(3,4-Dimethoxyphenyl)acetonitrile

Synonym(s):(3,4-Dimethoxyphenyl)acetonitrile;3,4-Dimethoxybenzylcyanide;Homoveratronitrile

CAS NO.：93-17-4
Empirical Formula: C10H11NO2
Molecular Weight: 177.2
MDL number: MFCD00001911
EINECS: 202-225-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-19 20:33:22

(3,4-Dimethoxyphenyl)acetonitrile Structural

What is (3,4-Dimethoxyphenyl)acetonitrile?

Chemical properties

white to almost white crystals or cryst. needles

The Uses of (3,4-Dimethoxyphenyl)acetonitrile

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

The Uses of (3,4-Dimethoxyphenyl)acetonitrile

An Impurity of Verapamil (V125000). An intermediate in the preparation of the muscle relaxant Papverine (P190500).

Synthesis Reference(s)

Journal of the American Chemical Society, 57, p. 1126, 1935 DOI: 10.1021/ja01309a053
Tetrahedron Letters, 24, p. 4533, 1983 DOI: 10.1016/S0040-4039(00)85947-X

Purification Methods

Its solubility is 10% in MeOH, and it has been recrystallised from EtOH or MeOH. Purify it also by distillation followed by recrystallisation. [Price & Rogers Org Synth Coll Vol III 174 1955, Niederl & Ziering J Am Chem Soc 64 885 1952, Julian & Sturgis J Am Chem Soc 57 1126 1935, Beilstein 10 I 198.]

Properties of (3,4-Dimethoxyphenyl)acetonitrile

Melting point:	54-57 °C(lit.)
Boiling point:	171-178 °C10 mm Hg(lit.)
Density	1.1607 (rough estimate)
refractive index	1.5168 (estimate)
Flash point:	>230 °F
storage temp.	Sealed in dry,Room Temperature
solubility	methanol: 0.1 g/mL, clear
form	Crystals or Crystalline Needles
color	yellow
Water Solubility	insoluble
BRN	1956100
Exposure limits	NIOSH: IDLH 25 mg/m3
CAS DataBase Reference	93-17-4(CAS DataBase Reference)
NIST Chemistry Reference	Benzeneacetonitrile, 3,4-dimethoxy-(93-17-4)