CN105037165B - 1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound and preparation method thereof - Google Patents
1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound and preparation method thereof Download PDFInfo
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- CN105037165B CN105037165B CN201510380492.6A CN201510380492A CN105037165B CN 105037165 B CN105037165 B CN 105037165B CN 201510380492 A CN201510380492 A CN 201510380492A CN 105037165 B CN105037165 B CN 105037165B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- -1 1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound Chemical class 0.000 title abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 41
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000000605 extraction Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract description 3
- 239000000706 filtrate Substances 0.000 claims abstract description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- JHZYGPAIKZFVOS-UHFFFAOYSA-N 1-(2-bromoethenyl)-3-methoxybenzene Chemical class COC1=CC=CC(C=CBr)=C1 JHZYGPAIKZFVOS-UHFFFAOYSA-N 0.000 claims description 11
- 239000011787 zinc oxide Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 229910000416 bismuth oxide Inorganic materials 0.000 claims description 3
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 5
- 239000002917 insecticide Substances 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 2
- JSTMQHZKDFPMPS-UHFFFAOYSA-N 2,4-bis[2-(2-bromo-5-methoxyphenyl)ethenyl]-1,3,5-trinitrobenzene Chemical compound BrC1=C(C=CC2=C(C(=C(C=C2[N+](=O)[O-])[N+](=O)[O-])C=CC2=C(C=CC(=C2)OC)Br)[N+](=O)[O-])C=C(C=C1)OC JSTMQHZKDFPMPS-UHFFFAOYSA-N 0.000 abstract 2
- CECJKTQRYSIMMJ-UHFFFAOYSA-N 2,4-bis[2-(3-methoxyphenyl)ethenyl]-1,3,5-trinitrobenzene Chemical compound O(C)C=1C=C(C=CC2=C(C(=C(C=C2[N+](=O)[O-])[N+](=O)[O-])C=CC2=CC(=CC=C2)OC)[N+](=O)[O-])C=CC=1 CECJKTQRYSIMMJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003779 heat-resistant material Substances 0.000 abstract 1
- 239000008204 material by function Substances 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 238000002390 rotary evaporation Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 235000015655 Crocus sativus Nutrition 0.000 description 16
- 244000124209 Crocus sativus Species 0.000 description 16
- 235000013974 saffron Nutrition 0.000 description 16
- 239000004248 saffron Substances 0.000 description 16
- 239000012043 crude product Substances 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000004237 Crocus Nutrition 0.000 description 1
- 241000596148 Crocus Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 229910007938 ZrBr4 Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 238000013379 physicochemical characterization Methods 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a 1, 3-bis (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene compound and a preparation method thereof, wherein 1, 3-bis (3-methoxystyryl) -2, 4, 6-trinitrobenzene, liquid bromine and a catalyst are added into a reactor, dichloromethane is used as a solvent, after the reaction is finished at normal temperature, the filtration is carried out, saturated sodium carbonate solution is used for neutralizing the filtrate, dichloromethane is used for extraction, rotary evaporation is carried out, and drying is carried out to obtain 1, 3-bis (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene. The 1, 3-di (2-bromo-5-methoxystyryl) -2, 4, 6-trinitrobenzene of the invention has a bromine atom on each benzene ring at the periphery and good symmetry, and the central benzene ring is connected with the other two benzene rings by two conjugated double bonds, thereby greatly improving the stability of the compound and being used for functional materials such as medicines, insecticides, heat-resistant materials and the like.
Description
Technical field
The present invention relates to one kind 1,3- bis-（The bromo- 5- methoxyl-styrenes of 2-）- 2,4,6- trinitrobenzene compounds and system
Preparation Method, belongs to fire retardant, insecticide and medicine intermediate.
