Chloracetamide

Among the three 2-halo-acetamides, chloro-, bromo- and iodo-acetamide, 2-chloracetamide is the one with the lowest antimicrobial efficacy, although because of the high electronegativity of the chloro atom, it is the more reactive compound. But its lipoid solubility is much lower than that of bromo- and iodo-acetamide. Comparison data of the three 2-halo-acetamides are listed in Table 76. Nevertheless 2-chloracetamide only has gained significant importance as a preservative for the protection of aqueous functional fluids because of its good water solubility and in consequence its favourable partition coefficient. 

Other advantages of 2-chloracetamide are the following properties colourless, odourless, effective over a wide range of pH values (4-9), compatible with anionic and non-ionic compounds. The antimicrobial activity increases even in... 

Table 77. Minimum Inhibition Concentrations (MIC) of 2-Chloracetamide in Nutrient Agar...

Dichloracetamide (pAT, = 13.55) also shows evidence of ionisation but mono-chloracetamide (pXi = 14.17) does not moreover Bruylants and Kezdy also found evidence for a termolecular mechanism in the hydrolysis of chlor-acetamide. 

Chemiluminescence, of firefly lanterns, 421 Chemotherapeutic activity, 152 Chichibabin reaction. 12 in synthesis of 2-aminothiazole. 12 a-Chloracetamide, with acetamidothiazoles. 

SYNS CHLORACETAMID (GERMAN) CHLORO-ACETAMIDE (X-CHLOROACETAMIDE 2-CHLOROETHANAMIDE USAF DO-29... 

N-(Phenyl-o-arsinic acid)-glycineamide, AsO(OH)2.C6H4.NH. CH2.CO.NHjj, obtained from o-arsanilic acid and chloracetamide, crystallises from hydrochloric acid solution in flat, microscopic needles, decomposing at 198° to 199° C. From boiling water or 50 per cent, alcohol it crystallises in narrow plates. 

N-(2-Methylphenyl-5-arsinic acid)-glycineamide, AsO(OH)2. C8H8(CH3)NH.CHa.CO.NH2.—This is formed by the condensation of chloracetamide and 3-amino-4.-methylphenylarsinic acid. It crystallises in delicate, interlaced needles, which do not melt below 285° C., and are sparingly soluble in water, alcohol, and acetic acid, soluble in methyl alcohol. The corresponding i-arsinic add yields a glycineamide which forms diamond-shaped platelets, M.pt. 203° to 205° C. 

N-(Phenyl-l-amino-4-arsinic acid)-glycine-amide, (HO)20As. C8Hj(NHg).NH.CH2.CO.NH2, is obtained when 3 4-diaminophenyl-arsinie acid in alkaline solution is treated with chloracetamide. It begins to darken at 215° C. and melts with decomposition at 234° to 241° C. If about 25 per cent, more alkali is used in the preparation, 3-amino-6-arsino-l 2-dihydroquinoxaline results ... 

Other sources of preservatives are topical medicaments and body care products. Parabens, chloracetamide, and formaldehyde-releasing preservatives, like diazoUdinyl urea, imidazoUdinyl urea, bronopol, and quaternium 15, should also be considered (15). 

Well then, certain chlor-ethers can be obtained by the reaction of chloracids upon alcohols, with a similar elimination of water and nearly all these chlor-ethers when submitted to the action of anhydrous ammonia, of an alcohol, of potash, and even of heat, divide themselves into products belonging to the families of the acid and of the alcohol which served to produce them. Thus acetic ether for example, gives origin to acetamide chloracetic ether to chloracetamide, c. Numerous examples of these changes may be seen in a very lucid resume, that has been published upon this subject by Gerhardt. 

Figure 22 Undirected ABPP probes exploiting sulfonate esters and a-chloracetamide as reactive groups, (a) A probe library with diverse sulfonate esters appended via a linker either to rhodamine or biotin, (b) a-Cloracetamide probes with a variable peptide backbone linked to a rhodamine tag.

Figure 23 A set of undirected probes with diverse electrophilic reactive groups such as sulfonate esters (SE), epoxides (EP), Q-chloracetamide (CA), Michael acceptor (UK), and spiroepoxide (SP).

R = Me, CH2Ph) with tri-n-butyl tin hydride followed by NaBHjCN reduction affords the 7-exo cyclization products (165 R = Me, CHzPh), even if in only poor to moderate yield <9ITL2829>. In a similar reaction, 2,2-dichloro-iV-methyl-iV-(o-allylphenyl)-acetamide furnishes the 1-exo product, 4-methyl-2,3,4,5-tetrahydro-l/7-benz[Z)]azepine (166) in 49% yield <91JCS(P1)353>. The established photo-induced cyclization of chloracetamides has been applied to a synthesis of the azepino[3,4,5-c,ring system isomeric to that of the clavicipitic acids <88SC671>. 

Protection of amino groups as chloracetamides Removal of the protective group under mild conditions... 

The sensitizing potential of this preservative has been established in a modified Draize test (17% of 205 volunteers) (Maibach 1971). The industrial exposure is widespread (e. g., wood, leather, and tanning industries, wallpaper glue, nylon spin finish, cutting oils). Chloracetamide in cosmetics and pharmaceutical preparations has caused contact allergy (Nater 1971 Calnan 1971) of 27 contact allergic reactions to Hirudoid ointment 7 were caused by chloracetamide (Smeenk and Prins 1972),... 

Calnan CD (1967) Chlortetracycline sensitivity. Contact Dermatitis Newslett 1 16 Calnan CD (1968) Isopropyl myristate sensitivity. Contact Dermatitis Newslett 2 38 Calnan CD (1971) Chloracetamide dermatitis from a cosmetic. Contact Dermatitis Newslett 9 215... 

Smeenk G (1973) Contact allergy to bufexamac. Dermatologica 147 334-337 Smeenk G, Prins FJ (1972) Allergic contact eczema due to chloracetamide. Dermatologica 144 108-114... 

Chloor Chlor. See Chlorine Chloracel 40% Sol n., Chloracel Solid. See Sodium aluminum chlorohydroxy lactate Chloracetamide. See Chloroacetamide Chloracetic acid. See Chloroacetic acid Chloracetic chlroide. See Chloracetyl chloride Chloracetophenone. See Chloroacetophenone Chloracetyl chloride CAS 79-04-9 UN 1752... 

CAS 79-07-2 EINECS/ELINCS 201-174-2 Synonyms Acetamide, 2-chloro- Chloracetamide 2-Chloroacetamide o-Chloroacetamide 2-Chloroethanamide Classification Chlorinated compd. 

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