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B32807

Sigma-Aldrich

Benzyltriphenylphosphonium chloride

99%

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Synonym(s):
BTPPC, NSC 116712, Triphenyl(phenylmethyl)phosphonium chloride
Linear Formula:
C6H5CH2P(Cl)(C6H5)3
CAS Number:
Molecular Weight:
388.87
Beilstein/REAXYS Number:
3599868
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

99%

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

≥300 °C (lit.)

SMILES string

[Cl-].C(c1ccccc1)[P+](c2ccccc2)(c3ccccc3)c4ccccc4

InChI

1S/C25H22P.ClH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1

InChI key

USFRYJRPHFMVBZ-UHFFFAOYSA-M

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This Item
377015430056309567
vibrant-m

430056

Benzyltriphenylphosphonium bromide

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

assay

99%

assay

97%

assay

96%

assay

97%

form

powder

form

-

form

-

form

solid

mp

≥300 °C (lit.)

mp

262-264 °C (lit.)

mp

295-298 °C (lit.)

mp

185-195 °C (dec.) (lit.)

Application

Benzyltriphenylphosphonium chloride can be used as a reactant for the synthesis of:
  • Platinum chloro-tetrazole complexes via azidation.
  • Trans-stilbenes and cinnamates via Wittig olefination.
  • Achiral N-hydroxyformamide inhibitors of ADAM-TS4 and ADAM-TS5 for osteoarthritis treatment.
  • Pentiptycenes for use as light-driven molecular brakes.
  • Archipelago structures for formation of petroleum asphaltenes.


It is also used as a crosslinking agent for tube-like natural halloysite / fluorelastomer nanocomposites.
Crosslinking agent for tube-like natural halloysite / fluorelastomer nanocomposites

Reactant for synthesis of:
  • Platinum chloro tetrazole complexes via azidation
  • Trans-stilbenes and cinnamates via Wittig olefination
  • Achiral N-hydroxyformamide inhibitors of ADAM-TS4 and ADAM-TS5 for osteoarthritis treatment
  • Pentiptycenes for use as light-driven molecular brakes

Reactant for formation of archipelago structures for formation of petroleum asphaltenes

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - STOT RE 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

572.0 °F - closed cup

flash_point_c

300 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives.
Ismail T, et al.
Bioorganic Chemistry, 64, 97-102 (2016)
Pentiptycene?Derived Light?Driven Molecular Brakes: Substituent Effects of the Brake Component.
Sun W T, et al.
Chemistry?A European Journal , 16(38), 11594-11604 (2010)
Orally active achiral N-hydroxyformamide inhibitors of ADAM-TS4 (aggrecanase-1) and ADAM-TS5 (aggrecanase-2) for the treatment of osteoarthritis.
De Savi , et al.
Bioorganic & Medicinal Chemistry Letters, 21(11), 3301-3306 (2011)
Formation of archipelago structures during thermal cracking implicates a chemical mechanism for the formation of petroleum asphaltenes.
Alshareef A H, et al.
Energy and Fuels, 25(5), 2130-2136 (2011)
A new route to N (1)-5R-tetrazole complexes via azidation to nitriles coordinated to Pt (II) and Pt (IV).
Popova E A, et al.
Inorgorganica Chimica Acta, 375(1), 242-247 (2011)

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