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361747

Sigma-Aldrich

Chlorobis(trimethylsilyl)methane

97%

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Synonym(s):
Bis(trimethylsilyl)chloromethane
Linear Formula:
[(CH3)3Si]2CHCl
CAS Number:
5926-35-2
Molecular Weight:
194.85
Beilstein:
1736681
MDL number:
MFCD00054866
UNSPSC Code:
12352103
PubChem Substance ID:
24862252
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.449 (lit.)

bp

57-60 °C/15 mmHg (lit.)

density

0.892 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)C(Cl)[Si](C)(C)C

InChI

1S/C7H19ClSi2/c1-9(2,3)7(8)10(4,5)6/h7H,1-6H3

InChI key

XNJGZHVYPBNLEB-UHFFFAOYSA-N

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Application

Chlorobis(trimethylsilyl)methane can be used as a reagent for the preparation of:
  • Para-bis(trimethylsilyl)ethylstyrene (PBTES) monomer, which is used to synthesize corresponding network polymer of styrene.
  • Bis(trimethylsilyl)methyl magnesium chloride (Grignard reagent), which is used in the synthesis of bis(trimethylsilyl) allyl compounds by reacting with alkenyl bromide via the Kumada coupling reaction.
  • N-[Bis(trimethylsilyl)methyl]heterocumulenes.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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David R Williams et al.
Organic letters, 8(20), 4393-4396 (2006-09-22)
Allylation reagents, which possess geminal bis-trimethylsilyl substitution, are readily prepared from E- or Z-alkenyl bromides. The reactivity of 3,3-bis(trimethylsilyl)-2-methyl-1-propene (1) is described and predominantly provides ene reactions with aldehydes to give alcohol 2 in the presence of BF3.OEt2. Alternatively, Sakurai
Synthesis and Reactivity of N-[Bis (trimethylsilyl) methyl] heterocumulenes
Barbaro G, et al.
The Journal of Organic Chemistry, 60(19), 6032-6039 (1995)
Synthesis of some silyl mono-and polystyrenes with new properties
Assadi, MG and Hosseinzadeh, F
Designed Monomers and Polymers, 13(2), 181-191 (2010)

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