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.[1]
Racemic 2-chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2-chloropropionyl chloride.[1] Enantiomerically pure (S)-2-chloropropionic acid can be prepared from L-alanine via diazotization in hydrochloric acid.[2] Other α-amino acids undergo this reaction.
2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen.[1]
SafetyEdit
In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin.[4]
^Koppenhoefer, Bernhardt; Schurig, Volker (1988). "(S)-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid". Organic Syntheses. 66: 151. doi:10.15227/orgsyn.066.0151.
^Bernhard Koppenhoefer; Volker Schurig (1988). "(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids Via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane". Organic Syntheses. 66: 160. doi:10.15227/orgsyn.066.0160.
^Simpson MG, Wyatt I, Jones HB, Gyte AJ, Widdowson PS, Lock EA (1996). "Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid". Neurotoxicology. 17 (2): 471–480. PMID 8856742.
August 25, 2023
chloropropionic, acid, chloropropanoic, acid, chemical, compound, with, formula, ch3chclco2h, this, colorless, liquid, simplest, chiral, chlorocarboxylic, acid, noteworthy, being, readily, available, single, enantiomer, conjugate, base, chloropropionic, 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 1 2 Chloropropionic acid NamesPreferred IUPAC name 2 Chloropropanoic acidOther names a Chloropropanoic acida Chloropropionic acidIdentifiersCAS Number 598 78 7 racemate Y29617 66 1 S 7474 05 7 R 3D model JSmol Interactive imageChEMBL ChEMBL1743205ChemSpider 11241 YECHA InfoCard 100 009 049EC Number 209 952 3PubChem CID 11734RTECS number UE8575000UNII ADV1WUE1NB YUN number 2511CompTox Dashboard EPA DTXSID0021545InChI InChI 1S C3H5ClO2 c1 2 4 3 5 6 h2H 1H3 H 5 6 YKey GAWAYYRQGQZKCR UHFFFAOYSA N YInChI 1 C3H5ClO2 c1 2 4 3 5 6 h2H 1H3 H 5 6 Key GAWAYYRQGQZKCR UHFFFAOYAWSMILES ClC C O O CPropertiesChemical formula C 3H 5Cl O 2Molar mass 108 52 g mol 1Appearance Colorless liquidDensity 1 18 g mLMelting point 13 C 9 F 260 K Boiling point 78 C 172 F 351 K at 10 mmHgSolubility in water MiscibleHazardsOccupational safety and health OHS OSH Main hazards Toxic corrosiveGHS labelling PictogramsSignal word DangerHazard statements H301 H302 H310 H314 H331 H371 H373Precautionary statements P260 P261 P262 P264 P270 P271 P280 P301 P312 P301 P330 P331 P302 P350 P303 P361 P353 P304 P340 P305 P351 P338 P309 P311 P310 P311 P314 P321 P322 P330 P361 P363 P403 P233 P405 P501Flash point 101 C 214 F 374 K Safety data sheet SDS External MSDSRelated compoundsRelated compounds Propionic acidChloroacetic acidExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Reactions 3 Safety 4 See also 5 ReferencesPreparation EditRacemic 2 chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2 chloropropionyl chloride 1 Enantiomerically pure S 2 chloropropionic acid can be prepared from L alanine via diazotization in hydrochloric acid 2 Other a amino acids undergo this reaction Reactions EditReduction 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 3 2 Chloropropionyl chloride reacts with isobutylbenzene to give after hydrolysis ibuprofen 1 Safety EditIn general a halocarboxylic acids and their esters are good alkylating agents and should be handled with care 2 Chloropropionic acid is a neurotoxin 4 See also Edit2 2 Dichloropropionic acidReferences Edit a b c Samel Ulf Rainer Kohler Walter Gamer Armin Otto Keuser Ullrich 2005 Propionic Acid and Derivatives Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a22 223 Koppenhoefer Bernhardt Schurig Volker 1988 S 2 Chloroalkanoic Acids of High Enantiomeric Purity from S 2 Amino Acids S 2 Chloropropanoic Acid Organic Syntheses 66 151 doi 10 15227 orgsyn 066 0151 Bernhard Koppenhoefer Volker Schurig 1988 R Alkyloxiranes of High Enantiomeric Purity from S 2 Chloroalkanoic Acids Via S 2 Chloro 1 Alkanols R Methyloxirane Organic Syntheses 66 160 doi 10 15227 orgsyn 066 0160 Simpson MG Wyatt I Jones HB Gyte AJ Widdowson PS Lock EA 1996 Neuropathological changes in rat brain following oral administration of 2 chloropropionic acid Neurotoxicology 17 2 471 480 PMID 8856742 Retrieved from https en wikipedia org w index php title 2 Chloropropionic acid amp oldid 1157934052, wikipedia, wiki, book, books, library,
