ChemicalBook Product Catalog Organic Chemistry Phosphines Chlorodiphenylphosphine

Chlorodiphenylphosphine

Chlorodiphenylphosphine Basic information
Product Name:Chlorodiphenylphosphine
Synonyms:Diphenylphosphorus chloride;Chlorodiphenylphosphine, 95%, tech.;Diphenylchlorophosphine, min. 95%;Diphenylphosphinous chloride (DPC);CHLORODIPHENYLPHOSPHINE (DPPC);CHLORODIPHENYLPHOSPINE;Chlorodiphenylphosphine 98%;Bis(phenyl)chlorophosphine
CAS:1079-66-9
MF:C12H10ClP
MW:220.63
EINECS:214-093-2
Product Categories:Ligand;organophosphine halide;Achiral Phosphine;Aryl Phosphine;P-Cl;Phosphines;Pharmaceutical Intermediates;Chlorophosphines;1079-66-9
Mol File:1079-66-9.mol
Chlorodiphenylphosphine Structure
Chlorodiphenylphosphine Chemical Properties
Melting point 14-16°C
Boiling point 320 °C(lit.)
density 1.229 g/mL at 25 °C(lit.)
vapor density 7.8 (vs air)
vapor pressure 1.3 hPa (20 °C)
refractive index n20/D 1.636(lit.)
Fp >230 °F
storage temp. Store below +30°C.
solubility Miscible with alcohol. Slightly miscible with ammonia.
form Liquid
Specific Gravity1.229
color Colorless to yellow
Water Solubility Reacts violently
Sensitive Air & Moisture Sensitive
Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
BRN 512032
InChIKeyXGRJZXREYAXTGV-UHFFFAOYSA-N
LogP5.330 (est)
CAS DataBase Reference1079-66-9(CAS DataBase Reference)
NIST Chemistry ReferenceChlorodiphenylphosphine(1079-66-9)
EPA Substance Registry SystemPhosphinous chloride, diphenyl- (1079-66-9)
Safety Information
Hazard Codes C
Risk Statements 14-34-29-36
Safety Statements 26-36/37/39-45-8-30-25-27
RIDADR UN 3265 8/PG 2
WGK Germany 2
F 1-9-19
Autoignition Temperature320 °C
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29310095
ToxicityLD50 orally in Rabbit: 316 mg/kg
MSDS Information
ProviderLanguage
Chlorodiphenylphosphine English
SigmaAldrich English
ACROS English
ALFA English
Chlorodiphenylphosphine Usage And Synthesis
Chemical PropertiesColorless to light yellow liqui
UsesChlorodiphenylphosphine is used to introduce the diphenylphosphinyl moiety by aryl ortho-lithiation. It is also used as an intermediate to make antioxidants, flame retardants, stabilizers, catalysts, photoinitiators, and optical brighteners. Used as a halogenation reagent for the conversion of alcohols into halides, in the preparation of solid-phase reagent for the conversion of alcohols to alkyl halides.
Synthesis Reference(s)Journal of the American Chemical Society, 77, p. 3526, 1955 DOI: 10.1021/ja01618a030
Flammability and ExplosibilityNonflammable
Purification MethodsThis air-sensitive, pale yellow lachrymatory liquid is purified by careful fractional distillation and discarding the lower boiling fraction which contains the main impurity PhPCl2 (b 48-51o/0.7mm), and checking for impurities by NMR. [Weinberg J Org Chem 40 3586 1975, Honer et al. Chem Ber 94 2122 1961, Beilstein 16 IV 969.]
Chlorodiphenylphosphine Preparation Products And Raw materials
Preparation ProductsDiphenylphosphine-->1,1'-Bis(diphenylphosphino)ferrocene-->4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene-->(R)-1-[(1S)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLDI-TERT-BUTYLPHOSPHINE-->4-(DIMETHYLAMINO)PHENYLDIPHENYLPHOSPHINE-->VANADIUM(III) CHLORIDE-->(OXYDI-2,1-PHENYLENE)BIS(DIPHENYLPHOSPHINE)-->1-DIPHENYLPHOSPHINO-1'-(DI-TERT-BUTYLPH&-->Phosphine, 4-dibenzofuranyldiphenyl--->2-(Diphenylphosphino)-biphenyl-->2-Diphenylphosphinobenzaldehyde-->DIPHENYL(P-VINYLPHENYL)PHOSPHINE-->4,6-Bis(diphenylphosphino) dibenzofuran, 98%-->1,1-BIS(DIPHENYLPHOSPHINO)ETHYLENE-->Bis[(2-diphenylphosphino)ethyl]ammonium chloride, min. 97%-->(DIPHENYLPHOSPHORYL)METHANOL
Chlorodiphenylphosphine sulfide Diphenylphosphine Tris(triphenylphosphine)rhodiu Di-tert-butylchlorophosphane Tetrabutylphosphonium chloride DICHLOROTRIPHENYLPHOSPHORANE BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE Diphenylsilane Chlorodiphenylphosphine Chlorodi(p-tolyl)phosphine, 95% CHLORODIPHENYLPHOSPHINE (DIPHENYL CHLOROPHOSPHINE; DIPHENYLPHOSPHINOUS CHLORIDE) BIS(4-METHOXYPHENYL)CHLOROPHOSPHINE BIS(3,5-DI(TRIFLUOROMETHYL)PHENYL)CHLOROPHOSPHINE DI-O-TOLYLCHLOROPHOSPHINE Bis(triphenylphosphine)iminium chloride BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE 2-​[[(2-​ethylphenyl)​(2-​hydroxyethyl)​amino]​methyl]​-​3,​3-​difluoro-Propanenitrile Diphenylsilanediol
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