Bis(4-trifluoromethylphenyl)phosphine

Base Information

• Chemical Name: Bis(4-trifluoromethylphenyl)phosphine
• CAS No.: 99665-68-6
• Molecular Formula: C14H9F6P
• Molecular Weight: 322.19
• Hs Code.: 2903999090
• European Community (EC) Number: 633-713-6
• DSSTox Substance ID: DTXSID80402442
• Wikidata: Q82205854
• Mol file: 99665-68-6.mol

Synonyms:99665-68-6;BIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE;Bis(4-(trifluoromethyl)phenyl)phosphine;Bis[4-(trifluoromethyl)phenyl]phosphane;Phosphine, bis[4-(trifluoromethyl)phenyl]-;MFCD01630793;Bis[4-(trifluoromethyl)phenyl]phosphine;SCHEMBL1486411;DTXSID80402442;LLJITAAISCMRAR-UHFFFAOYSA-N;UFZSSXQUGHMWDK-UHFFFAOYSA-N;BCP22547;AKOS016009390;bis(4-trifluoromethyl phenyl)phosphine;AMY202003190;SY113127;Bis(4-trifluoromethylphenyl)phosphine, 97%;FT-0732821;A858439

Chemical Property of Bis(4-trifluoromethylphenyl)phosphine

Chemical Property:

• Refractive Index: n20/D1.512
• Boiling Point: 291.4 °C at 760 mmHg
• Flash Point: 130 °C
• PSA: 13.59000
• Density: 1.317 g/mL at 25 °C
• LogP: 4.35350
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 322.03460626
• Heavy Atom Count: 21
• Complexity: 289

Purity/Quality:

98% ^*data from raw suppliers

Bis(4-trifluoromethylphenyl)phosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-37-41
• Safety Statements: 26-39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(F)(F)F)PC2=CC=C(C=C2)C(F)(F)F
• Uses: Reactant for:Preparation of iron(II) chiral diimine diphosphine complexes as catalysts for asymmetric transfer hydrogenation of ketonesEnantioselective decarboxylative allylation and ring-closing metathesis

Technology Process of Bis(4-trifluoromethylphenyl)phosphine

There total 5 articles about Bis(4-trifluoromethylphenyl)phosphine 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: 87.0%

bis(4-(trifluoromethyl)phenyl)phosphine oxide (15929-43-8) → potassium bis(4-(trifluoromethyl)phenyl)phosphide (99665-68-6)

Guidance literature:

bis(4-(trifluoromethyl)phenyl)phosphine oxide; With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 20 ℃; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; tert-butyl methyl ether; water; toluene; at 5 ℃;

DOI:10.1007/s11164-018-3403-3

Reference yield: 79.0%

→ potassium bis(4-(trifluoromethyl)phenyl)phosphide (99665-68-6)

Guidance literature:

Reference yield:

4-(trifluoromethyl)phenylmagnesium bromide (402-51-7) → potassium bis(4-(trifluoromethyl)phenyl)phosphide (99665-68-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 2.33 h / 0 - 20 °C / Inert atmosphere

1.2: 0.42 h / 0 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 20 °C / Inert atmosphere

2.2: 5 °C

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1007/s11164-018-3403-3

upstream raw materials:

Benzyl-bis-(4-trifluoromethyl-phenyl)-phosphane

(4-trifluoromethylphenyl)lithium

bis(4-(trifluoromethyl)phenyl)phosphine oxide

4-(trifluoromethyl)phenylmagnesium bromide

Downstream raw materials:

(S)-2-(2-(bis(4-trifluoromethyl-phenyl)-phosphino))-5-(4-trifluoromethyl-phenyl)-4-tert-butyl-4,5-dihydro-oxazole

trans-1,2-ethenediylbis[di(4-trifluoromethylphenyl)phosphine]

(3-ethoxypropyl)bis[4-(trifluoromethyl)phenyl]phosphine

[3-(dimethylamino)propyl]bis[4-(trifluoromethyl)phenyl]phosphine

Refernces

• 1、 Barrett, Adam N.,Woof, Callum R.,Goult, Christopher A.,Gasperini, Danila,Mahon, Mary F.,Webster, Ruth L.. "Hydrogen/Halogen Exchange of Phosphines for the Rapid Formation of Cyclopolyphosphines". supporting information. p. 16826 - 16833. Retrieved 2021/11/04.
• 2、 Li, Chun-Jing,Lü, Jing,Zhang, Zhi-Xun,Zhou, Kun,Li, Yan,Qi, Guang-Hui. "Copper-catalyzed C–P cross-coupling of secondary phosphines with (hetero)aromatic bromide". . p. 4547 - 4562. Retrieved 2018/04/20.