Chloroacetic acid methyl

SYNS CHLOROACETIC ACID METHYL ESTER METHYL CHLOROACETATE (DOT) METHYLESTER KYSELINY CHLOROCTOVE METHYL MONOCHL-ORACETATE METHYL MONOCHLOROACETATE MONOCHLOROACETIC ACID METHYL ESTER... 

CHLOROACETIC ACID CHLORIDE see CEC250 CHLOROACETTC ACID, ETHYL ESTER see EHG500 CHLOROACETIC ACID METHYL ESTER see MF775 CHLOROACETIC ACID SODIUM SALT see SFU500 CHLOROACETIC ACID, soUd (UN 1751) (DOT) see CEAOOO... 

CHLOROACETIC ACID, METHYL ESTER (96-34-4) Forms explosive mixture with... 

Chloroacetic acid methyl ester CH2C1-C(0)0CH3 90.6 + 3.2 379.1 + 13.4 Derived from AfH° in ref. 1996NIST... 

Chloroacetic acid, methyl amine, dimethyl dithiophosphoric acid... 

The AC may react with methyl chloride or alpha-chloroacetic acid via a direct displacement reaction (eq. 2). The derivatives would be methyl cellulose or carboxymethyl cellulose. 

Dichloroacetic acid is produced in the laboratory by the reaction of chloral hydrate [302-17-0] with sodium cyanide (31). It has been manufactured by the chlorination of acetic and chloroacetic acids (32), reduction of trichloroacetic acid (33), hydrolysis of pentachloroethane [76-01-7] (34), and hydrolysis of dichloroacetyl chloride. Due to similar boiling points, the separation of dichloroacetic acid from chloroacetic acid is not practical by conventional distillation. However, this separation has been accompHshed by the addition of a eotropeforming hydrocarbons such as bromoben2ene (35) or by distillation of the methyl or ethyl ester. 

Chloroacetate esters are usually made by removing water from a mixture of chloroacetic acid and the corresponding alcohol. Reaction of alcohol with chloroacetyl chloride is an anhydrous process which Hberates HCl. Chloroacetic acid will react with olefins in the presence of a catalyst to yield chloroacetate esters. Dichloroacetic and trichloroacetic acid esters are also known. These esters are usehil in synthesis. They are more reactive than the parent acids. Ethyl chloroacetate can be converted to sodium fluoroacetate by reaction with potassium fluoride (see Fluorine compounds, organic). Both methyl and ethyl chloroacetate are used as agricultural and pharmaceutical intermediates, specialty solvents, flavors, and fragrances. Methyl chloroacetate and P ionone undergo a Dar2ens reaction to form an intermediate in the synthesis of Vitamin A. Reaction of methyl chloroacetate with ammonia produces chloroacetamide [79-07-2] C2H ClNO (53). 

R,7R)-7-[2-[2-(2-Chloroacetamido)-4-thiazolyl] -2-(methoxyimino) acetamido] -8-oxo-3-[ ((1,4,5,6-tetrahydro-4-methyl-5,6-dioxo-as-triazin-3-yl)thiol methyl 1 -5-thia-1 -azabicycio (4.2.01 oct-2-ene-2-carboxylic acid Ceftriaxone sodium Chloroacetic acid Carbocysteine Isobornyl thiocyanoacetate... 

Numerous other derivatives of guar have been prepared by attaching modifying molecules to the guar backbone. Illustrative of the modifying molecules are chloroacetic acid(122), acrolein(123), ethylenimine(124), acrylamide(125), aminomethylphosphonic acid(126), and methyl bromide(127). None of these have achieved widespread use... 

Similarly, 3-(5-mercapto-l,2,4-triazol-3-yl)-7-methyl-l,4-dihydro-4-oxo-l,8-naphthyridines 432, after reaction with substituted benzaldehydes, chloroacetic acid in the presence of the mixture of acetic anhydride and acetic acid, gives the corresponding 3-(6-arylidene-5-oxo-5,6-dihydro-thiazolo[3,2- ]-l,2,4-triazol-2-yl)-7-methyl-l,4-dihydro4-oxo-1,8-naphthyridines 433 (Equation 92) <2002EJC323>. 

Analogously, 5-(pyrimidylsulfanyl)methyl-l,2,4-triazolidine-3-thione 436 reacts with chloroacetic acid, sodium acetate in acetic acid, to give 188 in 77% yield (Equation 94) <2003PS(178)2431>. 

Ethyl, n-propyl and isopropyl fluoroacetates were also readily prepared by heating the corresponding esters of chloroacetic acid with potassium fluoride in the rotating autoclave. Their toxicities were similar to that of methyl fluoroacetate. (It... 

It was obviously of interest to determine whether other esters of fluoroacetic acid would prove to be more or less toxic than the methyl ester. In the phosphorofluoridate series, for example, we found that esters of secondary alcohols were far more potent than those of primary alcohols for instance, di-isopropyl fluorophosphonate (I) was a compound of considerable activity. Accordingly ethyl, ra-propyl and isopropyl fluoroacetates were prepared by heating the corresponding esters of chloroacetic acid in the rotating autoclave with potassium fluoride. The toxicity figures of these esters were very similar to those of methyl fluoroacetate. 

It is interesting to compare the toxicity of fluoroacetyl chloride with the isomeric chloroacetyl fluoride. The former possessed a toxicity comparable to that of methyl fluoroacetate, whereas the latter was relatively non-toxic. This is readily understandable in that fluoroacetyl chloride gives the toxic fluoroacetic acid, whereas chloroacetyl fluoride hydrolyses to chloroacetic acid and the relatively non-toxic (at the concentrations employed) hydrogen fluoride. Fluoroacetyl fluoride also possessed a toxicity comparable with that of fluoroacetyl chloride or of methyl fluoroacetate, again showing that the COF group contributed practically nothing. Acetyl fluoride was also non-toxic. 

Uses Manufacture of acetate rayon, acetic anhydride, acetone, acetyl compounds, cellulose acetates, chloroacetic acid, ethyl alcohol, ketene, methyl ethyl ketone, vinyl acetate, plastics and rubbers in tanning laundry sour acidulate and preservative in foods printing calico and dyeing silk solvent for gums, resins, volatile oils and other substances manufacture of nylon and fiber, vitamins, antibiotics and hormones production of insecticides, dyes, photographic chemicals, stain removers latex coagulant textile printing. 

The reaction of saccharin with sodium hydroxide results in substitution of the imide hydrogen atom of saccharin with sodium, giving a sodium salt (3.2.75). The resulting product is reacted with methyl chloroacetate, giving the saccharin-substituted acetic acid methyl ester (3.2.76). Upon reaction with sodium methoxide in dimethylsuhoxide, the product undergoes... 

A reactor was charged with methyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta-[b]furan-7-carboxylate (25.0 g) and 2-chloroacetic acid chloride (16.0 g) dissolved in 180 ml of THF and then cooled to below 20°C and treated with the drop-wise addition of pyridine (10.7 g). The solution was stirred at ambient temperature for 1 hour and then combined with 5% aqueous solution of sodium hydrogen carbonate (40 g). Following an ordinary posttreatment workup, 31.5 g of product were isolated after recrystallization from isopropyl ether. 

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