2-Aminophenylboronic acid Chemical Properties

Melting point:

188-190°C

Boiling point:

346.9±44.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

8.83±0.53(Predicted)

color 

light yellow

BRN 

2962939

CAS DataBase Reference

5570-18-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-37-36

Hazard Note 

Harmful

HS Code 

29310095

MSDS

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2-Aminophenylboronic acid Usage And Synthesis

Chemical Properties

Crystalline powder

Uses

2-Aminobenzeneboronic acid derivative is used in the synthesis of quinolines by reacting with alpha, beta unsaturated ketones. Its hydrochloride derivative is used in the preparation of designed boronate ligands for glucose-selective holographic sensors.

Uses

2-Aminophenylboronic acid is used in the preparation of affinity sites for antibacterial drugs like ampicillin. A useful synthesis intermediate.

Synthesis

General procedure for the synthesis of 2-aminophenylboronic acid from 2-nitrophenylboronic acid: (i) Preparation of 2-aminophenylboronic acid: 2-nitrophenylboronic acid (500 mg, 2.99 mmol) was dissolved in methanol (10 mL) and 10% Pd/C (250 mg) was added. The reaction mixture was stirred at atmospheric pressure for 2 h under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, dichloromethane solution of 0-50% CMA) to afford the target compound 2-aminophenylboronic acid (182 mg).1H NMR (300 MHz, CD3OD) δ 6.69-7.75 (m, 4H).

References

[1] Patent: CN103214489, 2016, B. Location in patent: Paragraph 0063-0064
[2] Journal of the American Chemical Society, 1994, vol. 116, # 17, p. 7597 - 7605
[3] Patent: US2005/192310, 2005, A1. Location in patent: Page/Page column 47
[4] Patent: US8324264, 2012, B1. Location in patent: Page/Page column 116
[5] Patent: EP2712863, 2014, A1. Location in patent: Paragraph 0184-0185

2-Aminophenylboronic acid(5570-18-3)Related Product Information

• 2-Aminophenylboronic acid pinacol ester
• Sulfanilamide
• Sulfanilic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• p-Anisidine
• 4-Aminobenzoic acid
• Phenylboronic acid
• Aniline
• Methyl anthranilate
• Citric acid
• Ascoric Acid
• 3-AMINOPHENYLBORONIC ACID,3-Aminophenylboronic Acid Monohydrate (contains varying amounts of Anhydride),M-AMINOPHENYLBORONIC ACID
• (2-BOC-AMINOPHENYL)BORONIC ACID
• Anthranilic acid
• 2-Nitrobenzeneboronic acid pinacol ester
• 4-Ethoxycarbonyl-2-nitrophenylboronic acid
• 4-CARBOXY-2-NITROPHENYLBORONIC ACID