrole, output is not high, and a part becomes resinous substance.Pyrroles is a secondary amine in form, but dissolves very slow in diluted acid; After ring hydrogen is replaced by alkyl, alkalescence strengthens, and can form undissolved salt.Pyrroles can form salt with picric acid; Also reducible one-tenth dihydro and Pyrrolidine.
Pyrroles can produce with Isosorbide-5-Nitrae-dicarbonyl compound and ammonia react, and industrial pyrroles is prepared by katalysis by butynediol and ammonia.The compound that pyrroles and benzo join is called indoles, is an important compound.The derivative of some pyrroles has important physiological action, and such as, chlorophyll, protoheme are all the derivatives of the porphyrin ring system formed by 4 pyrrole rings.Pyrrolidine is an important reagent, and it and reactive ketone dehydration form enamine, and namely there is a carbon-to-carbon double bond on amino side.The enamine that such as pimelinketone and Pyrrolidine are formed has multiple use in organic synthesis.Generally speaking, be, before raw material is tested, re-use after re-distillation with pyrroles, because pyrroles exposes in atmosphere easily polymerization for a long time generate polypyrrole (black solid).
Summary of the invention
The invention provides that a kind of reaction conditions is simple, productive rate is high, cost is low and the synthetic method of 3, the 5-dimethoxy pyrroles-2-formic acid that contaminate environment is less.
For achieving the above object, the synthetic route of the present invention 3,5-dimethoxy pyrroles-2-formic acid is:
The building-up process of 3, the 5-dimethoxy pyrroles-2-formic acid that the present invention relates to comprises the following steps:
(1) in the there-necked flask of 500mL that thermometer is housed, 50 ~ 60mL ethyl acetate is added, add 50 ~ 55mL acetone and 200mL anhydrous diethyl ether more wherein, with vigorous stirring, put into cryosel bath and be cooled to-3 ~ 1 DEG C, at remaining on-3 ~ 1 DEG C, 10 ~ 15g sodium Metal 99.5 is cut into superfine fritter, slowly join in flask in 2 ~ 3h, continuation stirring 1 hour is carried out after adding sodium block, then ice bath is removed, continue stirring reaction 5 ~ 6h, carry out suction filtration after reaction terminates and remove ether, to obtain after filter residue washed with diethylether 2 ~ 3 times suction filtration again, vacuum-drying is put into after suction filtration, obtain faint yellow solid, be 3-oxo-2-amylene-2-sodium alkoxide,
(2) in the there-necked flask of 250mL, add the above-mentioned obtained 2-methyl-3-oxo-1-butylene-1-sodium alkoxide of 3 ~ 4g, 15 ~ 30mL Glacial acetic acid and 30 ~ 40mL distilled water wherein, after mixing and stirring, three-necked bottle is vacuumized, exhaust rear argon replaces 2 ~ 3 times, reaction system is in argon atmosphere all the time, under magnetic stirring, flask is heated to 80 ~ 85 DEG C, add 3 ~ 5g diethyl aminomalonate and 5 ~ 10mL distilled water wherein, continue to be heated to backflow simultaneously, keep back flow reaction 2 ~ 3h, after reaction terminates, reaction mixture is under agitation poured in trash ice, now have solid to generate, then suction filtration is carried out, obtain solid and be 3, 5-dimethyl pyrrole-2-ethyl formate,
(3) by above-mentioned for 15 ~ 30g obtained 3,5-dimethyl pyrrole-2-ethyl formate joins in the there-necked flask of 250mL, add the water of 120 ~ 130mL wherein, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38 ~ 40% is wherein 4 ~ 5, filter and remove insolubles, in filtrate, add 5 ~ 10g Potassium monofluoride, then to be acidified to pH with massfraction 40% concentrated hydrochloric acid be 1, crystallization at 0 DEG C afterwards, filtration obtains 3,5-difluoro pyrroles-2-ethyl formate;
(4) getting above-mentioned 3, the 5-obtained difluoro pyrroles-2-ethyl formates of 10 ~ 12g adds in the reaction vessel of 250mL, adds 20 ~ 25mLCH wherein
3cOOH solvent, under the condition stirred, the temperature controlled in reaction vessel is 10 ~ 20 DEG C, adds the NaS of 15 ~ 20g at this temperature in batches, carries out stirring reaction 50 ~ 60min, pours in clear water, can produce layering, by water layer C after reaction terminates by reactant
2h
4cl extracts, and merges organic layer after extraction, with distilled water wash organic layer 2 ~ 3 times, is poured in reaction vessel by the organic layer obtained again, adds solvent C H
3oH and CH
3oNa etherifying reagent, reacting by heating container to 60 ~ 70 DEG C, under agitation react 3 ~ 5h, after reaction terminates, product is poured into water, add massfraction 60 ~ 70%NaOH solution wherein, carry out stirring, leave standstill, suction filtration, the filter residue obtained by suction filtration adds ethyl acetate and carries out recrystallization, 3,5-dimethoxy pyrroles-2-formic acid.
