TRIPHOSGENE
Bis(trichloromethyl)carbonate
CAS: 32315-10-9
Molecular Formula: C3Cl6O3
TRIPHOSGENE - Names and Identifiers
| Name | Bis(trichloromethyl)carbonate |
| Synonyms | BTC btc Triphosgen triphosgene TRIPHOSGENE Triphosgene TriphosgeneForSynthesis TRICHLOROMETHANOLCARBONATE Bis(trichloromethyl)carbonate bis(trichloromethyl) carbonate bis-(trichloromethyl)-carbonat BIS(TRICHLOROMETHYL) CARBONATE CARBONIC ACID BISTRICHLOR METHYL ESTER carbonic acid bistrichlor methyl ester |
| CAS | 32315-10-9 |
| EINECS | 250-986-3 |
| InChI | InChI=1/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9 |
| InChIKey | UCPYLLCMEDAXFR-UHFFFAOYSA-N |
TRIPHOSGENE - Physico-chemical Properties
| Molecular Formula | C3Cl6O3 |
| Molar Mass | 296.73 |
| Density | 1.78 |
| Melting Point | 79-83 °C (lit.) |
| Boling Point | 203-206 °C (lit.) |
| Flash Point | 203-206°C |
| Water Solubility | practically insoluble |
| Vapor Presure | 16 hPa (90 °C) |
| Appearance | Crystalline Powder, Crystals and/or Chunks |
| Color | White to off-white |
| BRN | 1787583 |
| Storage Condition | 2-8°C |
| Sensitive | Moisture Sensitive |
| Refractive Index | 1.532 |
| Physical and Chemical Properties | Properties: White or almost white crystals, with similar light odor Melting Point: 79 ℃-81 ℃ Boiling Point: 205 ℃-206 ℃ (partial decomposition) density: 1.78g/cm3 soluble in organic solvents such as ethanol, benzene, diethyl ether and dichloromethane. In case of hot water and hydroxide alkali decomposition, cold water-based role. |
| Use | For the synthesis of chloroformate, isocyanate, polycarbonate and acid chloride; Solid phosgene, also known as triphosgene, synthesis of raw materials for dimethyl carbonate-a green chemical raw materials, is a highly reactive material, can replace phosgene for a variety of chemical reactions, the main types of reactions can be involved in: chloromethanes, carbonation, urea, isocyanate, chlorination, isonitriles, ring forming reactions, α-chloro-chloroformylation of aldehydes, oxidation of alcohols, etc. In the aspect of organic synthesis, solid phosgene can replace oxalyl chloride as an activator of dimethyl sulfoxide in the oxidation reaction of alcohols, which is convenient and safe for the preparation of hydroxyl compounds; solid phosgene can also change different types of alcohols to the corresponding chlorides. In the pharmaceutical industry, solid phosgene can replace phosgene to synthesize a large number of medicines |
TRIPHOSGENE - Risk and Safety
| Risk Codes | R26 - Very Toxic by inhalation R34 - Causes burns R29 - Contact with water liberates toxic gas R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. |
| Safety Description | 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.) S9 - Keep container in a well-ventilated place. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S7/9 - |
| UN IDs | UN 2928 6.1/PG 2 |
| WGK Germany | 2 |
| FLUKA BRAND F CODES | 10-19-21 |
| TSCA | Yes |
| HS Code | 29209010 |
| Hazard Class | 6.1 |
| Packing Group | II |
TRIPHOSGENE - Upstream Downstream Industry
| Raw Materials | Formaldehyde Chlorine |
TRIPHOSGENE - Reference Information
| Introduction | bis (trichloromethyl) carbonate or trichloromethyl carbonate is a stable white crystal, melting point of 78~82 ℃, boiling point of 203~206 ℃, similar to the smell of phosgene, its molecular formula is CO (occil3) 2, molecular weight of 296.75, the specific gravity of the solid was 1.78g/cm3, and the specific gravity in the molten state was 1.629g/cm3. Since one mole of BTC can produce three moles of phosgene under certain conditions, it is also called "triphosgene". This product is solid, so it is also called "solid phosgene". |
