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ChemicalBook--->CAS DataBase List--->99349-68-5

99349-68-5

99349-68-5 Structure

99349-68-5 Structure
IdentificationBack Directory
[Name]

(M-ACRYLAMIDOPHENYL)BORONIC ACID
[CAS]

99349-68-5
[Synonyms]

(m-AcryL
amidophenyL
3-(Propenamido)
Boronic acid acrylamide
Phenylboronate acrylamide
3-Acrylamidobenzeneboronic Acid
(M-ACRYLAMIDOPHENYL)BORONIC ACID
3-(Propenamido)phenylboronic acid
N-Acryloyl-m-aminophenylboronic acid
3-(Acryloylamino)benzeneboronic acid
3-(AcrylaMido)phenylboronic acid 98%
N-Acryloyl-3-aminophenylboronic acid
Boronic acid, B-[3-[(1-oxo-2-propen-1-yl)amino]phenyl]-
3-Acrylamidophenylboronic Acid (contains varying amounts of Anhydride)
3-(Acrylamido)phenylboronic acid, 3-[(Prop-2-enoyl)amino]benzeneboronic acid
[Molecular Formula]

C9H10BNO3
[MDL Number]

MFCD09025755
[MOL File]

99349-68-5.mol
[Molecular Weight]

190.992
Chemical PropertiesBack Directory
[Melting point ]

129-146°C
[density ]

1.22±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[form ]

powder to crystal
[pka]

8.05±0.10(Predicted)
[color ]

White to Amber
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312+H332
[Precautionary statements ]

P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
[Hazard Codes ]

Xn
[Risk Statements ]

22
[WGK Germany ]

3
[HS Code ]

2931900090
Hazard InformationBack Directory
[Uses]

suzuki reaction
[Synthesis]

3-Aminobenzeneboronic acid

30418-59-8

Acryloyl chloride

814-68-6

(M-ACRYLAMIDOPHENYL)BORONIC ACID

99349-68-5

General procedure for the synthesis of 3-acrylamidophenylboronic acid from 3-aminophenylboronic acid and acryloyl chloride: 3-aminophenylboronic acid (0.566 g, 3.65 mmol) and Na2CO3 (0.67 g, 80.3 mmol) were added to 20 mL of a 1:1 (v/v) solvent mixture of tetrahydrofuran and water and the mixture was cooled to 0 °C. Acryloyl chloride (960 mg, 8.06 mmol) was slowly added dropwise under stirring conditions. After the dropwise addition, the mixture was allowed to warm up naturally to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, 10 mL of water was added to terminate the reaction, followed by extraction of the reaction mixture with ethyl acetate (20 mL x 3). The organic phases were combined, washed with saturated NaCl solution (10 mL) and finally the organic layer was dried with anhydrous Na2SO4. After concentrating the organic layer, it was purified by column chromatography to give the light yellow solid product 3-acrylamidophenylboronic acid (0.32 g, 40.1% yield).

[References]

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 11, p. 4636 - 4656
[2] Soft Matter, 2014, vol. 10, # 6, p. 911 - 920
[3] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19832 - 19838
[4] Patent: CN104945411, 2018, B. Location in patent: Paragraph 0077; 0078; 0079
[5] New Journal of Chemistry, 2012, vol. 36, # 2, p. 438 - 451
Spectrum DetailBack Directory
[Spectrum Detail]

(M-ACRYLAMIDOPHENYL)BORONIC ACID(99349-68-5)1HNMR
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