Ethyl 3-mercaptopropionate

Base Information

• Chemical Name: Ethyl 3-mercaptopropionate
• CAS No.: 5466-06-8
• Molecular Formula: C5H10 O2 S
• Molecular Weight: 134.199
• Hs Code.: 2930909090
• European Community (EC) Number: 226-771-5
• NSC Number: 25754
• UNII: 22GQZ8P70D
• DSSTox Substance ID: DTXSID7063922
• Nikkaji Number: J101.168E
• Wikidata: Q27253650
• Metabolomics Workbench ID: 49027
• ChEMBL ID: CHEMBL3234723
• Mol file: 5466-06-8.mol

Synonyms:ethyl 3-mercaptopropionate

Chemical Property of Ethyl 3-mercaptopropionate

Chemical Property:

• Appearance/Colour: colourless liquid with an unpleasant smell
• Vapor Pressure: 0.445mmHg at 25°C
• Refractive Index: n20/D 1.457(lit.)
• Boiling Point: 194.3°Cat760mmHg
• PKA: 9.72±0.10(Predicted)
• Flash Point: 72.8°C
• PSA: 65.10000
• Density: 1.043g/cm³
• LogP: 0.86940
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 134.04015073
• Heavy Atom Count: 8
• Complexity: 72.8

Purity/Quality:

99% ^*data from raw suppliers

Ethyl3-Mercaptopropanoate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: CCOC(=O)CCS
• Uses: Ethyl 3-Mercaptopropanoate is a useful synthetic intermediate. It can be used to prepare acylaminobutyldecahydroisoquinolines with HIV protease-inhibiting activities. It can also be used to prepare new anti-MRSA cephalosporins (cephalosporins C zinc salt, C258750).

Technology Process of Ethyl 3-mercaptopropionate

There total 12 articles about Ethyl 3-mercaptopropionate 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: 77.0%

ethanol (64-17-5) + 3-mercaptopropionic acid (107-96-0) → 3-mercaptopropionic acid ethyl ester (5466-06-8)

Guidance literature:

With toluene-4-sulfonic acid; for 15h; Heating;

DOI:10.1080/00304949609356537

Reference yield: 61.0%

ethyl acetate (141-78-6) + 3-mercaptopropionic acid (107-96-0) → 3-mercaptopropionic acid ethyl ester (5466-06-8)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 14h; Reflux;

DOI:10.1002/chem.201201370

Reference yield:

3-acetylsulfanyl-propionic acid ethyl ester (221219-13-2) → 3-mercaptopropionic acid ethyl ester (5466-06-8)

Guidance literature:

With sodium hydroxide; In acetone; Ambient temperature;

DOI:10.1016/S0040-4039(98)02545-3

upstream raw materials:

diethyl 3,3'-thiobispropionate

Ethyl 3-bromopropionate

thiocarboxamide

ethanol

Downstream raw materials:

2-cyanothiophenol

o-(ethyl carboxy-3 ethyl)mercapto benzonitrile

ethyl (S)-3-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-phenylpropyl>thio>propanoate

C₁₁H₁₄ClO₂PS

Refernces

• 1、 Mustafaev,Efendieva, Kh. K.,Akchurina, T. Kh.. "Synthesis of 2-sulfanylidene-1,3-thiazolidin-4-one derivatives". . p. 1860 - 1863. Retrieved 2018/02/06.
• 2、 Zheng, Tu-Cai,Burkart, Maureen,Richardson, David E.. "A general and mild synthesis of thioesters and thiols from halides". . p. 603 - 606. Retrieved 2007/10/03.