CN108690063A - A kind of preparation method to chlorophenylboronic acid - Google Patents
A kind of preparation method to chlorophenylboronic acid Download PDFInfo
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- CN108690063A CN108690063A CN201810797300.5A CN201810797300A CN108690063A CN 108690063 A CN108690063 A CN 108690063A CN 201810797300 A CN201810797300 A CN 201810797300A CN 108690063 A CN108690063 A CN 108690063A
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- chlorophenylboronic acid
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- ZOQCZTRFTARYGJ-UHFFFAOYSA-N chlorooxy(phenyl)borinic acid Chemical compound ClOB(O)C1=CC=CC=C1 ZOQCZTRFTARYGJ-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000002904 solvent Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 claims description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 11
- 229910052749 magnesium Inorganic materials 0.000 claims description 11
- 239000011777 magnesium Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 239000012074 organic phase Substances 0.000 claims description 8
- 238000009413 insulation Methods 0.000 claims description 7
- -1 triisopropyl borate ester Chemical class 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical group COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000013517 stratification Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 claims description 2
- JLPJTCGUKOBWRJ-UHFFFAOYSA-N tripentyl borate Chemical compound CCCCCOB(OCCCCC)OCCCCC JLPJTCGUKOBWRJ-UHFFFAOYSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 abstract description 6
- 150000004795 grignard reagents Chemical class 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- 238000006467 substitution reaction Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 5
- 238000003747 Grignard reaction Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000008236 heating water Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000005740 Boscalid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 1
- 229940118790 boscalid Drugs 0.000 description 1
- OJFSXZCBGQGRNV-UHFFFAOYSA-N carbinoxamine Chemical compound C=1C=CC=NC=1C(OCCN(C)C)C1=CC=C(Cl)C=C1 OJFSXZCBGQGRNV-UHFFFAOYSA-N 0.000 description 1
- 229960000428 carbinoxamine Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a kind of preparation methods to chlorophenylboronic acid, it improves existing Grignard Reagent method, grignard reaction is merged into substitution reaction in a step and is carried out, so that without carrying out ultralow temperature control, substantially reduce energy consumption and operation difficulty, and the generation for reducing by-product improves the yield of target product.
Description
Technical field
The present invention relates to technical field of organic synthesis, more particularly to a kind of preparation method to chlorophenylboronic acid.
Background technology
In organic synthesis and the preparation of special material, it is a kind of important intermediate to chlorophenylboronic acid, can be used for preparing
A variety of drugs, such as Terazololine-one, Boscalid, carbinoxamine, it may also be used for synthesis electroluminescent organic material.
Mainly have to chlorophenylboronic acid customary preparation methods at present following two:One is para chlorobromobenzenes to generate under butyl lithium effect
Then aryl lithium is added borate and is obtained to chlorophenylboronic acid by condensation water solution, which generally requires to react at -78 DEG C,
Temperature condition is harsh, and lithium reagent used height is inflammable, and security risk is larger, is not suitable for industrialized production.Another kind is more often used
Method be Grignard Reagent method, para chlorobromobenzene and magnesium are first generated into Grignard Reagent, is then added dropwise in borate and hydrolyzes, is obtained pair
Chlorophenylboronic acid.It is long the time required to this method, and intermediate rubigan magnesium bromide(That is Grignard Reagent)It is very active, it carries out next
Easily generate such as coupled product, two substitution product impurity when step reaction, it is therefore desirable to ultralow temperature controls, consume energy when production compared with
Greatly.
In addition, Grignard Reagent method needs to carry out grignard reaction, three step of substitution reaction and hydrolysis, trouble complicated for operation, and receive
Rate is relatively low, only 40-55%.
