- Acetyl chloride
Chembox new
Name = Acetyl chloride
ImageFileL1 = Acetyl-chloride.png
ImageSizeL1 = 100px
ImageNameL1 = Skeletal formula of acetyl chloride
ImageFileR1 = Acetyl-chloride-3D-balls.png
ImageSizeR1 = 100px
ImageNameR1 = Ball-and-stick model of acetyl chloride
ImageFile2 = Acetyl-chloride-3D-vdW.png
ImageSize2 = 120px
ImageName2 = Space-filling model of acetyl chloride
IUPACName = Ethanoyl chloride
OtherNames = Acetyl chloride
Section1 = Chembox Identifiers
SMILES = CC(=O)Cl
CASNo = 75-36-5
RTECS = AO6390000
Section2 = Chembox Properties
Formula = CH3COCl
MolarMass = 78.5 g/mol
Appearance = colorless liquid
Density = 1.11 g/ml, liquid
Solubility = Reacts
MeltingPt = −112 °C
BoilingPt = 51 °C
Viscosity =
Section3 = Chembox Structure
Dipole = 2.45 D
Section7 = Chembox Hazards
ExternalMSDS =
EUClass = Flammable (F)
Corrosive (C)
RPhrases = R11, R14, R34
SPhrases = S1/2, S9, S16, S26, S45
FlashPt = 5 °C
Autoignition = 390 °C
ExploLimits = 7.3–19%
Section8 = Chembox Related
Function =acyl chloride s
OtherFunctn =Propionyl chloride Butyryl chloride
OtherCpds =Acetic acid Acetic anhydride Acetyl chloride, also known as ethanoyl chloride, is an
acid chloride (also known as anacyl chloride ) derived fromacetic acid (ethanoic acid ). It has the formula CH3COCl and it belongs to the class oforganic compound s calledacyl halide s. At room temperature and pressure, it is a clear colorlessliquid . Acetyl chloride does not exist in nature, because contact with water would hydrolyze it into acetic acid andhydrogen chloride . In fact, if handled in open air it gives off whitesmoke owing to the hydrolysis from the moisture in the air. The smoke is actuallygas eous hydrogen chloride which forms small droplets in the air with water vapour.ynthesis
Acetyl chloride is synthesized by the reaction of
acetic acid (CH3COO-H) withthionyl chloride (O=SCl2) under liberation ofsulfur dioxide (SO2).:CH3COO-H + O=SCl2 → CH3COCl + SO2 + H-Cl
Uses
It is a reagent for
acetylation in thesynthesis or derivatization ofchemical compound s. Examples of acetylation reactions includeacylation processes such asesterification (see below) and theFriedel-Crafts reaction ).:CH3COCl + HO-CH2-CH3 → CH3-COO-CH2-CH3 + H-Cl
Frequently such acylations are carried out in the presence of a base such as
pyridine ,triethylamine , or DMAP, which ascatalyst s help to promote the reaction and as bases neutralize the resulting HCl.Acetylation is the introduction of an
acetyl group viaacylation using areactant such as acetyl chloride oracetic anhydride . An acetyl group is anacyl group having the formula:-C(=O)-CH3For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see
acyl halide .References
External links
* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc02/icsc0210.htm International Chemical Safety Card 0210]
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