CAS 13716-10-4 Di-tert-butylchlorophosphine - Catalysts / Alfa Chemistry

Synonyms

(tert-C4H9)2PCl; ZINC95719226; PubChem6477; 716D104; AKOS015910830; di-t-Butylchlorophosphine; (t-Bu)2PCl; DTXSID70160089; Jsp002238; Di-tert-butylchlorophosphanec;

IUPAC Name

ditert-butyl(chloro)phosphane;

Molecular Weight

180.656g/mol

Molecular Formula

C8H18ClP;

Canonical SMILES

CC(C)(C)P(C(C)(C)C)Cl;

InChI

InChI=1S/C8H18ClP/c1-7(2,3)10(9)8(4,5)6/h1-6H3;

InChI Key

MCRSZLVSRGTMIH-UHFFFAOYSA-N;

Complexity

93.4

Covalently-Bonded Unit Count

EC Number

604-003-3

Exact Mass

180.083g/mol

Heavy Atom Count

Monoisotopic Mass

180.083g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

Di-tert-butylchlorophosphine is a colorless to light yellow liquid that serves a pivotal role in organic synthesis, particularly in the formation of catalysts and ligands. It functions as a bulky ligand when paired with palladium(II) acetate to enhance the efficiency of Suzuki-Miyaura cross-couplings between arylboronic acids and aryl bromides or chlorides. Additionally, it is instrumental in creating mono- and bidentate phosphine ligands within metal complexes, which are crucial for catalytic chiral asymmetric hydrogenations. Beyond these applications, Di-tert-butylchlorophosphine is utilized in both asymmetric and transition metal coupling reactions and plays a significant role in the synthesis of other phosphines required for catalytic polymerization processes.

February 10, 2025

Essential Catalyst for Efficient Cross-Couplings

Di-tert-butylchlorophosphine is invaluable in my lab's Suzuki-Miyaura reactions. As a ligand with Pd(OAc)2, it boosts efficiency and yields, making complex organic synthesis tasks remarkably smoother. A must-have for advanced chemical research!