3-Carboxy-5-nitrophenylboronic acid Chemical Properties

Melting point:

229°C(lit.)

Boiling point:

502.6±60.0 °C(Predicted)

Density 

1.62±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.49±0.10(Predicted)

color 

White to Light yellow

CAS DataBase Reference

101084-81-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

3-Carboxy-5-nitrophenylboronic acid Usage And Synthesis

Chemical Properties

White solid

Uses

Reactant for:

• Copper-catalyzed chlorination
• Parallel solid-phase synthesis of azabicyclooctylidenemethylbenzamides as μ- and d-opioid agonists

• Immobilization of glucose oxidase and acetylcholinesterase on boronic acid-activated silica surfaces

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 3-carboxy-5-nitrophenylboronic acid from 3-carboxyphenylboronic acid is as follows: first, 7.5 g of 3-carboxyphenylboronic acid (45.2 mmol) was mixed with 25 ml of concentrated sulphuric acid, and 25 ml of fuming nitric acid was slowly added under rapid stirring conditions while cooling using an ice water bath. The reaction mixture was stirred for 15 min, then the ice water bath was removed and the reaction continued to be stirred for 15 min. Subsequently, the reaction solution was poured into ice water to produce a precipitate, which was filtered and then the precipitate was washed with ice water for 5 times, and finally 6.01 g of 3-nitro-5-carboxyphenylboronic acid as a white solid was obtained by aqueous recrystallization in 63.0% yield. Next, 1.50 g of 3-carboxy-5-nitrophenylboronic acid (7.1 mmol) was dissolved in 20 ml of methanol, and 2 g of 10% Pd/C catalyst was added in a 50 ml three-necked flask for a catalytic hydrogenolysis reaction for 6 hours. After completion of the reaction, the Pd/C catalyst was removed by filtration and the filtrate was evaporated to dryness to give 1.25 g of 3-amino-5-carboxyphenylboronic acid as a white powdery solid in 97.1% yield.

References

[1] Patent: CN103497211, 2016, B. Location in patent: Paragraph 0190
[2] Organic Preparations and Procedures International, 1991, vol. 23, # 6, p. 729 - 734
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 3017
[4] Arkiv foer Kemi, 1957, vol. 10, p. 497,503

3-Carboxy-5-nitrophenylboronic acid(101084-81-5)Related Product Information

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• 3-Carboxyphenylboronic acid
• Phenylboronic acid
• 4-Nitrobenzenesulfonyl chloride
• 3-Nitrobenzaldehyde
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• 3-Nitroacetophenone
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• 3-METHOXYCARBONYL-5-NITROPHENYLBORONIC ACID
• Nitrobenzene