Ethyl chloroformate

Structural formula
General
Surname	Ethyl chloroformate
other names	Ethyl chloromethanate Ethyl chloroformate Ethoxycarbonyl chloride
Molecular formula	C 3 H 5 ClO 2
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 541-41-3 EC number 208-778-5 ECHA InfoCard 100.007.981 PubChem 10928 Wikidata Q288339
properties
Molar mass	108.53 g · mol -1
Physical state	liquid
density	1.14 g cm −3 (20 ° C)
Melting point	−81 ° C
boiling point	95 ° C
Vapor pressure	54 h Pa (20 ° C)
solubility	reacts with water
Refractive index	1.3974 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 225-301-314-330 P: 210-303 + 361 + 353-310-280-301 + 330 + 331-305 + 351 + 338
Toxicological data	204 mg kg −1 ( LD 50 ,  rat ,  oral )
Thermodynamic properties
ΔH f 0	−505.3 kJ / mol
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Ethyl chloroformate is a chemical compound that serves as an intermediate in the production of various carbonic acid derivatives.

Extraction and presentation

Ethyl chloroformate is obtained from phosgene and anhydrous ethanol .

Chemical properties

Chloroformic acid ethyl ester belongs to the group of chloroformic acid esters , as well as chloroformic acid methyl ester , chloroformic acid n- butyl ester , chloroformic acid phenyl ester and chloroformic acid benzyl ester . The connection is thermally unstable. A DSC measurement shows an exothermic decomposition reaction from 136 ° C with an exothermicity of −344 kJ kg ⁻¹ or −37.3 kJ mol ⁻¹ .

use

Ethyl chloroformate is a widely used intermediate in the production of carbonates and carbamates , which are used in the pharmaceutical industry as starting materials for syntheses.

nomenclature

The common name "ethyl chloroformate" is incorrect, as it is a derivative of carbonic acid , not a derivative of formic acid . It is the monochloride and at the same time the monoethyl ester of carbonic acid.

safety instructions

In concentrations between 3.2 and 27.5 percent by volume, the vapors of ethyl chloroformate form an explosive mixture with air ( flash point 16 ° C, ignition temperature 450 ° C). The compound decomposes when exposed to heat, releasing hydrogen chloride , phosgene, chlorine and other toxic substances.

Individual evidence

1. ↑ ^{a b c} Data sheet ethyl chloroformate (PDF) from Merck , accessed on February 4, 2018.
2. ↑ ^{a b} Entry on chloroformic acid ester. In: Römpp Online . Georg Thieme Verlag, accessed on August 29, 2012.
3. ↑ ^{a b c} data sheet Ethyl chloroformate at AlfaAesar, accessed on February 4, 2018 ( PDF )(JavaScript required) .
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-240.
5. ↑ ^{a b} Entry on ethyl chloroformate in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
6. ↑ Entry on Ethyl chloroformate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
7. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-23.
8. ↑ ^{a b} chemicalland21.com: Product information .
9. ↑ Sperry, JB; Minteer, CJ; Tao, J .; Johnson, R .; Duzguner, R .; Hawksworth, M .; Oke, S .; Richardson, PF; Barnhart, R .; Bill, DR; Giusto, RA; Weaver, JD: Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing in Org. Process Res. Dev. 22 (2018) 1262-1275, doi : 10.1021 / acs.oprd.8b00193 .