4104-90-9

Basic information

• Product Name: triphenyl(propadienyl)stannane
• Synonyms: 1-Triphenylstannyl-1,2-propadiene; Triphenyl propargyltin; Triphenyl(1,2-propadienyl)stannane; Triphenyl(2-propynyl)stannane
• CAS NO: 4104-90-9
• Molecular Formula: C₂₁H₁₈Sn
• Molecular Weight: 389.0776
• Mol File: 4104-90-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 432.1°C at 760 mmHg
• Flash Point: 217.9°C
• Vapor Pressure: 2.87E-07mmHg at 25°C
• CAS DataBase Reference: triphenyl(propadienyl)stannane(CAS DataBase Reference)
• NIST Chemistry Reference: triphenyl(propadienyl)stannane(4104-90-9)
• EPA Substance Registry System: triphenyl(propadienyl)stannane(4104-90-9)

Safety Data

• Hazardous Substances Data: 4104-90-9(Hazardous Substances Data)

Usage

General Description

Triphenyl(propadienyl)stannane is a chemical compound that belongs to the family of organotin compounds. It is a type of tin compound that contains a stannane (tin) group attached to a propadienyl group, which consists of three phenyl rings attached to a propadienyl backbone. triphenyl(propadienyl)stannane is mainly used as a precursor in organic synthesis reactions, particularly in the production of new functionalized materials and complex organic molecules. It is also used as a reagent in the formation of carbon-carbon and carbon-heteroatom bonds in various organic reactions. However, it is important to handle this compound with caution as organotin compounds like triphenyl(propadienyl)stannane have been found to have toxic effects on the environment and human health.

Upstream product

• 639-58-7 triphenyltin chloride 
• 106-96-7 propargyl bromide 
• 67-66-3 chloroform 
• 4104-89-6 triphenylpropargyl stannane 
• 10147-36-1 n-propanesulfonyl chloride 
• 4167-90-2 lithium triphenylstannide 
• 4167-90-2 triphenylstannyllithium 
• 962-89-0 triphenyltin bromide 
• 894-09-7 iodotriphenylstannane 
• 1247-08-1 Triphenyl-phenylethynyl-stannane 
• 161838-12-6 (C₆H₅)3SnCH₂CHCHC₆H₅ 
• 4104-91-0 Triphenyl-butin-⁽¹⁾-yl-⁽³⁾-zinn 
• 1092-86-0 dimethylamidotriphenyltin(IV) 
• 127916-72-7 triphenyl tin ⁽¹⁺⁾; 3,3-diethoxy-prop-1-yneide 

Downstream Products

• 34819-62-0 4,4,4-trichloro-1,2-butadiene 
• 83682-41-1 4,4-dichloro-1,2-butadiene 
• 95019-51-5 1-(propane-1-sulfonyl)propa-1,2-diene 
• 2525-42-0 phenylsulfonylpropa-1,2-diene 
• 125488-49-5 1-Acetyl-2-(2-propynyl)cyclohexane 
• 122621-07-2 1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)thymine 
• 167641-89-6 3'-α-C-allenyl-5'-O-benzoyl-2',3'-dideoxythymidine 
• 135263-87-5 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2S)-2-<(tert-butoxycarbonyl)amino>pent-4-ynoate 
• 135263-87-5 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2R)-2-<(tert-butoxycarbonyl)amino>pent-4-ynoate 
• 5424-25-9 ethyltriphenylstannate 
• 42903-26-4 (C₆H₅)3SnOCH(CCl₃)CHCCH₂ 
• 95626-30-5 (C₆H₅)3SnC(CH₃)CCH₂ 
• 1954-34-3 triphenyltin isothiocyanate 
• 4104-92-1 Triphenyl-butadien-(1,2)-yl-⁽¹⁾-zinn 

Relevant articles and documents

Erratum: Total synthesis of (-)-histrionicotoxin (Org. Lett. (2011) 13: 16 (4466-4449) DOI: 10.1021/ol2018032)

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Free-Radical Chain Substitution Reactions (SH2') of Alkenyl-, Alkynyl-, and (Alkenyloxy)stannanes

Free-radical chain substitution reactions of allyltributylstannane were observed with PhSSPh, PhCH2SSCH2Ph, PhSeSePh, PhSO2Cl, n-PrSO2Cl, or CCl3SO2Cl, where the attacking radicals leading to allylic rearrangement with displacement of Bu3Sn(radical) were PhS(radical), PhCH2S(radical), PhSe(radical), PhSO2(radical), n-PrSO2(radical), and CCl3(radical), respectively.Allylic rearrangement was also observed in the SH2' reaction of crotyltributylstannane with PhSSPh, PhCH2SSCH2Ph, PhSO2Cl, or n-PrSO2Cl.Propargyltriphenylstannane underwent SH2' substitution to form the allenic substitution products with PhSO2Cl, n-PrSO2Cl, CCl4, and CHCl3 while 2-butynyltriphenylstannane formed the 1,2-butadiene with PhSO2Cl or n-PrSO2Cl.Reaction of (1-cyclohexenyloxy)tributylstannane with CCl4 or BrCCl3 formed α-(trichloromethyl)cyclohexanone.With HCBr3 the initially formed α-(dibromomethyl)cyclohexanone readily underwent dehydrobromination to form α-(bromomethylene)cyclohexanone. tributylstannane formed α-(trichloromethyl)isobutyraldehyde with CCl4 or BrCCl3.Reaction with HCBr3 gave a mixture of α-(dibromomethyl)isobutyraldehyde and 1-(dibromomethyl)-2,2-dimethyloxirane.