2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE Chemical Properties

Melting point:

46-56 °C(lit.)

Boiling point:

372.4±25.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

solid

color 

white

Stability:

Hygroscopic

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

No

HS Code 

2931900090

MSDS

• Language:English Provider:SigmaAldrich

2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE Usage And Synthesis

Chemical Properties

White powder

Uses

2-(2-Cyanophenyl)-1,3,2-dioxaborinane is used in the synthesis of AMPA receptor antagonists in the treatment of neurological diseases causing dysfunction of glutamatergic neurotransmission. Also used in the small scale synthesis of Perampanel (P285520), an AMPA receptor antagonist.

Synthesis

The general procedure for the synthesis of 2-cyanophenylboronic acid-1,3-propanediol cyclic ester from 2-cyanophenylboronic acid and 1,3-propanediol is as follows: 3.69 g (48.5 mmol) of 1,3-propanediol was added to the organic phase obtained from Example 1 and the reaction mixture was stirred for 1 hour at room temperature. Upon completion of the reaction, the aqueous phase was separated and removed, followed by distillation using a rotary evaporator to remove the organic solvent. To the residual oily substance, 2 ml of toluene and 120 ml of heptane were added to induce crystallization. The resulting crystals were washed with 30 mL of heptane and 7.44 g (yield: 82.4%) of the target product 1,3-propanediol ester (2-(1,3,2-dioxaborolan-2-yl)benzonitrile) was obtained after drying. The crystals were analyzed to contain 0.40% impurity of 1-phenyl-1-(2,2,6,6-tetramethylpiperidin-1-yl)methanimine.

References

[1] Patent: JP2015/160823, 2015, A. Location in patent: Paragraph 0056
[2] Patent: EP2243785, 2010, A1
[3] Patent: US9281483, 2016, B2. Location in patent: Page/Page column 93
[4] Patent: KR2016/30582, 2016, A. Location in patent: Paragraph 0258; 0259; 0260; 0261; 0262
[5] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 3867 - 3876

2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(172732-52-4)Related Product Information

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