Chlorodicyclohexylphosphine

Base Information

• Chemical Name: Chlorodicyclohexylphosphine
• CAS No.: 16523-54-9
• Molecular Formula: C12H22ClP
• Molecular Weight: 232.733
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID10370140
• Nikkaji Number: J1.405.865F
• Wikidata: Q72468654
• Mol file: 16523-54-9.mol

Synonyms:Chlorodicyclohexylphosphine;16523-54-9;DICYCLOHEXYLCHLOROPHOSPHINE;chloro(dicyclohexyl)phosphane;chlorodicyclohexylphosphane;Chlorodicyclohexyl phosphine;Phosphinous chloride, dicyclohexyl-;Dicyclohexylphosphinous Chloride;ClPCy2;PCy2Cl;MFCD00014294;Phosphinous chloride, P,P-dicyclohexyl-;Dicyclohexylchlorophosphin;chlorodicyclohexvlphosphine;dicyclohexylchlorophosphane;Dicyclohexylchlorophosphine?;SCHEMBL496220;Chlorodicyclohexylphosphine, 97%;DTXSID10370140;AKJFBIZAEPTXIL-UHFFFAOYSA-N;AKOS015914536;MB00232;SC11225;BB 0221065;C1658;FT-0623639;EN300-105513;T70383;A852563;J-010189;J-520255;Dicyclohexylchlorophosphine;CHLORODICYCLOHEXYLPHOSPHANE;CHLORODICYCLOHEXYLPHOSPHINE;DICYCLOHEXYLPHOSPHINE CHLORIDE;DICYCLOHEXYLPHOSPHINOUS CHLORIDE

Chemical Property of Chlorodicyclohexylphosphine

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.00238mmHg at 25°C
• Melting Point: 126-128 °C
• Refractive Index: n20/D 1.533(lit.)
• Boiling Point: 297.5 °C at 760 mmHg
• Flash Point: 133.7 °C
• PSA: 13.59000
• Density: 1.054g/mLat 25°C(lit.)
• LogP: 5.28750
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: reacts violently
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 232.1147654
• Heavy Atom Count: 14
• Complexity: 142

Purity/Quality:

99% ^*data from raw suppliers

Dicyclohexylchlorophosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-27-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)P(C2CCCCC2)Cl
• Uses: Dicyclohexylchlorophosphine is used as pharmaceutical intermediate. It is also used in the synthesis of various phosphines. Chlorodicyclohexylphosphine can be used as a reactant in the synthesis of: 1,2-Bis(dicyclohexylphosphinoxy)ethane ligand by reacting with ethylene glycol in the presence of triethylamine via Michaelis?Arbuzov type rearrangements.1,1,2,2-tetracyclohexyldiphosphine monosulfide ligand by treating with LiS.It can be also used as a starting material for the preparation of some other ligands such as dicyclohexylphosphine oxide , phosphino substituted N-aryl pyrroles , di-tert-butyl((dicyclohexylphosphino)methyl)phosphine , dicyclohexylcyclopentylphosphine. These ligands are used in Pd-catalyzed cross-coupling reactions.

Technology Process of Chlorodicyclohexylphosphine

There total 13 articles about Chlorodicyclohexylphosphine 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: 80.6%

dicyclohexylphosphane (829-84-5) → chlorodicyclohexylphosphane (16523-54-9)

Guidance literature:

With Ethyl trichloroacetate; In chlorobenzene; at 80 ℃; for 2.46667h; Product distribution / selectivity;

Reference yield:

cyclohexylmagnesiumchloride (931-51-1) → chlorodicyclohexylphosphane (16523-54-9)

Guidance literature:

With phosphorus trichloride;

Reference yield:

cyclohexyl chloride (542-18-7) → chlorodicyclohexylphosphane (16523-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Mg / diethyl ether / 2.5 h / Heating

2: PCl₃ / diethyl ether

With magnesium; phosphorus trichloride; In diethyl ether;

DOI:10.1039/b210114a

upstream raw materials:

cyclohexylmagnesiumchloride

dichlorocyclohexylphosphine

cyclohexane

1-bromocyclohexane

Downstream raw materials:

1.1-Dibutoxy-2.2-dicyclohexyldiphosphin

[1-(Dicyclohexyl-phosphinoyl)-3-methyl-buta-1,2-dienyl]-benzene

keYPhos

C₂₄H₄₄OP₂

Refernces

• 1、 -. "DIALKYL(2-ALKOXY-6-AMINOPHENYL)PHOSPHINE, THE PREPARATION METHOD AND USE THEREOF". Paragraph 0033; 0034. . Retrieved 2014/10/29.
• 2、 -. "STRUCTURE AND METHOD FOR SYNTHESIZING AND USING DIALKYL(2,4,6- OR 2,6-ALKOXYPHENYL)PHOSPHINE AND ITS TETRAFLUOROBORATE". Page/Page column 4-5. . Retrieved 2012/08/08.