Ethoxycarbonyl Isothiocyanate

Ethoxycarbonyl Isothiocyanate Property

Boiling point:

56 °C18 mm Hg(lit.)

Density 

1.112 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.500(lit.)

Flash point:

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)

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H331Toxic if inhaled

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethoxycarbonyl Isothiocyanate Chemical Properties,Usage,Production

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
[4] Patent: US2014/100381, 2014, A1. Location in patent: Page/Page column
[5] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5230 - 5231