|
|
| | Ethoxycarbonyl Isothiocyanate Basic information |
| Product Name: | Ethoxycarbonyl Isothiocyanate | | Synonyms: | Ethyl isothiocyanatidocarbonate;ETHYL ISOTHIOCYANATOFORMATE,98%;(Ethoxyoxomethyl) isothiocyanate;Ethoxy(oxo)methyl isothiocyanate;Isothiocyanatoformic acid ethyl;CARBETHOXYISOTHIOCYANATE;CARBON(ISOTHIOCYANATIDIC)ACID, ETHYL ESTER;ISOTHIOCYANATOFORMIC ACID ETHYL ESTER | | CAS: | 16182-04-0 | | MF: | C4H5NO2S | | MW: | 131.15 | | EINECS: | 240-318-9 | | Product Categories: | Miscellaneous Reagents | | Mol File: | 16182-04-0.mol |  |
| | Ethoxycarbonyl Isothiocyanate Chemical Properties |
| Boiling point | 56 °C18 mm Hg(lit.) | | density | 1.112 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.500(lit.) | | Fp | 123 °F | | storage temp. | 2-8°C | | solubility | Soluble in chloroform and ether. | | form | Oil | | Specific Gravity | 1.112 | | color | Light Yellow | | Sensitive | Moisture Sensitive/Lachrymatory | | BRN | 606091 | | InChI | InChI=1S/C4H5NO2S/c1-2-7-4(6)5-3-8/h2H2,1H3 | | InChIKey | BDTDECDAHYOJRO-UHFFFAOYSA-N | | SMILES | C(N=C=S)(=O)OCC | | CAS DataBase Reference | 16182-04-0(CAS DataBase Reference) |
| Hazard Codes | T,Xi | | Risk 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 | | HS Code | 29309090 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Acute Tox. 3 Inhalation
Eye Irrit. 2
Flam. Liq. 3
Resp. Sens. 1
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| | Ethoxycarbonyl Isothiocyanate Usage And Synthesis |
| Chemical Properties | Light Yellow Oil | | 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. | | Uses | Ethoxycarbonyl isothiocyanate has been used in the synthesis of:
- pyrazolo[1,5-a][1,3,5]triazine derivatives, potential inhibitors of protein kinase CK2
- fused thiophene derivatives, having antibacterial and antifungal activities
- 4-thiouracil derivatives
- thiocarbamides from stannylarenes
- 1,3,5-triazin-2-one-4-thiones from 2-amino-2-oxazolines
- N-acylthioureas from aminodeoxy sugars
| | Application | Ethoxycarbonyl isothiocyanate reacts with 2-amino-tetrahydrobenzo[b]thiophene derivatives to yield tetrahydrobenzo[b]thiophen-2-thiourea derivatives.
Ethoxycarbonyl isothiocyanate has been used in the synthesis of:
pyrazolo[1,5-a][1,3,5]triazine derivatives, potential inhibitors of protein kinase CK2
fused thiophene derivatives, having antibacterial and antifungal activities
4-thiouracil derivatives
thiocarbamides from stannylarenes
1,3,5-triazin-2-one-4-thiones from 2-amino-2-oxazolines
N-acylthioureas from aminodeoxy sugars | | 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 | | General Description | Ethoxycarbonyl isothiocyanate reacts with 2-amino-tetrahydrobenzo[b]thiophene derivatives to yield tetrahydrobenzo[b]thiophen-2-thiourea derivatives. | | Hazard | Lachrymator. | | Synthesis | Example 1: Preparation of ethoxycarbonyl isothiocyanate
To a 1 liter jacketed reactor was added sodium thiocyanate (39.1 g, 0.48 mol) and 310 g of toluene. After heating the mixture to 30°C, pyridine (0.4 g, 0.005 mol) and water (0.9 g, 0.05 mol) were added sequentially. Subsequently, ethyl chloroformate (52.9 g, 0.49 mol) was added slowly and dropwise to the reaction system over 40 minutes. The reaction solution was maintained under stirring for 3 hours, during which time the progress of the reaction was monitored by gas chromatography (GC) to confirm that the ethyl chloroformate was almost completely consumed. Upon completion of the reaction, the reaction solution was filtered and analyzed by gas chromatography combined with quantitative internal standard method and the yield of ethoxycarbonyl isothiocyanate was measured to be 99%. | | References | [1] Patent: US2014/100381, 2014, A1. Location in patent: Page/Page column
[2] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5230 - 5231
[3] Research on Chemical Intermediates, 2012, vol. 38, # 3-5, p. 903 - 909 |
| | Ethoxycarbonyl Isothiocyanate Preparation Products And Raw materials |
|