(S)-(-)-2-Chloropropionic acid

Base Information

• Chemical Name: (S)-(-)-2-Chloropropionic acid
• CAS No.: 29617-66-1
• Molecular Formula: C3H5ClO2
• Molecular Weight: 108.525
• Hs Code.: 29159080
• European Community (EC) Number: 411-150-5,608-381-0
• UN Number: 2511
• UNII: PCC7J322CM
• DSSTox Substance ID: DTXSID50896915
• Nikkaji Number: J669F
• Wikidata: Q27144279
• Metabolomics Workbench ID: 66743
• Mol file: 29617-66-1.mol

Synonyms:(2S)-2-chloropropanoic acid;(S)-2-Chloropropionic acid;Propionic acid, 2-chloro-, L- (8CI);Propanoic acid, 2-chloro-, (S)-;alpha-L-Chloropropionic acid;S-2-Chloropropionic acid;(S)-2-Chloropropanoic acid;L-2-Chloropropanoic acid;(2S)-Chloropropanoic acid;L-2-chloropropinonical;

Chemical Property of (S)-(-)-2-Chloropropionic acid

Chemical Property:

• Appearance/Colour: colourless oil
• Vapor Pressure: 7.01mmHg at 25°C
• Melting Point: 4 °C
• Refractive Index: 1.479
• Boiling Point: 189 °C at 760 mmHg
• PKA: 2.83(at 25℃)
• Flash Point: 68.1 °C
• PSA: 37.30000
• Density: 1.285 g/cm³
• LogP: 0.69830
• Storage Temp.: 2-8°C
• Water Solubility.: soluble
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 107.9978071
• Heavy Atom Count: 6
• Complexity: 61.8
• Transport DOT Label: Corrosive

Purity/Quality:

99.9% ^*data from raw suppliers

(S)-(-)-2-Chloropropionic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 21/22-35-48/22
• Safety Statements: 23-26-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)O)Cl
• Isomeric SMILES: C[C@@H](C(=O)O)Cl
• Uses: Through the stereo displacement of (S)-(-)-2-Chloropropionic acid PPAR Agonist can be synthesized via asymmetric hydrogenation of a cinnamic acid derivative.

Technology Process of (S)-(-)-2-Chloropropionic acid

There total 29 articles about (S)-(-)-2-Chloropropionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

L-alanin (56-41-7,25191-17-7,18875-37-1) → (S)-2-chloropropanoic acid (29617-66-1)

Guidance literature:

With hydrogenchloride; nitrosylchloride; In water; at 0 ℃; for 1h; Temperature;

Reference yield: 93.0%

(1R,2R)-2-(naphthalen-2-yloxy)cyclohexyl (S)-2-chloropropanoate → (S)-2-chloropropanoic acid (29617-66-1) + trans-2-(naphthalen-2-yloxy)cyclohexan-1-ol

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 50 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c8ob02896f

Reference yield: 86.0%

(S)-2-Chloro-propionic acid (R)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester → (S)-2-chloropropanoic acid (29617-66-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0957-4166(98)00194-3

upstream raw materials:

(2R,3S)-(+)-3-chlorobutane-2-ol

L-alanin

methyl-(S)-2-chloropropionate

(RS)-1-Pentylpropynyl (L)-2-chloropropanoate

Downstream raw materials:

(S)-2-chloropropionyl chloride

(R)-2-(benzylthio)propanoic acid

(R)-2-((3aS,4R,4aR,6R,8aR,9aS)-2-Oxo-6-phenyl-octahydro-1,5,7-trioxa-3-aza-cyclopenta[b]naphthalen-4-yloxy)-propionic acid

Benzyl 2-(benzyloxycarbonylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

Refernces

• 1、 Jain, Nilesh,Bedekar, Ashutosh V.. "Roof shape chiral alcohol: auxiliary for asymmetric synthesis of α-halo acid derivatives". . p. 692 - 695. Retrieved 2016.
• 2、 Lagoa, Ana L.C.,Diogo, Herminio P.,Minas da Piedade, Manuel E.,Amaral, Luisa M.P.F.,Guedes, Rita C.,Costa Cabral, Benedito J.,Kulikov, Dmitry V.,Verevkin, Sergey P.,Siedler, Michael,Epple, Matthias. "Energetics of the C-Cl bond in CH3CH(Cl)COOH. Enthalpy of formation of (S)-(-)-2-chloropropionic acid and of the 1-carboxyethyl radical". . p. 9855 - 9861. Retrieved 2002.
• 3、 Khanvilkar, Aditya N.,Samanta, Sudeep G.,Bedekar, Ashutosh V.. "Applications of chiral naphthyloxycyclohexanols in deracemization of α-substituted carboxylic acids by dynamic thermodynamic resolution". . p. 2670 - 2683. Retrieved 2019/03/12.
• 4、 -. "Synthesis method of pesticide intermediate (S)-(-)-2-chloropropionic acid". Paragraph 0033-0050. . Retrieved 2020/05/19.