Ethyl chloroacetate

Base Information

• Chemical Name: Ethyl chloroacetate
• CAS No.: 105-39-5
• Molecular Formula: C4H7ClO2
• Molecular Weight: 122.551
• Hs Code.: 2905199090
• European Community (EC) Number: 203-294-0
• ICSC Number: 1081
• NSC Number: 8833
• UN Number: 1181
• UNII: 6H07TEH4TF
• DSSTox Substance ID: DTXSID4026715
• Nikkaji Number: J55.313A
• Wikipedia: Ethyl_chloroacetate
• Wikidata: Q424825
• ChEMBL ID: CHEMBL3186148
• Mol file: 105-39-5.mol

Synonyms:EMCA;ethyl monochloroacetate;monochloroacetic acid ethyl ester

Chemical Property of Ethyl chloroacetate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 4.39mmHg at 25°C
• Melting Point: -27 ºC
• Refractive Index: 1.420 - 1.422
• Boiling Point: 147.6 ºC at 760 mmHg
• Flash Point: 65.6 ºC
• PSA: 26.30000
• Density: 1.119 g/cm³
• LogP: 0.78830
• Water Solubility.: 20 g/L (20℃)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 122.0134572
• Heavy Atom Count: 7
• Complexity: 62.7
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): T; N
• Hazard Codes: T:Toxic;;
• Statements: R10:; R23/24/25:; R50:
• Safety Statements: S16:; S45:; S61:; S7/9:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Chloroacetic Acid Derivatives
• Canonical SMILES: CCOC(=O)CCl
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is moderately irritating to the skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.

Technology Process of Ethyl chloroacetate

There total 84 articles about Ethyl chloroacetate 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: 97.4%

ethanol (64-17-5) + chloroacetic acid (79-11-8) → chloroacetic acid ethyl ester (105-39-5)

Guidance literature:

With Candida antarctica lipase B; at 20 ℃; for 36h; Enzymatic reaction;

DOI:10.1002/ejoc.200500388

Reference yield: 83.0%

chloroacetic acid (79-11-8) → chloroacetic acid ethyl ester (105-39-5)

Guidance literature:

With thionyl chloride; In ethanol; dichloromethane; for 0.583333h; Cooling with ice;

DOI:10.21577/0103-5053.20200219

Reference yield: 73.0%

diazoacetic acid ethyl ester (623-73-4) → chloroacetic acid ethyl ester (105-39-5)

Guidance literature:

With tertiary butyl chloride; [HB(3,5-(CF₃)2Pz)3]Ag(THF);

DOI:10.1021/ja034801o

upstream raw materials:

diazoacetic acid ethyl ester

tertiary butyl chloride

methanol

(E)-1,2-dichloro-1-ethoxy-ethene

Downstream raw materials:

girard's reagent P

1-(ethoxycarbonylmethyl)pyridinium chloride

(3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid ethyl ester

1,3-bis(2-ethoxy-2-oxoethyl)-1H-imidazol-3-ium chloride

Refernces

• 1、 Wang, Li-Sheng,Song, Guo-Qiang,Meng, Ying,Li, Shou-Gao,Li, Fu-Xiang. "Microwave synthesis of chloroacetic acid with acetic anhydride catalyzing chlorination of acetic acid". . p. 8997 - 8999. Retrieved 2013.
• 2、 Marchetti, Fabio,Pampaloni, Guido,Biancalana, Lorenzo. "Activation reactions of 1,1-dialkoxoalkanes and unsaturated O-donors by titanium tetrafluoride". . p. 135 - 139. Retrieved 2012.
• 3、 Li, Yi-Qun. "Catalytic esterifications of carboxylic acids and alcohols by sodium bisulfate monohydrate". . p. 3901 - 3903. Retrieved 1999.
• 4、 Kornilova, Tatiana A.,Ukolov, Anton I.,Kostikov, Rafael R.,Zenkevich, Igor G.. "A simple criterion for gas chromatography/mass spectrometric analysis of thermally unstable compounds, and reassessment of the by-products of alkyl diazoacetate synthesis". . p. 461 - 466. Retrieved 2013.
• 5、 Zav'yalov, S. I.,Sitkareva, I. V.,Ezhova, G. I. "CHLORINATING PROPERTIES OF THE TRIMETHYLCHLOROSILANE-POTASSIUM BROMATE-DMF SYSTEM". . p. 356 - 358. Retrieved 1992.
• 6、 Barbosa-Filho, José M.,Brand?o, Maria Cláudia R.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes D.,Souza, Helivaldo D. S.,Trindade, Emmely O.,de Athayde-Filho, Petr?nio F.. "New Diesters Derived from Piperine: In silico Study and Evaluation of Their Antimicrobial Potential". . p. 1668 - 1678. Retrieved 2020/10/09.