Allyltributylstannane

Base Information

• Chemical Name: Allyltributylstannane
• CAS No.: 24850-33-7
• Molecular Formula: C15H32Sn
• Molecular Weight: 331.129
• Hs Code.: 29319019
• European Community (EC) Number: 246-494-3
• UNII: AOR8OD4103
• DSSTox Substance ID: DTXSID50179553
• Wikidata: Q27274038
• Mol file: 24850-33-7.mol

Synonyms:Allyltributyltin;Allyltributylstannane;24850-33-7;Allyltri-n-Butyltin;Stannane, tributyl-2-propenyl-;tributyl(prop-2-enyl)stannane;tributyl(prop-2-en-1-yl)stannane;allyltributyl tin;allyl tributylstannane;MFCD00010346;UNII-AOR8OD4103;AOR8OD4103;Tributyl-2-propen-1-ylstannane;EINECS 246-494-3;Allyl(tributyl)stannane;Tributyl-2-propenylstannane;tri-n-butyl-2-propenylstannane;allyitri pound-n pound-butyltin;allyl tributyltin;allyl-tributyltin;allyl tributyl tin;allyl(tributyl)tin;tributyl(allyl)tin;allyltribuylstannane;allyl-(tributyl)tin;allyl tri-n-butyltin;allyl-tri-n-butyltin;allyltri(n-butyl)tin;allyltri-n-butyl tin;tri n-butyl allyltin;allyltributyl-stannane;allyl tri-n-butyl tin;allyltributyltin (IV);allyl tributyl stannane;allyl-tributyl-stannane;prop-2-enyltributyltin;tributyl allyl stannane;tributyl-2-propenyltin;allyltri-n-butylstannane;allyl tri-n-butylstannane;tributyl(1-allyl)stannane;Allyl(tributyl)stannane #;Allyltributylstannane, 97%;ghl.PD_Mitscher_leg0.523;C15-H32-Sn;tributyl(2-propen-1-yl)stannane;ALLYLTRIBUTYLSTANNANE [MI];DTXSID50179553;AMY18348;STR02624;tributyl (prop-2-en-1-yl)stannane;Stannane, tributyl-2-propen-1-yl-;AKOS015843291;A1222;CS-0112876;FT-0622056;EN300-104205;H10117;J-015698;J-519559;Q27274038

Chemical Property of Allyltributylstannane

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Vapor Pressure: 0.00098mmHg at 25°C
• Melting Point: 134-135 °C
• Refractive Index: n20/D 1.486(lit.)
• Boiling Point: 312.3 °C at 760 mmHg
• Flash Point: 146.6 °C
• PSA: 0.00000
• Density: 1.068 g/mL at 25 °C(lit.)
• LogP: 6.02150
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Immiscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 11
• Exact Mass: 332.152604
• Heavy Atom Count: 16
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

Allyltributyltin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53-23/24/25
• Safety Statements: 35-36/37/39-45-60-61-28-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)CC=C
• Uses: 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 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.

Technology Process of Allyltributylstannane

There total 54 articles about Allyltributylstannane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tri-n-butyltin lithium (4226-01-1) + 1,2-propanediene (463-49-0) + copper(l) cyanide → allyltributylstanane (24850-33-7)

Guidance literature:

With ammonium chloride; In tetrahydrofuran; (under Ar); addn. of CuCN to soln. of stannyllithium in THF at -100°C, stirring at this temp. for 30 min, dropwise addn. of the allene to this soln., stirring for 30 min, addn. of NH4Cl, quenching with methanol at -100 °C; extg., drying, chromy.;

Reference yield: 99.0%

2Li(1+)*(C6H5)(CH3)2Si(Sn(C4H9)3)Cu(1-)*CN(1-) = (C6H5)(CH3)2Si(Sn(C4H9)3)CuLi*LiCN + 1,2-propanediene (463-49-0) → allyltributylstanane (24850-33-7)

Guidance literature:

In tetrahydrofuran; substrate added to the Cu compound at -78°C, mixt. allowed to warm to room temp.; aq. work-up; extd. (diethyl ether), chromd. (SiO2, hexane);

Reference yield: 96.0%

tributyltin oxide (14937-35-0,80883-02-9) + allyl bromide (106-95-6) → allyltributylstanane (24850-33-7)

Guidance literature:

allyl bromide; With iodine; magnesium; In diethyl ether; for 1.5h; Inert atmosphere; Reflux;

tributyltin oxide; In diethyl ether; at 20 - 38 ℃; Concentration; Inert atmosphere; Reflux;

upstream raw materials:

tributyltin chloride

allyllithium

n-butyllithium

2-propenyl diphenylphosphinate

Downstream raw materials:

tributylphenylstannane

2-allyl-3-pentanone

3-<3-(trifluoromethyl)phenyl>propene

1-p-tolyl-3-buten-1-ol

Refernces

• 1、 Lahournere,Valade. "". . p. C3. Retrieved 1970.
• 2、 Naruta, Yoshinori,Nishigaichi, Yutaka,Maruyama, Kazuhiro. "Extremely Facile and Stereoselective Preparation of Allylstannanes with Use of Ultrasound". . p. 1857 - 1860. Retrieved 1986.
• 3、 -. "Novel compound 6,6-dimethyl tetrahydropyran-2-methanol and preparing method thereof". Paragraph 0014; 0019-0020; 0026; 0032. . Retrieved 2018/04/03.
• 4、 -. "METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND". . . Retrieved 2016/10/31.