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Merck
CN

146498

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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24848783
EC Number:
213-917-8
Beilstein/REAXYS Number:
3535111
MDL number:
MFCD00000520

Key Documents

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InChI key

KWTSZCJMWHGPOS-UHFFFAOYSA-M

InChI

1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1

SMILES string

C[Sn](C)(C)Cl

form

crystals

mp

37-39 °C (lit.)

Quality Level

100

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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.

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.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM8264
SHBS6197
SHBS1490
SHBR9125
SHBP7075

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Chlorotrimethylstannane.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2009)
Chlorotrimethylstannane
Yoshinori Yamamoto, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2007)
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)
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)
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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