Pentyl isocyanate

Pentyl isocyanate

Skeletal formula of pentyl isocyanate
Names
IUPAC name 1-isocyanatopentane
Other names 1-pentyl isocyanate n-pentyl isocyanate pentylisocyanate
Identifiers
CAS Number	3954-13-0
3D model (JSmol)	Interactive image
ChemSpider	178519
ECHA InfoCard	100.154.472
EC Number	626-033-6
PubChem CID	206036
CompTox Dashboard (EPA)	DTXSID10192662
InChI InChI=1S/C6H11NO/c1-2-3-4-5-7-6-8/h2-5H2,1H3 Key: VRVUKQWNRPNACD-UHFFFAOYSA-N
SMILES CCCCCN=C=O
Properties
Chemical formula	C6H11NO
Molar mass	113.160 g·mol−1
Appearance	clear liquid
Density	0.878 g/mL at 25 °C
Boiling point	136–137 °C (277–279 °F; 409–410 K)
Hazards
GHS labelling: [1]
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H312, H315, H317, H318, H332, H334, H335
Precautionary statements	P210, P233, P240, P280, P303, P305, P338, P351, P353, P361
Flash point	32 °C (90 °F; 305 K)
Related compounds
Related compounds	Methyl isocyanate Ethyl isocyanate Propyl isocyanate Butyl isocyanate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pentyl isocyanate is an organic chemical compound of carbon, hydrogen, nitrogen, and oxygen with the linear formula CH₃(CH₂)₄NCO. ^{[2] [3] [4]}

Synthesis

The most common industrial route to obtain the compound involves reacting n-pentylamine with phosgene. ^[5] The reaction typically occurs in an inert organic solvent (like chlorobenzene) to form a carbamoyl chloride intermediate, followed by heating (100–200 °C) to complete the conversion and remove hydrogen chloride (HCl).

CH₃(CH₂)₄NH₂ + COCl₂ → CH₃(CH₂)₄NCO + 2 HCl

Physical properties

Pentyl isocyanate forms a clear, flammable colorless liquid. It is highly toxic. ^[6]

Uses

The compound is used in a variety of research applications. ^[7]

References

1. PubChem. "Pentane, 1-isocyanato-". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-20.
2. "389951 Sigma-Aldrich Pentyl isocyanate". Sigma Aldrich . Retrieved 21 January 2026.
3. "Pentyl isocyanate | CAS 3954-13-0 | SCBT - Santa Cruz Biotechnology". scbt.com . Retrieved 21 January 2026.
4. Yaws, Carl L. (20 June 2014). Thermophysical Properties of Chemicals and Hydrocarbons. William Andrew. p. 528. ISBN   978-0-323-29060-9 . Retrieved 21 January 2026.
5. Navarro, Rodrigo; García, Carolina; Rodríguez-Hernández, Juan; Elvira, Carlos; Marcos-Fernández, Angel; Gallardo, Alberto; Reinecke, Helmut (2020). "General approach to prepare polymers bearing pendant isocyanate groups". Polymer Chemistry . 11 (32): 5140–5146. doi:10.1039/D0PY00989J . Retrieved 21 January 2026.
6. "Product name: Pentyl isocyanate" (PDF). AK Scientific. Retrieved 21 January 2026.
7. "1-Pentyl isocyanate". georganics.sk. Retrieved 21 January 2026.