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93-17-4 - 3,4-Dimethoxyphenylacetonitrile, 98% - 3,4-Dimethoxybenzyl cyanide - Homoveratronitrile - A12003 - Alfa Aesar

A12003 3,4-Dimethoxyphenylacetonitrile, 98%

CAS Number
93-17-4
Synonyms
3,4-Dimethoxybenzyl cyanide
Homoveratronitrile

Size Price ($) Quantity Availability
25g 17.92
100g 37.90
500g 133.20
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3,4-Dimethoxyphenylacetonitrile, 98%

MDL
MFCD00001911
EINECS
202-225-1

Chemical Properties

Formula
C10H11NO2
Formula Weight
177.20
Melting point
62-65°
Boiling Point
177-178°/10mm
Solubility
Insoluble in water. Soluble in methanol.

Applications

It is employed as an intermediate in the preparation of the muscle relaxant papverin. 3,4-Dimethoxyphenyl)acetonitrile has been used in the synthesis of (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile1. It has also been used in the preparation of modified diterpene (±) nimbidiol which relies on a sulfenium ion promoted polyene cyclization.

Notes

Store in cool place. Keep away from oxidizing agents.

Literature References

Eide-Dittmar Luebs.; Alberto Cohen.; Edward J. Zaleski.; Richard J. Bing. Effect of nitroglycerin, intensain, isoptin and papaverine on coronary blood flow in man ?: Measured by the coincidence counting technic and rubidium. The American Journal of Cardiology. 1966, 17 (4),535-541.

A. Carpy, J.-M. Léger.; C. Melchiorre. Structure of [alpha]-isopropyl-[alpha]-[(N-methyl-N-homoveratryl)-[gamma]-aminopropyl]-3,4-dimethoxyphenylacetonitrile hydrochloride, verapamil, C27H38N2O4.HCl. Acta Cryst. 1985, (C41),624-627.

Reaction with dimethylamine in the presence of CuCl gives the N,N-dimethylamidine, which, on borohydride reduction, provides an efficient route to the N,N-dimethylphenethylamine: Tetrahedron Lett., 34, 6395 (1993); Org. Synth., 76, 133 (1998). The method is applicable to other alkyl nitriles and to both primary and secondary amines, providing a general route to secondary and tertiary amines from the corresponding nitriles:

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H312

Harmful if swallowed. Harmful in contact with skin.

Precautionary Statements: P280h

Wear protective gloves/clothing.

Other References

Beilstein
1956100
Harmonized Tariff Code
2926.90
TSCA
No
RTECS
AL9325000

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