301558

Di-tert-butylchlorophosphine

96%

• Synonym(s): P, P-bis(1 1-dimethylethyl), Phosphinous chloride
• Linear Formula: [(CH₃)₃C]₂PCl
• CAS Number: 13716-10-4
• Molecular Weight: 180.66
• MDL number: MFCD00008815
• UNSPSC Code: 12352001
• PubChem Substance ID: 24858196

Properties

• Assay: 96%
• form: liquid
• reaction suitability: reagent type: ligand; reaction type: Suzuki-Miyaura Coupling
• refractive index: n20/D 1.482 (lit.)
• bp: 48 °C/3 mmHg (lit.)
• density: 0.951 g/mL at 25 °C (lit.)
• functional group: phosphine
• SMILES string: CC(C)(C)P(Cl)C(C)(C)C
• InChI: 1S/C8H18ClP/c1-7(2,3)10(9)8(4,5)6/h1-6H3
• InChI key: MCRSZLVSRGTMIH-UHFFFAOYSA-N

Description

General description

Di-tert-butylchlorophosphine belongs to the class of phosphine ligands. It is used for cross-coupling reactions because of the flexibility of its electronic and steric properties. It plays a key role in stabilizing and activating the central metal atom and is used in reactions such as transition metal-catalyzed C-O, C-N, and C-C bond-forming reactions.

Application

Di-tert-butylchlorophosphine can be used as a ligand in:      

• The Pd-catalyzed amination reaction with aryl halides.      
• The Pd-catalyzed Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides and chlorides.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): 143.6 °F - closed cup
• Flash Point(C): 62 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves