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146498

Trimethyltin chloride

Synonym(s):

Chlorotrimethylstannane

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5 g

Available to ship TODAY

$76.70
10 g

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$127.00
50 g

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$320.00

About This Item

Linear Formula:
(CH3)3SnCl
CAS Number:
Molecular Weight:
199.27
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
213-917-8
Beilstein/REAXYS Number:
3535111
MDL number:
Form:
crystals

$76.70


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form

crystals

Quality Segment

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

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.

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This Item
375195375187344923
description

-

description

1.0 M in THF

description

1.0 M in hexanes

description

96%

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

mp

37-39 °C (lit.)

mp

-

mp

-

mp

150 °C (dec.) (lit.)

form

crystals

form

liquid

form

liquid

form

solid


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Pictograms

Skull and crossbonesEnvironment

Signal Word

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 (personal protective equipment)

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



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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    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/418/501/product-dating-information-06-25-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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