3-Dimethylaminophenylboronic acid Chemical Properties

Melting point:

191-193°C

Boiling point:

344.0±44.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

8.54±0.10(Predicted)

color 

Pale Green to Pale Grey

InChI

InChI=1S/C8H12BNO2/c1-10(2)8-5-3-4-7(6-8)9(11)12/h3-6,11-12H,1-2H3

InChIKey

YZQQHZXHCXAJAV-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(N(C)C)=C1)(O)O

CAS DataBase Reference

178752-79-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

UN 3335

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

3-Dimethylaminophenylboronic acid Usage And Synthesis

Chemical Properties

Solid

Uses

Reactant involved in synthesis of different protein effector including:

• Modulators of survival motor neuron protein
• Glucokinase activators
• Aryl ethers for use as Bacillus anthracis enoyl-ACP reductase inhibitors

Reactant involved in synthesis of:

• Thiourea-functionalized paracyclophanes
• Low-background fluorescent imaging agents for nitric oxide

Reactant to undergo regioselective iodination and bromination

Uses

3-Dimethylaminophenylboronic acid, HCl

General Description

May contain varying amounts of anhydride

Synthesis

The general procedure for the synthesis of 3-(N,N-dimethylamino)phenylboronic acid from 3-bromo-N,N-dimethylaniline was as follows: 3-bromo-N,N-dimethylaniline (500 mg, 2.50 mmol) was dissolved in tetrahydrofuran (THF, 8 mL) and the solution was cooled to -78 °C. At -78 °C, n-butyllithium (1.6 M in hexane, 1.56 mL, 3.75 mmol) was slowly added dropwise, and after the drop was completed, the reaction mixture continued to be stirred for 5 min by maintaining this temperature. Subsequently, trimethyl borate (1.11 mL, 10.0 mmol) was added and stirred at -78 °C for 1 h, followed by a slow warming to -20 °C over 20 min. 2 M hydrochloric acid (3 mL) was added and after stirring for 5 min, the reaction mixture was neutralized with saturated sodium bicarbonate (NaHCO3) solution. The mixture was extracted with ethyl acetate (3 × 10 mL), the organic phases were combined, and the crude product was concentrated under reduced pressure. Purification by silica gel fast column chromatography with acetone/dichloromethane (1:1, v/v) as eluent gave the target product 3-(N,N-dimethylamino)phenylboronic acid (251 mg, 61% yield).

References

[1] Patent: US2006/270686, 2006, A1. Location in patent: Page/Page column 26
[2] Patent: WO2008/8059, 2008, A1. Location in patent: Page/Page column 68
[3] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[4] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4

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