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194409

Sigma-Aldrich

Bromotrimethylsilane

97%

Synonym(s):

TMBS, Trimethylbromosilane, Trimethylsilyl bromide

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About This Item

Linear Formula:
(CH3)3SiBr
CAS Number:
2857-97-8
Molecular Weight:
153.09
Beilstein/REAXYS Number:
1731135
EC Number:
220-672-0
MDL number:
MFCD00000048
UNSPSC Code:
12352103
PubChem Substance ID:
24851651
NACRES:
NA.22

Quality Level

200

assay

97%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.424 (lit.)

bp

79 °C (lit.)

density

1.16 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)Br

InChI

1S/C3H9BrSi/c1-5(2,3)4/h1-3H3

InChI key

IYYIVELXUANFED-UHFFFAOYSA-N

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Application

Used with InCl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

89.6 °F

flash_point_c

32 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Aldrichimica Acta, 14, 31-31 (1981)
Takahiro Saito et al.
The Journal of organic chemistry, 71(22), 8516-8522 (2006-10-27)
The combination of InCl3 and Me3SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced
J. Chem. Soc. Perkin Trans. II, 263-263 (1991)
J L Hughes et al.
Peptide research, 8(5), 298-300 (1995-09-01)
The cleavage of a peptide resin attached to a phenylacetomidomethyl (PAM) resin was investigated using bromotrimethylsilane (TMSBr) with thioanisole in trifluoroacetic acid (TFA), and by chlorotrimethylsilane (TMSCl) in the same reagents with lithium bromide. Both TMSBr and TMSCl cleaved the
A Otaka
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 120(1), 54-67 (2000-02-03)
This review summarizes the development of deprotecting methodologies for peptides and their practical application to the synthesis of disulfide bond- or phosphoamino acid-containing peptides. Acidic deprotecting systems utilizing Brønsted acid (HF, trifluoromethanesulfonic acid (TFMSA) and HBr etc.) have been used
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