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
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 | n |
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) |
Flame Flammables GHS02 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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