Isopropyl isothiocyanate
[CAS# 2253-73-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanate ester / isocyanate
• Name: Isopropyl isothiocyanate
• Synonyms: 2-isothiocyanatopropane
• Molecular Formula: C₄H₇NS
• Molecular Weight: 101.17
• CAS Registry Number: 2253-73-8
• EC Number: 218-851-3
• SMILES: CC(C)N=C=S

Properties

• Density: 0.948
• Boiling point: 136-137 ºC
• Refractive index: 1.491
• Flash point: 40 ºC

Safety Data

• Hazard Symbols: GHS02;GHS06 Danger
• Hazard Statements: H301-H313-H315-H319-H225
• Precautionary Statements: P501-P270-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P312-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P301+P310+P330-P403+P235-P405

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	3	H226
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H330
Respiratory sensitization	Resp. Sens.	1	H334
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	3	H311
Flammable liquids	Flam. Liq.	2	H225
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1993

Discovory and Applicatios

Isopropyl isothiocyanate is an organic compound with the molecular formula (CH₃)₂CHNCS. The compound is known for its unique isothiocyanate group and is widely used in organic synthesis and various industrial applications.

Isopropyl isothiocyanate was first synthesized in the mid-20th century as part of the study of isothiocyanates, a class of compounds characterized by the -N=C=S functional group. The synthesis of isopropyl isothiocyanate generally involves the reaction of isopropylamine with carbon disulfide, followed by treatment with an oxidizing agent such as hydrogen peroxide to form the isothiocyanate.

Isopropyl isothiocyanate is a colorless to pale yellow liquid with a pungent odor. It is moderately soluble in water but highly soluble in organic solvents such as ethanol, ether, and chloroform. The presence of the isothiocyanate group imparts significant reactivity to the compound, enabling the compound to participate in a variety of chemical reactions, especially those involving nucleophiles.

One of the main uses of isopropyl isothiocyanate is in organic synthesis. Its reactivity makes it a valuable reagent for introducing isothiocyanate functional groups into organic molecules. This ability is particularly useful in the synthesis of thioureas, dithiocarbamates, and other sulfur-containing compounds.

Isopropyl isothiocyanate reacts with amines to form thioureas, which are valuable intermediates in the synthesis of pharmaceuticals and agrochemicals. Thioureas can be further converted into a variety of bioactive molecules, including antiviral and anticancer agents. The isothiocyanate group can participate in cyclization reactions to form heterocyclic compounds, which are essential building blocks in pharmaceutical chemistry. For example, isopropyl isothiocyanate can be used to synthesize thiazoles and thiadiazoles, structures that are commonly found in pharmaceuticals and agrochemicals.

In addition to its role in organic synthesis, isopropyl isothiocyanate has a variety of industrial applications: Isopropyl isothiocyanate is used in the formulation of pesticides and herbicides. Its ability to act as a potent biocide makes it effective in controlling a variety of pests and weeds. The compound disrupts essential biological processes within the target organism, leading to its elimination. In the rubber industry, isopropyl isothiocyanate is used as a vulcanization accelerator. It helps cross-link the rubber molecules, enhancing the mechanical properties and durability of the final product.

Isopropyl isothiocyanate is a reactive compound and should be handled with care. It can irritate the skin, eyes, and respiratory system, and prolonged exposure can lead to serious health effects. When handling this compound, proper safety measures must be taken, such as wearing protective gloves, goggles, and working in a well-ventilated area. It should also be stored in a cool, dry place, away from sources of ignition and incompatible materials.

References

2024. Chalcone derivatives containing 1,2,4-triazole and pyridine moiety: design, synthesis, and antiviral activity. *Molecular Diversity*, 28(6).
DOI: 10.1007/s11030-024-11049-7

2024. Isothiocyanate-Rich Essential Oil from Leaves of Drypetes assamica and Its Antioxidant Activity. *Chemistry of Natural Compounds*, 60(3).
DOI: 10.1007/s10600-024-04380-w

2015. Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard. *Journal of Natural Products*, 78(8).
DOI: 10.1021/acs.jnatprod.5b00272