2-Chloropropionic acid

From Wikipedia, the free encyclopedia
2-Chloropropionic acid
2-Chloropropionic acid
Names
Preferred IUPAC name
2-Chloropropanoic acid
Other names
α-Chloropropanoic acid
α-Chloropropionic acid
Identifiers
  • 598-78-7 (racemate) checkY
  • 29617-66-1 (S)
  • 7474-05-7 (R)
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.049 Edit this at Wikidata
EC Number
  • 209-952-3
RTECS number
  • UE8575000
UNII
UN number 2511
  • InChI=1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) checkY
    Key: GAWAYYRQGQZKCR-UHFFFAOYSA-N checkY
  • InChI=1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)
    Key: GAWAYYRQGQZKCR-UHFFFAOYAW
  • ClC(C(=O)O)C
Properties
C3H5ClO2
Molar mass 108.52 g·mol−1
Appearance Colorless liquid
Density 1.18 g/mL
Melting point −13 °C (9 °F; 260 K)
Boiling point 78 °C (172 °F; 351 K) at 10 mmHg
Miscible
Hazards
Main hazards Very toxic, corrosive
Safety data sheet (SDS) External MSDS
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word
 Danger
H302, H310, H314, H331, H371, H373
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, P501
Flash point 101 °C (214 °F; 374 K)
Related compounds
Related compounds
 Propionic acid
Chloroacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  (what is checkY☒N ?)
Infobox references

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]

Preparation[]

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.

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).[3]

Methyloxirane from 2-chloropropionic acid.png

2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen.[1]

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.[4]

See also[]

References[]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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): 471–80. PMID 8856742.
Retrieved from ""