481408

Chlorodicyclohexylphosphine

97%

• Synonym(s): Dicyclohexylchlorophosphine, Dicyclohexylphosphine chloride, Dicyclohexylphosphinous chloride
• Linear Formula: (C₆H₁₁)₂PCl
• CAS Number: 16523-54-9
• Molecular Weight: 232.73
• MDL number: MFCD00014294
• UNSPSC Code: 12352101
• PubChem Substance ID: 24871756
• NACRES: NA.22

Properties

• assay: 97%
• reaction suitability: reaction type: Buchwald-Hartwig Cross Coupling Reaction; reaction type: Heck Reaction; reaction type: Hiyama Coupling; reaction type: Negishi Coupling; reaction type: Sonogashira Coupling; reaction type: Stille Coupling; reaction type: Suzuki-Miyaura Coupling; reagent type: ligand
• refractive index: n20/D 1.533 (lit.)
• bp: 165 °C/12 mmHg (lit.)
• density: 1.054 g/mL at 25 °C (lit.)
• functional group: phosphine
• SMILES string: ClP(C1CCCCC1)C2CCCCC2
• InChI: 1S/C12H22ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2
• InChI key: AKJFBIZAEPTXIL-UHFFFAOYSA-N

Description

Application

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.

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• supp_hazards: EUH014
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 235.4 °F - closed cup
• flash_point_c: 113 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter