Triphenylphosphine-d15

Base Information

• Chemical Name: Triphenylphosphine-d15
• CAS No.: 24762-44-5
• Molecular Formula: C18D15 P
• Molecular Weight: 277.172
• European Community (EC) Number: 693-171-1
• DSSTox Substance ID: DTXSID60452728
• Nikkaji Number: J2.274.563H
• Wikidata: Q82273529
• Mol file: 24762-44-5.mol

Synonyms:Triphenylphosphine-d15;24762-44-5;tris(2,3,4,5,6-pentadeuteriophenyl)phosphane;TRI(PHENYL-D5)PHOSPHINE;Triphenylphosphan-d15;Phosphine, tri(phenyl-d5)-;SCHEMBL1332780;DTXSID60452728;AKOS015915851;Triphenylphosphine-d15, 98 atom % D;Triphenylphosphine-d15, 99 atom % D;tris[(2,3,4,5,6-?H?)phenyl]phosphane;D98057;J-015664

Chemical Property of Triphenylphosphine-d15

Chemical Property:

• Melting Point: 78-80oC(lit.)
• Boiling Point: 377oC
• Flash Point: 220℃
• PSA: 13.59000
• LogP: 3.44480
• Storage Temp.: Room Temperature
• Solubility.: Chloroform (Slightly), Hexanes (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 277.185288665
• Heavy Atom Count: 19
• Complexity: 202

Purity/Quality:

98%min ^*data from raw suppliers

Triphenylphosphine-d15 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 20/21/22-36/37/38-50/53
• Safety Statements: 45-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: [2H]C1=C(C(=C(C(=C1[2H])[2H])P(C2=C(C(=C(C(=C2[2H])[2H])[2H])[2H])[2H])C3=C(C(=C(C(=C3[2H])[2H])[2H])[2H])[2H])[2H])[2H]
• Uses: Triphenylphosphine-d15 is the labelled version of Triphenylphosphine (T808975) which is used in the synthesis of Chlorambucil with cytotoxicity in breast and pancreatic cancers. Triphenylphosphine is also used in the preparation of α-Tocopherol analogues for monitoring antioxidant status. Employed in a mechanistic study of cis-bis(silylmethyl)platinum(II) complexes.

Technology Process of Triphenylphosphine-d15

There total 4 articles about Triphenylphosphine-d15 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: 75.0%

d5-iodobenzene (7379-67-1) → triphenylphosphine-d15 (24762-44-5)

Guidance literature:

d₅-iodobenzene; With tert.-butyl lithium; In pentane; at -75 ℃;

With triphenylphosphine; In diethyl ether; at -75 - 25 ℃; Further stages.;

DOI:10.1002/chem.200390061

Reference yield: 39.0%

bromobenzene-d5 (4165-57-5) → triphenylphosphine-d15 (24762-44-5)

Guidance literature:

bromobenzene-d5; With magnesium; In diethyl ether; at 20 - 40 ℃; for 1.5h; Inert atmosphere; Autoclave;

With phosphorus trichloride; In diethyl ether; for 16h; Inert atmosphere; Autoclave;

DOI:10.1002/anie.201205058

Reference yield:

benzene-d6 (1076-43-3) → triphenylphosphine-d15 (24762-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / t-BuOK / pentane / 20 h / 0 °C

1.2: 28 percent / I₂ / tetrahydrofuran; pentane / -75 °C

2.1: t-BuLi / pentane / -75 °C

2.2: 75 percent / Ph₃P / diethyl ether / -75 - 25 °C

With n-butyllithium; tert.-butyl lithium; potassium tert-butylate; In pentane;

DOI:10.1002/chem.200390061

upstream raw materials:

d₅-iodobenzene

benzene-d6

bromobenzene-d5

Downstream raw materials:

triphenylphosphane oxide-d15

3,3-dimethyl-butan-2-one

acetaldehyde

formaldehyd

Refernces

• 1、 Carpenter, Alex E.,Margulieux, Grant W.,Millard, Matthew D.,Moore, Curtis E.,Weidemann, Nils,Rheingold, Arnold L.,Figueroa, Joshua S.. "Zwitterionic stabilization of a reactive cobalt tris-isocyanide monoanion by cation coordination". supporting information. p. 9412 - 9416. Retrieved 2012/11/07.