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Chloroacetyl chloride is bifunctional—the acyl chloride easily forms esters [4] and amides, while the other end of the molecule is able to form other linkages, e.g. with amines. The use of chloroacetyl chloride in the synthesis of lidocaine is illustrative: [ 5 ]
Acetyl halide, such as acetyl chloride in the presence of a base like triethylamine [2] Activated ester form of acetic acid, such as a N-hydroxysuccinimide ester, although this is not advisable due to higher costs and difficulties. [3] Acetic anhydride in the presence of base with a catalyst such as pyridine with a bit of DMAP added. [4]
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. [4]Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids (R−C(=O)OH). A specific example of an acyl chloride is acetyl chloride, CH 3 COCl.
Chloroacetic acid was first prepared (in impure form) by the French chemist Félix LeBlanc (1813–1886) in 1843 by chlorinating acetic acid in the presence of sunlight, [3] and in 1857 (in pure form) by the German chemist Reinhold Hoffmann (1831–1919) by refluxing glacial acetic acid in the presence of chlorine and sunlight, [4] and then by the French chemist Charles Adolphe Wurtz by ...
Thus, chloride ion is a better leaving group than acetate ion. The reactivity of acyl compounds towards nucleophiles decreases as the basicity of the leaving group increases, as the table shows. The reactivity of acyl compounds towards nucleophiles decreases as the basicity of the leaving group increases, as the table shows.
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Synonyms CAS number Ac 2 O 3: actinium(III) oxide: 12002-61-8 AgBF 4: Silver tetrafluoroborate: 14104-20-2 AgBr: silver bromide: 7785-23-1 AgBrO: silver hypobromite: AgBrO 2: silver bromite: AgBrO 3: silver bromate: 7783-89-3 AgBrO 4: silver perbromate: AgCl: silver chloride: 7783-90-6 AgCl 3 Cu 2: dicopper silver trichloride: 69569-03-5 AgClO ...