1-CHLORO-1-METHYLSILACYCLOBUTANE Property

Boiling point:

103 °C(lit.)

Density 

0.985 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.45(lit.)

Flash point:

37 °F

solubility 

soluble in most aprotic organic solvents.

Specific Gravity

0.985

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

Safety

Hazard Codes 

F,C

Risk Statements 

11-14-34

Safety Statements 

16-26-36/37/39-45

RIDADR 

UN 2985 3/PG 2

WGK Germany 

3

TSCA 

No

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

1-CHLORO-1-METHYLSILACYCLOBUTANE Chemical Properties,Usage,Production

Physical properties

bp 103°C; d 0.985 g cm?3.

Uses

Intermediate in the formation of enoxysilacyclobutanes.

Uses

Siletanes (silacyclobutanes) represent a unique class of silicon-based reagents that have enjoyed much success in a number of synthetic applications including aldol reactions, allylations, cross-coupling reactions, carbosilane oxidations, and ring expansions. The manifestation of their strain in enhanced Lewis acidity and in the ring opening to silanols accounts for their utility. 1-Chloro-1-methylsiletane can be used for the preparation of the various siletane derivatives for these applications.
Grignard reagents react efficiently with 1-chloro-1-methylsiletane to provide the corresponding aryl-, alkenyl-, or alkylsiletanes (eqs 1–3).On the contrary, reactions with alkyllithiums are limited to the reaction of 1 with a lithium acetylide (eq 4).The reaction of 1 with an intermediate vinylalane obtained by hydroalumination of 1-heptyne gave (E)-1-heptenylmethylsiletane in >99/1 isomeric purity (eq 5).The reaction of 1 with LiAlD4 afforded 1-deuterio-1-methylsiletane (eq 6).

Preparation

siletane can be prepared in large quantities byWurtz coupling reaction of dichloro-3-chloropropylmethylsilane with Mg.It is commercially available from Gelest and Aldrich chemical company.