CAS 5926-35-2 Bis(trimethylsilyl)chloromethane (HCID 552583)

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Basic information

CAS: 5926-35-2
Standard SMILES: C[Si](C)(C)C(Cl)[Si](C)(C)C
InChIKey: XNJGZHVYPBNLEB-UHFFFAOYSA-N
Molecular formula: C7H19ClSi2
Average molar mass: 194.85 g/mol
Monoisotopic mass: 194.07138135

Names & identifiers

Preferred name: Bis(trimethylsilyl)chloromethane
IUPAC: [chloro(trimethylsilyl)methyl]-trimethylsilane
English name: Bis(trimethylsilyl)chloromethane
Molecular formula: C7H19ClSi2
Molecular weight: 194.85

Names & synonyms

Bis(trimethylsilyl)chloromethane5926-35-2DTXSID80339002RefChem:569328DTXCID40290084628-127-2Chlorobis(trimethylsilyl)methane[chloro(trimethylsilyl)methyl]-trimethylsilaneBis(trimethylsilyl)methyl chloride(chloromethylene)bis(trimethylsilane)Bis(trimethylsilyl) methyl chloridechloro-bis(trimethylsilanyl)-methane

Show more names

Chloro-bis(trimethylsilyl)methaneChloro-bis-trimethylsilanyl-methaneChlorobis(trimethylsilyl)methane 97%chloro(trimethylsilyl)methyl]-trimethylsilaneSilane, 1,1'-(chloromethylene)bis[1,1,1-trimethyl-

MFCD00054866Silane, (chloromethylene)bis[trimethyl-SCHEMBL1645069AKOS032949272Chlorobis(trimethylsilyl)methane, 97%Silane, (chloromethylene)bis*trimethyl-CS-0204327[chloro(trimethylsilyl)methyl]-trimethyl-silane

Database identifiers

CAS: 5926-35-2
PubChem CID: 552583
DTXSID

Properties

Computed structural properties

Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 2
Heavy atoms: 10
Formal charge: 0
Complexity: 95.8

Experimental & physicochemical properties

SpringerMaterials Properties29Si nuclear magnetic resonance spectrum

Physicochemical properties

Boiling point: 57 · 57-60 °C/15 mmHg (lit.)
Density: 0.892 g/mL · 0.892 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.449(lit.)
Flash point: 120 °F · 120 °F
solubility: soluble in common organic solvents (DMF, THF, Et2O, CH2Cl2).
form: liquid
Specific Gravity: 0.892 · 0.892
Hydrolytic Sensitivity: 4 · 4: no reaction with water under neutral conditions
BRN: 1736681 · 1736681
InChI: 1S/C7H19ClSi2/c1-9(2,3)7(8)10(4,5)6/h7H,1-6H3
InChIKey: XNJGZHVYPBNLEB-UHFFFAOYSA-N
SMILES: C[Si](C)(C)C(Cl)[Si](C)(C)C
UNSPSC Code

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

F: 21
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: No
ridadr: UN 1993 3/PG 3
risk_code: 10-36/37/38
Signal word: Warning
Symbol(GHS): GHS02,GHS07
hazard_code: Xi
safety_code: 26-36/37/39
hazard_class: 3.2
Storage Class: 3 - Flammable liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H226-H315-H319-H335
Hazard Classifications: Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3

Chemistry & industry

Applications · 2 items

UsesSilane, 1,1-(Chloromethylene)bis[1,1,1]- trimethyl- can be used as versatile C1 building block; broad application in Peterson olefination reactions; Grignard reagent participates readily in Kumada cross-coupling reactions with aryl and vinyl halides; useful in synthesis of methylenephosphine analogs and as sterically demanding ligand for a number of main group and transition metal complexes.

UsesChlorobis(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.

Preparation methods · 1 item

Preparationa convenient one-pot procedure has been developed by Kemp and Cowley in which trimethylsilylchloride reacts with dichloromethane in the presence of nBuLi at 110°Cto give bis(trimethylsilyl)dichloromethane.1 This intermediate is sequentially treated with nBuLi and ethanol to yield chlorobis(trimethylsilyl)methane. A number of other syntheses have been described