Invention content
For the drawbacks described above of the prior art, the present invention provides a kind of preparation method to chlorophenylboronic acid, and it includes following
Step:
1) para chlorobromobenzene is added in the first solvent, forms solution A, wherein para chlorobromobenzene:The mass ratio of first solvent is 1:
0.8-1.5;
2) trialkyl borate is added in the second solvent, forms solution B, wherein trialkyl borate:The quality of second solvent
Than being 1:0.7-1.4;
3) magnesium chips, initiator and solution B are added in third solvent, 40-50 DEG C is heated with stirring to, solution A is added dropwise later, are dripped
Insulation reaction 2-3h after the completion of adding, wherein magnesium chips:The mass ratio of third solvent is 1:6;
4) in the reactive mixture agitation and dropping dilute hydrochloric acid to pH 2-3, during which temperature control at 20 DEG C hereinafter, later at 20-30 DEG C
Lower insulation reaction 3h;
5) stratification recycles upper organic phase, obtains described to chlorophenylboronic acid.
Preferably, para chlorobromobenzene:Magnesium:The molar ratio of trialkyl borate is 1:1-1.2:1-1.2.
First solvent, the second solvent and third solvent are identical or different, respectively tetrahydrofuran, methyltetrahydrofuran, first
Benzene or methyl tertiary butyl ether(MTBE).Preferably, the first solvent is toluene, and the second solvent and third solvent are tetrahydrofuran.
Specifically, initiator is 0.5-1g iodine grains.
Specifically, trialkyl borate is selected from trimethylborate, triethyl borate, triproylborate, three isopropyl of boric acid
Ester, three isobutyl ester of boric acid or triamylborate or combinations thereof.Preferably, trialkyl borate is trimethylborate.
Preferably, in the step 3), the drop rate of the solution A is 3mL/min.
Preferably, step 1) -3) it is to carry out under nitrogen protection.
Beneficial effects of the present invention are that grignard reaction and substitution reaction are completed in one step, and operation is simpler, and can
Shorten reaction time.And due to being that the solution A containing para chlorobromobenzene is added dropwise in the solution of magnesium chips and trialkyl borate,
Another reactant trialkyl borate of substitution reaction almost remains excessive, and Grignard Reagent rubigan magnesium bromide is once raw
Rubigan borate is generated at being reacted with trialkyl borate, coupled product and two substitution product impurity are few, therefore nothing
Ultralow temperature control is needed, energy consumption is substantially reduced, simplifies operation.In addition, since by-product is less, the method for the present invention to chlorophenylboronic acid
Yield is higher, up to 75-80%.
Specific implementation mode
For a better understanding of the present invention, below with specific example come the technical solution that the present invention will be described in detail, but this
Invention is not limited thereto.
Embodiment 1
The present embodiment provides a kind of preparation methods to chlorophenylboronic acid, and it includes following steps:
1) 314g toluene under nitrogen protection, is added into 1L reaction bulbs, 382g para chlorobromobenzenes are added later, stirs evenly, obtains
To solution A;
2) 160g tetrahydrofurans under nitrogen protection, are added into 1L reaction bulbs, 207.8g trimethylborates are added later, stir
It mixes uniformly, obtains solution B;
3) 314g tetrahydrofurans, 48.6g magnesium chips and 0.5g iodine grains under nitrogen protection, are added into 2L reaction bulbs, under stiring
The solution B is added, heating water bath is warming up to 40-50 DEG C, and the solution A is added dropwise with the rate of 3mL/min later, is added dropwise
Insulation reaction 2.5 hours afterwards;
4) reaction mixture is transferred to 3L reaction bulbs, 18% dilute hydrochloric acid is slowly added dropwise under stiring to pH 2-3, during which temperature control
At 20 DEG C hereinafter, keeping the temperature 20-30 DEG C later, react 3 hours;
5) stop stirring, reaction mixture sat is made to be layered, separation upper organic phase and lower layer's water phase use 200g toluene later
Aqueous phase extracted is primary, then secondary clearing, merges organic phase, by merged organic layer with≤65 under the vacuum not less than -0.08MPa
It is concentrated under reduced pressure at a temperature of DEG C, is dried at 65-70 DEG C, obtain 246g in pale powder to chlorophenylboronic acid, yield 77%,
Purity >=99%.
