| Identification | More | [Name]
Di-tert-butylchlorophosphane | [CAS]
13716-10-4 | [Synonyms]
AURORA KA-1319
Bis(1,1-dimethylethyl)-phosphinous chloride
DI-T-BUTYLCHLOROPHOSPHINE
DI-T-BUTYLPHOSPHINOUS CHLORIDE
DI-TERT-BUTYLCHLOROPHOSPHANE
DI-TERT-BUTYLCHLOROPHOSPHINE
DI-TERT-BUTYLPHOSPHORUS CHLORIDE
(tert-C4H9)2PCl
Chlorodi-tert-butylphosphine
Di-tert-Butylphosphinous chloride
Phosphinous chloride, di-tert-butyl-
DI-TERT-BUTYLCHLOROPHOSPHINE (DTBCP)
Di-t-butylchlorophosphine,min.98%
Phosphonous dichloride
Di-tert-B-butylchlorophosphine, 96%
Di-t-butylchlorophosphine, min. 98% | [EINECS(EC#)]
237-266-4 | [Molecular Formula]
C8H18ClP | [MDL Number]
MFCD00008815 | [Molecular Weight]
180.66 | [MOL File]
13716-10-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [Melting point ]
2-3°C | [Boiling point ]
48 °C/3 mmHg (lit.) | [density ]
0.951 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.482(lit.)
| [Fp ]
142 °F
| [solubility ]
Miscible with terahydrofuran. | [form ]
Liquid | [color ]
Clear colorless | [Specific Gravity]
0.951 | [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) | [Storage Precautions]
Moisture sensitive;Air sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S25:Avoid contact with eyes . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [TSCA ]
No | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29310099 |
| Hazard Information | Back Directory | [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.? | [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]
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 |
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