Specific embodiments
The building-up process of one 3, the 5-dimethoxy pyrroles-2-formic acid that the present invention relates to comprises the following steps:
First in the there-necked flask of 500mL that thermometer is housed, 50 ~ 60mL ethyl acetate is added, add 50 ~ 55mL acetone and 200mL anhydrous diethyl ether more wherein, with vigorous stirring, put into cryosel bath and be cooled to-3 ~ 1 DEG C, at remaining on-3 ~ 1 DEG C, 10 ~ 15g sodium Metal 99.5 is cut into superfine fritter, slowly join in flask in 2 ~ 3h, continuation stirring 1 hour is carried out after adding sodium block, then ice bath is removed, continue stirring reaction 5 ~ 6h, carry out suction filtration after reaction terminates and remove ether, to obtain after filter residue washed with diethylether 2 ~ 3 times suction filtration again, vacuum-drying is put into after suction filtration, obtain faint yellow solid, be 3-oxo-2-amylene-2-sodium alkoxide, the above-mentioned obtained 2-methyl-3-oxo-1-butylene-1-sodium alkoxide of 3 ~ 4g is added in the there-necked flask of 250mL, 15 ~ 30mL Glacial acetic acid and 30 ~ 40mL distilled water wherein, after mixing and stirring, three-necked bottle is vacuumized, exhaust rear argon replaces 2 ~ 3 times, reaction system is in argon atmosphere all the time, under magnetic stirring, flask is heated to 80 ~ 85 DEG C, add 3 ~ 5g diethyl aminomalonate and 5 ~ 10mL distilled water wherein, continue to be heated to backflow simultaneously, keep back flow reaction 2 ~ 3h, after reaction terminates, reaction mixture is under agitation poured in trash ice, now have solid to generate, then suction filtration is carried out, obtain solid and be 3, 5-dimethyl pyrrole-2-ethyl formate, by obtained for 15 ~ 30g 3,5-dimethyl pyrrole-2-ethyl formate joins in the there-necked flask of 250mL, add the water of 120 ~ 130mL wherein, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38 ~ 40% is wherein 4 ~ 5, filter and remove insolubles, in filtrate, add 5 ~ 10g Potassium monofluoride, then to be acidified to pH with massfraction 40% concentrated hydrochloric acid be 1, crystallization at 0 DEG C afterwards, filtration obtains 3,5-difluoro pyrroles-2-ethyl formate, 3, the 5-difluoro pyrroles-2-ethyl formates getting 10 ~ 12g obtained add in the reaction vessel of 250mL, add 20 ~ 25mLCH wherein
3cOOH solvent, under the condition stirred, the temperature controlled in reaction vessel is 10 ~ 20 DEG C, adds the NaS of 15 ~ 20g at this temperature in batches, carries out stirring reaction 50 ~ 60min, pours in clear water, can produce layering, by water layer C after reaction terminates by reactant
2h
4cl extracts, and merges organic layer after extraction, with distilled water wash organic layer 2 ~ 3 times, is poured in reaction vessel by the organic layer obtained again, adds solvent C H
3oH and CH
3oNa etherifying reagent, reacting by heating container to 60 ~ 70 DEG C, under agitation react 3 ~ 5h, after reaction terminates, product is poured into water, add massfraction 60 ~ 70%NaOH solution wherein, carry out stirring, leave standstill, suction filtration, the filter residue obtained by suction filtration adds ethyl acetate and carries out recrystallization, 3,5-dimethoxy pyrroles-2-formic acid.
Example 1
First in the there-necked flask of 500mL that thermometer is housed, 50mL ethyl acetate is added, add 50mL acetone and 200mL anhydrous diethyl ether more wherein, put into cryosel bath with vigorous stirring and be cooled to-3 DEG C, at remaining on-3 DEG C, 10g sodium Metal 99.5 is cut into superfine fritter, slowly join in flask in 2h, continuation stirring 1 hour is carried out after adding sodium block, then ice bath is removed, continue stirring reaction 5h, carry out suction filtration after reaction terminates and remove ether, to obtain after filter residue washed with diethylether 2 times suction filtration again, vacuum-drying is put into after suction filtration, obtain faint yellow solid, be 3-oxo-2-amylene-2-sodium alkoxide, the above-mentioned obtained 2-methyl-3-oxo-1-butylene-1-sodium alkoxide of 3g is added in the there-necked flask of 250mL, 15mL Glacial acetic acid and 30mL distilled water wherein, after mixing and stirring, three-necked bottle is vacuumized, exhaust rear argon replaces 2 times, reaction system is in argon atmosphere all the time, under magnetic stirring, flask is heated to 80 DEG C, add 3g diethyl aminomalonate and 5mL distilled water wherein, continue to be heated to backflow simultaneously, keep back flow reaction 2h, after reaction terminates, reaction mixture is under agitation poured in trash ice, now have solid to generate, then suction filtration is carried out, obtain solid and be 3, 5-dimethyl pyrrole-2-ethyl formate, by obtained for 15g 3,5-dimethyl pyrrole-2-ethyl formate joins in the there-necked flask of 250mL, add the water of 120mL wherein, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38% is wherein 4, filter and remove insolubles, in filtrate, add 5g Potassium monofluoride, then to be acidified to pH with massfraction 40% concentrated hydrochloric acid be 1, crystallization at 0 DEG C afterwards, filtration obtains 3,5-difluoro pyrroles-2-ethyl formate, 3, the 5-difluoro pyrroles-2-ethyl formates getting 10g obtained add in the reaction vessel of 250mL, add 20mLCH wherein
3cOOH solvent, under the condition stirred, the temperature controlled in reaction vessel is 10 DEG C, adds the NaS of 15g at this temperature in batches, carries out stirring reaction 50min, pours in clear water, can produce layering, by water layer C after reaction terminates by reactant
2h
4cl extracts, and merges organic layer after extraction, with distilled water wash organic layer 2 times, is poured in reaction vessel by the organic layer obtained again, adds solvent C H
3oH and CH
3oNa etherifying reagent, reacting by heating container to 60 DEG C, under agitation react 3h, after reaction terminates, product is poured into water, add massfraction 60%NaOH solution wherein, carry out stirring, leave standstill, suction filtration, the filter residue obtained by suction filtration adds ethyl acetate and carries out recrystallization, 3,5-dimethoxy pyrroles-2-formic acid.
Example 2
First in the there-necked flask of 500mL that thermometer is housed, 55mL ethyl acetate is added, add 53mL acetone and 200mL anhydrous diethyl ether more wherein, put into cryosel bath with vigorous stirring and be cooled to-0 DEG C, at remaining on 0 DEG C, 13g sodium Metal 99.5 is cut into superfine fritter, slowly join in flask in 2.5h, continuation stirring 1 hour is carried out after adding sodium block, then ice bath is removed, continue stirring reaction 5.5h, carry out suction filtration after reaction terminates and remove ether, to obtain after filter residue washed with diethylether 2.5 times suction filtration again, vacuum-drying is put into after suction filtration, obtain faint yellow solid, be 3-oxo-2-amylene-2-sodium alkoxide, the above-mentioned obtained 2-methyl-3-oxo-1-butylene-1-sodium alkoxide of 3.5g is added in the there-necked flask of 250mL, 123mL Glacial acetic acid and 35mL distilled water wherein, after mixing and stirring, three-necked bottle is vacuumized, exhaust rear argon replaces 2 times, reaction system is in argon atmosphere all the time, under magnetic stirring, flask is heated to 83 DEG C, add 4g diethyl aminomalonate and 8mL distilled water wherein, continue to be heated to backflow simultaneously, keep back flow reaction 2.5h, after reaction terminates, reaction mixture is under agitation poured in trash ice, now have solid to generate, then suction filtration is carried out, obtain solid and be 3, 5-dimethyl pyrrole-2-ethyl formate, by obtained for 23g 3,5-dimethyl pyrrole-2-ethyl formate joins in the there-necked flask of 250mL, add the water of 125mL wherein, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 39% is wherein 4.5, filter and remove insolubles, in filtrate, add 7g Potassium monofluoride, then to be acidified to pH with massfraction 40% concentrated hydrochloric acid be 1, crystallization at 0 DEG C afterwards, filtration obtains 3,5-difluoro pyrroles-2-ethyl formate, 3, the 5-difluoro pyrroles-2-ethyl formates getting 11g obtained add in the reaction vessel of 250mL, add 23mLCH wherein
3cOOH solvent, under the condition stirred, the temperature controlled in reaction vessel is 15 DEG C, adds the NaS of 18g at this temperature in batches, carries out stirring reaction 55min, pours in clear water, can produce layering, by water layer C after reaction terminates by reactant
2h
4cl extracts, and merges organic layer after extraction, with distilled water wash organic layer 2.5 times, is poured in reaction vessel by the organic layer obtained again, adds solvent C H
3oH and CH
3oNa etherifying reagent, reacting by heating container to 65 DEG C, under agitation react 4h, after reaction terminates, product is poured into water, add massfraction 65%NaOH solution wherein, carry out stirring, leave standstill, suction filtration, the filter residue obtained by suction filtration adds ethyl acetate and carries out recrystallization, 3,5-dimethoxy pyrroles-2-formic acid.
