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Butyryl chloride

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Identification
Molecular formula
C4H7ClO
CAS number
141-75-3
IUPAC name
butanoyl chloride
State
State

Butyryl chloride is a liquid at room temperature. It is typically stored under anhydrous conditions to prevent reaction with atmospheric moisture.

Melting point (Celsius)
-87.30
Melting point (Kelvin)
185.85
Boiling point (Celsius)
102.00
Boiling point (Kelvin)
375.15
General information
Molecular weight
106.56g/mol
Molar mass
106.5500g/mol
Density
0.9390g/cm3
Appearence

Butyryl chloride is a colorless liquid with a pungent odor. It is highly reactive, particularly in the presence of water or moisture, due to its acid chloride functional group.

Comment on solubility

Solubility of Butanoyl Chloride

Butanoyl chloride, also known by its IUPAC name butanoyl chloride and the chemical formula C4H7ClO, exhibits interesting solubility characteristics that are significant for its applications in organic synthesis.

Solubility Behavior

In terms of its solubility, butanoyl chloride can be characterized as follows:

  • Polar Solvents: It is soluble in polar aprotic solvents like acetone and dimethylformamide (DMF). This is due to the molecule's polarity and the presence of the carbonyl group.
  • Water: Butanoyl chloride is not soluble in water. This is primarily because it reacts with water to produce butanoic acid and hydrochloric acid, rather than simply dissolving.
  • Nonpolar Solvents: While it shows limited solubility in nonpolar solvents, caution is advised as it may react rather than dissolve.

The solubility of butanoyl chloride is crucial for chemical reactions where it serves as an acylating agent. Understanding its solubility properties enables chemists to plan experiments that maximize efficiency and minimize by-product formation.

Key Points to Remember

  • Soluble in polar aprotic solvents.
  • Insoluble in water, reacting instead.
  • Limited solubility in nonpolar solvents.

Overall, the solubility profile of butanoyl chloride is essential for its handling and application in synthetic organic chemistry.

Interesting facts

Interesting Facts About Butanoyl Chloride

Butanoyl chloride, also known as butanoic acid chloride, is an important acyl chloride that plays a crucial role in organic synthesis. Here are some engaging insights about this compound:

  • Functional Group: Butanoyl chloride features the acyl chloride functional group, which is highly reactive due to the electron-withdrawing nature of the chlorine atom. This reactivity makes it useful in various chemical reactions.
  • Key Reactions: It is primarily used for acylation reactions, where it introduces the butanoyl group into various substrates. This can facilitate the synthesis of esters, amides, and other derivatives.
  • Preparation: One common method to synthesize butanoyl chloride is through the reaction of butanoic acid with thionyl chloride (SOCl2). This reaction not only produces butanoyl chloride but also generates byproducts that make isolation easier.
  • Applications: Butanoyl chloride is utilized in the pharmaceutical and agrochemical industries. It is a crucial building block in the synthesis of bioactive compounds, pharmaceuticals, and herbicides.
  • Safety Considerations: As a reactive compound, butanoyl chloride is corrosive and can cause severe burns upon contact with skin. It's imperative to handle it with proper safety precautions, such as working in a fume hood and using appropriate personal protective equipment.
  • Environmental Impact: Understanding the environmental impact of using such chlorinated compounds is essential. They can produce toxic byproducts, making it vital to implement proper waste disposal practices when working with or producing butanoyl chloride.

It's intriguing to see how a seemingly simple compound like butanoyl chloride can have a significant impact on various fields, showcasing the intricate interplay of chemistry and its applications in real-world scenarios. As molecular structures become increasingly complex, the role of acyl chlorides such as butanoyl chloride will undoubtedly remain pivotal in synthetic chemistry.

Synonyms
Butyryl chloride
Butanoyl chloride
141-75-3
N-BUTYRYL CHLORIDE
Butyrylchloride
Butyric acid chloride
Butyric chloride
Butyroyl chloride
CCRIS 5989
n-Butyric acid chloride
HSDB 6016
UNII-2XVM8E16IR
EINECS 205-498-5
UN2353
DTXSID5024710
N-BUTANOYL CHLORIDE
2XVM8E16IR
DTXCID104710
N-BUTYRYL CHLORIDE [MI]
EC 205-498-5
N-BUTYRYL CHLORIDE [HSDB]
UN 2353
butryl chloride
butyroylchloride
n-PrCOCl
MFCD00000752
butanoic acid chloride
BUTYROL CHLORIDE
methylpropionyl chloride
Butyryl chloride, 98%
SCHEMBL2819
Butyryl chloride, >=99%
propanecarboxylic acid chloride
CHEMBL1300263
Tox21_200294
BBL011417
STL146523
AKOS000121193
FB34825
HY-W245950
NCGC00091749-01
NCGC00091749-02
NCGC00257848-01
CAS-141-75-3
VS-02944
B0770
NS00003156
EN300-19257
Butyryl chloride [UN2353] [Flammable liquid]
Q5003202
F2190-0011
205-498-5