Propyl isothiocyanate
[CAS# 628-30-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiocyanate / isothiocyanate
• Name: Propyl isothiocyanate
• Synonyms: 1-isothiocyanatopropane
• Molecular Formula: C₄H₇NS
• Molecular Weight: 101.17
• CAS Registry Number: 628-30-8
• EC Number: 211-035-8
• SMILES: CCCN=C=S

Properties

• Density: 0.978
• Boiling point: 153 °C
• Refractive index: 1.503-1.505
• Flash point: -15 °C

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H225-H226-H302-H312-H314-H332-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P261-P264-P270-P271-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P319-P321-P330-P362+P364-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Flammable liquids	Flam. Liq.	2	H225
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	2	H330
Skin sensitization	Skin Sens.	1	H317
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	2	H310

• Transport Information: UN 2924

Discovery and Applications

Propyl isothiocyanate (also known as 1-isothiocyanatopropane) is a valuable organic compound with a wide range of applications in chemical synthesis and industry. Its unique structure and reactivity make it a versatile reagent in various fields of chemistry.

Propyl isothiocyanate was first synthesized in the early 20th century as part of the ongoing research on isothiocyanates, a class of compounds known for their reactivity and usefulness in organic chemistry. The compound has the chemical formula C₃H₇NS and has a propyl group attached to an isothiocyanate functional group (−NCS).

It is typically a colorless to pale yellow liquid with a pungent odor. Propyl isothiocyanate is soluble in organic solvents such as ethanol and ether, but is not easily soluble in water. Its reactivity stems from the isothiocyanate group, which is highly nucleophilic and can participate in a variety of chemical reactions.

Propyl isothiocyanate is used in the synthesis of thiourea, an important intermediate in organic synthesis. Thiourea can be further converted into a range of other compounds, including pharmaceuticals and agrochemicals.

This compound generates other isothiocyanate derivatives by reacting with different nucleophiles. These derivatives are useful in medicinal chemistry and materials science.

Propyl isothiocyanate reacts with primary and secondary amines to form various substituted thiourea derivatives. These reactions can be used to prepare compounds with potential biological activity.

In polymer chemistry, propyl isothiocyanate is used to make polymers with isothiocyanate groups. These polymers can have specific properties and applications, including coatings and adhesives.

Propyl isothiocyanate is used as a reagent in qualitative analysis to detect the presence of certain metal ions and organic compounds. It forms unique complexes or precipitates that can be used to identify and quantify various substances.

In biochemical assays, propyl isothiocyanate can be used as a labeling agent to tag specific molecules or proteins. This labeling is essential for studying protein interactions and tracking biological processes.

Because propyl isothiocyanate has a pungent odor and is potentially irritating, it should be handled with care. It can irritate the skin, eyes, and respiratory system. Appropriate safety measures include the use of personal protective equipment such as gloves, goggles, and working in a well-ventilated area. The compound should be stored in a cool, dry place away from heat and open flame.

References

1994. Synthesis of thiocyanato-, isothiocyanato-, and halo derivatives of 1-arylpropanes and their antimicrobial properties. Pharmaceutical Chemistry Journal, 28(3).
DOI: 10.1007/bf02219207

2006. Leaching of isothiocyanates through intact soil following simulated biofumigation. Plant and Soil, 284(1-2).
DOI: 10.1007/s11104-006-9176-2

2019. Quantification of Total Glucosinolates and Isothiocyanates for Common Brassicaceous Vegetables Consumed in the US Market Using Cyclocondensation and Thiocyanate Ion Measurement Methods. Journal of Analysis and Testing, 3(3).
DOI: 10.1007/s41664-019-00114-y