Triphenylphosphine dibromide

Base Information

• Chemical Name: Triphenylphosphine dibromide
• CAS No.: 1034-39-5
• Molecular Formula: C18H15Br2P
• Molecular Weight: 422.099
• Hs Code.: 29319019
• European Community (EC) Number: 213-855-1
• NSC Number: 87871
• UNII: 7Y0J6R63JD
• DSSTox Substance ID: DTXSID3061423
• Nikkaji Number: J80.055D
• Wikidata: Q27268998
• Mol file: 1034-39-5.mol

Synonyms:Triphenylphosphine dibromide;1034-39-5;Dibromotriphenylphosphorane;Triphenyldibromophosphorane;Phosphorane, dibromotriphenyl-;Phosphorane,dibromotriphenyl-;Triphenylphosphonium dibromide;C18H15Br2P;dibromo(triphenyl)-lambda5-phosphane;Dibromo triphenyl phosphine;UNII-7Y0J6R63JD;7Y0J6R63JD;EINECS 213-855-1;MFCD00000054;NSC 87871;NSC-87871;triphenylphosphinedibromide;Bromotriphenylphosphonium bromide;dibromotriphenylphosphine;dibromtriphenylphosphorane;dibromo triphenylphosphorane;dibromo-triphenylphosphorane;dibromotriphenyl phosphorane;dibromo-triphenyl-phosphorane;Dibromo(triphenyl)phosphorane;SCHEMBL63774;DTXSID3061423;C18-H15-Br2-P;dibromotriphenyl-lambda5-phosphane;Triphenylphosphine dibromide, 96%;NSC87871;AKOS015889774;TRIPHENYLPHOSPHINE DIBROMIDE [MI];AS-10060;CS-0046124;FT-0633258;D72725;EN300-1664590;J-000966;Q27268998

Chemical Property of Triphenylphosphine dibromide

Chemical Property:

• Appearance/Colour: light yellow to light pink crystalline powder
• Melting Point: 235 °C (dec.)(lit.)
• PSA: 13.59000
• LogP: 5.13600
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in water, dichloromethane, acetonitrile, phenyl cyanide, dimethyl formamide, ether, chloroform, alcohol, carbon tetrachl
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 421.92576
• Heavy Atom Count: 21
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

Triphenylphosphine dibromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)(C3=CC=CC=C3)(Br)Br
• Uses: Triphenylphosphine dibromide is used as a reagent for conversion of aldoximes into nitriles. It acts as a reagent for cleavage of acetals. It reacts with amines to give iminophosphoranes. Further, it serves as a reagent in the preparation of alkyl and aryl bromides from alcohols and phenols without rearrangement.

Technology Process of Triphenylphosphine dibromide

There total 39 articles about Triphenylphosphine dibromide 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: 85.0%

caprinaldehyde (112-31-2) + carbon tetrabromide (558-13-4) + triphenylphosphine (603-35-0) → 1,1-dibromo-1-undecene (77295-69-3) + Triphenylphosphine oxide (791-28-6) + dibromotriphenylphosphorane (1034-39-5)

Guidance literature:

In dichloromethane; for 0.5h; Ambient temperature;

Reference yield: 83.0%

pentanal (110-62-3) + carbon tetrabromide (558-13-4) + triphenylphosphine (603-35-0) → 1,1-dibromo 1-hexene (73383-23-0) + Triphenylphosphine oxide (791-28-6) + dibromotriphenylphosphorane (1034-39-5)

Guidance literature:

In dichloromethane; for 0.5h; Ambient temperature;

Reference yield: 81.0%

carbon tetrabromide (558-13-4) + terephthalaldehyde, (623-27-8) + triphenylphosphine (603-35-0) → 1,4-bis(2,2-dibromoethenyl)benzene (77295-67-1) + Triphenylphosphine oxide (791-28-6) + dibromotriphenylphosphorane (1034-39-5)

Guidance literature:

In dichloromethane; for 0.5h; Ambient temperature;

upstream raw materials:

pentaphenylphosphorane

triphenylphosphine

thiophene-2-carbaldehyde

carbon tetrabromide

Downstream raw materials:

N-(triphenylphosphoranylidene)pyridin-2-amine

N-p-tolylsulfonylphosphine imide

P,P,P-triphenyl-N-phenylsulfonylphosphine imide

1-bromo dodecane

Refernces

C45-and C50-Carotenoids. Synthesis of an Optically Active Cyclic C20-Building Block and of (2R,2'S)-3',4'-Didehydro-1',2'-dihydro-2-(4-hydroxy-3-methylbut-2-enyl)-2'-(3-methylbut-2-enyl)-β,Ψ-caroten-1'-ol (=C.p. 473)

10.1002/hlca.19860690622

The research details the synthesis of an optically active cyclic C40 building block and the optically active C40-carotenoid (2R,2’S)-3’,4’-Didehydro-1’,2’-dihydro-2-(4-hydroxy-3-methylbut-2-enyl)-2’-(3-methylbut-2-enyl)-β,γ-caroten-1’-ol (C.p. 473). The purpose of this study was to develop synthetic methods for producing optically active carotenoids, which are important for understanding their natural structures and potential applications in biological and chemical contexts. The synthesis of the optically active C40 building block (R)-16 and the carotenoid C.p. 473 (1) started from (-)-β-pinene. Key chemicals used in the process included acetic anhydride, pyridine, sodium borohydride, triphenylphosphine dibromide, and various reagents for Wittig reactions such as phosphonium salts and organometallic compounds like butyllithium. The synthesis involved multiple steps, including acetylation, hydrolysis, reduction, bromination, and Wittig reactions to extend carbon chains and introduce functional groups. The final products were characterized by spectroscopic methods, confirming their structures. The research successfully demonstrated the synthesis of these complex molecules, contributing to the field of organic chemistry and providing a methodological framework for producing optically active carotenoids.