| physical and chemical properties | 1. Physical properties BTC is a white crystal with a molecular weight of 296. 75; The melting point is 79~83 degrees C; Boiling Point: 203 C/0.1 MPa,124 C/6. 6kPa; Solid density of 1.78g/cm3; Melt density of 1.629g/cm3, soluble in carbon tetrachloride, ethane, benzene, chloroform, ether and tetrahydrofuran, room temperature preservation. BTC stability is very strong, only a small amount of decomposition at the boiling point, the formation of trichloromethyl chloroformate and phosgene. 2. Chemically active BTC under the action of auxiliary nucleophile Nu (such as pyridine, triethylamine, etc.) (reaction with amine does not require auxiliary nucleophile), one molecule of BTC produces a trimolecular reactive intermediate (ClCONu Cl-) that can react with various nucleophiles under mild conditions. |
| Application | phosgene and primary amine carbonylation reaction, can be prepared from a variety of isocyanates, but because phosgene is difficult to accurately measure, side reactions often occur. Triphosgene is a solid, can be accurately measured, and the use of triphosgene instead of phosgene, its safety is greatly improved, so can safely replace phosgene. The reaction of triphosgene with amine compounds is a widely used field, the reaction selectivity is strong, some functional groups do not need to be protected, can directly generate isocyanate, urea and other compounds. Various isocyanates can be synthesized by carbonylation reaction of triphosgene and various primary amines. The target product can be obtained by accurately controlling the ratio of triphosgene to amine in the reaction without by-products. For example, 2, 4-dimethyldiisocyanate (TDI) can be synthesized by the reaction of triphosgene with 2, 4-diaminotoluene; The reaction of triphosgene with 4,4 '-diaminodiphenylmethane can produce 4,4'-diphenylmethane diisocyanate (MDI); Triphosgene and hexamethylene diamine can form hexamethylene diisocyanate sodium (HDI). The cyclization condensation reaction can also be carried out in the carbonylation reaction by BTC. In such reactions, triphosgene is widely used to prepare both N-carbonyl anhydrides and various important heterocyclic compounds and cyclic carbonate compounds. The former can be used to prepare active amino acids and polypeptide compounds, and the latter can be used to prepare various pharmaceutical and pesticide intermediates. |
| preparation | in a methanol liquid, bis (trichloromethyl) carbonate is added in a proportion of 10% of the mol amount of methanol, by the first reaction of BIS (trichloromethyl) carbonate and methanol to produce carbon ester dimethyl ester, then the chlorine gas into the liquid, placed in 180nm ultraviolet light, bis (trichloromethyl) carbonate and hydrochloric acid were synthesized by reacting carbon ester dimethyl ester with chlorine gas. The HCl gas generated in the reaction process was absorbed by water and 5% soda ash. After completion of the reaction, the mixture was degassed, cooled to crystallize, filtered, and dried under vacuum to obtain the final product as solid bis (trichloromethyl) carbonate. |
| Chemical properties | bis (trichloromethyl) carbonate, also known as triphosgene, or solid phosgene. Boiling point 203-206 ℃ (partial decomposition); Similar to the smell of phosgene; Insoluble in water, soluble in ether, Tetrahydrofuran, benzene, cyclohexane, chloroform and other organic solvents. The replacement can be achieved in almost all reactions of the extremely toxic phosgene and the extremely potent diphosgene. |
| Use | as a substitute product of highly toxic phosgene and diphosgene in synthesis, this product has low toxicity, safe and convenient use, and the reaction conditions are mild, the selectivity is good, the yield is high. for the synthesis of chloroformates, isocyanates, polycarbonates and acid chlorides, etc. |
| EPA chemical substance information | information is provided by: ofmpeb.epa.gov (external link) |
Last Update：2024-04-10 22:29:15
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Raw Materials for TRIPHOSGENE