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| | 2,2,2-Trichloroethyl chloroformate Basic information |
| Product Name: | 2,2,2-Trichloroethyl chloroformate | | Synonyms: | 2,2,2-Trichloroethyl chloroforMate puruM, >=98.0% (NT);NALPHA-tert-Butoxycarbonyl-NEPSILON-trifluoroacetyl-D -lysine;(Trichloroethoxy)chloroformate;2,2,2-Trichloroethyl chloroformate ,97%;(2,2,2-Trichloroethoxy)formic acid chloride;(Carbonic acid 2,2,2-trichloroethyl) chloride;Chloridocarbonic acid 2,2,2-trichloroethyl ester;Chloroformic acid 2,2,2-trichloroethyl | | CAS: | 17341-93-4 | | MF: | C3H2Cl4O2 | | MW: | 211.86 | | EINECS: | 241-363-7 | | Product Categories: | Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Miscellaneous;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;CHLOROFORMATES;bc0001;KT00001 | | Mol File: | 17341-93-4.mol |  |
| | 2,2,2-Trichloroethyl chloroformate Chemical Properties |
| Melting point | 1°C | | Boiling point | 171-172 °C (lit.) | | density | 1.539 g/mL at 25 °C (lit.) | | vapor pressure | 0.06 psi ( 20 °C) | | refractive index | n20/D 1.471(lit.) | | Fp | >100°C | | storage temp. | 2-8°C | | solubility | soluble in Chloroform, Ethyl Acetate | | form | Liquid | | color | Clear light yellow | | Water Solubility | Soluble in Ether, Benzene, Chloroform, Ethanol. Insoluble in water. | | Sensitive | Moisture Sensitive | | BRN | 970619 | | InChI | 1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 | | InChIKey | LJCZNYWLQZZIOS-UHFFFAOYSA-N | | SMILES | ClC(=O)OCC(Cl)(Cl)Cl | | CAS DataBase Reference | 17341-93-4(CAS DataBase Reference) | | NIST Chemistry Reference | Carbonochloridic acid, 2,2,2-trichloroethyl ester(17341-93-4) | | EPA Substance Registry System | Carbonochloridic acid, 2,2,2-trichloroethyl ester (17341-93-4) |
| Hazard Codes | T | | Risk Statements | 23-34-36 | | Safety Statements | 26-36/37/39-45-7/9 | | RIDADR | UN 3277 6.1/PG 2 | | WGK Germany | 3 | | F | 10-19 | | TSCA | TSCA listed | | HazardClass | 6.1 | | PackingGroup | II | | HS Code | 29159000 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 3 Inhalation
Eye Dam. 1
Skin Corr. 1B |
| | 2,2,2-Trichloroethyl chloroformate Usage And Synthesis |
| Chemical Properties | Clear light yellow liquid | | Uses | 2,2,2-Trichloroethyl chloroformate is used as a protecting reagent for aliphatic and aromatic hydroxyl and amino groups. It is used as derivatizing reagent in gas chromatographic/mass spectrometric determination of a large range of amphetamine-related drugs and ephedrines in plasma, urine and hair samples, during N-demethylation of dextromethorphan. It was used as starting reagent during the synthesis of 6-Nor-9,10-dihydrolysergic acid methyl ester. | | Uses | 2,2,2-Trichloroethyl chloroformate was used as:
- derivatizing reagent in gas chromatographic/mass spectrometric determination of a large range of amphetamine-related drugs and ephedrines in plasma, urine and hair samples
- starting reagent during the synthesis of 6-nor-9,10-dihydrolysergic acid methyl ester (IV)
- reagent during N-demethylation of dextromethorphan
- protecting group reagent for amines and alcohols
| | Application | 2,2,2-Trichloroethyl chloroformate is a protecting agent for various functional groups; a net carboxylating agent for organometallic reagents; achieves N-demethylation and N-debenzylation of tertiary amines; and activates N-heteroaromatic rings for reaction with organostannanes. | | Preparation | 2,2,2-Trichloroethyl chloroformate is widely available commercially. It can be readily prepared by passing Phosgene into a solution of 2,2,2- Trichloroethanol in benzene/diethylaniline or benzene/ether/pyridine. An alternate two-step approach (93% yield) has been described that employs S-Ethyl Chlorothioformate instead of phosgene. |
| | 2,2,2-Trichloroethyl chloroformate Preparation Products And Raw materials |
| Raw materials | Ethyl acetate-->Dichloromethane-->Toluene-->Pyridine-->PHOSGENE-->tert-Butyl methyl ether-->Triphosgene-->Magnesium sulfate heptahydrate-->Trichloroethanol | | Preparation Products | 1,1,1,2-TETRACHLOROETHANE-->(αR,βS)-β-(BenzoylaMino)-α-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-benzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodeca-->1,2-Pyrrolidinedicarboxylic acid, 1-(2,2,2-trichloroethyl) ester, (2S)--->2,2,2-trichloroethyl 3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-ylcarbamate |
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