(Trimethylsilyl)methyllithium

HCID 3482579CAS 1822-00-0

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Basic information

Standard SMILES: [CH2-][Si](C)(C)C.[Li+]
InChIKey: KVWLUDFGXDFFON-UHFFFAOYSA-N
Molecular formula: C4H11LiSi
Average molar mass: 94.159 g/mol
Monoisotopic mass: 94.07900643

Names & identifiers

Preferred name: (Trimethylsilyl)methyllithium
IUPAC: Lithium (trimethylsilyl)methanide
English name: (Trimethylsilyl)methyllithium
Molecular formula: C4H11LiSi
Molecular weight: 94.16

Names & synonyms

LithiomethyltrimethylsilaneRIMETHYLSILYL)METHYLLITHIUMmethanidyl(trimethyl)silaneTrimethyl(lithiomethyl)silaneLithio(trimethylsilyl)methaneTrimethylsiloxy-Methyllithium(Trimethylsilyl)methyllithiumLithium, (trimethylsilyl)methyl-lithium,methanidyl(trimethyl)silane(trimethylsilyl)methyllithiumsolution

Database identifiers

CAS: 1822-00-0
PubChem CID: 3482579
DTXSID: DTXSID90392901
EC Number: 629-440-7
Nikkaji: J337.666D

Properties

Physicochemical properties

Melting point: 112 · 112-117 °C (decomp)
Boiling point: 35 · 35-36 °C
Density: 0.65 g/mL · 0.65 g/mL at 25 °C
Flash point: 57 °F · −57 °F
storage temp.: 2 · 2-8°C
solubility: Sol ethereal solvents; reacts with protic solvents.
Specific Gravity: 0.66 · 0.66
Hydrolytic Sensitivity: 8 · 8: reacts rapidly with moisture, water, protic solvents
BRN: 4123225 · 4123225
InChI: InChI=1S/C4H11Si.Li/c1-5(2,3)4;/h1H2,2-4H3;
InChIKey: RJPBNMJOQNIBQW-UHFFFAOYSA-N
SMILES: [Si](C)(C)(C)C[Li]
UNSPSC Code: 12352103 · 12352103
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS05,GHS07,GHS08,GHS09
Signal word: Danger
Hazard statements: 224 · H224-H304-H314-H336-H411
Precautionary statements: 210 · P210-P261-P273-P280-P301+P310-P305+P351+P338
target organs: Central nervous system
PPE: Faceshields, Gloves, Goggles
Hazard Codes: F,C,N,F+
Risk Statements: 11 · 11-14-34-51/53-65-66-67-12-2
Safety Statements: 16 · 16-26-33-36/37/39-43-45-61-62
RIDADR: 3399 · UN 3399 4.3/PG 1
WGK Germany: 1 · 1
F: 10 · 10
HazardClass: 4.2 · 4.2
PackingGroup: I
HS Code: 29319090 · 29319090
Storage Class: 4.3 · 4.3 - Hazardous materials which set free flammable gases upon contact with water
Hazard Classifications: 2 Asp · Aquatic Chronic 2Asp. Tox. 1Eye Dam. 1Flam. Liq. 1Skin Corr. 1BSTOT SE 3
REACH Registrations: Active

Safety & regulation

Safety data

F: 10
PPE: Faceshields, Gloves, Goggles
wgk: 1
ridadr: UN 3399 4.3/PG 1
hs_code: 29319090
risk_code: 11-14-34-51/53-65-66-67-12-2
Signal word: Danger
Symbol(GHS): GHS02,GHS05,GHS07,GHS08,GHS09
hazard_code: F,C,N,F+
safety_code: 16-26-33-36/37/39-43-45-61-62
hazard_class: 4.2
Storage Class: 4.3 - Hazardous materials which set free flammable gases upon contact with water
packing_group: I
target organs: Central nervous system
Hazard statements: H224-H304-H314-H336-H411
REACH Registrations: Active
Hazard Classifications: Aquatic Chronic 2Asp. Tox. 1Eye Dam. 1Flam. Liq. 1Skin Corr. 1BSTOT SE 3
Precautionary statements: P210-P261-P273-P280-P301+P310-P305+P351+P338

Chemistry & industry

Applications · 3 items

UsesTrimethylsilylmethyllithium is a reagent used in the methylenation of carbonyl compounds; reacts with carboxylic acid derivatives to provide α-silyl ketones; synthesis of allylsilanes. It participates in the reactions of Peterson Alkenation, Reaction with Carboxylic Acid Derivatives, Other Electrophiles, etc.

UsesInitiates polymerization and copolymerization of cyclosiloxanes. Alkylates metal complexes.

UsesInitiates polymerization and copolymerization of cyclosiloxanes.1 Alkylates metal complexes.2

Preparation methods

PreparationTrimethylsilylmethyllithium is obtained by reaction of (chloromethyl)- trimethylsilane with lithium metal in an inert solvent. It is also available by displacement of a heteroatom group based on sulfur, silicon, or tin.

Upstream & downstream products

Downstream products

alpha-cyclopropylstyrene Phenyl-(4-trimethylsilanylmethyl-phenyl)-methanone

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

湖北万得化工有限公司15377098680 15377098680 · [email protected]

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