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271411

Sigma-Aldrich

Allyltributylstannane

97%

Synonym(s):

Allyltri-n-butyltin, Allyltributyltin, Tributyl-2-propenylstannane

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About This Item

Linear Formula:
CH2=CHCH2Sn(CH2CH2CH2CH3)3
CAS Number:
Molecular Weight:
331.12
Beilstein:
3588340
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

refractive index

n20/D 1.486 (lit.)

bp

88-92 °C/0.2 mmHg (lit.)

density

1.068 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)CC=C

InChI

1S/3C4H9.C3H5.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;3H,1-2H2;

InChI key

YLGRTLMDMVAFNI-UHFFFAOYSA-N

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Application

Allylation reagent for aldehydes catalyzed by chiral Lewis acids and ytterbium(III) trifluoromethanesulfonate (cat. no. 430595). Undergoes tetrakis(triphenylphosphine)palladium(0) (cat. no. 216666) catalyzed coupling with iodoquinones and allyl acetates.
Efficient allylation of aldehydes leading to homoallylic alcohols with trichloro-1,3,5-triazene.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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Aldrichimica Acta, 20, 45-45 (1987)
Tetrahedron Letters, 34, 7827-7827 (1993)
Journal of the American Chemical Society, 115, 8467-8467 (1993)
Journal of the American Chemical Society, 35, 4639-4639 (1994)
Tetrahedron, 50, 2003-2003 (1994)

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