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146498

Sigma-Aldrich

Trimethyltin chloride

Sinónimos:

Chlorotrimethylstannane

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5 G
$53.88
10 G
$112.00
50 G
$288.00

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5 G
$53.88
10 G
$112.00
50 G
$288.00

About This Item

Fórmula lineal:
(CH3)3SnCl
Número de CAS:
1066-45-1
Peso molecular:
199.27
Beilstein:
3535111
Número CE:
213-917-8
Número MDL:
MFCD00000520
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
24848783
NACRES:
NA.22

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Formulario

crystals

mp

37-39 °C (lit.)

cadena SMILES

C[Sn](C)(C)Cl

InChI

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

Clave InChI

KWTSZCJMWHGPOS-UHFFFAOYSA-M

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Descripción general

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.

Aplicación

Trimethyltin chloride can be used as a precursor to synthesize trimethyltin hydride, cyanide, methoxide, azide, and lithium compounds.[1]
It can also be used as a reagent to prepare:
  • Organotrimethyltin derivatives by reacting with organocopper compounds via transmetalation reaction.[1]
  • Acetophenone by palladium-catalyzed coupling reaction with benzoyl chloride.[1]
  • Optically active propargyl trimethylstannane by treating with chiral allenyltitanium.[1]
  • Trimethylstannyl nucleophiles, which are applicable in the formation of Sn-C bonds via SN2 reactions, SRN1 reactions, and halogen-metal exchanges.[1]
  • Carbocycles by reacting with unactivated dienes or trienes via radical-mediated carbocyclization reaction in the presence of NaBH3CN and a catalytic amount of AIBN.[1]

Me3SnCl can also be used as a Lewis acid catalyst in asymmetric allylic alkylation reactions.[1]

Pictogramas

Skull and crossbonesEnvironment
GHS06,GHS09

Palabra de señalización

Danger

Frases de peligro

H300 + H310 + H330,H410

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

206.6 °F - closed cup

Punto de inflamabilidad (°C)

97 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
SHBS6197
SHBS1490
SHBR9125
SHBP7075
STBD4008V

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Milstein D and Stille J K
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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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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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