Trimethyltin chloride

Name: Trimethyltin chloride
Brand: ALDRICH

Synonym(s):

Chlorotrimethylstannane

Select a Size

Change View

About This Item

Linear Formula:

(CH₃)₃SnCl

CAS Number:

1066-45-1

Molecular Weight:

199.27

UNSPSC Code:

12352103

NACRES:

NA.22

PubChem Substance ID:

24848783

EC Number:

213-917-8

Beilstein/REAXYS Number:

3535111

MDL number:

MFCD00000520

Form:

crystals

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

form

crystals

Quality Level

100

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.