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384410

Sigma-Aldrich

Chlorotrimethylsilane solution

1.0 M in THF

Synonym(s):

Trimethylchlorosilane

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About This Item

Linear Formula:
(CH3)3SiCl
CAS Number:
75-77-4
Molecular Weight:
108.64
Beilstein:
1209232
MDL number:
MFCD00000502
UNSPSC Code:
12352302
PubChem Substance ID:
24863995
NACRES:
NA.22

form

liquid

concentration

1.0 M in THF

density

0.88 g/mL at 25 °C

SMILES string

C[Si](C)(C)Cl

InChI

1S/C3H9ClSi/c1-5(2,3)4/h1-3H3

InChI key

IJOOHPMOJXWVHK-UHFFFAOYSA-N

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General description

Chlorotrimethylsilane (TMSCl) is a silylating agent employed in the silylation of alcohols, amines, carboxylic acids, thiols, and other functional groups. Silyl group serves as a protecting group for these original functional groups.

Application

Chlorotrimethylsilane (TMSCl) can be used as a reagent:
  • To synthesize allenylsilane via carbolithiation of conjugated enynes with aryllithium.
  • In the reductive coupling of aldehydes and ketones to produce corresponding 1,2 diols in the presence of zirconocene dichloride and magnesium.
  • To prepare 4,4′-bis(trimethylsilyl)bicyclohexyl-2,2′-diene from 1,3-cyclohexadiene by reductive disilylation reaction.

Signal Word

Danger

Hazard Statements

H225,H302,H314,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1A - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-4.0 °F - closed cup

Flash Point(C)

-20 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Carbolithiation of conjugated enynes with aryllithiums in microflow system and applications to synthesis of allenylsilanes
Tomida Y, et al.
Organic Letters, 11(16), 3614-3617 (2009)
Zirconocene dichloride-catalyzed pinacol coupling of aromatic aldehydes and ketones
Lakshmi Kantam M, et al.
Synthetic Communications, 36(10), 1437-1445 (2006)
Ti-catalyzed reactions of 4, 4?-bis (trimethylsilyl) bicyclohexyl-2, 2?-diene with various electrophiles
A Chahinez, et al.
Tetrahedron Letters, 49(31), 4630-4632 (2008)
Malin Persson et al.
Langmuir : the ACS journal of surfaces and colloids, 26(12), 9927-9936 (2010-03-27)
In the in vitro motility assay, actin filaments are propelled by surface-adsorbed myosin motors, or rather, myosin motor fragments such as heavy meromyosin (HMM). Recently, efforts have been made to develop actomyosin powered nanodevices on the basis of this assay
Mark Sundberg et al.
Langmuir : the ACS journal of surfaces and colloids, 22(17), 7302-7312 (2006-08-09)
We have previously described the efficient guidance and unidirectional sliding of actin filaments along nanosized tracks with adsorbed heavy meromyosin (HMM; myosin II motor fragment). In those experiments, the tracks were functionalized with trimethylchlorosilane (TMCS) by chemical vapor deposition (CVD)
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