3,5-DIMETHOXYPHENYLACETONITRILE Chemical Properties

Melting point:

54-57 °C(lit.)

Boiling point:

316.7±27.0 °C(Predicted)

Density 

1.082±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Dichloromethane, Ethyl Acetate

form 

powder to crystal

color 

White to Orange to Green

BRN 

2096481

InChI

InChI=1S/C10H11NO2/c1-12-9-5-8(3-4-11)6-10(7-9)13-2/h5-7H,3H2,1-2H3

InChIKey

UUNRWZQWCNTSCV-UHFFFAOYSA-N

SMILES

C1(CC#N)=CC(OC)=CC(OC)=C1

CAS DataBase Reference

13388-75-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

22

Safety Statements 

36/37-24/25

RIDADR 

3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3,5-DIMETHOXYPHENYLACETONITRILE Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

(3,5-Dimethoxyphenyl)acetonitrile (cas# 13388-75-5) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of 3,5-dimethoxyphenylacetonitrile from trimethylsilyl cyanide and 3,5-dimethoxybenzyl bromide: In 100 mL of acetonitrile, 2.310 g (0.01 mol) of 3,5-dimethoxy-4-bromobenzyl bromide, 1.485 g (0.015 mol) of trimethylsilyl cyanide, and 4.725 g (0.015 mol) of tetra butylammonium fluoride in a 30 mL three-neck flask. The mixture was stirred and heated to reflux and the reaction was carried out for 6 hours, during which time the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, it was cooled to room temperature and the reaction solution was poured into 100 mL of ice water and stirred until a white solid precipitated. The solid was collected by filtration, washed with 50% methanol and dried to afford the target compound 3,5-dimethoxyphenylacetonitrile in 66.7% yield.

Purification Methods

Crystallise the nitrile from MeOH or pet ether (b 90-110o). [Adams et al. J Am Chem Soc 70 664 1948, Sankaraman et al. J Am Chem Soc 109 5235 1987, Beilstein 10 I 198, 10 II 269, 10 III 1470.]

References

[1] Patent: CN105503652, 2016, A. Location in patent: Paragraph 0048; 0049
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 1, p. 81 - 85

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