16182-04-0

Basic information

• Product Name: ETHOXYCARBONYL ISOTHIOCYANATE
• Synonyms: CARBETHOXYISOTHIOCYANATE;CARBON(ISOTHIOCYANATIDIC)ACID, ETHYL ESTER;ISOTHIOCYANATOFORMIC ACID ETHYL ESTER;ETHOXYCARBONYL ISOTHIOCYANATE;ETHYL ISOTHIOCYANATOFORMATE;Ethyl isothiocyanatidocarbonate;ETHYL ISOTHIOCYANATOFORMATE,98%;(Ethoxyoxomethyl) isothiocyanate
• CAS NO: 16182-04-0
• Molecular Formula: C₄H₅NO₂S
• Molecular Weight: 131.15
• EINECS: 240-318-9
• Product Categories: Miscellaneous Reagents
• Mol File: 16182-04-0.mol

Chemical Properties

• Boiling Point: 56 °C18 mm Hg(lit.)
• Flash Point: 123 °F
• Appearance: light yellow oil
• Density: 1.112 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.05mmHg at 25°C
• Refractive Index: n20/D 1.500(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform and ether.
• Sensitive: Moisture Sensitive/Lachrymatory
• BRN: 606091
• CAS DataBase Reference: ETHOXYCARBONYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHOXYCARBONYL ISOTHIOCYANATE(16182-04-0)
• EPA Substance Registry System: ETHOXYCARBONYL ISOTHIOCYANATE(16182-04-0)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23-36/37/38-42
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2929 6.1/PG 2
• WGK Germany: 3
• F: 9-13-19-21
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 16182-04-0(Hazardous Substances Data)

Usage

Uses

Used in 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, making it an important raw material and intermediate in organic synthesis.
Used in Pharmaceutical Industry:
ETHOXYCARBONYL ISOTHIOCYANATE is used as a key intermediate in the development of pharmaceuticals, contributing to the synthesis of potential inhibitors of protein kinase CK2, such as pyrazolo[1,5-a][1,3,5]triazine derivatives.
Used in Agrochemical Industry:
In the agrochemical industry, ETHOXYCARBONYL ISOTHIOCYANATE is utilized for the synthesis of fused thiophene derivatives, which possess antibacterial and antifungal activities, making them valuable for the development of new agrochemical products.
Used in Dye Industry:
ETHOXYCARBONYL ISOTHIOCYANATE is employed in the synthesis of various dyes, including 4-thiouracil derivatives, thiocarbamides from stannylarenes, 1,3,5-triazin-2-one-4-thiones from 2-amino-2-oxazolines, and N-acylthioureas from aminodeoxy sugars, showcasing its versatility in the dye industry.

Synthesis Reference(s)

Using Schiff base as a phase transfer catalyst, ethoxycarbonyl isothiocyanate was synthesized by reacting ethyl chloroformate with sodium thiocyanate. www.semanticscholar.org

Hazard

Lachrymator.

InChI:InChI=1/C4H5NO2S/c1-2-7-4(6)5-3-8/h2H2,1H3

Upstream product

• 333-20-0 potassium thioacyanate 
• 541-41-3 chloroformic acid ethyl ester 
• 592-87-0 lead(II) thiocyanate 
• 64-17-5 ethanol 
• 78366-54-8 Carbonyl-chlorid-isothiocyanat 
• 1147550-11-5 ammonium thiocyanate 
• 79-03-8 propionyl chloride 
• 540-72-7 sodium thiocyanide 
• 99-56-9 4-Nitrophenylene-1,2-diamine 

Downstream Products

• 52009-44-6 N-(p-methylphenyl)-N'-(ethoxycarbonyl)thiourea 
• 13906-09-7 2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 24774-92-3 N¹-Aethoxycarbonyl-N²-phenylthioharnstoff 
• 103122-66-3 <(2-Methylpropoxy)(thiocarbonyl)>-carbamic Acid Ethyl Ester 
• 859481-43-9 (5-amino-4-methyl-thiazol-2-yl)-carbamic acid ethyl ester 
• 136646-34-9 4-(2,4-dimethyl-phenyl)-3-thio-allophanic acid ethyl ester 
• 859481-35-9 (5-amino-4-phenyl-thiazol-2-yl)-carbamic acid ethyl ester 
• 33017-85-5 6-Chlor-4-oxo-2-thioxo-1,2,3,4-tetrahydrochinazolin 
• 51863-43-5 N-Ethoxycarbonyl-N'-methylthioharnstoff 
• 54035-70-0 ethyl N-(benzylcarbamothioyl)carbamate 
• 412311-64-9 (5-amino-thiazol-2-yl)-carbamic acid ethyl ester 
• 59965-72-9 Ethyl N-(benzyloxythiocarbonyl)carbamate 
• 3673-38-9 N-ethoxycarbonylthiourea 
• 3673-34-5 thiazole-2-ylcarbamic acid ethyl ester 

Relevant articles and documents

Lipid membrane adhesion and fusion driven by designed, minimally multivalent hydrogen-bonding lipids

Cyanuric acid (CA) and melamine (M) functionalized lipids can form membranes that exhibit robust hydrogen-bond driven surface recognition in water, facilitated by multivalent surface clustering of recognition groups and variable hydration at the lipid-water interface. Here we describe a minimal lipid recognition cluster: three CA or M recognition groups are forced into proximity by covalent attachment to a single lipid headgroup. This trivalent lipid system guides recognition at the lipid-water interface using cyanurate-melamine hydrogen bonding when incorporated at 0.1-5 mol percent in fluid phospholipid membranes, inducing both vesicle-vesicle binding and membrane fusion. Fusion was accelerated when the antimicrobial peptide magainin was used to anchor trivalent recognition, or when added exogenously to a preassembled lipid vesicle complex, underscoring the importance of coupling recognition with membrane disruption in membrane fusion. Membrane apposition and fusion were studied in vesicle suspensions using light scattering, FRET assays for lipid mixing, surface plasmon resonance, and cryo-electron microscopy. Recognition was found to be highly spatially selective as judged by vesicular adhesion to surface patterned supported lipid bilayers (SLBs). Fusion to SLBs was also readily observed by fluorescence microscopy. Together, these studies indicate effective and functional recognition of trivalent phospholipids, despite low mole percentage concentration, solvent competition for hydrogen bond donor/acceptor sites, and simplicity of structure. This novel designed molecular recognition motif may be useful for directing aqueous-phase assembly and biomolecular interactions.

A novel dithiourea and its response to metal ions

The synthesis, characterization, and its response to metal ions of a novel thiourea N,N′-diethoxycarbonyl-N″,N?-(1,2-ethylidene) dithiourea was reported. The results show that this dithiourea with new structure can react with Cu2+ and Ni2+ separately, and has a best selectivity to Fe3+ ions. Bench-scale flotation tests were also carried out, verifying it has higher copper flotation recovery and better selectivity to sulfide ores containing Cu compared with universal collectors.

Visualized detection of melamine in milk by supramolecular hydrogelations

We reported a visualized detection system for melamine based on supramolecular dydrogelations.

Synthesis and reaction with metal ions of a new thionocarbamate

The synthesis and research of a novel thionocarbamate N,N′-diethoxy- carbonyl-O,O′-(1,4-butylidene) dithionocarbamate which contains two ester and two thioamide groups are reported. This compound was characterized by elemental analysis, UV spectrum, infrared spectrum, mass spectrum, and 1H NMR and 13C NMR spectroscopy. Additionally, the metal ion-collector interaction in organic solution was put into practice. The results of UV spectroscopic analysis showed that this dithionocarbamate with a new structure exhibited a stronger complex ability with Cu2+ than with Ni2+ or Fe3+. Furthermore, infrared spectroscopic analysis implicated that this dithionocarbamate binds to Cu2+ through both the C=O and C=S groups. Bench-scale flotation tests were also carried out, verifying that it has a higher copper flotation recovery and better selectivity to sulfide ores containing Cu compared with universal collectors. Springer Science+Business Media B.V. 2011.

Fusion reactions of N-heterocyclic moieties to thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidines

Derivatives of the novel heterocyclic parent systems imidazolo[1,2-a]thiopyrano[4′,3′:4,5]thieno[2,3-d]-pyrimidine (B) and thiopyrano[4′,3′:4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (C) have been synthesized by fusing pyrimidine moieties to 2-amino-4,7-dihydro-5H-thieno[2,3-c]thiopyran-3-car-boxylic acid ethyl ester (1) and -3-carbonitrile (10), followed by cyclization reactions of the title intermediates A thus obtained.

