4,5-Dimethoxy-1-cyanobenzocyclobutane Chemical Properties

Melting point:

83-84 °C

Boiling point:

345.9±42.0 °C(Predicted)

Density 

1.18

vapor pressure 

0.004Pa at 25℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO, Methanol

form 

Solid

color 

Light Brown

InChI

InChI=1S/C11H11NO2/c1-13-10-4-7-3-8(6-12)9(7)5-11(10)14-2/h4-5,8H,3H2,1-2H3

InChIKey

HJTHVTHXHHFXMJ-UHFFFAOYSA-N

SMILES

C12C(C(C#N)C1)=CC(OC)=C(OC)C=2

LogP

1.22 at 30℃ and pH7

CAS DataBase Reference

35202-54-1(CAS DataBase Reference)

Safety Information

HS Code 

2926907090

4,5-Dimethoxy-1-cyanobenzocyclobutane Usage And Synthesis

Uses

4,5-Dimethoxy-1-benzocyclobutenecarbonitrile is used in the preparation of selective bradycardic agents.

Uses

4,5-Dimethoxy-1-cyanobenzocyclobutane is used in the preparation of selective bradycardic agents.

Synthesis

NaNH2 (39.0 g, 1.0 mol) was added in portions to a solution of hydrocinnamonitrile 8 (224.0 g, 0.83 mol) in liquid ammonia at -45°C, and the reaction mixture was stirred at -45 °C for 2 h. After evaporation of the excess NH3, NH4Cl (20.0 g) and water (1000 mL) were added in portions. After standing at room temperature, greyish crystals separated and were collected and recrystallised with ethanol to give 4,5-Dimethoxy-1-cyanobenzocyclobutane as a colourless powder. Yield 116.5 g (74%).

References

[1] Patent: WO2011/138625, 2011, A1. Location in patent: Page/Page column 31-32
[2] Journal of Chemical Research, 2009, # 7, p. 420 - 422
[3] Patent: US2014/107334, 2014, A1. Location in patent: Paragraph 0048-0051
[4] Patent: US2014/128598, 2014, A1. Location in patent: Paragraph 0040-0043
[5] Patent: US2014/163220, 2014, A1. Location in patent: Paragraph 0034-0037

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