Embodiment 2
The present embodiment provides a kind of preparation methods to chlorophenylboronic acid, and it includes following steps:
1) 568g toluene under nitrogen protection, is added into 1L reaction bulbs, 382g para chlorobromobenzenes are added later, stirs evenly, obtains
To solution A;
2) 279g tetrahydrofurans under nitrogen protection, are added into 1L reaction bulbs, 207.8g triproylborates are added later, stir
It mixes uniformly, obtains solution B;
3) 316g tetrahydrofurans, 48.6g magnesium chips and 0.5g iodine grains under nitrogen protection, are added into 2L reaction bulbs, under stiring
The solution B is added, heating water bath is warming up to 40-50 DEG C, and the solution A is added dropwise with the rate of 3mL/min later, is added dropwise
Insulation reaction 2.5 hours afterwards;
4) reaction mixture is transferred to 3L reaction bulbs, 18% dilute hydrochloric acid is slowly added dropwise under stiring to pH 2-3, during which temperature control
At 20 DEG C hereinafter, keeping the temperature 20-30 DEG C later, react 3 hours;
5) stop stirring, reaction mixture sat is made to be layered, separation upper organic phase and lower layer's water phase use 200g toluene later
Aqueous phase extracted is primary, then secondary clearing, merges organic phase, by merged organic layer with≤65 under the vacuum not less than -0.08MPa
It is concentrated under reduced pressure at a temperature of DEG C, is dried at 65-70 DEG C, obtain 250g in pale powder to chlorophenylboronic acid, yield 80%,
Purity >=99%.
Embodiment 3
The present embodiment provides a kind of preparation methods to chlorophenylboronic acid, and it includes following steps:
1) 402g methyl tertiary butyl ethers under nitrogen protection, are added into 1L reaction bulbs, 382g para chlorobromobenzenes, stirring are added later
Uniformly, solution A is obtained;
2) 226g methyltetrahydrofurans under nitrogen protection, are added into 1L reaction bulbs, three isobutyl of 205g boric acid is added later
Ester stirs evenly, and obtains solution B;
3) 313g tetrahydrofurans, 48.6g magnesium chips and 0.5g iodine grains under nitrogen protection, are added into 2L reaction bulbs, under stiring
The solution B is added, heating water bath is warming up to 40-50 DEG C, and the solution A is added dropwise with the rate of 3mL/min later, is added dropwise
Insulation reaction 2.5 hours afterwards;
4) reaction mixture is transferred to 3L reaction bulbs, 18% dilute hydrochloric acid is slowly added dropwise under stiring to pH 2-3, during which temperature control
At 20 DEG C hereinafter, keeping the temperature 20-30 DEG C later, react 3 hours;
5) stop stirring, reaction mixture sat is made to be layered, separation upper organic phase and lower layer's water phase use 200g toluene later
Aqueous phase extracted is primary, then secondary clearing, merges organic phase, by merged organic layer with≤65 under the vacuum not less than -0.08MPa
It is concentrated under reduced pressure at a temperature of DEG C, is dried at 65-70 DEG C, obtain 248g in pale powder to chlorophenylboronic acid, yield 79%,
Purity >=99%.
The above embodiment of the present invention is only preferred embodiment, is not limited to the scope of the present invention.This field
Those of ordinary skill can understand the spirit of the present invention according to above-described embodiment, and make a variety of different modifications and variations.It is not taking off
In the case of spirit from the present invention, all such modifications and variations are all within the scope of the present invention.
Claims (9)
1. a kind of preparation method to chlorophenylboronic acid, which is characterized in that comprise the steps of:
1) para chlorobromobenzene is added in the first solvent, forms solution A, wherein para chlorobromobenzene:The mass ratio of first solvent is 1:
0.8-1.5;
2) trialkyl borate is added in the second solvent, forms solution B, wherein trialkyl borate:The quality of second solvent
Than being 1:0.7-1.4;
3) magnesium chips, initiator and solution B are added in third solvent, are heated with stirring to 40-50 DEG C, solution is slowly added dropwise later
A is added dropwise to complete rear insulation reaction 2-3h, wherein magnesium chips:The mass ratio of third solvent is 1:6;
4) in the reactive mixture agitation and dropping dilute hydrochloric acid to pH 2-3, during which temperature control at 20 DEG C hereinafter, later at 20-30 DEG C
Lower insulation reaction 3h;
5) stratification recycles upper organic phase, obtains described to chlorophenylboronic acid.
