N-Cyanoimido-S,S-dimethyl-dithiocarbonate
[CAS 10191-60-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: N-Cyanoimido-S,S-dimethyl-dithiocarbonate
• Synonyms: S,S-Dimethyl cyanoimidodithiocarbonate; N-Cyano-S,S-dimethyldithioimidocarbonate; {[Bis(methylthio)methylene]amino}(nitrilo)methane
• Molecular Formula: C₄H₆N₂S₂
• Molecular Weight: 146.22
• CAS Registry Number: 10191-60-3
• EC Number: 233-467-6
• SMILES: CSC(=NC#N)SC

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Melting point: 45 - 50 °C (Expl.)
• Boiling point: 229.6±23.0 °C 760 mmHg (Calc.)^*
• Flash point: 92.6±22.6 °C (Calc.)^*, 113 °C (Expl.)
• Index of refraction: 1.571 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H302-H311-H314-H317-H330
• Safety Statements: P260-P261-P262-P264-P270-P271-P272-P280-P284-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P320-P321-P330-P333+P317-P361+P364-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 1759

chemBlink Chemical Story

N-Cyanoimido-S,S-dimethyl-dithiocarbonate, CAS 10191-60-3, is a small, highly activated sulfur- and nitrogen-containing synthetic reagent. Its chemical story is best understood by looking at how its structure creates function rather than by treating the name as a simple catalog label. The molecule or material combines two methylthio groups surrounding an electrophilic carbon and a cyanoimino unit, a combination that explains its relevance to cimetidine manufacture and nitrogen-rich heterocycle synthesis.

Published literature identifies dimethyl cyanocarbonimidodithioate as a raw material used by some manufacturers in cimetidine synthesis. Its methylthio groups provide positions that can be displaced by nitrogen nucleophiles, while the cyanoimino functionality helps establish carbon-nitrogen frameworks. Related chemistry uses the reagent to prepare cyanoguanidines, pyrimidines and fused nitrogen heterocycles.

A published occupational case described severe allergic dermatitis after exposure during pharmaceutical manufacture, illustrating that a reactive intermediate can have hazards quite different from those of the final medicine.

A broader lesson follows from this example. Chemical identity is only the starting point for performance. In polymers and surfactants, composition, molecular distribution and formulation can dominate behavior; in synthetic intermediates, the value may lie in transformations that occur only in later steps; in biologically active compounds, mechanism must be separated from clinical evidence. For N-Cyanoimido-S,S-dimethyl-dithiocarbonate, the most reliable interpretation is therefore the one supported by its documented chemistry and literature rather than an assumed application.

The compound also illustrates why specialty chemicals often look more complicated than their job description suggests. Functional groups are selected to solve different parts of a practical problem: one region may provide reactivity, another solubility or interfacial affinity, and another stability or a controllable breaking point. Once those roles are separated, the long chemical name becomes a map of molecular design.

References:
NIST Chemistry WebBook, SRD 69, CAS 10191-60-3; PubChem, CID 66289; Kim et al. Contact Dermatitis. 1992;27:85-87. PMID: 1355116; ChemicalBook, CAS 10191-60-3.

Read more stories