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Succinyl chloride

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Identification
Molecular formula
C4H4Cl2O2
CAS number
156-29-4
IUPAC name
butanedioyl dichloride
State
State

Succinyl chloride is a liquid at room temperature. This contrasts with many other carboxylic dichlorides which are often solid. Its liquid state contributes to its use in various chemical syntheses where reagents must be mixed in the liquid phase.

Melting point (Celsius)
-20.00
Melting point (Kelvin)
253.15
Boiling point (Celsius)
190.00
Boiling point (Kelvin)
463.15
General information
Molecular weight
155.00g/mol
Molar mass
155.0030g/mol
Density
1.3820g/cm3
Appearence

Succinyl chloride is a colorless to pale yellow liquid with a pungent scent. It is often stored in a tightly sealed container due to its reactive nature, especially towards moisture in the air, which can cause it to degrade or release corrosive fumes.

Comment on solubility

Solubility of Butanedioyl Dichloride

Butanedioyl dichloride, also known as succinyl chloride and with the chemical formula C4H4Cl2O2, exhibits intriguing solubility characteristics that are important for its applications in organic synthesis.

This compound is primarily soluble in non-polar solvents, demonstrating a strong affinity for solvents such as:

  • Chloroform
  • Ether
  • Carbon tetrachloride

However, it is insoluble in water due to its hydrophobic nature and the presence of multiple chlorine atoms, which prevents adequate interaction with polar water molecules. To further understand this behavior, it can be useful to consider some fundamental aspects of solubility:

  1. The principle of like dissolves like - polar solvents dissolve polar solutes, and non-polar solvents dissolve non-polar solutes.
  2. The molecular structure of butanedioyl dichloride promotes its preference for non-polar environments.

Thus, it is crucial for chemists to select the appropriate solvent when working with butanedioyl dichloride, as its solubility profile plays a vital role in its reactivity and functionality in chemical reactions.

Interesting facts

Interesting Facts About Butanedioyl Dichloride

Butanedioyl dichloride, also known as succinyl chloride, is an intriguing compound in organic chemistry with several noteworthy attributes:

  • Versatile Intermediate: This compound serves as a significant intermediate in the synthesis of various chemical compounds, including pharmaceuticals and agrochemicals.
  • Functional Group Reactivity: With its two chlorides, butanedioyl dichloride is highly reactive towards nucleophiles, making it a vital player in acylation reactions.
  • Enhancing Synthesis: Researchers utilize butanedioyl dichloride to introduce succinyl groups into molecules. This process is crucial in modifying natural products and synthesizing complex compounds.
  • Family of Acyl Chlorides: It belongs to the broader family of acyl chlorides, which are known for their reactivity and utility as halide precursors in organic chemistry.
  • Health and Safety: While useful, caution is essential when handling this compound due to its irritant properties and potential to react vigorously with water.

As a valuable tool in organic synthesis, butanedioyl dichloride continues to be a subject of interest for chemists striving to develop new methodologies and compounds. As stated by a prominent chemist, "The potential of acyl chlorides in transforming complex structures opens up a realm of possibilities for innovative design in medicinal chemistry." This highlights both the challenges and the excitement of working with butanedioyl dichloride.

Synonyms
SUCCINYL CHLORIDE
Butanedioyl dichloride
Succinyl dichloride
Succinic acid dichloride
Succinoyl chloride
Succinic chloride
1,2-Bis(chlorocarbonyl)ethane
1,2-Ethanediylbis(chloroformate)
EINECS 208-838-0
NSC 87873
UNII-GDN09V9867
BRN 0507064
AI3-17465
GDN09V9867
NSC-87873
SUCCINYL CHLORIDE [MI]
DTXSID6060260
4-02-00-01921 (Beilstein Handbook Reference)
DTXCID7041671
inchi=1/c4h4cl2o2/c5-3(7)1-2-4(6)8/h1-2h
irxbnhgnhknoji-uhfffaoysa-n
543-20-4
Succinoyl dichloride
MFCD00000749
Butanedioyl chloride
succinic dichloride
succinic acid chloride
Succinyl chloride, 95%
WLN: GV2VG
NCIOpen2_000998
SCHEMBL43375
BCP22924
NSC87873
AKOS000121271
BP-13425
BS-43814
DB-052537
NS00043233
EN300-19228
D95385
Q27279047