2. the preparation method according to claim 1 to chlorophenylboronic acid, which is characterized in that para chlorobromobenzene:Magnesium:Three alkane of boric acid
The molar ratio of base ester is 1:1-1.2:1-1.2.
3. the preparation method according to claim 1 to chlorophenylboronic acid, which is characterized in that first solvent, second molten
Agent and third solvent are identical or different, respectively tetrahydrofuran, methyltetrahydrofuran, toluene or methyl tertiary butyl ether(MTBE).
4. the preparation method according to claim 3 to chlorophenylboronic acid, which is characterized in that first solvent is toluene,
Second solvent and third solvent are tetrahydrofuran.
5. the preparation method according to claim 1 to chlorophenylboronic acid, which is characterized in that the initiator is 0.5-1g iodine
Grain.
6. the preparation method according to claim 1 to chlorophenylboronic acid, which is characterized in that the trialkyl borate is selected from
Trimethylborate, triethyl borate, triproylborate, triisopropyl borate ester, three isobutyl ester of boric acid or triamylborate or its group
It closes.
7. the preparation method according to claim 6 to chlorophenylboronic acid, which is characterized in that the trialkyl borate is boron
Sour trimethyl.
8. the preparation method according to claim 1 to chlorophenylboronic acid, which is characterized in that described in the step 3)
The drop rate of solution A is 3mL/min.
9. the preparation method according to any one of claim 1 to 8 to chlorophenylboronic acid, which is characterized in that the step
1) it is -3) to carry out under nitrogen protection.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810797300.5A CN108690063A (en) | 2018-07-19 | 2018-07-19 | A kind of preparation method to chlorophenylboronic acid |
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|---|---|---|---|
| CN201810797300.5A CN108690063A (en) | 2018-07-19 | 2018-07-19 | A kind of preparation method to chlorophenylboronic acid |
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| CN108690063A true CN108690063A (en) | 2018-10-23 |
Family
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| CN201810797300.5A Pending CN108690063A (en) | 2018-07-19 | 2018-07-19 | A kind of preparation method to chlorophenylboronic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110054642A (en) * | 2019-04-24 | 2019-07-26 | 京博农化科技有限公司 | A kind of preparation method of pair of chlorophenylboronic acid |
| CN111004262A (en) * | 2019-12-13 | 2020-04-14 | 京博农化科技有限公司 | Synthetic method of p-chlorophenylboronic acid |
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| CN103570753A (en) * | 2013-11-13 | 2014-02-12 | 大连九信生物化工科技有限公司 | Preparation method of arylboronic acid compound |
| CN106748804A (en) * | 2016-11-18 | 2017-05-31 | 浙江荣凯科技发展股份有限公司 | A kind of Boscalid intermediate 2（4 chlorphenyls）Aniline synthesis technique |
| CN106946915A (en) * | 2017-03-16 | 2017-07-14 | 安徽至善新材料有限公司 | A kind of high-purity, method to chlorophenylboronic acid is prepared in high yield |
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2018
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| CN103570753A (en) * | 2013-11-13 | 2014-02-12 | 大连九信生物化工科技有限公司 | Preparation method of arylboronic acid compound |
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| CN106946915A (en) * | 2017-03-16 | 2017-07-14 | 安徽至善新材料有限公司 | A kind of high-purity, method to chlorophenylboronic acid is prepared in high yield |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110054642A (en) * | 2019-04-24 | 2019-07-26 | 京博农化科技有限公司 | A kind of preparation method of pair of chlorophenylboronic acid |
| CN111004262A (en) * | 2019-12-13 | 2020-04-14 | 京博农化科技有限公司 | Synthetic method of p-chlorophenylboronic acid |
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Application publication date: 20181023 |