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Phenacyl bromide is the organic compound with the formula C 6 H 5 C(O)CH 2 Br. This colourless solid is a powerful lachrymator as well as a useful precursor to other organic compounds. It is prepared by bromination of acetophenone: [2] C 6 H 5 C(O)CH 3 + Br 2 → C 6 H 5 C(O)CH 2 Br + HBr. The compound was first reported in 1871. [3]
In organic chemistry, a phenacyl group is an aromatic substituent that consists of a phenyl group attached to an acyl group. A molecule containing a phenacyl group has the formula RCH 2 (CO)C 6 H 5 and the structure shown to the right. Here, R denotes the remainder of the molecule; for instance, if R is Br, then the compound could be called ...
Tear gas in use in France 2007 Exploded tear gas canister in the air in Greece. Tear gas, also known as a lachrymatory agent or lachrymator (from Latin lacrima 'tear'), sometimes colloquially known as "mace" after the early commercial self-defense spray, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears.
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Illustrative is the preparation of isopropyl thiocyanate by treatment of isopropyl bromide with sodium thiocyanate in boiling ethanol. [5] The main complication with this route is the competing formation of alkyisothiocyanates. "SN1-type" substrates (e.g., benzyl halides) tend to give the isothiocyanate derivatives.
The alkylation between N-methyl-2-nitrobenzylamine [56222-08-3] (1) and phenacyl bromide (2) gives CID:15326127 (3). Catalytic hydrogenation over Raney Nickel reduces the nitro group to give CID:15113381 (4). The reduction of the ketone group with sodium borohydride to alcohol gives [65514-97-8] (5).
Mace is the brand name of an early type of aerosol self-defense spray invented by Alan Lee Litman in the 1960s. The first commercial product of its type, Litman's design packaged phenacyl chloride (CN) tear gas dissolved in hydrocarbon solvents into a small aerosol spray can, [1] usable in many environments and strong enough to act as a deterrent and incapacitant when sprayed in the face.
EA-3148 (Substance 100A) is a "V-series" nerve agent related to the better-known compounds VX and VR. [1] It was studied by both the US and Soviet chemical weapons programmes during the Cold War, and is notable as the only V-series organophosphate nerve agent specifically identified in public domain sources as having a higher absolute potency as an acetylcholinesterase inhibitor than VX ...