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Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl (Cbz or Z) group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow.
Benzyl ethers are often derived from benzyl chloride. Benzyl chloride reacts with aqueous sodium hydroxide to give dibenzyl ether. In organic synthesis, benzyl chloride is used to introduce the benzyl protecting group in reaction with alcohols, yielding the corresponding benzyl ether, carboxylic acids, and benzyl ester. Benzoic acid (C 6 H 5 ...
Benzyl group and derivatives: Benzyl group, benzyl radical, benzyl amine, benzyl bromide, benzyl chloroformate, and benzyl methyl ether. R = heteroatom, alkyl, aryl, allyl etc. or other substituents. In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH 2 −C 6 H 5.
The (Z) group is another carbamate-type amine protecting group, discovered by Leonidas Zervas in the early 1930s and usually added via reaction with benzyl chloroformate. [34] Introduction of the Z protecting group from reaction with benzyl chloroformate (Z-chloride)
[70] [71] Can be formed from diazomethane in diethyl ether, [72] [73] [74] caesium carbonate and methyl iodide in N,N‑dimethylformamide, [75] or methanol and catalytic trimethylsilyl chloride [76] Benzyl esters — Also removed by hydrogenolysis. [77] Benzhydryl esters — Same as benzyl, but easier to cleave [78]
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Some phase transfer catalysts (PTC) can be prepared according to the Menshutkin reaction, for instance the synthesis of triethyl benzyl ammonium chloride (TEBA) from triethylamine and benzyl chloride: Menshutkin reaction