146498

Trimethyltin chloride

• Synonym(s): Chlorotrimethylstannane
• Linear Formula: (CH₃)₃SnCl
• CAS Number: 1066-45-1
• Molecular Weight: 199.27
• Beilstein/REAXYS Number: 3535111
• EC Number: 213-917-8
• MDL number: MFCD00000520
• UNSPSC Code: 12352103
• PubChem Substance ID: 24848783
• NACRES: NA.22

Properties

• form: crystals
• mp: 37-39 °C (lit.)
• SMILES string: C[Sn](C)(C)Cl
• InChI: 1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1
• InChI key: KWTSZCJMWHGPOS-UHFFFAOYSA-M

Description

General description

Trimethyltin chloride is an organotin reagent widely used in transferring trimethylstannyl groups onto the substrates to synthesize various organostannanes. Trimethylstannyl compounds derived from this reagent, are extensively used in the palladium-catalyzed Stille coupling reactions.

Application

Trimethyltin chloride can be used as a precursor to synthesize trimethyltin hydride, cyanide, methoxide, azide, and lithium compounds.
It can also be used as a reagent to prepare:

• Organotrimethyltin derivatives by reacting with organocopper compounds via transmetalation reaction.
• Acetophenone by palladium-catalyzed coupling reaction with benzoyl chloride.
• Optically active propargyl trimethylstannane by treating with chiral allenyltitanium.
• Trimethylstannyl nucleophiles, which are applicable in the formation of Sn-C bonds via SN2 reactions, SRN1 reactions, and halogen-metal exchanges.
• Carbocycles by reacting with unactivated dienes or trienes via radical-mediated carbocyclization reaction in the presence of NaBH₃CN and a catalytic amount of AIBN.

Me₃SnCl can also be used as a Lewis acid catalyst in asymmetric allylic alkylation reactions.

Safety Information

• pictograms: GHS06,GHS09
• signalword: Danger
• hcodes: H300 + H310 + H330,H410
• pcodes: P262 - P264 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 2
• flash_point_f: 206.6 °F - closed cup
• flash_point_c: 97 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges