378755
Dichlorotriphenylphosphorane
95%
Synonym(s):
Triphenylphosphine dichloride
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About This Item
Linear Formula:
(C6H5)3PCl2
CAS Number:
Molecular Weight:
333.19
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
95%
form
solid
mp
85 °C (dec.) (lit.)
functional group
phosphine
SMILES string
ClP(Cl)(c1ccccc1)(c2ccccc2)c3ccccc3
InChI
1S/C18H15Cl2P/c19-21(20,16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
InChI key
ASWXNYNXAOQCCD-UHFFFAOYSA-N
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General description
Dichlorotriphenylphosphorane (Triphenylphosphine dichloride, PPh3Cl2) is a phosphorous halide. Stability and reactivity of dichlorotriphenylphosphorane have been studied by solid state 31P NMR spectroscopy. It participates in the conversion of carboxylic esters to acid halides and mechanism of this cleavage has been investigated. Modified method has been proposed in which dichlorotriphenylphosphorane participates in the synthesis of tertiary amides.
Application
Dichlorotriphenylphosphorane may be used in the synthesis of the following:
- tertiary benzanilide derivatives
- N-phosphodipeptides
- dialkyl phosphorochloridites based on the reaction of trialkyl phosphites
- naphthalene ring-based calix[3]amide, via reaction with 6-amino-2-naphthoic acid
- C2v-symmetrical cyclic tetramers of aromatic amides
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 1B - Eye Dam. 1 - Flam. Sol. 2 - Skin Corr. 1B
Storage Class Code
4.1B - Flammable solid hazardous materials
WGK
WGK 3
Flash Point(F)
68.0 °F - closed cup
Flash Point(C)
20 °C - closed cup
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Construction of anomalously bent biphenyl structure using conformational properties of calix [4] amide.
Tominaga M, et al.
Tetrahedron Letters, 47(52), 346-350 (2006)
The preparation of dimethyl phosphorochloridite and its homologs from trialkyl phosphites and dichlorotriphenylphosphorane.
Majewski P.
Phosph. Sulfur Relat. Elem., 33(1-2), 37-39 (1987)
Synthesis of N-Phosphopeptides Coupled by Dichlorotriphenylphosphorane.
Dong S-Z, et al.
Synthetic Communications, 31(13), 2067-2075 (2001)
Cleavage of carboxylic acid esters to acid chlorides with dichlorotriphenylphosphorane.
Burton DKJ and Koppes WM.
The Journal of Organic Chemistry, 40(21), 3026-3032 (1975)
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