Iodoacetonitrile Chemical Properties

Boiling point:

182-184 °C/720 mmHg (lit.)

Density 

2.307 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.574(lit.)

RTECS 

AM0740000

Flash point:

187 °F

storage temp. 

2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

Specific Gravity

2.307

color 

Clear red to brown

Water Solubility 

Soluble in benzene, alcohol, acetone, ether. Slightly soluble in water. Insoluble in hexane.

Sensitive 

Light Sensitive

BRN 

1734628

Exposure limits

NIOSH: IDLH 25 mg/m3

Stability:

Light Sensitive

CAS DataBase Reference

624-75-9(CAS DataBase Reference)

NIST Chemistry Reference

Iodoacetonitrile(624-75-9)

EPA Substance Registry System

Acetonitrile, iodo- (624-75-9)

Safety Information

Hazard Codes 

C,T

Risk Statements 

22-34-36/37/38-23/24/25

Safety Statements 

26-36/37/39-45-24/25

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

8-10-19-21

HazardClass 

8

PackingGroup 

II

HS Code 

29269090

MSDS

• Language:English Provider:Iodoacetonitrile
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Iodoacetonitrile Usage And Synthesis

Chemical Properties

clear red to brown liquid

Uses

Iodoacetonitrile is used for alkylation of nucleophiles. It undergoes Reformatsky and Wittig-type reactions with aldehydes.

Synthesis

Step 2. The method followed the synthesis of literature S5: 2,6-piperidinedimethanol (3.80 g, 26.21 mmol), iodoacetonitrile (5.24 g, 31.45 mmol), triethylamine (Et3N, 4.38 mL, 31.45 mmol) and anhydrous N,N-dimethylformamide (DMF, 20 mL) were added to the reaction system. Upon completion of the reaction, the product was purified by fast column chromatography using a solvent mixture of dichloromethane (CH2Cl2) and methanol (CH3OH) (9:1, v/v) as eluent to afford iodoacetonitrile as a straw-colored oily substance (2.5 g, 53% yield). the molecular ion peak m/z (M + H)+ was determined by FAB MS to be 185. iodoacetonitrile was prepared using the Finkelstein reaction: Bromoacetonitrile (BrCH2CN, 3.77 g, 0.0314 mmol) was added dropwise to an acetone solution of sodium iodide (NaI, 4.71 g, 0.031 mmol) under stirring. A precipitate of sodium bromide (NaBr) was produced within a few minutes of the reaction, indicating that a halogen exchange reaction had occurred. The sodium bromide was removed by filtration and the acetone was subsequently evaporated under vacuum to give the crude product iodoacetonitrile (5.24 g, 100% yield).

References

[1] Patent: WO2005/61453, 2005, A1. Location in patent: Page/Page column 15
[2] Journal of the American Chemical Society, 1980, vol. 102, # 4, p. 1367 - 1371

Iodoacetonitrile(624-75-9)Related Product Information

• Sodium sulfide nonahydrate
• 3-Aminopropionitrile
• Iminodiacetonitrile
• Benzeneacetonitrile
• Glycolonitrile
• Iodoethane
• Ammonium iodide
• Iodoacetonitrile (Iodomethyl cyanide)
• FLUOROIODOACETONITRILE 97
• Iodoacetonitrile