DIMETHYLTHEXYLSILYL CHLORIDE Property

Melting point:

15 °C

Boiling point:

55-56 °C10 mm Hg(lit.)

Density 

0.909 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.449(lit.)

Flash point:

125 °F

storage temp. 

Sealed in dry,2-8°C

solubility 

sol in THF, DMF, CH2Cl2.

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

0.911

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

Sensitive 

Moisture Sensitive

BRN 

3647960

InChIKey

KIGALSBMRYYLFJ-UHFFFAOYSA-N

CAS DataBase Reference

67373-56-2(CAS DataBase Reference)

Safety

Hazard Codes 

C

Risk Statements 

10-34-37

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2986 8/PG 2

WGK Germany 

3

F 

10-21

TSCA 

No

HazardClass 

8

PackingGroup 

II

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable 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.

DIMETHYLTHEXYLSILYL CHLORIDE Chemical Properties,Usage,Production

Chemical Properties

clear colorless to almost colorless liquid

Physical properties

mp 14–15 °C; bp 55–56 °C/10 mmHg; d 0.909 g cm?3.

Uses

Silylating reagent for the protection of 1? and 2? alcohols and N-silylation of amines and amides; used in the preparation of thexyldimethylsilyl triflate; formation of α-silyl hydrazones; formylation of polyfluoroalkyl halides. Thexyldimethylsilyl chloride (TDS-Cl) was first introduced as a more easily prepared alternative to the more commonly used t-butyldimethylsilyl chloride for the protection of alcohols.

Uses

Protecting reagent for alcohols and other functional groups. Employed in the synthesis of silicon naphthocyanine and cyclodextrin derivatives, which are useful as antitumor dyes and chiral stationary phases, respectively.

Preparation

To a mixture of dimethylchlorosilane (10 mL, 92 mmol) and AlCl3 (0.680 g, 5 mmol) at 25°Cwas added 2,3-dimethyl-2-butene (11 mL, 91 mmol). After stirring for 4 h at ambient temperature, the mixture was filtered and distilled to yield 15.2 g of TDS-Cl (93%).

Purification Methods

Purify it by fractional distillation and store it in small aliquots in sealed ampoules. It is very sensitive to moisture and is estimated by dissolving an aliquot in excess of 0.1M NaOH and titrating with 0.1M HCl using methyl red as indicator [Szabó et al. Helv Chim Acta 67 2128 1984].