Methyl 4-(chloroformyl)butyrate

Base Information

• Chemical Name: Methyl 4-(chloroformyl)butyrate
• CAS No.: 1501-26-4
• Molecular Formula: C6H9ClO3
• Molecular Weight: 164.589
• Hs Code.: 2918300090
• European Community (EC) Number: 216-115-6
• NSC Number: 93892
• UNII: U7H8283W54
• DSSTox Substance ID: DTXSID60164470
• Nikkaji Number: J206.706D
• Wikidata: Q63409003
• Mol file: 1501-26-4.mol

Synonyms:4-(Chlorocarbonyl)butanoic acidmethyl ester;4-(Methoxycarbonyl)butyryl chloride;4-Chlorocarbonylbutyric acidmethyl ester;5-Chloro-5-oxopentanoic acid methyl ester;Glutaric acidmonomethyl ester chloride;Glutaryl chloride methyl ester;Methyl4-(chlorocarbonyl)butanoate;Methyl 4-(chloroformyl)butanoate;Methyl 5-chloro-5-oxopentanoate;Methyl5-chloro-5-oxovalerate;Methyl glutaroyl chloride;Methyl glutaryl chloride;NSC 93892;g-(Carbomethoxy)butyryl chloride;4-(Carbomethoxy)butanoylchloride;4-(Carbomethoxy)butyryl chloride;

Chemical Property of Methyl 4-(chloroformyl)butyrate

Chemical Property:

• Appearance/Colour: clear colourless to light yellow liquid
• Vapor Pressure: 0.0932mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 224 °C at 760 mmHg
• Flash Point: 82.2 °C
• PSA: 43.37000
• Density: 1.179 g/cm³
• LogP: 1.09510
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform, Hexane
• Water Solubility.: reacts
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 164.0240218
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-(Chloroformyl)butyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)CCCC(=O)Cl
• Uses: Methyl 4-(Chloroformyl)butyrate is used in the synthesis of Leukotriene B4, a proinflammatory agent produced from leukocytes.

Technology Process of Methyl 4-(chloroformyl)butyrate

There total 8 articles about Methyl 4-(chloroformyl)butyrate 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: 90.0%

Pentanedioic acid, monomethyl ester (1501-27-5) → methyl 4-(chlorocarbonyl)butyrate (1501-26-4)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1002/chem.201502073

Reference yield: 86.4%

methanol (67-56-1) + glutaric anhydride, (108-55-4) → methyl 4-(chlorocarbonyl)butyrate (1501-26-4)

Guidance literature:

methanol; glutaric anhydride,; for 1h; Reflux;

With thionyl chloride; In N,N-dimethyl-formamide; for 2h;

Reference yield:

glutaric anhydride, (108-55-4) → methyl 4-(chlorocarbonyl)butyrate (1501-26-4)

Guidance literature:

Multi-step reaction with 2 steps

1: CHCl₃ / 5 h / Heating

2: SOCl₂ / 2 h / Heating

With thionyl chloride; In chloroform;

DOI:10.1016/j.bmcl.2003.12.095

upstream raw materials:

Pentanedioic acid, monomethyl ester

methanol

glutaric anhydride,

thionyl chloride

Downstream raw materials:

methyl 5-(2-thienyl)-5-oxopentanoate

5-(4-benzyl-phenyl)-5-oxo-valeric acid methyl ester

5,5'-dioxo-5,5'-(4,4'-methanediyl-di-phenyl)-di-valeric acid

methyl 4-formylbutanoate

Refernces

• 1、 Micich,Cinfield. "". . p. 264. Retrieved 1977.
• 2、 Montembault, Mickael,Vo-Thanh, Giang,Deyine, Abdallah,Fargeas, Valerie,Villieras, Monique,Adjou, Ane,Dubreuil, Didier,Esquieu, Didier,Gregoire, Catherine,Opi, Sandrine,Peloponese, Jean-Marie,Campbell, Grant,Watkins, Jennifer,De Mareuil, Jean,Aubertin, Anne-Marie,Bailly, Christian,Loret, Erwann,Lebreton, Jacques. "A possible improvement for structure-based drug design illustrated by the discovery of a Tat HIV-1 inhibitor". . p. 1543 - 1546. Retrieved 2004.
• 3、 Yoo, Jakyung,Kim, So-Jin,Son, Dohyun,Seo, Heewon,Baek, Seung Yeop,Maeng, Cheol-Young,Lee, Changsik,Kim, In Su,Jung, Young Hoon,Lee, Sun-Mee,Park, Hyun-Ju. "Computer-aided identification of new histone deacetylase 6 selective inhibitor with anti-sepsis activity". . p. 126 - 135. Retrieved 2016.
• 4、 Gao, Min,Lee, Sun Hyeok,Park, Sang Hyuk,Ciaramicoli, Larissa Miasiro,Kwon, Haw-Young,Cho, Heewon,Jeong, Joseph,Chang, Young-Tae. "Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction". supporting information. p. 23743 - 23749. Retrieved 2021/10/14.
• 5、 Vigliotta, Giovanni,Giordano, Deborah,Verdino, Anna,Caputo, Ivana,Martucciello, Stefania,Soriente, Annunziata,Marabotti, Anna,De Rosa, Margherita. "New compounds for a good old class: Synthesis of two Β-lactam bearing cephalosporins and their evaluation with a multidisciplinary approach". supporting information. . Retrieved 2020/01/22.