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Diphenylphosphinic Chloride
(CAS RN:1499-21-4 Product Number:C1415)

Structure

Diphenylphosphinic Chloride
Synonym Chlorodiphenylphosphine Oxide

General Information

Product Number C1415

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Purity/Analysis Method >98.0%(GC)(T)
Storage Temperature
M.F. / M.W. C12H10ClOP=236.63
CAS RN 1499-21-4
Related CAS RN
MDL Number MFCD00002077
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Appearance Colorless to Light orange to Yellow clear liquid
Purity(GC) min. 98.0 %
Purity(Argentmetric Titration) min. 98.0 %

Data of Reference

flp 26°C(lit.)
bp 222°C/16mmHg(lit.)

References

Beilstein 16(4)1038
Reaxys-RN 975191
PubChem SID 87566421
F&F 15,150
EC Number 216-107-2

GHS

Pictogram
Signal Word Danger
Hazard Statements
  • H226
  • :Flammable liquid and vapour.
  • H314
  • :Causes severe skin burns and eye damage.
  • H341
  • :Suspected of causing genetic defects.
Precautionary Statements
  • P260
  • :Do not breathe dusts or mists.
  • P301+P330+P331+P310
  • :IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Immediately call a POISON CENTER or doctor.
  • P303+P361+P353+P310+P363
  • :IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water or shower. Immediately call a POISON CENTER or doctor. 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 or 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 or doctor.
  • P370+P378
  • :In case of fire: Use dry chemical or dry sand to extinguish.

Transport Information

UN Number 2920
Class 8/3
Packing Group II
HS Number 2931399090

Application

Condensing Agent

Experimental procedure: N-Benzyloxycarbonylvaline (30.15 g, 0.12 mol) is dissolved in dichloromethane (200 mL) and cooled to 0 °C at which temperature NMM (13.2 mL, 0.12 mol) and a solution of DppCl (28.38 g, 0.12 mol) in dichloromethane (200 mL) are added in quick succession. After an activation period of 15 min a precooled solution of alanine phenyl ester tosylate (33.74 g, 0.1 mol) in dry, distilled DMF (80 mL) is added immediately followed by NMM (11 mL, 0.1 mol) and the mixture is stirred for 30 min. Removal of the reaction solvent left a pale yellow oil which is partitioned between ethyl acetate and water. The organic phase is washed with saturated NaHCO3 (5 times), 5% citric acid (3 times), water (2 times), saturated NaHCO3 (2 times), water (2 times) and brine (2 times) before drying over anhydrous magnesium sulfate. Evaporation of solvent under reduced pressure from the final dried solution afforded a white powder which is crystallized from ethyl acetate with light petroleum to give 1 (38.73 g, 81%).

References

Protection of Amino Groups

Introduction of the diphenylphosphinyl (Dpp) group: To a vigorously stirred suspension of the amine hydrochloride (0.2 mol) in dichloromethane (500 mL) at 0 °C are added NMM (43.5 mL, 0.4 mol) and DppCl (47.4 g, 0.2 mol) in dichloromethane (90 mL) in such a way as to maintain the temperature of the reaction mixture at 0 °C. The reactants are then stirred for 2 h during which time the temperature rises to ca. 15 °C. Removal of the reaction solvent left a pale yellow oil which is partitioned between ethyl acetate and water. The organic phase is washed with saturated NaHCO3 (5 times), 5% citric acid (3 times), water (2 times), saturated NaHCO3 (2 times), water (2 times) and brine (2 times) before drying over anhydrous magnesium sulfate. Following evaporation of the solution, the desired product is crystallized from the residue with appropriate crystallization solvent to afford the protected amine.
Cleavage of the Dpp group: A 1.5 mol/L solution of HCl in methanol (3.5 mL, 5.3 mmol) is added to DppTrp-Met-Asp(OtBu)-PheNH2 (750 mg, 0.9 mmol) and the mixture is stirred. After 90 min white crystals begin to precipitate out of solution and 1 h later optimum cleavage is considered to have occurred. The reaction mixture is poured into vigorously stirred cold, anhydrous diethyl ether (200 mL) and after stirring for a further 1 h at low temperature. HCl·H2NTrp-Met-Asp(OtBu)-PheNH2 (470 mg, 78%) is filtered off, washed with cold diethyl ether, and dried.

References

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