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Ethyl chloroformate

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Identification
Molecular formula
C3H5ClO2
CAS number
541-41-3
IUPAC name
ethyl carbonochloridate
State
State

Ethyl chloroformate is typically a liquid at room temperature. Its liquid state is maintained under standard conditions (20°C or 68°F and 1 atm pressure).

Melting point (Celsius)
-80.00
Melting point (Kelvin)
193.15
Boiling point (Celsius)
93.70
Boiling point (Kelvin)
366.85
General information
Molecular weight
108.52g/mol
Molar mass
108.5200g/mol
Density
1.1390g/cm3
Appearence

Ethyl chloroformate is a colorless to pale yellow liquid. It may also appear as a clear liquid depending on purity and storage conditions. It possesses a sharp, pungent odor similar to that of phosgene or other acid chlorides.

Comment on solubility

Solubility of Ethyl Carbonochloridate

Ethyl carbonochloridate, also known as ethyl chloroformate, exhibits specific characteristics regarding its solubility. It is a colorless liquid with a significant presence in organic synthesis, primarily due to its reactive nature.

Solubility Characteristics

When considering the solubility of ethyl carbonochloridate, the following points are critical:

  • Polar Solvents: Ethyl carbonochloridate is soluble in polar solvents such as water to a limited extent, primarily due to the presence of the carbonyl and chloro functional groups.
  • Non-Polar Solvents: It is readily soluble in non-polar organic solvents like ether, benzene, and chloroform, making it ideal for various organic reactions.
  • Temperature Impact: The solubility may also vary with temperature; generally, increased temperatures enhance solubility in organic solvents.

As a versatile reagent, understanding its solubility is essential for optimizing reaction conditions and ensuring effective use in synthesizing other compounds. According to general solubility principles, the affinity for similar solvent types proves to be a guiding factor for ethyl carbonochloridate's behavior in various chemical environments. Remember that proper handling and storage conditions must be adhered to, owing to the compound's reactive nature.

Interesting facts

Interesting Facts about Ethyl Carbonochloridate

Ethyl carbonochloridate, often known for its role as an important reagent in organic synthesis, is a chemical compound that brings several fascinating aspects to the forefront of chemistry. This compound is predominantly used in the preparation of various esters, which are essential constituents in the synthesis of pharmaceuticals, agrochemicals, and fragrances.

Key Applications

  • Reagent in Organic Chemistry: Ethyl carbonochloridate is mainly utilized in acylation reactions, where it functions as a powerful acylating agent.
  • Production of Esters: It enables the formation of a variety of esters by reacting with alcohols, thus expanding the scope of synthetic capabilities.
  • Pesticide and Pharmaceutical Synthesis: This compound plays a critical role in the production of certain pesticides and pharmaceuticals, showcasing its importance in agriculture and medicine.

Historical Insights

The use of carbonochloridates can be traced back to innovative synthetic methodologies developed in the mid-20th century. Its introduction enabled chemists to explore new pathways for complex molecule synthesis, marking significant advancements in medicinal chemistry.

Caution and Handling

Despite its usefulness, it is vital to handle ethyl carbonochloridate with care due to its reactive nature. Safety precautions are crucial when working with this compound, particularly considering the potential risks associated with exposure.

In summary, ethyl carbonochloridate is a remarkable compound that exemplifies the intersection of synthesis and practicality in the chemical sciences. Its versatility and applications signify its value to both academic research and industrial applications.

Synonyms
ETHYL CHLOROFORMATE
541-41-3
Ethyl carbonochloridate
Ethyl chlorocarbonate
Cathyl chloride
Ethoxycarbonyl chloride
Chloroformic acid ethyl ester
Carbonochloridic acid, ethyl ester
Etil cloroformiato
Ethylchloorformiaat
ETHYLCHLOROFORMATE
Etil clorocarbonato
Formic acid, chloro-, ethyl ester
Chlorocarbonic acid ethyl ester
Ethyl chloromethanoate
Chlorocarbonate D'ethyle
Ethyle, chloroformiat D'
Clhorameisensaeureaethylester
Ethylchloorformiaat [Dutch]
Etil cloroformiato [Italian]
Cloroformiato de etilo
Etil clorocarbonato [Italian]
TL 423
HSDB 409
Ethylester kyseliny chlormravenci
Cloroformiato de etilo [Spanish]
Chlorocarbonate d'ethyle [French]
Ethyle, chloroformiat d' [French]
Chlorameisensaeureaethylester
EINECS 208-778-5
UN1182
Chlorameisensaeureaethylester [German]
Clhorameisensaeureaethylester [German]
BRN 0385653
Ethylester kyseliny chlormravenci [Czech]
DTXSID1027186
AI3-19852
09601EZP9R
Chloroformic acid, ethyl ester
DTXCID707186
ETHYL CHLOROFORMATE [MI]
EC 208-778-5
ETHYL CHLOROFORMATE [HSDB]
Cloroformiato de etilo (Spanish)
ETHYLCHLOORFORMIAAT (DUTCH)
ETIL CLOROFORMIATO (ITALIAN)
ETIL CLOROCARBONATO (ITALIAN)
CHLOROCARBONATE D'ETHYLE (FRENCH)
ETHYLE, CHLOROFORMIAT D' (FRENCH)
CHLORAMEISENSAEUREAETHYLESTER (GERMAN)
carbonochloridic acid ethyl ester
Ethyle, chloroformiat d
Formic acid, chloro, ethyl ester
208-778-5
Ethyl chloridocarbonate
ECF
chloro(ethoxy)methanone
UNII-09601EZP9R
ethylcloroformate
ethyl chlorformate
ethyl choroformate
ethyl cloroformate
ethylchorocarbonate
ethvl chloroformate
ethyl chioroformate
ClCOOEt
ethylchlorocarbanate
ethylchlorocarbonate
EtOCOCl
carboethoxy chloride
ethyl chlorcarbonate
Ethyl chloroforrnate
chloro ethyl formate
ethyl chloro-formate
ethyl chloroform ate
ethyl-chloro-formate
ClCO2Et
ethoxycarbonylchloride
ethyl carbonchloridate
ethyl chloro-carbonate
ethyl-carbonochloridate
EtOC(O)Cl
ethyl chloroformic acid
CH3CH2OCOCl
C2H5OCOCl
ClCOOC2H5
chloroformic ethyl ester
Ethoxy carbonyl chloride
ClCO2CH2CH3
ethyl chlorocarbonic acid
ClCO2C2H5
Ethyl chloridocarbonate #
SCHEMBL342
Ethyl chloroformate, 97%
chloroformic acid ethylester
CHEMBL3183406
Chlorocarbonic acid, ethyl ester
RIFGWPKJUGCATF-UHFFFAOYSA-
Tox21_201034
BBL011487
MFCD00000644
STL146599
AKOS000119319
UN 1182
NCGC00248902-01
NCGC00258587-01
CAS-541-41-3
VS-02959
Ethyl chloroformate [UN1182] [Poison]
DB-052494
NS00005955
EN300-19001
Ethyl chloroformate, purum, >=98.0% (GC)
Q288339
InChI=1/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3