N-Cyanoimido-S,S-dimethyl-dithiocarbonate Chemical Properties

Melting point:

45-50 °C (lit.)

Boiling point:

229.6±23.0 °C(Predicted)

Density 

1.298 (estimate)

refractive index 

1.5000 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Slightly soluble in methanol.

form 

solid

pka

-5.10±0.50(Predicted)

Appearance

White to off-white Solid

BRN 

635998

InChI

InChI=1S/C4H6N2S2/c1-7-4(8-2)6-3-5/h1-2H3

InChIKey

IULFXBLVJIPESI-UHFFFAOYSA-N

SMILES

C(=N/C#N)(/SC)\SC

CAS DataBase Reference

10191-60-3(CAS DataBase Reference)

NIST Chemistry Reference

N-Cyano-s,s'-dimethyldithioimido carbonate(10191-60-3)

EPA Substance Registry System

Carbonimidodithioic acid, cyano-, dimethyl ester (10191-60-3)

Safety Information

Hazard Codes 

C,T

Risk Statements 

22-34-23/24/25-36/37

Safety Statements 

26-36/37/39-45-38-28A-7/9

RIDADR 

UN 1759 8/PG 2

WGK Germany 

3

F 

13-19

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29309090

MSDS

• Language:English Provider:{[Bis(methylthio)methylene]amino}(nitrilo)methane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Cyanoimido-S,S-dimethyl-dithiocarbonate Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

Dimethyl cyanodithioiminocarbonate has been used in the synthesis of 4-methylthiopyrazolo[1,5-a]-1,3,5-triazines, methylsulfanylpyrimidines, cyanoguanidines and N-aryl-6-methylsulfanyl-4-oxopyrimidine-5-carbonitriles. It has been also used in the synthesis of methylsulfanyl derivatives of azoloazines and azoloazoles.

Synthesis

Dimethyl N-cyanoimido-S,S-dithiocarbonate was synthesized according to the method reported in the literature. The procedure was as follows: cyanamide (0.02 mol, 50% aqueous solution) was dissolved in 80 mL of water, followed by addition of potassium hydroxide (0.04 mol) and stirred for 45 min at room temperature. Carbon disulfide was then added and the reaction mixture was heated to 40°C. After complete dissolution of carbon disulfide (about 2 hours), iodomethane (0.04 mole) was added and stirred overnight at room temperature. After completion of the reaction, the precipitate was collected by filtration, the solid product was washed with water, dried under vacuum at room temperature to constant weight and finally purified by recrystallization from ethanol. The resulting product was dimethyl cyanodithioiminocarbonate (1c) in 71% yield with a melting point of 58-60°C. Infrared spectra (FT-IR, ν/cm?1): 1678, 2176. nuclear magnetic resonance hydrogen spectra (1H NMR, 300 MHz, DMSO-d6) δ: 2.90 (s, 6H, 2×SCH3). NMR carbon spectra (13C NMR, 75 MHz, CDCl3) δ: 18.8, 115.3, 186.8.

References

[1] Tetrahedron, 2008, vol. 64, # 39, p. 9309 - 9314
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 5, p. 759 - 764
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2309 - 2314
[4] Synthetic Communications, 2004, vol. 34, # 5, p. 805 - 815
[5] Synthetic Communications, 2006, vol. 36, # 6, p. 743 - 753

N-Cyanoimido-S,S-dimethyl-dithiocarbonate(10191-60-3)Related Product Information

• ALTRENOGEST
• Dimethyl disulfide
• N,N-Dimethylformamide
• ISOMETHIOZIN
• ETHANE
• Dimethyl phthalate
• Dimethyl sulfate
• Dimethyl sulfoxide
• Glycine
• Dacthal
• Dimethyl fumarate
• Dimethyl ether
• Dimethyl carbonate
• Cimetidine
• 4,4'-Diphenylmethane diisocyanate
• Methylene Blue
• Dimethoxymethane
• ETHYL 2-CYANOACRYLATE