Methyl 2-chloroacetoacetate

Base Information

• Chemical Name: Methyl 2-chloroacetoacetate
• CAS No.: 4755-81-1
• Deprecated CAS: 165397-10-4
• Molecular Formula: C5H7ClO3
• Molecular Weight: 150.562
• Hs Code.: 29183000
• European Community (EC) Number: 225-286-6
• UNII: 09T3687932
• DSSTox Substance ID: DTXSID10884111
• Nikkaji Number: J24.755C
• Wikidata: Q27236497
• Mol file: 4755-81-1.mol

Synonyms:Methyl 2-chloroacetoacetate;4755-81-1;Methyl 2-chloro-3-oxobutanoate;Butanoic acid, 2-chloro-3-oxo-, methyl ester;2-Chloroacetoacetic Acid Methyl Ester;methyl-2-chloroacetoacetate;EINECS 225-286-6;MFCD00008757;2-chloro-3-oxo-butyric acid methyl ester;09T3687932;vitaminb1;2-Aminobenzoesaure;SCHEMBL269783;Methyl-alpha-Chloroacetoacetate;2-chloroacetoacetate methyl ester;GYQRIAVRKLRQKP-UHFFFAOYSA-;DTXSID10884111;Methyl 2-chloro-3-oxobutanoate #;UNII-09T3687932;AKOS009156889;METHYL 2-CHLORO-3-OXOBUTYRATE;CS-W018135;2-chloro-3-oxobutyric acid methyl ester;METHYL .ALPHA.-CHLOROACETOACETATE;2-Chloro-3-oxobutanoic acid methyl ester;BS-17095;SY051760;FT-0635430;EN300-48598;Q27236497

Chemical Property of Methyl 2-chloroacetoacetate

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 7.19mmHg at 25°C
• Melting Point: -33--32.7 °C(lit.)
• Refractive Index: n20/D 1.446(lit.)
• Boiling Point: 229 °C at 760 mmHg
• PKA: 7.89±0.46(Predicted)
• Flash Point: 102.8 °C
• PSA: 43.37000
• Density: 1.223 g/cm³
• LogP: 0.35580
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 150.0083718
• Heavy Atom Count: 9
• Complexity: 132

Purity/Quality:

98%, ^*data from raw suppliers

Methyl 2-chloroacetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-27-28-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C(C(=O)OC)Cl
• Uses: Methyl 2-chloroacetoacetate was used in one-pot synthesis of 2-arylimidazole-4-carboxylic acids. It was also used in synthesis of 3,5-disubstituted 1,2,4-triazoles.

Technology Process of Methyl 2-chloroacetoacetate

There total 4 articles about Methyl 2-chloroacetoacetate 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: 100.0%

acetoacetic acid methyl ester (105-45-3) → methyl 2-chloroacetoacetate (4755-81-1,935731-92-3)

Guidance literature:

With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); In benzene; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm800412d

Reference yield:

ethyl acetoacetate (141-97-9) → methyl 2-chloroacetoacetate (4755-81-1,935731-92-3) + ethyl 2-chloro-3-oxo-butyrate (609-15-4)

Guidance literature:

With 1,3-dichloro-5,5-dimethylhydantoin; silica gel; In methanol; for 1h; Reflux;

DOI:10.1039/b815169e

Reference yield:

methyl 2,2-dichloro-3-oxobutanoate (6134-69-6) → methyl 2-chloroacetoacetate (4755-81-1,935731-92-3)

Guidance literature:

Multistep reaction; (i) iPrMgCl, THF, (ii) aq. HCl;

DOI:10.1016/S0022-328X(00)88279-0

upstream raw materials:

acetoacetic acid methyl ester

methyl 2,2-dichloro-3-oxobutanoate

ethyl acetoacetate

Downstream raw materials:

(E)-mevinphos

dimethyl 2-carbomethoxy-1-methylvinyl phosphate

methyl 2-(phenylthio) acetoacetate

2-(4-Methoxy-phenylsulfanyl)-3-oxo-butyric acid methyl ester

Refernces

• 1、 Chen, Zizhan,Zhou, Bin,Cai, Huihua,Zhu, Wei,Zou, Xinzhuo. "Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH". experimental part. p. 275 - 278. Retrieved 2010/04/22.
• 2、 Ranu, Brindaban C.,Adak, Laksmikanta,Banerjee, Subhash. "Halogenation of carbonyl compounds by an ionic liquid, [AcMIm]X, and Ceric Ammonium Nitrate (CAN)". . p. 358 - 362. Retrieved 2008/02/13.