Bis(3,5-dimethylphenyl)chlorophosphine

Base Information

• Chemical Name: Bis(3,5-dimethylphenyl)chlorophosphine
• CAS No.: 74289-57-9
• Molecular Formula: C16H18 Cl P
• Molecular Weight: 276.746
• European Community (EC) Number: 636-136-8
• DSSTox Substance ID: DTXSID50400511
• Nikkaji Number: J1.273.144B
• Wikidata: Q72445256
• Mol file: 74289-57-9.mol

Synonyms:BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE;74289-57-9;Chlorobis(3,5-dimethylphenyl)phosphine;Chloro-bis(3,5-dimethylphenyl)phosphane;Bis(3,5-dimethylphenyl)phosphinous chloride;Phosphinous chloride, bis(3,5-dimethylphenyl)-;SCHEMBL460419;DTXSID50400511;FCEBDAANWYNQMO-UHFFFAOYSA-N;MFCD01630841;CS-0108686;FT-0752955;E84318;A901461

Chemical Property of Bis(3,5-dimethylphenyl)chlorophosphine

Chemical Property:

• Vapor Pressure: 1.81E-06mmHg at 25°C
• Refractive Index: n20/D 1.606
• Boiling Point: 407.2°C at 760 mmHg
• Flash Point: 110 °C
• PSA: 13.59000
• Density: 1.102 g/mL at 25 °C
• LogP: 4.50670
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 276.0834653
• Heavy Atom Count: 18
• Complexity: 222

Purity/Quality:

97% ^*data from raw suppliers

Bis(3,5-dimethylphenyl)chlorophosphine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-43-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)P(C2=CC(=CC(=C2)C)C)Cl)C
• Uses: Chlorobis(3,5-dimethylphenyl)phosphine is used in the synthesis of (S)- and (R)-2,2?-Bis[bis(3,5-dimethylphenyl)phosphinoyl]-5,5?,6,6?,7,7?,8,8?-octahydro-1,1?-binaphthyl (Xyl-H 8 -BINAPO).

Technology Process of Bis(3,5-dimethylphenyl)chlorophosphine

There total 11 articles about Bis(3,5-dimethylphenyl)chlorophosphine 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: 100.0%

diethylphosphoramidous dichloride (1069-08-5) + 5-bromo-1,3-xylene (556-96-7) → bis-(3,5-dimethylphenyl)chlorophosphine (74289-57-9)

Guidance literature:

5-bromo-1,3-xylene; With n-butyllithium; In diethyl ether; hexane; at 0 ℃; for 4h; Inert atmosphere; Sealed tube;

diethylphosphoramidous dichloride; In diethyl ether; hexane; at 0 ℃; for 0.166667h; Inert atmosphere; Sealed tube;

With hydrogenchloride; In 1,4-dioxane; diethyl ether; hexane; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c00142

Reference yield: 94.0%

tris(3,5-dimethylphenyl)phosphine (69227-47-0) → bis-(3,5-dimethylphenyl)chlorophosphine (74289-57-9)

Guidance literature:

With zinc trifluoromethanesulfonate; phosphorus trichloride; In tetrachloromethane; at 0 - 60 ℃; for 12h;

Reference yield: 91.0%

C21H29N2P → bis-(3,5-dimethylphenyl)chlorophosphine (74289-57-9)

Guidance literature:

With hydrogenchloride; In hexane; for 1h;

upstream raw materials:

bis(3,5-dimethylphenyl)phosphine oxide

[bis-(3,5-dimethylphenyl)](diethylamino)phosphine

diethylphosphoramidous dichloride

3,5-dimethyphenylmagnesium bromide

Downstream raw materials:

2-[bis(3,5-dimethylphenyl)phosphino]benzaldehyde

(R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-6,6'-dimethyl-1,1'-binaphthyl

Refernces

• 1、 Tan, Xuefeng,Gao, Shuang,Zeng, Weijun,Xin, Shan,Yin, Qin,Zhang, Xumu. "Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2". supporting information. p. 2024 - 2027. Retrieved 2018/02/19.
• 2、 -. "A 2,2 the [...] -bis [(3,5- xylyl ) phosphorus] dinaphthalene method for the preparation of". Paragraph 0028; 0039; 0040. . Retrieved 2017/02/28.