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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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