Methyl 4-chlorobutyrate

Base Information

• Chemical Name: Methyl 4-chlorobutyrate
• CAS No.: 3153-37-5
• Molecular Formula: C5H9ClO2
• Molecular Weight: 136.578
• Hs Code.: 29159080
• European Community (EC) Number: 221-592-9
• NSC Number: 66271
• DSSTox Substance ID: DTXSID7062873
• Nikkaji Number: J26.255B
• Wikidata: Q63396643
• Mol file: 3153-37-5.mol

Synonyms:Methyl 4-chlorobutyrate;3153-37-5;Methyl 4-chlorobutanoate;4-Chlorobutyric acid methyl ester;Butanoic acid, 4-chloro-, methyl ester;methyl-4-chlorobutyrate;C5H9ClO2;Butyric acid, 4-chloro-, methyl ester;4-Chlorobutanoic acid methyl ester;gamma-Chlorobutyric acid methyl ester;MFCD00001003;Methyl omega-chlorobutyrate;Methyl .omega.-chlorobutyrate;EINECS 221-592-9;NSC 66271;.gamma.-Chlorobutyric acid methyl ester;methyl4-chlorobutyrate;methyl 4-chloro-butanoate;Methyl gamma-chlorobutyrate;4-Chlorbutansauremethylester;4-Chlorobutyric acid methyl;SCHEMBL83390;Methyl .gamma.-chlorobutyrate;ClCH2(CH2)2C(O)OCH3;DTXSID7062873;Methyl 4-chlorobutyrate, >=98%;NSC66271;4-Chloro Butyric Acid Methyl Ester;BBL011535;NSC-66271;STL146654;AKOS005287838;VS-02970;C0823;CS-0001466;FT-0618202;EN300-39776;GAMMA-CHLORO-N-BUTYRIC ACID METHYL ESTER;Q-200457;Q63396643

Chemical Property of Methyl 4-chlorobutyrate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 1.14mmHg at 25°C
• Refractive Index: n20/D 1.433(lit.)
• Boiling Point: 175-176 °C(lit.)
• Flash Point: 139 °F
• PSA: 26.30000
• Density: 1.12 g/mL at 25 °C(lit.)
• LogP: 1.17840
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 136.0291072
• Heavy Atom Count: 8
• Complexity: 72.8

Purity/Quality:

99% ^*data from raw suppliers

4-Chlorobutanoicacidmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: COC(=O)CCCCl
• Uses: Methyl 4-chlorobutyrate is used as a pharmaceutical synthesis, industrial dye intermediates.

Technology Process of Methyl 4-chlorobutyrate

There total 18 articles about Methyl 4-chlorobutyrate 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: 93.1%

4-butanolide (96-48-0) + methanol (67-56-1) → methyl 4-chlorobutyrate (3153-37-5)

Guidance literature:

4-butanolide; With dichlorotriphenoxyphosphorane; In dichloromethane; at -5 - 0 ℃;

methanol; In dichloromethane; at 45 - 50 ℃; Temperature;

Reference yield: 77.0%

methanol (67-56-1) + 4-Chlorobutanoyl chloride (4635-59-0) → methyl 4-chlorobutyrate (3153-37-5)

Guidance literature:

With pyridine; at 25 ℃; for 18h;

DOI:10.1139/v93-152

Reference yield: 76.0%

5-chloro-2-pentanone (5891-21-4) + acetic anhydride (108-24-7) → methyl 4-chlorobutyrate (3153-37-5) + methyl 3-chloropropionate (6001-87-2)

Guidance literature:

With oxygen; manganese(III) triacetate dihydrate; at 90 ℃; for 10h; under 3750.38 Torr; Autoclave;

DOI:10.1002/cssc.201300325

upstream raw materials:

methanol

4-Chlorobutyronitrile

γ-chlorobutyric acid

4-hydroxy-1-butanitrile

Downstream raw materials:

4-(3-methoxycarbonyl-propoxy)-benzoic acid methyl ester

4-hydroxy-4,4-diphenylbutyl chloride

methyl 4-<3-(p-t-butylphenyl)-2-methylpropylthio>butanoate

4-chlorobutyraldehyde

Refernces

• 1、 Liu, Junxia,Du, Zhongtian,Lu, Tianliang,Xu, Jie. "Conversion of levulinate into succinate through catalytic oxidative carbon-carbon bond cleavage with dioxygen". . p. 2255 - 2258. Retrieved 2014/01/06.
• 2、 Ndibwami, Alexis,Lamothe, Serge,Guay, Daniel,Plante, Raymond,Soucy, Pierre,et al.. "Transannular Diels-Alder reactions on 14-membered macrocyclic trienes. Part I: stereoselective syntheses of the macrocyclic trienes precursors". . p. 695 - 713. Retrieved 2007/10/02.