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CAS RN: 1499-21-4 | Product Number: C1415
Diphenylphosphinic Chloride
Purity: >98.0%(GC)(T)
Synonyms:
- Chlorodiphenylphosphine Oxide
Product Documents:
Size | Unit Price | Same Day | 2-3 Business Days |
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5G |
$45.00
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3 | Contact Us |
25G |
$145.00
|
33 | ≥100 |
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Product Number | C1415 |
Purity / Analysis Method | >98.0%(GC)(T) |
Molecular Formula / Molecular Weight | C__1__2H__1__0ClOP = 236.63 |
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 | Moisture Sensitive |
CAS RN | 1499-21-4 |
Reaxys Registry Number | 975191 |
PubChem Substance ID | 87566421 |
SDBS (AIST Spectral DB) | 23276 |
MDL Number | MFCD00002077 |
Specifications
Appearance | Colorless to Light orange to Yellow clear liquid |
Purity(GC) | min. 98.0 % |
Purity(Argentometric Titration) | min. 98.0 % |
Properties (reference)
Boiling Point | 222 °C/16 mmHg |
Flash point | 26 °C |
Specific Gravity (20/20) | 1.27 |
Refractive Index | 1.61 |
GHS
Pictogram | |
Signal Word | Danger |
Hazard Statements | H314 : Causes severe skin burns and eye damage. H341 : Suspected of causing genetic defects. H226 : Flammable liquid and vapor. |
Precautionary Statements | P501 : Dispose of contents/ container to an approved waste disposal plant. P202 : Do not handle until all safety precautions have been read and understood. P240 : Ground/bond container and receiving equipment. P210 : Keep away from heat/sparks/open flames/hot surfaces. No smoking. P233 : Keep container tightly closed. P201 : Obtain special instructions before use. P243 : Take precautionary measures against static discharge. P241 : Use explosion-proof electrical/ ventilating/ lighting/ equipment. P242 : Use only non-sparking tools. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish. P308 + P313 : IF exposed or concerned: Get medical advice/ attention. 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. P403 + P235 : Store in a well-ventilated place. Keep cool. P405 : Store locked up. |
Related Laws:
Transport Information:
UN Number | UN2920 |
Class | 8 / 3 |
Packing Group | II |
H.S.code* | 2931.59-000 |
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
- Application of diphenylphosphinic carboxylic mixed anhydrides to peptide synthesis
Application
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.
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
- Phosphinamides: a new class of amino protecting groups in peptide synthesis
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