Di-tert-butylchlorophosphane CAS 13716-10-4
Di-tert-butylchlorophosphane Basic information
| Product Name: | Di-tert-butylchlorophosphane |
| Synonyms: | AURORA KA-1319;Bis(1,1-dimethylethyl)-phosphinous chloride;DI-T-BUTYLCHLOROPHOSPHINE;DI-T-BUTYLPHOSPHINOUS CHLORIDE;DI-TERT-BUTYLPHOSPHORUS CHLORIDE;DI-TERT-BUTYLCHLOROPHOSPHANE;DI-TERT-BUTYLCHLOROPHOSPHINE;DI-TERT-BUTYLCHLOROPHO |
| CAS: | 13716-10-4 |
| MF: | C8H18ClP |
| MW: | 180.66 |
| EINECS: | 237-266-4 |
| Product Categories: | organophosphine halide;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors;Phosphines;Ligand;Chlorophosphines;Achiral Phosphine;Alkyl Phosphine;P-Cl |
| Mol File: | 13716-10-4.mol |
Di-tert-butylchlorophosphane Chemical Properties
| Melting point | 2-3°C |
| Boiling point | 48 °C/3 mmHg (lit.) |
| density | 0.951 g/mL at 25 °C (lit.) |
| refractive index | n |
| Fp | 142 °F |
| solubility | Miscible with terahydrofuran. |
| form | Liquid |
| Specific Gravity | 0.951 |
| color | Clear colorless |
| Sensitive | Air & Moisture Sensitive |
| InChI | InChI=1S/C8H18ClP/c1-7(2,3)10(9)8(4,5)6/h1-6H3 |
| InChIKey | MCRSZLVSRGTMIH-UHFFFAOYSA-N |
| SMILES | P(C(C)(C)C)(C(C)(C)C)Cl |
| CAS DataBase Reference | 13716-10-4(CAS DataBase Reference) |
| NIST Chemistry Reference | Phosphinous chloride, bis(1,1-dimethylethyl)-(13716-10-4) |
Safety Information
| Hazard Codes | C |
| Risk Statements | 34 |
| Safety Statements | 26-36/37/39-45-25 |
| RIDADR | UN 3265 8/PG 2 |
| WGK Germany | 3 |
| TSCA | No |
| HazardClass | 8 |
| PackingGroup | II |
| HS Code | 29310099 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Skin Corr. 1B |
| Chemical Properties | Colorless to light yellow liqui |
| Uses | Di-tert-butylchlorophosphine is associated with palladium(II) acetate and used in Suzuki-Miyaura cross-couplings of arylboronic acids with aryl bromides and chlorides. It serves as a ligand and used in the preparation of mono- and bidentate phosphine ligands in metal complexes for catalytic chiral asymmetric hydrogenations. Further, it is used in asymmetric and transition metal coupling reactions. In addition to this, it plays an important role in the preparation of other phosphines in catalytic polymerization reactions. |
| Uses | Di-tert-butylchlorophosphine is used as a catalyst in organic synthesis. |
| Uses | Bulky ligand used with Pd(OAc)2 in efficient Suzuki-Miyaura cross-couplings of arylboronic acids with aryl bromides and chlorides. |
| Application | Bulky ligand used with Pd(OAc)2 in efficient Suzuki-Miyaura cross-couplings of arylboronic acids with aryl bromides and chlorides. |
| reaction suitability | reagent type: ligand reaction type: Suzuki-Miyaura Coupling |
| Synthesis | 819-19-2 13716-10-4 General procedure for the synthesis of di-tert-butylphosphonium chloride from di-tert-butylphosphine: Di-tert-butylphosphine (13.5 g, 92 mmol) was added to a three-necked round-bottomed flask fitted with a thermometer, a charging funnel and a condenser under the protection of nitrogen and heated to 83-84 °C. The synthesis of di-tert-butylphosphonium chloride from di-tert-butylphosphine was carried out by the following procedure. Octyl trichloroacetate (25.4 g, 92 mmol) was slowly added dropwise over a period of 20 minutes. After the dropwise addition, the reaction mixture was continued to be stirred at 70 °C for 20 min, which showed 0.6% unreacted di-tert-butylphosphine by GC analysis. The addition funnel was removed and the short-circuit distillation head was adapted for distillation. Two fractions were collected and the former fraction (1.24 g) was discarded. The second fraction was collected to give 13 g (78.2% yield) of di-tert-butylphosphonium chloride as a clear, colorless liquid with a boiling point of 48-52 °C/3.2 mbar (literature value 48 °C/3 mm Hg). The purity of the product was 97% by GC-FID. |
| Precautions | Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents and strong reducing agents. |
| References | [1] Patent: WO2009/147495, 2009, A2. Location in patent: Page/Page column 17 [2] J. Gen. Chem. USSR (Engl. Transl.), 1991, vol. 61, # 1.1, p. 114 - 118 |
Di-tert-butylchlorophosphane Preparation Products And Raw materials
| Raw materials | Tetrahydrofuran-->Sodium-->Nitrogen-->Magnesium-->Phosphorus trichloride-->Pentane-->tert-Butyllithium-->2-Chloro-2-methylpropane-->Di-tert-butylphosphine |
| Preparation Products | 1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride,-->1,1'-Bis(di-tert-butylphosphino)ferrocene-->Di-t-butylmethylphosphine-->1-DIPHENYLPHOSPHINO-1'-(DI-TERT-BUTYLPH&-->RAC-2-(DI-T-BUTYLPHOSPHINO)-1,1'-BINAPHTHYL-->2-DI-TERT-BUTYLPHOSPHINO-3,4,5,6-TETRAM&-->DI-T-BUTYLNEOPENTYLPHOSPHINE, MIN. 95-->1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE-->PNN-->DI-TERT-BUTYLPHENYLPHOSPHINE-->2-(Di-tert-butylphosphino)biphenyl |