Background technology
The conjugation of double bond present in diphenylethylene compounds structure and phenyl ring so that the compound chemical property
It is more stable.If multiple nitros being introduced on phenyl ring so as to more stable, and then brominating conditions becoming harsher.So far
Till, very Polybrominated method, such as NBS H has been developed2SO4˗TFA、DBUHBr3、Br2˗Lewis acids、 KBr/
BTPPMS 、 ZrBr4/ diaziene, IQBC and [BMPy] Br3Etc..Although these methods are widely used,
They still have the significant shortcoming of several comparisons：1st, applicable compound is than relatively limited；2nd, there are side chain side reaction and excessive bromination；
3rd, bromination result is single；4th, regioselectivity is poor, causes the waste of raw material and produces a large amount of waste liquids.With bromination process ground it is fluffy
The exhibition of breaking out, it is important to develop green synthesis method, therefore, it is to solve problem above to find a kind of bromination catalyst of Novel clean
One of effective ways.And nowadays, existing catalyst is zeolitic catalyst, clay class catalyst, ion exchange resin
Catalyst, immobilized liquid acid catalyst, metal-oxide and metal salt catalyst, heteropolyacid catalyst and solid super-strong acid
Catalyst.Wherein zeolitic catalyst can not only improve the regioselectivity of bromination, and reduce pollutant emission, while using
Last a long time, reduce industrial cost.However, in zeolitic catalyst, H-Beta type zeolite catalysises effect is preferable, selectivity
Good and long service life.Based on this, we have selected H-Beta type zeolites bromination 1,3- bis-（3- methoxyl-styrenes）- 2,4,
6- trinitrobenzenes.Bromine-containing compound is important industrial chemicals, is extensively applied in each department of national economy, and sending out with science and technology
Exhibition, researchs and develops the quickening of speed, and the new application of bromine-containing compound is constantly expanding.
The content of the invention
It is an object of the invention to：There is provided one kind 1,3- bis-（The bromo- 5- methoxyl-styrenes of 2-）- 2,4,6- trinitro-s
Benzene compound and preparation method, not only symmetry is good for the compound, and stable, can potential application in fire retardant, insecticide and
Medicine intermediate etc..
The present invention technical solution be：The compound it is as follows with structure：
The compound physicochemical characterization is as follows：IR (KBr, ν, cm-1): 3095, 1634, 1590, 1539, 1332,
970; m.p. 211.2-213.2℃; 1H NMR (300 MHz, CDCl3), δ 8.85 (s, 1H), 7.52 (d, J=
8.7Hz, 2H), 7.18-7.15 (m, 6H), 6.86-6.82 (m, 2H), 3.88 (s, 6H); 13C NMR (75
MHz, DMSO-d6), δ 159.36, 147.12, 135.50, 134.68, 134.26, 130.58, 123.35,
121.66, 117.85, 114.57, 112.95, 56.04。
Wherein, 1,3- bis-（The bromo- 5- methoxyl-styrenes of 2-）The preparation method of -2,4,6- trinitrobenzene compounds includes
Following steps：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes, bromine, catalyst are added in reactor,
Solvent is done with dichloromethane, is reacted at normal temperatures；After the completion of reaction, filter, with saturated sodium carbonate solution and filtrate, dichloromethane
Alkane is extracted, and revolving, drying obtain 1,3- bis-（The bromo- 5- methoxyl-styrenes of 2-）- 2,4,6- trinitrobenzenes.
Wherein, described catalyst selects H-Beta/ Zinc Oxide, H-Beta/ bismuth oxide, H-Beta/ ferrum oxides, H-
One of in Beta/ titanium oxides.
Wherein, described 1,3- bis-（3- methoxyl-styrenes）The amount of the material of -2,4,6- trinitrobenzenes and bromine it
Than for 1 ~ 2.
Wherein, described catalyst amount is 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzene materials
The 10% of amount.
Compared with prior art, it is an advantage of the invention that：（1）One kind 1,3- bis- is synthesized（The bromo- 5- methoxy styrenes of 2-
Base）- 2,4,6- trinitrobenzenes；（2）From in structure, on each phenyl ring of compound periphery, contain a bromine atoms, center benzene
Ring is connected with conjugated double bond respectively with other two phenyl ring, and symmetry is good；（3）From in application, the compound can be used to hinder
Combustion agent, insecticide and medicine intermediate etc..
