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338389

Sigma-Aldrich

Triphenylphosphine hydrobromide

97%

Synonym(s):

Ph3P · HBr, Ph3P · HBr, Triphenylphosphonium bromide

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About This Item

Linear Formula:
(C6H5)3P · HBr
CAS Number:
6399-81-1
Molecular Weight:
343.20
Beilstein:
3633387
EC Number:
229-012-6
MDL number:
MFCD00035107
UNSPSC Code:
12352002
PubChem Substance ID:
24860541
NACRES:
NA.22

Assay

97%

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

mp

196 °C (dec.) (lit.)

functional group

phosphine

SMILES string

Br.c1ccc(cc1)P(c2ccccc2)c3ccccc3

InChI

1S/C18H15P.BrH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H

InChI key

CMSYDJVRTHCWFP-UHFFFAOYSA-N

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Application

Used as mild source of anhydrous HBr; catalyst for formation of THP ethers from tertiary alcohols; preparation of phosphonium salts.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH8608
BCCG0579
BCCD0019
BCBM2830V
BCBM2829V

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Hamanaka, N.; Kosuge, S.; Iguchi, S.
Synlett, 139-139 (1990)
Kaila, N.; Blumenstein, M. et al.
The Journal of Organic Chemistry, 57, 4576-4576 (1992)
Jun Hu et al.
Chemical communications (Cambridge, England), 48(91), 11256-11258 (2012-10-17)
In the presence of triphenylphosphine, copper(II) chloride can catalyze an intermolecular ortho-acylation reaction of phenols with aryl aldehydes. The reaction proceeds smoothly with a wide range of starting materials, and furthermore, it can be used to synthesize xanthone derivatives in
Graham A Bowmaker et al.
Dalton transactions (Cambridge, England : 2003), 40(27), 7210-7218 (2011-06-11)
Syntheses of a number of adducts of silver(I) (bi-)carbonate with triphenylphosphine, both mechanochemically, and from solution, are described, together with their infra-red spectra, (31)P CP MAS NMR and crystal structures. Ag(HCO(3)):PPh(3) (1:4) has been isolated in the ionic form [Ag(PPh(3))(4)](HCO(3))·2EtOH·3H(2)O.
Catherine J Smith et al.
Organic & biomolecular chemistry, 9(6), 1927-1937 (2011-02-02)
Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of
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