Dicyclohexylchlorophosphine CAS 16523-54-9
Introduction：Basic information about Dicyclohexylchlorophosphine CAS 16523-54-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Dicyclohexylchlorophosphine Basic information
| Product Name: | Dicyclohexylchlorophosphine |
| Synonyms: | Chlorodicyclohexylphosphine ,96%;Chlorodicyclohexylphosphine, 97% 5GR;98% (C6H11)2PCl;chlorodicyclohexylphosphane;Phosphinous chloride, P,P-dicyclohexyl-;Chlorodicyclohexylphosphine 97%;Chlorodicyclohexylphosphine Synonyms Dicyclohexylchlorophosphine;Dicyclohexylphosphine chloride |
| CAS: | 16523-54-9 |
| MF: | C12H22ClP |
| MW: | 232.73 |
| EINECS: | |
| Product Categories: | organophosphine halide;Achiral Phosphine;Alkyl Phosphine;P-Cl;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors;Chlorophosphines;Phosphines |
| Mol File: | 16523-54-9.mol |
Dicyclohexylchlorophosphine Chemical Properties
| Melting point | 126-128 °C |
| Boiling point | 165 °C/12 mmHg (lit.) |
| density | 1.054 g/mL at 25 °C (lit.) |
| refractive index | n |
| Fp | >230 °F |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| form | Liquid |
| color | Colorless to pale yellow |
| Specific Gravity | 1.054 |
| Water Solubility | reacts violently |
| Sensitive | Air & Moisture Sensitive |
| InChI | InChI=1S/C12H22ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2 |
| InChIKey | AKJFBIZAEPTXIL-UHFFFAOYSA-N |
| SMILES | P(C1CCCCC1)(C1CCCCC1)Cl |
| CAS DataBase Reference | 16523-54-9(CAS DataBase Reference) |
Safety Information
| Hazard Codes | C |
| Risk Statements | 14-34 |
| Safety Statements | 26-27-36/37/39-45-8 |
| RIDADR | UN 3265 8/PG 2 |
| WGK Germany | 3 |
| TSCA | No |
| HazardClass | 8 |
| PackingGroup | II |
| HS Code | 29319090 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Eye Dam. 1 Skin Corr. 1B |
| Chemical Properties | clear colorless liquid |
| Uses | Dicyclohexylchlorophosphine is used as pharmaceutical intermediate. It is also used in the synthesis of various phosphines. |
| Uses | Chlorodicyclohexylphosphine can be used as a reactant in the synthesis of:
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. |
| 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. |
| 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 |
| Synthesis | Dicyclohexylphosphine (98.8%,10.68 g,53.8 mmol) was added to the reaction flask followed by THF (10.85 g). Ethyl trichloroacetate (97%,10.52g,55mmol) was added dropwise to the resulting solution over a period of 30 minutes under stirring (the temperature of the reaction mixture was varied from 18??C to 33??C by applying external cooling during the addition). The reaction mixture was aged at ambient temperature for two hours (aging means keeping the reaction mixture under specified conditions for a specified time, optionally under stirring). After aging, the reaction mixture was a clear and colorless low viscosity liquid. The crude reaction mixture was subjected to vacuum distillation (96-100 ??C/3.6 mbar), which resulted in the isolation of dicyclohexylphosphonium chloride in 53% yield and high purity as a clear and colorless low-viscous liquid (31P NMR: 98.78% ;GC-FID: 97.26%). |
| Precautions | Store in cool, dry conditions in well sealed containers. Protect from humidity and water. Store under dry inert gas. It is sensitive to air and moisture. Incompatible with strong oxidizing agents. |
Dicyclohexylchlorophosphine Preparation Products And Raw materials
| Preparation Products | X-PHOS-->2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl-->CPhos-->1,2-BIS(DICYCLOHEXYLPHOSPHINO)ETHANE-->Tricyclohexyl phosphine-->Dicyclohexylphosphine oxide-->2-(Dicyclohexylphosphino)-2'-methoxybiphenyl-->T-BUTYLDICYCLOHEXYLPHOSPHINE-->Phosphine, dicyclohexyl[2-(9-phenanthrenyl)phenyl]--->2-DICYCLOHEXYLPHOSPHINO-2',6'-DIISOPROPOXYBIPHENYL-->2-(Dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-Imidazole-->2-(Dicyclohexylphosphino)-2'-methylbiphenyl-->2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl |
