Ethoxycarbonyl isothiocyanate

Base Information

• Chemical Name: Ethoxycarbonyl isothiocyanate
• CAS No.: 16182-04-0
• Molecular Formula: C4H5NO2S
• Molecular Weight: 131.155
• Hs Code.: 29309090
• European Community (EC) Number: 240-318-9
• NSC Number: 158480
• UNII: WQY39AV49E
• DSSTox Substance ID: DTXSID50167253
• Nikkaji Number: J281J
• Mol file: 16182-04-0.mol

Synonyms:Ethoxycarbonyl isothiocyanate;16182-04-0;Ethyl isothiocyanatoformate;Ethoxycarbonylisothiocyanate;Carbethoxy isothiocyanate;ethyl N-(sulfanylidenemethylidene)carbamate;O-ethyl carbonisothiocyanatidate;Carbon(isothiocyanatidic) acid, ethyl ester;MFCD00004814;Carbon(isothiocyanatidic)acid Ethyl Ester;EINECS 240-318-9;ETHYL CARBONISOTHIOCYANATIDATE;NSC-158480;CARBON(ISOTHIOCYANATIDIC)ACID, ETHYL ESTER;ethyl N-carbothioylcarbamate;CARBETHOXYISOTHIOCYANATE;ethoxycarbonylisothiocyanat;ethoxycarbonyl-isothiocyanat;ethoxy carbonylisothiocyanate;ethoxycarbonyli-sothiocyanate;ethyl isothiocyanatocarbonate;ethylmethanoyl isothiocyanate;WQY39AV49E;SCHEMBL42860;ethoxy carbonyl isothiocyanate;ethoxy-carbonyl isothiocyanate;Ethyl isothiocyanatidocarbonate;Ethyl isothiocyanatidocarbonate #;DTXSID50167253;Ethoxycarbonyl isothiocyanate, 98%;AMY10862;Isothiocyanatoformic Acid Ethyl Ester;NSC158480;AKOS005198535;AB00381;NSC 158480;Carbonisothiocyanatidic acid, ethyl ester;E0440;FT-0625742;EN300-51998;A26273;J-520459;J-670007;J-801006

Chemical Property of Ethoxycarbonyl isothiocyanate

Chemical Property:

• Appearance/Colour: light yellow oil
• Vapor Pressure: 3.05mmHg at 25°C
• Refractive Index: n20/D 1.500(lit.)
• Boiling Point: 155.3 °C at 760 mmHg
• Flash Point: 50.6 °C
• PSA: 70.75000
• Density: 1.16 g/cm³
• LogP: 1.24570
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive/Lachrymatory
• Solubility.: Soluble in chloroform and ether.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 131.00409958
• Heavy Atom Count: 8
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

Ethoxycarbonyl isothiocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 23-36/37/38-42
• Safety Statements: 23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)N=C=S
• Uses: Versatile reagent for organic synthesis.Ethoxycarbonyl isothiocyanate is used as a building block in the synthesis of various heterocycles. It is also used for the synthesis of 1,2,4-oxadiazolidine-3,5-dione. It is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. Ethoxycarbonyl isothiocyanate has been used in the synthesis of:pyrazolo[1,5-a][1,3,5]triazine derivatives, potential inhibitors of protein kinase CK2fused thiophene derivatives, having antibacterial and antifungal activities4-thiouracil derivativesthiocarbamides from stannylarenes1,3,5-triazin-2-one-4-thiones from 2-amino-2-oxazolines N-acylthioureas from aminodeoxy sugars

Technology Process of Ethoxycarbonyl isothiocyanate

There total 13 articles about Ethoxycarbonyl isothiocyanate 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: 99.0%

sodium thiocyanide (540-72-7) + chloroformic acid ethyl ester (541-41-3) → Ethoxycarbonyl isothiocyanate (16182-04-0)

Guidance literature:

With pyridine; In water; toluene;

Reference yield: 73.0%

potassium thioacyanate (333-20-0) + chloroformic acid ethyl ester (541-41-3) → Ethoxycarbonyl isothiocyanate (16182-04-0)

Guidance literature:

In acetonitrile; 1.) 15-20 min, 70-75 deg C, 2.) 10 min, 25 deg C;

DOI:10.1021/jo00330a004

Reference yield: 50.0%

ethanol (64-17-5) + Carbonyl-chlorid-isothiocyanat (78366-54-8) → Ethoxycarbonyl isothiocyanate (16182-04-0)

Guidance literature:

In tetrachloromethane; at 22 ℃; for 1h;

upstream raw materials:

potassium thioacyanate

chloroformic acid ethyl ester

lead(II) thiocyanate

ethanol

Downstream raw materials:

N-(p-methylphenyl)-N'-(ethoxycarbonyl)thiourea

2-thioxo-2,3-dihydro-1H-quinazolin-4-one

N¹-Aethoxycarbonyl-N²-phenylthioharnstoff

thiazole-2-ylcarbamic acid ethyl ester

Refernces

Discovery and kinetic evaluation of 6-substituted 4-benzylthio-1,3,5- triazin-2(1H)-ones as inhibitors of cathepsin B

10.1016/j.ejmech.2011.08.005

The research focuses on the discovery and kinetic evaluation of 6-substituted 4-benzylthio-1,3,5-triazin-2(1H)-ones as inhibitors of cathepsin B, a lysosomal cysteine protease with significant roles in both physiological and pathophysiological processes. The study involves the screening of a library of 2,4,6-trisubstituted 1,3,5-triazines and 1,3,5-triazin-2(1H)-ones against three human cathepsins (B, H, and L) and the synthesis of a focused library of new 1,3,5-triazin-2(1H)-ones. The experiments utilized various reactants, including amidine S-(benzyl)isothiourea hydrochloride, ethoxycarbonyl isothiocyanate, and different alkyl or aryl halides, to synthesize the compounds, which were then subjected to enzymatic evaluation. The analyses included detailed kinetics studies to determine the mode of inhibition and the calculation of inhibition constants (Ki and K0) for the compounds. The study revealed that these compounds act as reversible, partial mixed-type inhibitors of cathepsin B with low micromolar inhibitory constants, showing selectivity for cathepsin B over cathepsin H.

Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes

10.1016/j.ejmech.2006.11.006

The research focuses on the development and evaluation of a series of bis-2,5-[4-guanidinophenyl]thiophenes as potential antiparasitic agents. The researchers synthesized these compounds through a five-step process starting from 2,5-bis[trimethylstannyl]thiophene, involving Stille coupling, reduction, and subsequent reactions to introduce guanidino groups. Key chemicals used in the synthesis include 4-bromonitrobenzene, stannous chloride, ethyl isothiocyanatoformate, and various amines for N-alkyl and N-aryl substitutions. The synthesized compounds were evaluated for their DNA affinity and in vitro efficacy against Trypanosoma brucei rhodesiense (T. b. r.), Plasmodium falciparum (P. f.), Leishmania donovani (L. d.), and Trypanosoma cruzi (T. c.), as well as in vivo efficacy against T. b. r. in a mouse model. The results showed that certain compounds exhibited promising in vitro activity against T. b. r. and P. f., with some demonstrating superior in vivo activity against T. b. r. compared to existing drugs like pentamidine and furamidine. The study concludes that these bis-2,5-[4-guanidinophenyl]thiophenes merit further investigation as potential new treatments for parasitic diseases due to their strong DNA affinity and effective antiparasitic activity.