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Published TCIMAIL newest issue No.197
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CAS RN: 1079-66-9 | Product Number: C0597
Chlorodiphenylphosphine
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Purity: >97.0%(T)
Synonyms:
- Diphenylphosphinous Chloride
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 25G |
35,00 €
|
6 | ≥100 |
|
| 100G |
94,00 €
|
5 | ≥100 |
|
| 500G |
301,00 €
|
Contact Us | ≥40 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| 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 |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| 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 |
|
| 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. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. 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. |
Related Laws:
| EC Number | 214-093-2 |
Transport Information:
| UN Number | UN3265 |
| Class | 8 |
| Packing Group | II |
| HS Number | 2931599090 |
Application
A Novel Synthesis of Phenyleneethynylenes by Using Ph2P(O)-protected Ethynes
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%).
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
- 1a) X. Yang, D. Matsuo, Y. Suzuma, J.-K. Fang, F. Xu, A. Orita, J. Otera, S. Kajiyama, N. Koumura, K. Hara, Synlett 2011, 2402.
- 1b) X. Yang, S. Kajiyama, J.-K. Fang, F. Xu, Y. Uemura, N. Koumura, K. Hara, A. Orita, J. Otera, Bull. Chem. Soc. Jpn. 2012, 85, 687.
- 2a) L. Peng, F. Xu, Y. Suzuma, A. Orita, J. Otera, J. Org. Chem. 2013, 78, 12802.
- 2b) L. Peng, F. Xu, K. Shinohara, A. Orita, J. Otera, Chem. Lett. 2014, 43, 1610.
- 2c) L. Peng, F. Xu, K. Shinohara, T. Nishida, K. Wakamatsu, A. Orita, J. Otera, Org. Chem. Front. 2015, 2, 248.
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).
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
- A Convenient Method for the Preparation of Symmetrical or Unsymmetrical Ethers by the Coupling of Two Alcohols via a New Type of Oxidation–reduction Condensation Using Tetrafluoro-1,4-benzoquinone
- Efficient Methods for the Preparation of Alkyl－Aryl and Symmetrical or Unsymmetrical Dialkyl Ethers between Alcohols and Phenols or Two Alcohols by Oxidation－Reduction Condensation
PubMed Literature
Articles/Brochures
TCIMAIL
[Research Articles] A Novel Synthesis of Phenyleneethynylenes by Using Ph2P(O)-protected EthynesProduct Documents (Note: Some products will not have analytical charts available.)
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