1-chloroethyl carbonochloridate
1-Chloroethyl Chloroformate
CAS: 50893-53-3
Molecular Formula: C3H4Cl2O2
1-chloroethyl carbonochloridate - Names and Identifiers
1-chloroethyl carbonochloridate - Physico-chemical Properties
| Molecular Formula | C3H4Cl2O2 |
| Molar Mass | 142.97 |
| Density | 1.325 g/mL at 25 °C (lit.) |
| Melting Point | -65°C |
| Boling Point | 118-119 °C (lit.) |
| Flash Point | 105°F |
| Solubility | Miscible with most organic solvents. |
| Vapor Presure | 3.25 psi ( 20 °C) |
| Appearance | Liquid |
| Color | Clear colorless |
| BRN | 1747601 |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic, Moisture Sensitive |
| Sensitive | Moisture Sensitive |
| Refractive Index | n20/D 1.422(lit.) |
| Physical and Chemical Properties | Melting Point -65°C boiling point 118-119°C(lit.) density 1.325g/mL at 25°C(lit.) vapor pressure 3.25 psi (20°C) refractive index n20/D 1.422(lit.) flash point 105 °F Storage Conditions 2-8°C Sensitive moiety BRN 1747601 |
1-chloroethyl carbonochloridate - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R10 - Flammable R22 - Harmful if swallowed R23 - Toxic by inhalation R34 - Causes burns |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 2742 6.1/PG 2 |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-19-21 |
| TSCA | No |
| HS Code | 29159000 |
| Hazard Class | 6.1 |
| Packing Group | II |
1-chloroethyl carbonochloridate - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| introduction | 1-chloroethyl chloroformate is a pharmaceutical intermediate. it has been reported in the literature that it can be used to prepare a drug for the treatment of hypertension and an antidepressant drug duloxetine hydrochloride. |
| application | 1-chloroethyl chloroformate is a highly efficient and mild debenzyl protecting group reagent, especially for compounds containing easily reduced functional groups, the use of this reagent will not affect other functional groups in the molecule; It is also applied to remove the alkyl group from the tertiary amine, and the obtained urethane is heated in methanol to remove the formate group to obtain the secondary amine with high yield; pharmaceutical synthesis is used for cefpodoxime proxetil, candesartan proxetil, cefotiam proxil, parampicillin, ampixicam, etc. |
| synthesis method | the two synthesis methods of 1-chloroethyl chloroformate are as follows: 1. in the carbonate method laboratory, ethylene carbonate and phosphorus pentachloride can be prepared by reacting ethylene carbonate and phosphorus pentachloride in the round bottom three-mouth bottle equipped with reflux condenser, thermometer and stirrer, 17.6g ethylene carbonate and 41.7g phosphorus pentachloride can be added, stirred, heated and refluxed for 4 hours, and then cooled down, decompression distillation separates the product. The yield is 85% and the boiling point is 150~152 ℃. Ethylene carbonate can be obtained by cyclizing diethyl carbonate and ethylene glycol. Diethyl carbonate and ethylene glycol are added to the reaction pot, stirred and heated, potassium carbonate is added in steps at 100~150 ℃, and refluxed for 4~5h to obtain a clear liquid. After ethanol is recovered, it is cooled and crystallized, filtered, washed and dried with absolute ethanol to obtain ethylene carbonate with a 59.5% yield. 2. Industrial direct synthesis of chloroethanol and phosgene Add 24.4g of chloroethanol to a three-mouth bottle, cool with ice water to control the reaction temperature at 15~20 ℃, and the ventilation time is 3h until the measured phosgene is passed. Then the air is drilled to clear the remaining phosgene. The expelled phosgene is absorbed with lye, the reaction solution is taken out, and the product is 37.9g. |
| use | organic synthesis. It is a high-efficiency and mild debenzyl protecting group reagent, especially for compounds containing easily reduced functional groups. The use of this reagent will not affect other functional groups in the molecule; it is also used to remove the alkyl group from the tertiary amine, The obtained urethane is heated in methanol to remove the formate group to obtain a high yield of secondary amine; in pharmaceutical synthesis, it is used for cefpodoxime axetil, candesactazine axetil, cefotiam axetil, bamamicillin, Anxicam, etc. |
Last Update：2024-04-10 22:29:15
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