Structural, Hirshfeld surface and in?vitro cytotoxicity evaluation of five new N-aryl-N’-alkoxycarbonyl thiocarbamide derivatives

Five new compounds, N-(2, 4-dichlorophenyl)-N’-(methoxycarbonyl) thiocarbamide (1), N-(2, 4-dichlorophenyl)-N’-(ethoxycarbonyl) thiocarbamide (2), N-(2, 4-dichlorophenyl)-N’-(2, 2, 2-trichloroethoxycarbonyl) thiocarbamide (3), N-(2,4-dichlrophenyl)-N’-(pentoxycarbonyl) thiocarbamide (4) and N-(4-nitrophenyl)-N’-(pentoxycarbonyl) thiocarbamide (5), have been synthesized by the reaction of various alkoxy chloroformates with 2, 4-dichloroaniline/4-nitroaniline.The molecular structures of the compounds were elucidated by using spectroscopic methods (FT-IR, 1H and 13C NMR) and single-crystal X-ray structure analysis of compounds 2 and 5. Antiperiplanar orientation of C = O and C = S group across C–N bonds of thiocarbamide core may be due to the presence of intramolecular (N–H···O–C) hydrogen bond in the crystal structure of both the compounds. The presence of intermolecular interactions (C–H···S, C–H···O and N–H···S) in the molecular structure of the compounds has been studied in detail using Hirshfeld surfaces and their associated two-dimensional fingerprint plots. In vitro cytotoxicity screening of the synthesized compounds evaluated on a panel of seven human cancer cell lines (cervical carcinoma (2008, C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1)) demonstrated significant inhibitory properties.

Weak interaction and supramolecular structure of N-ethoxycarbonyl-N′- arylthiourea

Two kinds of N-ethoxycarbonyl-N′-arylthiourea were synthesized, and their structure was determined by X-ray diffraction. There are inter-and intramolecular hydrogen bonds in these compounds. In the crystals, the compounds were assembled to one-dimensional catenulate supramolecular structure by intermolecular hydrogen bonds. Copyright Taylor & Francis Group, LLC.

Preparation process of alkoxycarbonyl thiourea

The invention relates to a preparation process of alkoxycarbonyl thiourea. The process comprises the following steps: 1, preparing alkoxycarbonyl isothiocyanate by using chloroformate and thiocyanateas raw materials; and 2, adding an aqueous solution of an amine compound to the bottom of a reaction kettle, slowly dropwise adding the alkoxycarbonyl isothiocyanate prepared in the step 1, controlling the dropwise adding temperature at 0-50 DEG C, continuously heating to 60-90 DEG C after the dropwise adding is completed, and standing for layering to obtain an organic phase product. According tothe preparation process of the alkoxycarbonyl thiourea, the feeding mode is changed, and production operation control is better facilitated; the heat release rate of the alkoxycarbonyl thiourea synthesis reaction is favorably reduced; safe production is facilitated; and no flammable and explosive organic solvent with high cost and large pollution is used. The process is simple to operate, and is more beneficial to industrial production control operation, so that safe production of the alkoxycarbonyl thiourea is realized.

Synthetic method of 1,3,4-thiadiazole derivative

The invention discloses a synthetic method of a 1,3,4-thiadiazole derivative. The method comprises the following steps: (1) using hydrazine hydrate as a raw material, under the action of a catalyst, reacting with acid, to obtain a hydrazide compound I; (2) using alkyl chloroformate and thiocyanate to react in a condition of a solvent, to obtain an isothiocyanate compound II; (3) in a reaction system of the isothiocyanate compound II, adding solution containing the compound I, reacting to obtain solution containing a compound III; (4) processing the solution of the compound III by dehydrating,neutralizing, and washing, to obtain a compound IV; (5) in the conditions of an acid-binding agent and a solvent, adding alkyl halide or sulfuric acid diester into the compound IV, reacting to obtaina compound V; and (6) enabling the compound V to perform an amination reaction with primary amine, to obtain the 1,3,4-thiadiazole derivative VI. The preparation method has the advantages of green andno pollution, simple and convenient operation, higher yield, mild reaction condition and the like.

Synthesis, crystal structure and herbicidal activity of a series of [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds

With the aim of obtaining efficient, safe and environmentally friendly green herbicide, a series of [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds (8a-8f) were synthesized by reacting 2-amino-5,7-(bis-substituted)- 1,2,4-triazolo[1,5-a]pyrimidine (4a and 4b) with 2-substituted-6-trifluoromethyl-benzenesulfonyl chloride (7a-7c). And their structures were characterized by H-NMR, C-NMR, HRMS, FTIR, single-crystal X-ray diffraction, elemental analysis. Moreover, their herbicidal activities against six species of weeds were evaluated. Three target compounds such as 8a, 8c and 8e, exhibited significant postemergence herbicidal activity against some common dicotyledons and monocotyledons under different concentrations. The structure and activity relationship is discussed based on the herbicidal performances of the compounds with different substituents. The investigation results indicated that the above structures could serve as lead compounds for the development of new herbicides.