Example 3
First in the there-necked flask of 500mL that thermometer is housed, 60mL ethyl acetate is added, add 55mL acetone and 200mL anhydrous diethyl ether more wherein, put into cryosel bath with vigorous stirring and be cooled to 1 DEG C, at remaining on 1 DEG C, 15g sodium Metal 99.5 is cut into superfine fritter, slowly join in flask in 3h, continuation stirring 1 hour is carried out after adding sodium block, then ice bath is removed, continue stirring reaction 6h, carry out suction filtration after reaction terminates and remove ether, to obtain after filter residue washed with diethylether 3 times suction filtration again, vacuum-drying is put into after suction filtration, obtain faint yellow solid, be 3-oxo-2-amylene-2-sodium alkoxide, the above-mentioned obtained 2-methyl-3-oxo-1-butylene-1-sodium alkoxide of 4g is added in the there-necked flask of 250mL, 30mL Glacial acetic acid and 40mL distilled water wherein, after mixing and stirring, three-necked bottle is vacuumized, exhaust rear argon replaces 3 times, reaction system is in argon atmosphere all the time, under magnetic stirring, flask is heated to 85 DEG C, add 5g diethyl aminomalonate and 10mL distilled water wherein, continue to be heated to backflow simultaneously, keep back flow reaction 3h, after reaction terminates, reaction mixture is under agitation poured in trash ice, now have solid to generate, then suction filtration is carried out, obtain solid and be 3, 5-dimethyl pyrrole-2-ethyl formate, by obtained for 30g 3,5-dimethyl pyrrole-2-ethyl formate joins in the there-necked flask of 250mL, add the water of 130mL wherein, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 40% is wherein 5, filter and remove insolubles, in filtrate, add 10g Potassium monofluoride, then to be acidified to pH with massfraction 40% concentrated hydrochloric acid be 1, crystallization at 0 DEG C afterwards, filtration obtains 3,5-difluoro pyrroles-2-ethyl formate, 3, the 5-difluoro pyrroles-2-ethyl formates getting 12g obtained add in the reaction vessel of 250mL, add 25mLCH wherein
3cOOH solvent, under the condition stirred, the temperature controlled in reaction vessel is 20 DEG C, adds the NaS of 20g at this temperature in batches, carries out stirring reaction 60min, pours in clear water, can produce layering, by water layer C after reaction terminates by reactant
2h
4cl extracts, and merges organic layer after extraction, with distilled water wash organic layer 3 times, is poured in reaction vessel by the organic layer obtained again, adds solvent C H
3oH and CH
3oNa etherifying reagent, reacting by heating container to 70 DEG C, under agitation react 5h, after reaction terminates, product is poured into water, add massfraction 70%NaOH solution wherein, carry out stirring, leave standstill, suction filtration, the filter residue obtained by suction filtration adds ethyl acetate and carries out recrystallization, 3,5-dimethoxy pyrroles-2-formic acid.
