2-IODOPHENYLACETONITRILE Chemical Properties

Boiling point:

113-120 °C0.5 mm Hg(lit.)

Density 

1.75 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.618(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Appearance

White to light yellow Solid

Sensitive 

Light Sensitive

BRN 

2083106

CAS DataBase Reference

40400-15-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

23-26-36

RIDADR 

3276

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

MSDS

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

2-IODOPHENYLACETONITRILE Usage And Synthesis

Uses

2-Iodophenylacetonitrile may be used in the preparation of:

• 2?-aminobiphen-2-ylacetonitrile
• ethyl (2-iodophenyl)iminoacetate hydrochloride
• 3,4-disubstituted 2-naphthalenamines

• 2-(2-iodophenyl)-2-methylpropanenitrile
• 1-(2-iodophenyl)cyclopentanecarbonitrile
• 5-bromo-2-(2-iodophenyl)pentanenitrile
• 2-(2-iodophenyl)-2-propylpentanenitrile
• 1-(2-iodophenyl)cyclohexanecarbonitrile
• 1-(2-Iodophenyl)cyclopropanecarbonitrile

General Description

2-Iodophenylacetonitrile is a 2-aryl substituted nitrile. It reacts with lactams to form ring-fused isoquinolinones via palladium-catalyzed carboxamidation in tandem with aldol condensation.

Synthesis

Distilled dichloromethane (5 mL) was added to a 25 mL reaction tube under nitrogen protection. Subsequently, 161 mg (0.5 mmol) of iodobenzene diacetate was added. Next, 180 μL of trimethylsilyl trifluoromethanesulfonate (TMSOTf, 1.0 mmol) was added. The reaction mixture was stirred at room temperature for 5 min. After that, 198 mg (0.6 mmol) of 2-(tributylstannyl)acetonitrile was added at -78 °C and stirring was continued for 5 min, and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, 3 mL of saturated sodium bicarbonate solution was added to quench the reaction. The reaction was slowly warmed to room temperature and then extracted with dichloromethane (3 mL x 3). The organic phases were combined and dried over anhydrous sodium sulfate. It was subsequently concentrated under reduced pressure. Purification by column chromatography (Rf = 0.19, unfolding agent: petroleum ether/ethyl acetate = 40/1, v/v) afforded the target product 2-iodophenylacetonitrile as a white solid in 86% yield.

References

[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 29, p. 9078 - 9082
[2] Angew. Chem., 2018, vol. 130, # 29, p. 9216 - 9220,5
[3] Patent: CN108409602, 2018, A. Location in patent: Paragraph 0022; 0023; 0024

2-IODOPHENYLACETONITRILE(40400-15-5)Related Product Information

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