HandaPhos - CAS 1908442-13-6

HandaPhos forms a 1:1 complex with Pd(OAc)2 thereby arriving at a pre-catalyst, used at the ppm level, that enables Suzuki-Miyaura cross-couplings to be run under micellar catalysis in water at room temperature. To be used in tandem with Designer Surfactant TPGS-750-M.

Catalog Number

1908442-13-6

CAS

1908442-13-6

IUPAC Name

3-tert-butyl-4-(2,6-dimethoxyphenyl)-2-[[2,4,6-tri(propan-2-yl)phenyl]methyl]-2H-1,3-benzoxaphosphole

Synonyms

3-(tert-butyl)-4-(2,6- dimethoxyphenyl)-2-(2,4,6- triisopropylbenzyl)-2,3- dihydrobenzo[d][1,3]oxaph osphole; 3-(tert-butyl)-4-(2,6-dimet hoxyphenyl)-2-(2,4,6-triiso propylbenzyl)-2,3-dihydro benzo[d][1,3]oxaphosphole; 3-(tert-Butyl)-4-(2,6-dimethoxyphenyl)-2-(2,4,6-triisopropylbenzyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole

Molecular Weight

546.72

Molecular Formula

C35H47O3P

Product Information

Canonical SMILES

CC(C)C1=CC(=C(C(=C1)C(C)C)CC2OC3=CC=CC(=C3P2C(C)(C)C)C4=C(C=CC=C4OC)OC)C(C)C

InChI

InChI=1S/C35H47O3P/c1-21(2)24-18-26(22(3)4)28(27(19-24)23(5)6)20-32-38-31-17-12-14-25(34(31)39(32)35(7,8)9)33-29(36-10)15-13-16-30(33)37-11/h12-19,21-23,32H,20H2,1-11H3

InChI Key

RXGMKJPMNONITA-UHFFFAOYSA-N

Purity

≥95%

Storage

2-8°C

Flash Point

41.0 °F

Safety Information

Precautionary Statement

P201 - P210 - P273 - P301 + P310 + P331 - P302 + P352 - P308 + P313

Reference Reading

1. Handaphos: a general ligand enabling sustainable ppm levels of palladium-catalyzed cross-couplings in water at room temperature.

Sachin Handa, Fabrice Gallou, Martin P Andersson, Bruce H Lipshutz, John Reilly. Angew Chem Int Ed Engl. 2016 Apr 11; 55(16): 4914-8. DOI: 10.1002/anie.201510570. PMID: 26924396.

The new monophosphine ligand HandaPhos has been identified such that when complexed in a 1:1 ratio with Pd(OAc)2, enables Pd-catalyzed cross-couplings to be run using ≤1000 ppm of this pre-catalyst. Applications to Suzuki-Miyaura reactions involving highly funtionalized reaction partners are demonstrated, all run using environmentally benign nanoreactors in water at ambient temperatures. Comparisons with existing state-of-the-art ligands and catalysts are discussed herein.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass