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HomeProduct name listDIMETHYLTHEXYLSILYL CHLORIDE

DIMETHYLTHEXYLSILYL CHLORIDE

Synonym(s):TDSCl;Dimethylthexylsilyl chloride;Thexyldimethylsilyl chloride;Chlorodimethyl(1,1,2-trimethylpropyl)silane;Dimethyl-(2,3-dimethyl-2-butyl)chlorosilane

  • CAS NO.:67373-56-2
  • Empirical Formula: C8H19ClSi
  • Molecular Weight: 178.77
  • MDL number: MFCD00012175
  • EINECS: 629-449-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-06-08 17:06:38
DIMETHYLTHEXYLSILYL CHLORIDE Structural

What is DIMETHYLTHEXYLSILYL CHLORIDE?

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.

The Uses of DIMETHYLTHEXYLSILYL CHLORIDE

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.

The Uses of DIMETHYLTHEXYLSILYL CHLORIDE

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].

Properties of DIMETHYLTHEXYLSILYL CHLORIDE

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
Specific Gravity 0.911
color  Colorless to Almost colorless
Sensitive  Moisture Sensitive
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents
BRN  3647960
CAS DataBase Reference 67373-56-2(CAS DataBase Reference)

Safety information for DIMETHYLTHEXYLSILYL CHLORIDE

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H226:Flammable liquids
H314:Skin corrosion/irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P240:Ground/bond container and receiving equipment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for DIMETHYLTHEXYLSILYL CHLORIDE

InChIKey KIGALSBMRYYLFJ-UHFFFAOYSA-N

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