BIS(DIPHENYLPHOSPHINO)ACETYLENE

Base Information

• Chemical Name: BIS(DIPHENYLPHOSPHINO)ACETYLENE
• CAS No.: 5112-95-8
• Molecular Formula: C26H20P2
• Molecular Weight: 394.392
• Hs Code.: 29310099
• European Community (EC) Number: 225-842-8
• NSC Number: 164872
• DSSTox Substance ID: DTXSID00199140
• Nikkaji Number: J145.406D
• Wikidata: Q83072041
• ChEMBL ID: CHEMBL70027
• Mol file: 5112-95-8.mol

Synonyms:Phosphine,1,2-ethynediylbis[diphenyl- (9CI);Phosphine, ethynylenebis[diphenyl-(6CI,7CI,8CI);((Diphenylphosphino)ethynyl)diphenylphosphine;1,2-Bis(diphenylphosphino)acetylene;1,2-Bis(diphenylphosphino)ethyne;Bis(diphenylphosphino)acetylene;Bis(diphenylphosphino)ethyne;NSC 164872;

Chemical Property of BIS(DIPHENYLPHOSPHINO)ACETYLENE

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 9.04E-11mmHg at 25°C
• Melting Point: 86-88 °C(lit.)
• Boiling Point: 529.6 °C at 760 mmHg
• Flash Point: 291.4 °C
• PSA: 27.18000
• LogP: 5.17060
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 6
• Exact Mass: 394.10402463
• Heavy Atom Count: 28
• Complexity: 425

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bis(diphenylphosphino)acetylene, 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C#CP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of BIS(DIPHENYLPHOSPHINO)ACETYLENE

There total 11 articles about BIS(DIPHENYLPHOSPHINO)ACETYLENE 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: 52.0%

diphenyl-prop-1-ynyl-phosphane (6224-94-8) → bis(diphenylphosphino)acetylene (5112-95-8)

Guidance literature:

With [(Ph₃SiO)₃Mo≡CC₆H₄OMe]; In toluene; at 20 ℃; for 2h; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201302320

Reference yield: 50.0%

Bis(diphenylphosphanyl)acetylene P,P'-dioxide (22428-64-4) → bis(diphenylphosphino)acetylene (5112-95-8)

Guidance literature:

Bis(diphenylphosphanyl)acetylene P,P'-dioxide; With trityl tetrakis(pentafluorophenyl)borate; In ⁽²⁾H₈-toluene; at 20 ℃; Glovebox; Inert atmosphere;

With phenylsilane; In ⁽²⁾H₈-toluene; at 80 ℃; for 1.5h; chemoselective reaction; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1002/adsc.202100189

Reference yield: 49.0%

trans-1,2-dichloroethylene (156-60-5,43695-79-0) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → bis(diphenylphosphino)acetylene (5112-95-8)

Guidance literature:

trans-1,2-dichloroethylene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃;

chloro-diphenylphosphine; In tetrahydrofuran; hexane; at 0 ℃;

chloro-diphenylphosphine; Further stages;

DOI:10.1002/anie.201108932

upstream raw materials:

ethynyldimagnesium dibromide

chloro-diphenylphosphine

acetylene

bis(diisopropylamino)phosphanylnitrile

Downstream raw materials:

(diphenylphosphino-ethynyl)-methyl-diphenyl-phosphonium; iodide

1,1,4,4-tetrakis(diphenylphosphanyl)butatriene

Tetraphenyldiphosphin

2,3-Bis-diphenylphosphanyl-4,6-diphenyl-phosphinine

Refernces

• 1、 Persich, Peter,Llaveria, Josep,Lhermet, Rudy,Deharo, Teresa,Stade, Robert,Kondoh, Azusa,Fuerstner, Alois. "Increasing the structural span of alkyne metathesis". supporting information. p. 13047 - 13058. Retrieved 2013/10/01.
• 2、 Ekkert, Olga,Kehr, Gerald,Froehlich, Roland,Erker, Gerhard. "P-C bond activation chemistry: Evidence for 1,1-carboboration reactions proceeding with phosphorus-carbon bond cleavage". supporting information; experimental part. p. 4610 - 4616. Retrieved 2011/05/17.