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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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Triphenylphosphine ≥95.0% (GC)

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Sigma-Aldrich

217646

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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)
Yong Ma et al.
Langmuir : the ACS journal of surfaces and colloids, 27(21), 13097-13103 (2011-09-21)
Chemically selective liposomal surface functionalization and liposomal microarray fabrication using azide-reactive liposomes are described. First, liposome carrying PEG-triphenylphosphine was prepared for Staudinger ligation with azide-containing biotin, which was conducted in PBS buffer (pH 7.4) at room temperature without a catalyst.
Tong Wang et al.
Organic & biomolecular chemistry, 9(14), 5260-5265 (2011-06-02)
The triphenylphosphine-catalyzed formal [3 + 2] cycloaddition of allenoates and trifluoromethylketones was realized to give the corresponding dihydrofurans in good yields with excellent γ-regioselectivities. Hydrogenation of the dihydrofurans gave 2,4,4-trisubstituted tetrahydrofurans in good yields with exclusive cis-selectivities.
Kirill Nikitin et al.
Chemical communications (Cambridge, England), 49(14), 1434-1436 (2013-01-17)
Triphenylhalophosphonium halides, Ph(3)PX(2), form crystals comprising bridged linear cations [Ph(3)P-X-X-X-PPh(3)](+) where the X(3) bridge is shortened from 6.56 Å in Cl-Cl-Cl to 6.37 Å in the Br-Br-Br system. It is proposed that this structure is stabilised by five-centre/six-electron (5c-6e) hypervalent
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