Ethyl 4-chlorobutyrate

Base Information

• Chemical Name: Ethyl 4-chlorobutyrate
• CAS No.: 3153-36-4
• Molecular Formula: C6H11ClO2
• Molecular Weight: 150.605
• Hs Code.: 29159000
• European Community (EC) Number: 221-591-3
• NSC Number: 81215
• UNII: 6TM3R4X5CX
• DSSTox Substance ID: DTXSID90185431
• Nikkaji Number: J26.254D
• Wikidata: Q72473561
• Mol file: 3153-36-4.mol

Synonyms:Ethyl 4-chlorobutyrate;3153-36-4;ETHYL 4-CHLOROBUTANOATE;Butanoic acid, 4-chloro-, ethyl ester;Ethyl gamma-chlorobutyrate;Butyric acid, 4-chloro-, ethyl ester;4-chloro-butyric acid ethyl ester;NSC 81215;6TM3R4X5CX;Ethyl .gamma.-chlorobutyrate;4-Chlorobutyric Acid Ethyl Ester;EINECS 221-591-3;NSC-81215;Ethyl-4-chlorobutyrate;MFCD00001004;Ethyl 4chlorobutyrate;UNII-6TM3R4X5CX;Ethyl .omega.-chlorobutyrate;Ethyl 4-chlorobutyrate, 98%;Cl(CH2)3C(O)OC2H5;SCHEMBL1364893;OPXNFHAILOHHFO-UHFFFAOYSA-;DTXSID90185431;4-Chlorobutanoic acid ethyl ester;NSC81215;gamma-Chlorobutyric acid ethyl ester;BBL011514;CCG-40422;STL146630;AKOS001090190;.gamma.-Chlorobutyric acid ethyl ester;AS-57727;FT-0618201;FT-0668199;EN300-17864;D89301;Ethyl 4-chlorobutyrate, purum, >=97.5% (GC);J-018453;F0001-2559

Chemical Property of Ethyl 4-chlorobutyrate

Chemical Property:

• Appearance/Colour: clear yellow to brownish liquid
• Vapor Pressure: 0.678mmHg at 25°C
• Melting Point: -70oC
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 186 °C at 760 mmHg
• Flash Point: 51.7 °C
• PSA: 26.30000
• Density: 1.057 g/cm³
• LogP: 1.56850
• Storage Temp.: Flammables area
• Water Solubility.: Insoluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 150.0447573
• Heavy Atom Count: 9
• Complexity: 83.1

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 4-chlorobutyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-10
• Safety Statements: 26-36-37/39-16-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CCOC(=O)CCCCl
• Uses: Ethyl 4-chlorobutyrate is a reagent used in the preparation of cyclopropane derivatives. Ethyl 4-chlorobutyrate is used in organic synthesis. And also used for producting 4-Iodo-butyric acid ethyl ester.

Technology Process of Ethyl 4-chlorobutyrate

There total 21 articles about Ethyl 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: 80.0%

4-butanolide (96-48-0) + ethanol (64-17-5) → 4-chloro-butyric acid ethyl ester (3153-36-4)

Guidance literature:

With thionyl chloride; for 16h; Heating;

DOI:10.1021/jo00291a045

Reference yield: 43.0%

cyclobutanone (1191-95-3) + oxovanadium(V) ethoxydichloride (1801-77-0) → 4-chloro-butyric acid ethyl ester (3153-36-4)

Guidance literature:

With lithium chloride; In diethyl ether; for 13h; Ambient temperature;

DOI:10.1021/jo00006a061

Reference yield: 30.0%

ethyl 4-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate → 4-chloro-butyric acid ethyl ester (3153-36-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4-tert-Butylcatechol; 2-methoxybenzo[d][1,3,2]dioxaborole; trans-di-O-tert-butyl hyponitrite; In methanol; dichloromethane; benzene; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.202004012

upstream raw materials:

1,4-dioxane

4-ethoxy-butyryl chloride

4-butanolide

ethanol

Downstream raw materials:

ethyl 4-<(2-ethoxy-2-oxoethyl)sulfanyl>butanoate

2-cyano-2-phenyldiethyl adipate

3,4-dihydronaphthalene-1(2H)-one

ethylbenzene

Refernces

• 1、 Saegusa et al.. "". . p. 3599. Retrieved 1967.
• 2、 El Aissi, Radhia,Liu, Jianrong,Besse, Sophie,Canitrot, Damien,Chavignon, Olivier,Chezal, Jean-Michel,Miot-Noirault, Elisabeth,Moreau, Emmanuel. "Synthesis and biological evaluation of new quinoxaline derivatives of ICF01012 as melanoma-targeting probes". supporting information. p. 468 - 473. Retrieved 2014/06/09.
• 3、 Bois, Joackim,Espinas, Jeff,Darbost, Ulrich,Felix, Caroline,Duchamp, Christian,Bouchu, Denis,Taoufik, Mostafa,Bonnamour, Isabelle. "Easy and selective method for the synthesis of various mono-O- functionalized Calix[4]arenes: De-O-functionalization using TiCl4". experimental part. p. 7550 - 7558. Retrieved 2011/02/25.