2-Chloropropionic acid

changed changed 477195788 2-Chloropropionic acid Enantiomers Structural Formulae.svg 2-Chloropropionic acid 2-Chloropropanoic acid α-Chloropropanoic acidα-Chloropropionic acid ClC(C(=O)O)C 1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) GAWAYYRQGQZKCR-UHFFFAOYAW correct chemspider 1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) correct chemspider GAWAYYRQGQZKCR-UHFFFAOYSA-N correct CAS 598-78-7 (racemate) 29617-66-1 (S) 7474-05-7 (R) correct FDA ADV1WUE1NB correct chemspider 11241 11734 209-952-3 UE8575000 2511 1743205 3 5 1 2 Colorless liquid 1.18 g/mL Miscible -13 78 at 10 mmHg External MSDS Toxic, corrosive 101 05 06 07 08 Danger 301 302 310 314 331 371 373 260 261 262 264 270 271 280 301+312 301+330+331 302+350 303+361+353 304+340 305+351+338 309+311 310 311 314 321 322 330 361 363 403+233 405 501 Propionic acidChloroacetic acid 2-Chloropropionic acid (2-chloropropanoic acid) is the chemical compound with the formula CH3CHClCO2H. This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer. The conjugate base of 2-chloropropionic acid (CH3CHClCO2−), as well as its salts and esters, are known as 2-chloropropionates or 2-chloropropanoates.2005 Ulf-Rainer Samel Walter Kohler Armin Otto Gamer Ullrich Keuser Propionic Acid and Derivatives 10.1002/14356007.a22_223 Preparation Racemic 2-chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2-chloropropionyl chloride. Enantiomerically pure (S)-2-chloropropionic acid can be prepared from L-alanine via diazotization in hydrochloric acid.10.15227/orgsyn.066.0151 free (S)-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid Organic Syntheses 1988 66 Koppenhoefer Bernhardt Schurig Volker 151 Other α-amino acids undergo this reaction. Reactions Reduction of (S)-2-chloropropionic acid with lithium aluminium hydride affords (S)-2-chloropropanol, the simplest chiral chloro-alcohol. This alcohol undergoes cyclization upon treatment with potassium hydroxide, which causes dehydrohalogenation to give the epoxide, (R)-propylene oxide (methyloxirane). 10.15227/orgsyn.066.0160 free (R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids Via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane Organic Syntheses 1988 66 160 Bernhard Koppenhoefer Volker Schurig 400px 2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen. Applications Some of the known uses include in the synthesis of: Dichlorprop, Flamprop, Haloxyfop Safety In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin. Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid Simpson MG, Wyatt I, Jones HB, Gyte AJ, Widdowson PS, Lock EA Neurotoxicology 1996 17 2 471–480 8856742 See also 2,2-Dichloropropionic acid References Category:Carboxylic acids Category:Organochlorides