1,1-diiodoethane

1,1-diiodoethane Property

Melting point:

63.01°C (estimate)

Boiling point:

223.38°C (estimate)

Density 

2.7600

refractive index 

1.6500

storage temp. 

-20°C

form 

liquid

BRN 

1730848

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1,1-diiodoethane Chemical Properties,Usage,Production

Uses

1,1-diiodoethane is a reagent for methylcyclopropanation of alkenes and ethylidenation of carbonyl compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4476, 1951 DOI: 10.1021/ja01153a524

Synthesis

The Preparative Methods of 1,1-diiodoethane: mix 39.6 g (0.40 mol) of 1,1-dichloroethane, 187 g (1.2 mol) of ethyl iodide, and 2.0 g of Aluminum Chloride and heat on a steam bath for 3 h; wash the mixture with H2O and then NaHSO3, and dry over MgSO4; distillation provides 67.3 g (60%) of the product 1,1-diiodoethane boiling at 75-76 °C/25 mmHg. An alternative procedure utilizes the reaction of Iodine, Triethylamine, and the hydrazone of Acetaldehyde: from 1 mol of acetaldehyde, 95 g (34% from acetaldehyde) of 1,1-diiodoethane can be isolated; this procedure is a little more involved but provides a viable alternative if 1,1-dichloroethane is not available.

Precautions

Corrosive and irritant; emits toxic fumes if heated to decomposition or mes in contact with acids. Use in a fume hood; store over copper powder and protect from light.