384410
Chlorotrimethylsilane solution
1.0 M in THF
Synonym(s):
Trimethylchlorosilane
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About This Item
Linear Formula:
(CH3)3SiCl
CAS Number:
Molecular Weight:
108.64
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1209232
Form:
liquid
form
liquid
Quality Level
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
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1A - STOT SE 3
target_organs
Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 1
flash_point_f
-4.0 °F - closed cup
flash_point_c
-20 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Zirconocene dichloride-catalyzed pinacol coupling of aromatic aldehydes and ketones
Lakshmi Kantam M, et al.
Synthetic Communications, 36(10), 1437-1445 (2006)
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)
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)