2-Bromomethylphenylboronic acid Chemical Properties

Melting point:

158-162 °C

Boiling point:

358.5±44.0 °C(Predicted)

Density 

1.57±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

8.44±0.58(Predicted)

form 

crystalline powder

color 

Faint orange

InChI

InChI=1S/C7H8BBrO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,10-11H,5H2

InChIKey

MYVJCOQGXCONPE-UHFFFAOYSA-N

SMILES

B(C1=CC=CC=C1CBr)(O)O

CAS DataBase Reference

91983-14-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-36/37-36

RIDADR 

3261

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2931900090

2-Bromomethylphenylboronic acid Usage And Synthesis

Uses

suzuki reaction

Uses

Reactant involved in:

• Studies of carbon-boron bond cleavage of phenylboronate-pendant cyclen
• Development of a sensory system to detect glucose or other monosaccharides and hydroxycarboxylates
• Synthesis of boronated triaryl and tetraaryl phosphonium salts used in cytotoxicity studies
• Colorimetry and fluorometry mercury determination with chemosensors composed of rhodamine and boronic acid groups
• Synthesis of imidazolium-containing boronic acids used as fluoride ion sensors
• Reactions with adenine for molecules with antiinflammatory antitumor activities?

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 835, 1958 DOI: 10.1021/ja01537a021

General Description

May contain varying amounts of anhydride.

Synthesis

General procedure for the synthesis of 2-(bromomethyl)benzeneboronic acid from 2-methylbenzeneboronic acid: 14.8 g (0.11 mol) of 2-methylbenzeneboronic acid was added to a 500 mL round bottom flask, followed by the addition of 380 mL of carbon tetrachloride, which was heated slightly until dissolved. A bromine solution was prepared by dissolving 17.9 g of bromine in 85 mL of carbon tetrachloride under light conditions. At the beginning of the reaction, a portion of the bromine solution was added quickly to keep the reaction solution light yellow. After the reaction was carried out for 2 hours, the reaction mixture was bleached with alkaline solution and subsequently filtered. The filter cake was washed five times with carbon tetrachloride and three times with hexane. Finally, the product was dried under vacuum to give 19.97 g of white powdery solid in 84.6% yield.

References

[1] Patent: CN103497211, 2016, B. Location in patent: Paragraph 0242; 0243
[2] Tetrahedron Letters, 2001, vol. 42, # 34, p. 5875 - 5877
[3] Russian Chemical Bulletin, 2005, vol. 54, # 11, p. 2602 - 2611
[4] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
[5] Chinese Journal of Chemistry, 2011, vol. 29, # 11, p. 2445 - 2450

2-Bromomethylphenylboronic acid(91983-14-1)Related Product Information

• Glycine
• BROMOPENTAMETHYLBENZENE
• Ethyl 2-(Chlorosulfonyl)acetate
• Bromotrimethylsilane
• Phenylboronic acid
• Folic acid
• Benzyl bromide
• 4-Tolylboronic acid
• 3,5-Dimethylphenylboronic acid
• Methyl 4-(bromomethyl)benzoate
• 2-Bromomethyl-4-fluorophenylboronic acid neopentyl glycol ester
• (2-BROMOMETHYL-4-FLUOROBENZENE)BORONIC ACID
• 2-Bromomethyl-4-fluorophenylboronic acid pinacol ester
• (2-BROMOMETHYLPHENYL)BORONIC ACID, PINACOL ESTER
• 4-BROMOMETHYLPHENYLBORONIC ACID
• 2-BROMOMETHYLPHENYLBORONIC ACID, MONO(2,2-DIMETHYLPROPYL) ESTER
• 3-BROMOMETHYLPHENYLBORONIC ACID
• Methyl bromide