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CAS RN: 1079-66-9 | Product Number: C0597

Chlorodiphenylphosphine


Purity: >97.0%(T)
Chemical Substance Law (ENCS):   3-3943
Synonyms:
  • Diphenylphosphinous Chloride
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Product Number C0597
Purity / Analysis Method >97.0%(T)
Molecular Formula / Molecular Weight C__1__2H__1__0ClP = 220.64  
Physical State (20 deg.C) Liquid
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive,Moisture Sensitive
CAS RN 1079-66-9
Reaxys Registry Number 512032
PubChem Substance ID 87565694
SDBS (AIST Spectral DB) 10853
MDL Number

MFCD00000529

Specifications
Appearance Colorless to Light yellow to Light orange clear liquid
Purity(Argentometric Titration) min. 97.0 %
Properties (reference)
Boiling Point 215 °C/57 mmHg
Flash point 138 °C
Specific Gravity (20/20) 1.20
Refractive Index 1.64
Solubility in water Decomposes in contact with water,Insoluble
GHS
Pictogram Pictogram
Signal Word Danger
Hazard Statements H314 : Causes severe skin burns and eye damage.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P363 : Wash contaminated clothing before reuse.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P405 : Store locked up.
Related Laws:
Chemical Substance Law (ENCS) 3-3943
Fire Defense Law Group-4-3-III
Transport Information:
UN Number UN3265
Class 8
Packing Group II
Application
A Novel Synthesis of Phenyleneethynylenes by Using Ph2P(O)-protected Ethynes

C0597

Typical Procedure1a):
A toluene (10 mL) solution of 4-ethynylanisole (132 mg, 1.0 mmol), CuI (19 mg, 0.1 mmol), Ph2PCl (265 mg, 1.2 mmol) and Et3N (202 mg, 2.0 mmol) is stirred at 80 °C for 8 h. After workup with CH2Cl2 and NH4Cl(aq), the combined organic layer is washed with brine, and dried over MgSO4. After evaporation, the residue is purified by column chromatography on silica gel (eluent: hexane/CH2Cl2 = 6/1-4/1) to give ((4-methoxyphenyl)ethynyl)diphenylphosphine as pale yellow sticky gel (193 mg, 61%).
To a THF (10 mL) solution of ((4-methoxyphenyl)ethynyl)diphenylphosphine (316 mg, 1.0 mmol) is added H2O2(aq) (30%, 2.5 mL, 20 mmol) at 0 °C, and the mixture is stirred at rt for 2 h. After workup with CH2Cl2 and water, the combined organic layer is washed with brine and dried over MgSO4. After evaporation, the residue is purified by column chromatography on silica gel (eluent: hexane/AcOEt = 2/1) to afford ((4-methoxyphenyl)ethynyl)diphenylphosphine oxide as white powder (312 mg, 94%).
To a THF solution (10 mL) of ((4-methoxyphenyl)ethynyl)diphenylphosphine oxide (166 mg, 0.5 mmol) is added t-BuOK (84 mg, 0.75 mmol), and the mixture is stirred at rt for 2 h. After workup with CH2Cl2 and NH4Cl(aq), the combined organic layer is washed with brine and dried over MgSO4. After evaporation, the residue is purified by column chromatography on silica gel (eluent: hexane) to afford 4-ethynylanisole as pale yellow oil (60 mg, 91%).

References


Application
Mukaiyama Oxidation-Reduction Condensation

[Experimental procedure]
to a mixture of alkoxydiphenylphosphine (2, 0.60 mmol), prepared from the alcohol (1), n-BuLi and chlorodiphenylphosphine, and tetrafluoro-1,4-benzoquinone (0.72 mmol) under argon atmosphere is added a dichloromethane (0.50 mL) solution of alcohol (3, 0.72 mmol) at room temperature. After the reaction that is monitored by TLC was completed, the reaction mixture is quenched by adding water and the aqueous layer is extracted with dichloromethane. The organic layers are dried over anhydrous sodium sulfate. After filtration and evaporation, the resulted residue is purified by preparative TLC to afford the corresponding ether (4).

References


PubMed Literature


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