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2-Chloroacetyl chloride

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Identification
Molecular formula
C2H2Cl2O
CAS number
79-04-9
IUPAC name
2-chloroacetyl chloride
State
State

At room temperature, 2-chloroacetyl chloride is in a liquid state. It is a volatile compound noted for its reactive nature.

Melting point (Celsius)
-20.00
Melting point (Kelvin)
253.15
Boiling point (Celsius)
105.00
Boiling point (Kelvin)
378.15
General information
Molecular weight
112.95g/mol
Molar mass
112.9490g/mol
Density
1.4040g/cm3
Appearence

2-Chloroacetyl chloride is a colorless to pale yellow liquid with a pungent odor. The slight yellow color is mostly due to impurities.

Comment on solubility

Solubility of 2-chloroacetyl chloride

2-chloroacetyl chloride, a compound with the chemical formula C2HClOCl, exhibits some notable solubility characteristics that are essential to understand for practical applications. This compound is known to be highly soluble in organic solvents, such as:

  • Chloroform
  • Dichloromethane
  • Ether
  • Acetone

However, its solubility in water is limited. This limitation is due to the presence of the carbonyl and chlorine atoms, which can disrupt hydrogen bonding. Here are a few key points regarding its solubility:

  1. Hydrophobic Nature: The chlorinated structure imparts a hydrophobic character that makes it unfavorable for solubility in polar solvents like water.
  2. Effects of Temperature: Increased temperature can enhance solubility in organic solvents, making it more amenable for various chemical reactions.
  3. Reactivity Considerations: While assessing solubility, one should also consider that 2-chloroacetyl chloride is reactive and can participate in hydrolysis in the presence of water.

Overall, while 2-chloroacetyl chloride showcases excellent solubility in non-polar or weakly polar solvents, its behavior in aqueous environments is markedly different due to its structural properties. Understanding these solubility traits is crucial for chemists working with this compound.

Interesting facts

Interesting Facts about 2-Chloroacetyl Chloride

2-Chloroacetyl chloride is an intriguing compound with significant applications in organic synthesis and the pharmaceutical industry. Here are some fascinating aspects:

  • Versatile Reactivity: This compound serves as an essential reagent in the synthesis of various organic molecules. Its ability to introduce the –C(O)Cl functional group makes it pivotal in acylation reactions.
  • Intermediate for Pharmaceutical Development: 2-Chloroacetyl chloride is often utilized in the preparation of active pharmaceutical ingredients (APIs). Its reactivity plays a crucial role in developing drugs that can combat advanced diseases.
  • Chloride Group Benefits: The presence of the chloro group enhances electrophilic character, making reactions proceed more readily. This characteristic is particularly valuable in synthetic pathways where speed and efficiency are critical.
  • Formation of Derivatives: When reacted with amines or alcohols, 2-chloroacetyl chloride can yield various derivatives, such as amides and esters, which are important in numerous applications across chemical research.
  • Safety Precautions: As with many acyl chlorides, 2-chloroacetyl chloride is toxic and can cause severe irritations. Thus, proper handling and safety protocols, including the use of personal protective equipment (PPE) and fume hoods, are vital when working with this compound.
  • Historical Significance: The development of this compound has roots in classical organic chemistry, illustrating the evolution of synthetic methods that have shaped modern chemistry.

In summary, 2-chloroacetyl chloride stands out not only for its reactivity and utility in synthesis but also for its role in enhancing pharmaceutical innovations. Its diverse applications ensure that it remains a subject of interest for chemists and organic synthesis enthusiasts alike.

Synonyms
CHLOROACETYL CHLORIDE
79-04-9
2-chloroacetyl chloride
Acetyl chloride, chloro-
Chloracetyl chloride
Chloroacetic chloride
Monochloroacetyl chloride
ChloroacetylChloride
Chloroacetic acid chloride
Chloroethanoyl chloride
CCRIS 9145
HSDB 973
Chlorure de chloracetyle
UNII-K5UML06YUO
K5UML06YUO
chloracetylchloride
Chlorid kyseliny chloroctove
EINECS 201-171-6
Acetyl chloride, 2-chloro-
UN1752
.alpha.-Chloroacetyl chloride
CH2ClCOCl
BRN 0605439
chloro acetyl chloride
DTXSID4026472
MFCD00000725
alpha-Chloroacetyl chloride
monochloroacetic acid chloride
DTXCID306472
CHEBI:34624
EC 201-171-6
4-02-00-00488 (Beilstein Handbook Reference)
CHLOROACETYL CHLORIDE [HSDB]
UN 1752
chloro-acetyl chloride
Chlorure de chloracetyle [French]
Chlorid kyseliny chloroctove [Czech]
chloroacetylchlonde
chloroacetylchoride
chloroactylchloride
Chloroacetylchlorid
chloro acetylchlorid
chloroacetyl choride
chloroactyl chloride
choroacetyl chloride
Chloroacetic Acid Chloride; Chloroacetic Chloride; Chloroethanoyl Chloride; Monochloroacetyl Chloride;
chioroacetyl chloride
chloro-acetylchloride
chloroacetyl-chloride
Chloro acetylchloride
ClCH2COCl
chloro-actyl chloride
chloroacethyl chloride
2-chloroacetylchloride
chloroacetyl chloride-
a-chloroacetyl chloride
2-chloro acetylchloride
2-chloro-acetylchloride
2-chloroacetic chloride
Acetyl chloride, chloro
alpha-chloroacetylchloride
2-chloro-acetyl chloride
alpha-chloro-acetylchloride
2-chloranylethanoyl chloride
SCHEMBL9584
2-chloroacetic acid chloride
Chloroacetyl chloride, 98%
Chloroacetyl chloride (ACGIH)
CHEMBL3187685
CHLORACETYL CHLORIDE [MI]
BCP25293
Tox21_200644
BBL013127
STK399762
AKOS000121312
CAS-79-04-9
NCGC00248777-01
NCGC00258198-01
VS-03683
Chloroacetyl chloride [UN1752] [Poison]
NS00004813
EN300-19172
Chloroacetyl chloride, purum, >=99.0% (GC)
A839561
Q411258
F2190-0033
201-171-6