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146498

Sigma-Aldrich

Trimethyltin chloride

Sinonimo/i:

Chlorotrimethylstannane

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About This Item

Formula condensata:
(CH3)3SnCl
Numero CAS:
1066-45-1
Peso molecolare:
199.27
Beilstein:
3535111
Numero CE:
213-917-8
Numero MDL:
MFCD00000520
Codice UNSPSC:
12352103
ID PubChem:
24848783
NACRES:
NA.22

Stato

crystals

Punto di fusione

37-39 °C (lit.)

Stringa SMILE

C[Sn](C)(C)Cl

InChI

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

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Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Pittogrammi

Skull and crossbonesEnvironment
GHS06,GHS09

Avvertenze

Danger

Indicazioni di pericolo

H300 + H310 + H330,H410

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

206.6 °F - closed cup

Punto d’infiammabilità (°C)

97 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
SHBM8264
SHBM8262
SHBM8259
SHBM3682
MKCK4158

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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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