Allyltributyltin

Synonym(s):Allyltri-n-butyltin;Allyltributyltin;Tributyl-2-propenylstannane

CAS NO.：24850-33-7
Empirical Formula: C15H32Sn
Molecular Weight: 331.12
MDL number: MFCD00010346
EINECS: 246-494-3
SAFETY DATA SHEET (SDS)
Update Date: 2023-05-15 10:43:51

What is Allyltributyltin?

Chemical properties

CLEAR COLOURLESS LIQUID

The Uses of Allyltributyltin

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

The Uses of Allyltributyltin

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.

Purification Methods

A possible impurity is tributylchlorostannane — test for Cl as Cl ion after hydrolysing. Dissolve it in *C6H6 (or toluene), shake this with dilute aqueous NaOH, dry (CaCl2), filter, evaporate and distil the residue in a vacuum [Jones et al. J Chem Soc 1446 1947, Bristow Aldrichimica Acta 17 75 1984, Yamamoto Aldrichimica Acta 20 45 1987]. [Beilstein 4 IV 4317.]

Properties of Allyltributyltin

Melting point:	134-135 °C
Boiling point:	88-92 °C0.2 mm Hg(lit.)
Density	1.068 g/mL at 25 °C(lit.)
refractive index	n20/D 1.486(lit.)
Flash point:	>230 °F
storage temp.	2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Liquid
color	Clear colorless
Specific Gravity	1.068
Water Solubility	Immiscible with water.
Sensitive	Air Sensitive
Hydrolytic Sensitivity	1: no significant reaction with aqueous systems
BRN	3588340
Exposure limits	ACGIH: TWA 0.1 mg/m3; STEL 0.2 mg/m3 (Skin) NIOSH: IDLH 25 mg/m3; TWA 0.1 mg/m3
Stability:	Air Sensitive
CAS DataBase Reference	24850-33-7(CAS DataBase Reference)
NIST Chemistry Reference	Allyltributyltin(24850-33-7)

Safety information for Allyltributyltin

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06 Health Hazard GHS08 Environment GHS09
GHS Hazard Statements	H301:Acute toxicity,oral H312:Acute toxicity,dermal H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H372:Specific target organ toxicity, repeated exposure H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P201:Obtain special instructions before use. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.