Thiocyanatoacetic acid ethyl ester

Base Information

• Chemical Name: Thiocyanatoacetic acid ethyl ester
• CAS No.: 5349-28-0
• Molecular Formula: C5H7 N O2 S
• Molecular Weight: 145.182
• Hs Code.: 2930909090
• NSC Number: 1202
• DSSTox Substance ID: DTXSID80201674
• Nikkaji Number: J7.975H
• Wikidata: Q83074876
• Mol file: 5349-28-0.mol

Synonyms:ethyl 2-thiocyanatoacetate;5349-28-0;Thiocyanatoacetic acid ethyl ester;Ethyl thiocyanatoacetate;REE (acetate);Ethyl thiocyanoacetate;Thiocyano-essigsaeure-aethyl-ester;NSC 1202;ACETIC ACID, THIOCYANATO-, ETHYL ESTER;BRN 1761202;Thiocyano-essigsaeure-aethyl-ester [German];4-03-00-00618 (Beilstein Handbook Reference);ETHYL2-THIOCYANATOACETATE;Acetic acid,2-thiocyanato-, ethyl ester;ethyl 2-(cyanosulfanyl)acetate;ethyl thiocyano-acetate;WLN: NCS1VO2;SCHEMBL4867420;DTXSID80201674;NSC1202;thiocyanato-acetic acid ethyl ester;NSC-1202;MFCD00101190

Chemical Property of Thiocyanatoacetic acid ethyl ester

Chemical Property:

• Vapor Pressure: 2.15E-06mmHg at 25°C
• Refractive Index: 1.5216 (estimate)
• Boiling Point: 224.1°Cat760mmHg
• Flash Point: 89.4°C
• PSA: 75.39000
• Density: 1.19g/cm³
• LogP: 0.76378
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 145.01974964
• Heavy Atom Count: 9
• Complexity: 137

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl2-Thiocyanatoacetate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CSC#N

Technology Process of Thiocyanatoacetic acid ethyl ester

There total 11 articles about Thiocyanatoacetic acid ethyl ester 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: 98.3%

ethyl bromoacetate (105-36-2) → thiocyanato-acetic acid ethyl ester (5349-28-0)

Guidance literature:

With sodium thiocyanide; In water; at 20 ℃; for 5h;

DOI:10.1002/ejoc.201001227

Reference yield: 97.0%

potassium thioacyanate (333-20-0) + chloroacetic acid ethyl ester (105-39-5) → thiocyanato-acetic acid ethyl ester (5349-28-0)

Guidance literature:

In ethanol; for 3h; Heating / reflux;

Reference yield: 80.0%

potassium thioacyanate (333-20-0) + ethyl bromoacetate (105-36-2) → thiocyanato-acetic acid ethyl ester (5349-28-0)

Guidance literature:

With 18-crown-6 ether; In benzene; for 168h; Ambient temperature;

DOI:10.1246/bcsj.69.1769

upstream raw materials:

diazoacetic acid ethyl ester

potassium thioacyanate

ethanol

chloroacetic acid ethyl ester

Downstream raw materials:

ethyl isothiocyanate

ethyl bromoacetate

2-thioxo-4-thiazolidinone

pseudothiohydantoin

Refernces

• 1、 Pirenne, Vincent,Kurtay, Gülbin,Voci, Silvia,Bouffier, Laurent,Sojic, Neso,Robert, Frédéric,Bassani, Dario M.,Landais, Yannick. "Eosin-Mediated Alkylsulfonyl Cyanation of Olefins". supporting information. p. 4521 - 4525. Retrieved 2018/08/09.
• 2、 Li, Jing,Cao, Jing-Jing,Wei, Jun-Fa,Shi, Xian-Ying,Zhang, Li-Hui,Feng, Jin-Juan,Chen, Zhan-Guo. "Ionic liquid brush as a highly efficient and reusable catalyst for on-water nucleophilic substitutions". supporting information; experimental part. p. 229 - 233. Retrieved 2011/03/20.