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146498

Sigma-Aldrich

Trimethyltin chloride

Synonym(s):

Chlorotrimethylstannane

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About This Item

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

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

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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.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H410

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

206.6 °F - closed cup

Flash Point(C)

97 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chlorotrimethylstannane
Yoshinori Yamamoto, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2007)
Chlorotrimethylstannane.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2009)
Palladium-catalyzed coupling of tetraorganotin compounds with aryl and benzyl halides. Synthetic utility and mechanism.
Milstein D and Stille J K
Journal of the American Chemical Society, 101(17), 4992-4998 (1979)
Replacing alkoxy groups with alkylthienyl groups: a feasible approach to improve the properties of photovoltaic polymers.
Huo H, et al.
Angewandte Chemie (International Edition in English), 50(41), 9697-9702 (2011)
Yu Xi et al.
Journal of pineal research, 67(3), e12596-e12596 (2019-07-25)
Trimethyltin chloride (TMT) is a potent neurotoxin that causes neuroinflammation and neuronal cell death. Melatonin is a well-known anti-inflammatory agent with significant neuroprotective activity. Male C57BL/6J mice were intraperitoneally injected with a single dose of melatonin (10 mg/kg) before exposure to TMT (2.8 mg/kg, ip). Thereafter, the mice received
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