Ethyl 2-isothiocyanatopropanoate

Base Information

• Chemical Name: Ethyl 2-isothiocyanatopropanoate
• CAS No.: 39574-16-8
• Molecular Formula: C6H9NO2S
• Molecular Weight: 159.209
• Hs Code.: 2930909090
• European Community (EC) Number: 671-034-7
• DSSTox Substance ID: DTXSID20960177
• Nikkaji Number: J308.250D
• Mol file: 39574-16-8.mol

Synonyms:Ethyl 2-isothiocyanatopropanoate;39574-16-8;Ethyl 2-isothiocyanatopropionate;Propanoic acid, 2-isothiocyanato-, ethyl ester;ethyl N-(thioxomethylene)alaninate;SCHEMBL1457221;DTXSID20960177;ALJGYASQFZQQJX-UHFFFAOYSA-N;Ethyl 2-isothiocyanatopropanoate #;Ethyl L-2-isothiocyanatopropanoate;MFCD00070636;AKOS009461120;AS-61176;Ethyl N-(sulfanylidenemethylidene)alaninate;2-Isothiocyanato-propionic acid ethyl ester;BB 0254423;FT-0612729;EN300-1458863;A912690;J-802206

Chemical Property of Ethyl 2-isothiocyanatopropanoate

Chemical Property:

• Vapor Pressure: 0.128mmHg at 25°C
• Refractive Index: 1.4925
• Boiling Point: 218.2 °C at 760 mmHg
• Flash Point: 85.7 °C
• PSA: 70.75000
• Density: 1.1 g/cm³
• LogP: 1.04080
• Sensitive.: Moisture Sensitive
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 159.03539970
• Heavy Atom Count: 10
• Complexity: 163

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl2-Isothiocyanatopropionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)N=C=S

Technology Process of Ethyl 2-isothiocyanatopropanoate

There total 7 articles about Ethyl 2-isothiocyanatopropanoate 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%

potassium thioacyanate (333-20-0) + rac-2-(Trifluormethylsulfonyloxy)propionsaeure-ethylester (77902-90-0) → α-thiocyanato-propionic acid ethyl ester (55602-05-6) + 2-isothiocyanatopropionic acid ethyl ester (39574-16-8)

Guidance literature:

In acetonitrile; at 20 ℃; for 3h; Yields of byproduct given;

Reference yield: 72.0%

ethyl l-2-((methylsulfonyl)oxy)propionate (58742-64-6) + potassium thioacyanate (333-20-0) → α-thiocyanato-propionic acid ethyl ester (55602-05-6) + 2-isothiocyanatopropionic acid ethyl ester (39574-16-8)

Guidance literature:

In acetonitrile; Yields of byproduct given; 20 deg C, 24 h; 82 deg C, 3 h;

Reference yield: 45.0%

potassium thioacyanate (333-20-0) + Ethyl 2-bromopropionate (535-11-5,41978-69-2) → α-thiocyanato-propionic acid ethyl ester (55602-05-6) + 2-isothiocyanatopropionic acid ethyl ester (39574-16-8)

Guidance literature:

With 18-crown-6 ether; In benzene; for 72h; Heating;

DOI:10.1246/bcsj.69.1769

upstream raw materials:

thiophosgene

AlaOEt

carbon disulfide

DL-alanine ethyl ester hydrochloride

Downstream raw materials:

4-methyl-5t-phenyl-2-thioxo-oxazolidine-4r-carboxylic acid ethyl ester

4-methyl-5c-phenyl-2-thioxo-oxazolidine-4r-carboxylic acid ethyl ester

4-methyl-5-phenyl-2-thioxo-oxazolidine-4-carboxylic acid ethyl ester

4-methyl-2-oxo-5c-phenyl-oxazolidine-4r-carboxylic acid ethyl ester

Refernces

• 1、 Burkard, Ulrike,Effenberger, Franz. "Substitution of 2-(Sulfonyloxy)carboxylates with Oxygene and Sulfur Nucleophiles without Racemization". . p. 1594 - 1612. Retrieved 2016/06/15.