Claims (1)
1. the synthetic method of a dimethoxy pyrroles-2-formic acid, is characterized in that the synthesis of 3,5-dimethoxy pyrroles-2-formic acid:
(1) in the there-necked flask of 500mL that thermometer is housed, 50 ~ 60mL ethyl acetate is added, add 50 ~ 55mL acetone and 200mL anhydrous diethyl ether more wherein, put into cryosel bath with vigorous stirring and be cooled to-3 ~ 1 DEG C, at remaining on-3 ~ 1 DEG C, 10 ~ 15g sodium Metal 99.5 is cut into superfine fritter, slowly join in flask in 2 ~ 3h, continuation stirring 1 hour is carried out after adding sodium block, then ice bath is removed, continue stirring reaction 5 ~ 6h, carry out suction filtration after reaction terminates and remove ether, to obtain after filter residue washed with diethylether 2 ~ 3 times suction filtration again, vacuum-drying is put into after suction filtration, obtain faint yellow solid, be 3-oxo-2-amylene-2-sodium alkoxide,
(2) in the there-necked flask of 250mL, add the above-mentioned obtained 2-methyl-3-oxo-1-butylene-1-sodium alkoxide of 3 ~ 4g, 15 ~ 30mL Glacial acetic acid and 30 ~ 40mL distilled water wherein, after mixing and stirring, three-necked bottle is vacuumized, exhaust rear argon replaces 2 ~ 3 times, reaction system is in argon atmosphere all the time, under magnetic stirring, flask is heated to 80 ~ 85 DEG C, add 3 ~ 5g diethyl aminomalonate and 5 ~ 10mL distilled water wherein, continue to be heated to backflow simultaneously, keep back flow reaction 2 ~ 3h, after reaction terminates, reaction mixture is under agitation poured in trash ice, now have solid to generate, then suction filtration is carried out, obtain solid and be 3, 5-dimethyl pyrrole-2-ethyl formate,
(3) by above-mentioned for 15 ~ 30g obtained 3,5-dimethyl pyrrole-2-ethyl formate joins in the there-necked flask of 250mL, add the water of 120 ~ 130mL wherein, carry out stirring and make it to dissolve, the concentrated hydrochloric acid regulator solution pH value dripping massfraction 38 ~ 40% is wherein 4 ~ 5, filter and remove insolubles, in filtrate, add 5 ~ 10g Potassium monofluoride, then to be acidified to pH with massfraction 40% concentrated hydrochloric acid be 1, crystallization at 0 DEG C afterwards, filtration obtains 3,5-difluoro pyrroles-2-ethyl formate;
(4) getting above-mentioned 3, the 5-obtained difluoro pyrroles-2-ethyl formates of 10 ~ 12g adds in the reaction vessel of 250mL, adds 20 ~ 25mLCH wherein
3cOOH solvent, under the condition stirred, the temperature controlled in reaction vessel is 10 ~ 20 DEG C, adds the NaS of 15 ~ 20g at this temperature in batches, carries out stirring reaction 50 ~ 60min, pours in clear water, can produce layering, by water layer C after reaction terminates by reactant
2h
4cl extracts, and merges organic layer after extraction, with distilled water wash organic layer 2 ~ 3 times, is poured in reaction vessel by the organic layer obtained again, adds solvent C H
3oH and CH
3oNa etherifying reagent, reacting by heating container to 60 ~ 70 DEG C, under agitation react 3 ~ 5h, after reaction terminates, product is poured into water, add massfraction 60 ~ 70%NaOH solution wherein, carry out stirring, leave standstill, suction filtration, the filter residue obtained by suction filtration adds ethyl acetate and carries out recrystallization, 3,5-dimethoxy pyrroles-2-formic acid.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105801463A (en) * | 2016-03-31 | 2016-07-27 | 常州大学 | Synthetic method of 2-formic acid-3-propoxyl-5-methylpyrrole |
| CN110835351A (en) * | 2018-08-15 | 2020-02-25 | 江苏三月光电科技有限公司 | Organic compound with pyrromethene boron complex as core and preparation and application thereof |
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| CN102639135A (en) * | 2009-10-08 | 2012-08-15 | 先灵公司 | Iminothiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105801463A (en) * | 2016-03-31 | 2016-07-27 | 常州大学 | Synthetic method of 2-formic acid-3-propoxyl-5-methylpyrrole |
| CN110835351A (en) * | 2018-08-15 | 2020-02-25 | 江苏三月光电科技有限公司 | Organic compound with pyrromethene boron complex as core and preparation and application thereof |
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Address after: 213164 Changzhou Province, north of the New District, Jiangsu Biguiyuan, unit B, room 1601, room 32 Applicant after: Ding Yuqin Address before: 213164 Changzhou Province, north of the new North Industrial Park Road, one hundred environmental protection (Fan Qun drying equipment Co., Ltd.) Applicant before: Ding Yuqin |
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Application publication date: 20160106 |