Description of the drawings
Below in conjunction with the accompanying drawings the present invention is described in further detail.
Fig. 1 be 1 product 1 of embodiment, 3- bis-（The bromo- 5- methoxyl-styrenes of 2-）The proton magnetic of -2,4,6- trinitrobenzenes
Resonance collection of illustrative plates, abscissa is chemical shift.
Fig. 2 be 1 product 1 of embodiment, 3- bis-（The bromo- 5- methoxyl-styrenes of 2-）The carbon nuclear-magnetism of -2,4,6- trinitrobenzenes
Resonance collection of illustrative plates, abscissa is chemical shift.
Specific embodiment
The technical solution of the present invention is further illustrated with reference to embodiment, those skilled in the art is made more fully
Understand the present invention, and these embodiments are not to be construed as the restriction to technical scheme.
Raw material 1,3- bis-（3- methoxyl-styrenes）The preparation of -2,4,6- trinitrobenzenes：By 2, two between 4,6- trinitro-s
Toluene（0.24g）, m-methoxybenzaldehyde（0.27g）, piperidines（1mL）, benzene（40 mL）It is added in reactor, at 100 DEG C
Backflow, reacts 10h, boils off partial solvent, filters, and is successively washed with benzene and ethanol, dries to obtain 0.4g crocus solids.
Embodiment 1：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.32g）、
H-Beta molecular sieves（0.05g）, Zinc Oxide（0.05g）And dichloromethane（10mL）In adding reactor, under room temperature, 24h is reacted,
Filter, extraction, revolving obtain saffron crude product 0.61g, carry out recrystallization with acetone and ethanol, obtain saffron pure product
Product 0.59g, fusing point are 211.2-213.2 DEG C, and yield is 96.7%.
IR (KBr, ν, cm-1): 3095, 1634, 1590, 1539, 1332, 970; 1H NMR (300 MHz,
CDCl3), δ 8.85 (s, 1H), 7.52 (d, J=8.7Hz, 2H), 7.18-7.15 (m, 6H), 6.86-6.82
(m, 2H), 3.88 (s, 6H); 13C NMR (75 MHz, DMSO-d6), δ 159.36, 147.12, 135.50,
134.68, 134.26, 130.58, 123.35, 121.66, 117.85, 114.57, 112.95, 56.04。
Embodiment 2：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.32g）、
H-Beta molecular sieves（0.1g）, Zinc Oxide（0.05g）And dichloromethane（10mL）In adding reactor, 24h, mistake under room temperature, are reacted
Filter, extraction, revolving obtain saffron crude product 0.61g, carry out recrystallization with acetone and ethanol, obtain saffron net product
0.55g, yield are 90.2%.
Embodiment 3：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.32g）、
H-Beta molecular sieves（0.02g）, Zinc Oxide（0.05g）And dichloromethane（10mL）In adding reactor, under room temperature, 24h is reacted,
Filter, extraction, revolving obtain saffron crude product 0.53g, carry out recrystallization with acetone and ethanol, obtain saffron pure product
Product 0.42g, yield are 79.2%.
Embodiment 4：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.24g）、
H-Beta molecular sieves（0.05g）, Zinc Oxide（0.05g）And dichloromethane（10mL）In adding reactor, under room temperature, 24h is reacted,
Filter, extraction, revolving obtain saffron crude product 0.36g, carry out recrystallization with acetone and ethanol, obtain saffron pure product
Product 0.17g, yield are 47.2%.
Embodiment 5：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.16g）、
H-Beta molecular sieves（0.05g）, Zinc Oxide（0.05g）And dichloromethane（10mL）In adding reactor, under room temperature, 24h is reacted,
Filter, extraction, revolving obtain saffron crude product 0.34g, carry out recrystallization with acetone and ethanol, obtain saffron pure product
Product 0.16g, yield are 47.1%.
