tributyl(prop-2-en-1-yl)stannane

• ChemBase ID: 65051
• Molecular Formular: C15H32Sn
• Molecular Mass: 331.11558
• Monoisotopic Mass: 332.15259502
• SMILES: C=CC[Sn](CCCC)(CCCC)CCCC
• Canonical SMILES: C=CC[Sn](CCCC)(CCCC)CCCC
• InChI: InChI=1S/3C4H9.C3H5.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;3H,1-2H2
• InChIKey: YLGRTLMDMVAFNI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tributyl(prop-2-en-1-yl)stannane
• IUPAC Traditional name: tributyl(prop-2-en-1-yl)stannane
• Synonyms: Allyltributylstannane; Allyltri-n-butyltin; Allyltributyltin; Tributyl-2-propenylstannane; Allyltributylstannane; Allyltri-n-butylstannane; Tri-n-butyl-2-propenylstannane; Allyltri-n-butyltin; Allyltributylstannane; Allyltributyltin; 烯丙基三丁基锡; 丙烯基三丁基锡

Database IDs

• CAS Number: 24850-33-7
• EC Number: 246-494-3
• MDL Number: MFCD00010346
• Beilstein Number: 3588340
• PubChem SID: 24856436; 162030790
• PubChem CID: 90628

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.4548
• LogD (pH = 7.4): 7.4548
• Log P: 7.4548
• Molar Refractivity: 73.1767 cm^3
• Polarizability: 33.411934 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Boiling Point: 100-102°C/0.5mm; 88-92 °C/0.2 mmHg(lit.); 88-92°C/0.2mm
• Flash Point: >110°C; 103 °C; 103°C(217°F); 217.4 °F
• Density: 1.068; 1.068 g/mL at 25 °C(lit.); 1.079
• Refractive Index: 1.4860; n20/D 1.486; n20/D 1.486(lit.)

Safety Information

• Storage Warning: Air Sensitive; IRRITANT; Toxic
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2788; UN2788
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61; 36/37/39-45-60-61
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H315-H319-H372-H400-H410; H301-H312-H315-H319-H372-H410
• GHS Precautionary statements: P260-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P273-P280-P301 + P310-P305 + P351 + P338-P314-P501
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2788 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (GC); 97%
• Grade: purum
• Linear Formula: CH2=CHCH2Sn(CH2CH2CH2CH3)3

DETAILS

Sigma Aldrich - 271411

Packaging
5, 25, 100 g in glass bottle
Application
Allylation reagent for aldehydes catalyzed by chiral Lewis acids1,2 and ytterbium(III) trifluoromethanesulfonate (cat. no. 430595).3 Undergoes tetrakis(triphenylphosphine)palladium(0) (cat. no. 216666) catalyzed coupling with iodoquinones4 and allyl acetates.5,6Efficient allylation of aldehydes leading to homoallylic alcohols with trichloro-1,3,5-triazene.7

Sigma Aldrich - 06068

Other Notes
Reagent for allylation reactions1,2,3

REFERENCES

• Widely used nucleophilic, non-basic allylating agent.
• Couples with primary or secondary alkyl halides under free-radical conditions: J. Am. Chem. Soc., 104, 5829 (1982); Bull. Chem. Soc. Jpn., 56, 24801 (1983).
• Lewis acid-catalyzed stereoselective addition to aldehydes gives homoallylic alcohols: Chem. Lett., 919 (1979); Tetrahedron Lett., 25, 265, 1879 (1984); Synlett, 1694 (2002). For chemoselective allylation of aldehydes in the presence of ketones, see: Tetrahedron Lett., 36, 3723 (1995). In the presence of TI(O-i-Pr)₄ and BINOL, enantioselective allylation of ketones can be accomplished with high ee: Tetrahedron: Asym., 11, 4163 (2000).
• Similarly, homoallylamines are formed from aldimines with TiCl₄ or BF₃ etherate: J. Org. Chem., 50, 146 (1985). For allylation of quinones, see p-Benzoquinone, A13162.