Ethyl chloroformate

Last updated
Ethyl chloroformate [1]
Ethyl chloroformate.png
Ethyl chloroformate 3D ball.png
Names
Preferred IUPAC name
Ethyl carbonochloridate
Other names
  • Cathyl chloride
  • Chloroformic acid ethyl ester
  • Ethyl chlorocarbonate
  • TL-423
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.981 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-778-5
PubChem CID
RTECS number
  • LQ6125000
UNII
UN number 1182
  • InChI=1S/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3 Yes check.svgY
    Key: RIFGWPKJUGCATF-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3
    Key: RIFGWPKJUGCATF-UHFFFAOYAX
  • ClC(=O)OCC
Properties
ClCO2CH2CH3
Molar mass 108.52 g·mol−1
AppearanceColorless liquid
Odor Like hydrochloric acid [2]
Density 1.1403 g/cm3
Melting point −81 °C (−114 °F; 192 K)
Boiling point 95 °C (203 °F; 368 K)
Decomposes
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive
Flammable
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H225, H302, H314, H330
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
4
3
0
W
Flash point 61 °C (142 °F; 334 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ethyl chloroformate is an organic compound with the chemical formula ClCO2CH2CH3. It is the ethyl ester of chloroformic acid. It is a colorless, corrosive and highly toxic liquid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group [3] and for the formation of carboxylic anhydrides.

Contents

Preparation

Ethyl chloroformate can be prepared using ethanol and phosgene:

Synthesis Ethylchloroformiate A.svg

Safety

Ethyl chloroformate is a highly toxic, flammable, corrosive substance. It causes severe burns when comes in contact with eyes and/or skin, can be harmful if swallowed or inhaled. [4]

Related Research Articles

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<span class="mw-page-title-main">Propyne</span> Hydrocarbon compound (HC≡C–CH3)

Propyne (methylacetylene) is an alkyne with the chemical formula CH3C≡CH. It is a component of MAPD gas—along with its isomer propadiene (allene), which was commonly used in gas welding. Unlike acetylene, propyne can be safely condensed.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin carbon bonds. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

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Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow. It possesses a characteristic pungent odor and degrades in contact with water.

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<span class="mw-page-title-main">Dimethyl sulfate</span> Chemical compound

Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.

<span class="mw-page-title-main">Ethyl bromoacetate</span> Chemical compound

Ethyl bromoacetate is the chemical compound with the formula CH2BrCO2C2H5. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alkylating agent and may be fatal if inhaled.

<span class="mw-page-title-main">Fluorosulfuric acid</span> Chemical compound

Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula HSO3F. It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, H2SO4, substituting a fluorine atom for one of the hydroxyl groups. It is a colourless liquid, although commercial samples are often yellow.

<span class="mw-page-title-main">Ethyl lactate</span> Chemical compound

Ethyl lactate, also known as lactic acid ethyl ester, is the organic compound with the formula CH3CH(OH)CO2CH2CH3. It is the ethyl ester of lactic acid. A colorless liquid, it is a chiral ester. Being naturally derived, it is readily available as a single enantiomer. It is commonly used as a solvent. This compound is considered biodegradable and can be used as a water-rinsible degreaser. Ethyl lactate is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. The odor of ethyl lactate when dilute is mild, buttery, creamy, with hints of fruit and coconut.

<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States. Dimethyl carbonate is often considered to be a green reagent.

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Trimethylolpropane phosphite, C2H5C(CH2O)3P, is a phosphite ester used as a ligand in organometallic chemistry. Trimethylolpropane phosphite is sometimes abbreviated to EtCage. It is a white solid that is soluble in organic solvents. It is also highly toxic.

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Methyl chloroformate is the methyl ester of chloroformic acid. It is an oily colorless liquid, although aged samples appear yellow. It is also known for its pungent odor.

<span class="mw-page-title-main">Methyldichlorophosphine</span> Chemical compound

Methyldichlorophosphine (alternatively known as dichloro(methyl)phosphane and methyl phosphonous dichloride) is an organophosphorus compound with the chemical formula CH3PCl2. It is a colorless, corrosive, flammable, and highly reactive liquid with a pungent odor.

References

  1. Merck Index , 11th Edition, 3742.
  2. https://www.sigmaaldrich.com/GB/en/sds/aldrich/185892
  3. Protective Groups in Organic Synthesis, Third Edition, Theodora W. Greene and Peter G. M. Wuts, pages 504-506, ISBN   0-471-16019-9
  4. PubChem. "Ethyl chloroformate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-09-04.