Embodiment 6：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.32g）、
H-Beta molecular sieves（0.05g）, bismuth oxide（0.05g）And dichloromethane（10mL）In adding reactor, under room temperature, 24h is reacted,
Filter, extraction, revolving obtain saffron crude product 0.6g, carry out recrystallization with acetone and ethanol, obtain saffron pure product
Product 0.56g, yield are 93.3%.
Embodiment 7：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.32g）、
H-Beta molecular sieves（0.05g）, titanium oxide（0.05g）And dichloromethane（10mL）In adding reactor, under room temperature, 24h is reacted,
Filter, extraction, revolving obtain saffron crude product 0.58g, carry out recrystallization with acetone and ethanol, obtain saffron pure product
Product 0.45g, yield are 77.6%.
Embodiment 8：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes（0.48g）, bromine（0.32g）、
H-Beta molecular sieves（0.05g）, ferrum oxide（0.05g）And dichloromethane（10mL）In adding reactor, under room temperature, 24h is reacted,
Filter, extraction, revolving obtain saffron crude product 0.55g, carry out recrystallization with acetone and ethanol, obtain saffron pure product
Product 0.23g, yield are 41.8%.
1,3- bis- involved in the present invention（The bromo- 5- methoxyl-styrenes of 2-）The periphery of -2,4,6- trinitrobenzenes each
Contain a bromine atoms on phenyl ring, symmetry is good, and center phenyl ring is connected with two conjugated double bonds with other two phenyl ring, is carried significantly
High its stability, can be used for fire retardant, insecticide and medicine intermediate etc..
Claims (1)
1.1,3- bis-（The bromo- 5- methoxyl-styrenes of 2-）The preparation method of -2,4,6- trinitrobenzene compounds, including following step
Suddenly：By 1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes, bromine, catalyst are added in reactor, with dichloro
Methane makees solvent, reacts at normal temperatures；After the completion of reaction, filter, with saturated sodium carbonate solution and filtrate, dichloromethane extraction
Take, rotate, drying obtains 1,3- bis-（The bromo- 5- methoxyl-styrenes of 2-）- 2,4,6- trinitrobenzenes;It is characterized in that：Described
Catalyst is from one of H-Beta/ Zinc Oxide, H-Beta/ bismuth oxide, H-Beta/ ferrum oxides, H-Beta/ titanium oxides;It is described
1,3- bis-（3- methoxyl-styrenes）- 2,4,6- trinitrobenzenes are 1 ~ 2 with the ratio of the amount of the material of bromine;Described catalysis
Agent consumption is 1,3- bis-（3- methoxyl-styrenes）The 10% of the amount of -2,4,6- trinitrobenzene materials.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1016646A1 (en) * | 1991-12-12 | 2000-07-05 | Hoechst Marion Roussel | Intermediates for the preparation of cephalosporines containing on the 7-position a substituted benzyloximino radical |
| CN104016868A (en) * | 2014-04-03 | 2014-09-03 | 南京理工大学 | Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof |
| CN104016869A (en) * | 2014-05-16 | 2014-09-03 | 南京理工大学 | 2,4,6-trinitro-1,3-di(2',4',6'-trinitro-3'-hydroxystyryl)benzene, synthetic method and applciation |
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| WO2013049364A1 (en) * | 2011-09-27 | 2013-04-04 | The Trustees Of Columbia University In The City Of New York | Resveratrol-based compounds |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1016646A1 (en) * | 1991-12-12 | 2000-07-05 | Hoechst Marion Roussel | Intermediates for the preparation of cephalosporines containing on the 7-position a substituted benzyloximino radical |
| CN104016868A (en) * | 2014-04-03 | 2014-09-03 | 南京理工大学 | Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof |
| CN104016869A (en) * | 2014-05-16 | 2014-09-03 | 南京理工大学 | 2,4,6-trinitro-1,3-di(2',4',6'-trinitro-3'-hydroxystyryl)benzene, synthetic method and applciation |
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