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631922

Sigma-Aldrich

1,2-Bis(di-tert-butylphosphinomethyl)benzene

Synonym(s):

1,1′-[1,2-Phenylenebis(methylene)]bis[1,1-bis(1,1-dimethylethyl)phosphine, 1,2-Bis(di-tert-butylphosphino)xylene, 1,2-Bis[(di-tert-butylphosphino)methyl]benzene

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About This Item

Linear Formula:
C6H4[CH2P[C(CH3)2]2]
CAS Number:
121954-50-5
Molecular Weight:
394.55
MDL number:
MFCD03094573
UNSPSC Code:
12352002
PubChem Substance ID:
24882466
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

functional group

phosphine

SMILES string

CC(C)(C)P(Cc1ccccc1CP(C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI

1S/C24H44P2/c1-21(2,3)25(22(4,5)6)17-19-15-13-14-16-20(19)18-26(23(7,8)9)24(10,11)12/h13-16H,17-18H2,1-12H3

InChI key

SFCNPIUDAIFHRD-UHFFFAOYSA-N

General description

1,2-Bis(di-tert-butylphosphinomethyl)benzene (DTBPMB) is a bidentate phosphine ligand. DTBPMB in combination with Pd2(dba)3 (dba = trans,trans-dibenzylideneacetone) and a sulfonic acid can catalyze the methoxycarbonylation of ethane to form methyl propanoate.

Application

DTBPMB may be used as a ligand for the palladium-catalyzed hydroesterification of styrene and vinyl acetate to form branched esters in the presence of polymeric sulfonic acids promoters.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Highly active and selective palladium catalyst for hydroesterification of styrene and vinyl acetate promoted by polymeric sulfonic acids.
Ooka H, et al.
Chemical Communications (Cambridge, England), 9, 1173-1175 (2005)
Highly active and selective catalysts for the production of methyl propanoate via the methoxycarbonylation of ethene.
Clegg W, et al.
Chemical Communications (Cambridge, England), 18, 1877-1878 (1999)

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