This compound belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
Not applicable. No bioassay or immunoassay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For practical usage, refer to Reaction Conditions and Application notes in Reaction & Applications.
Biological Roles
Pentyl isocyanate is a synthetic, aliphatic isocyanate and does not have a native biological role.
General/toxicological context (literature)
Isocyanates are electrophiles that can react with biological nucleophiles (e.g., thiols on proteins), underlying their sensitization potential.
They are not metabolites nor cofactors; any biological interactions are typically adverse (e.g., haptenation) rather than functional roles.
Use in biochemical research (general):
Occasionally employed to derivatize amines/alcohols on biomolecules for analytical purposes, forming stable urea/carbamate linkages. Such applications must be conducted under strictly anhydrous conditions and with appropriate safety controls.
No clinical or therapeutic claims are made. For research use only.
Buffer Applications
This compound is not a buffering agent and is not used to prepare biological buffers. The isocyanate group reacts with water and amines in buffer systems, making it unsuitable for maintaining pH or for aqueous buffer formulations. For relevant use, see Reaction & Applications and Synthetic Utility.
Green Alternatives
Consider greener choices in both reagent and solvent dimensions while preserving reactivity and selectivity.
Solvent choices (literature/general)
Prefer 2-MeTHF or CPME over DCM/THF when feasible: lower toxicity, renewable (2-MeTHF), and good water-scavenging via azeotropy
Toluene can substitute for chlorinated solvents in many urethane/urea formations
Reagent strategy comparisons (general)
Direct isocyanate route vs. phosgene-free carbamoylations
Isocyanate (this product): atom-economical addition to alcohols/amines; hazards include sensitization and moisture reactivity
CDI or DSC methods: form carbamates/ureas via imidazole or succinimide leaving groups; often milder handling, but generate stoichiometric waste and may require base
Small comparison table (general)
| Approach | Pros | Cons |
| --- | --- | --- |
| Pentyl isocyanate + ROH/RNH2 | No external base needed; high atom economy; fast | Isocyanate sensitizer; moisture sensitive |
| CDI-mediated coupling | Phosgene-free; solid reagent; often safer to handle | Generates imidazole waste; slower with hindered substrates |
| DSC-mediated coupling | Efficient for phenols; mild | N-succinimide waste; may need base/catalyst |
| Solvent: 2-MeTHF | Greener, renewable; good for Dean–Stark | Slightly higher peroxide risk than toluene; ensure inhibitor monitoring |
Implement green metrics: minimize chlorinated solvents, scale with calorimetry, and recover solvents where possible.
Pharmaceutical Uses
Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet.
General context (literature/industry):
Pentyl isocyanate may serve as a synthetic intermediate or building block in API process development, enabling installation of urea or carbamate moieties common in drug-like molecules.
Not used as a pharmaceutical excipient due to reactivity and sensitization hazards.
For GMP or regulatory contexts, control of residual isocyanate and urea byproducts is critical; validated analytical methods (GC/IR for NCO, HPLC for ureas) are typically employed.
No therapeutic claims are made. Research and process development use only.
Physical Properties
Item-specific specifications for this product are not provided. Values below are literature/general references for pentyl isocyanate and are NOT product specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: typically ~145–150 °C at 1 atm (literature)
Melting point: typically below −60 °C (liquid at ambient) (literature)
Density: ~0.90–0.92 g/mL at 25 °C (literature)
Refractive index (n20 D): ~1.408–1.414 (literature)
Vapor pressure: expected low at 25 °C relative to lower alkyl isocyanates (literature)
Solubility: miscible with many aprotic organic solvents (e.g., hexane, toluene, Et2O, THF, DCM); reacts slowly with protic solvents and water (literature)
LogP: estimated >2 due to C5 chain (literature/computed trend)
pKa: not applicable; no ionizable protons; isocyanate carbon is electrophilic (literature)
Notes for practitioners (general):
Strong moisture sensitivity: hydrolyzes to a primary amine and CO2; can generate ureas by secondary reactions (literature).
Viscosity and volatility are moderate; handle in a well-ventilated hood to minimize exposure to isocyanate vapors (literature).
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for evaluating isocyanate quality (general):
Water content: Critical; moisture rapidly degrades isocyanates. Karl Fischer moisture specifications are commonly applied; request CoA.
Stabilizers: Some isocyanates are supplied without stabilizer; others contain traces of acid scavengers or inhibitors. For this item, stabilizer presence is not specified; refer to CoA/Spec Sheet.
Chromatographic suitability: If using for small-molecule synthesis or surface derivatization, low UV background and low non-volatile residue are beneficial; ask for HPLC/GC chromatograms if necessary.
Fit-for-purpose selection
Synthetic building block: look for high GC purity (≥98% typical in literature for fine chemicals) and low moisture
Polymer/urethane R&D: viscosity and NCO content (%NCO by titration) are key; request titration data if needed
Documentation: For this specific item, consult the CoA/SDS for exact purity, residual solvent profile, moisture, and any stabilizer content.
Reaction and Applications
Pentyl isocyanate serves as a versatile electrophilic partner in nucleophilic additions to the –N=C=O unit. Applications are broad across small-molecule synthesis, materials, and surface chemistry.
Key reactions (literature/general):
Urea formation: Rapid addition of primary/secondary amines to form mono- or substituted ureas, typically at 0–25 °C without added base. Useful for medicinal chemistry SAR (urea linkages) and linker installation.
Urethane (carbamate) formation: Reaction with alcohols; often requires catalyst (e.g., DBU, DABCO, tin carboxylates) or gentle heating. Basis of polyurethane chemistry when diols are used.
Thiocarbamate/thiourea: Reaction with thiols gives thiocarbamates; with thioamines gives thioureas.
Hydrolysis: With water to yield the corresponding pentylamine and CO2; subsequent dimerization to ureas is common.
Curtius analog workflows: While acyl azides/Curtius generate isocyanates in situ, preformed pentyl isocyanate can be used as an isocyanate source for selective urea/urethane installations without high-energy azides.
Electrophilic capture: Isocyanates can trap enolates or stabilized carbanions to form imide-like adducts (specialized applications).
Practical notes:
Exclude moisture rigorously; reactions are typically run under N2/Ar with dry solvents.
Control exotherms by slow addition of the nucleophile or isocyanate at 0–10 °C, especially with reactive amines/diols.
Monitor by IR: strong NCO stretch ~2265–2275 cm−1 disappears as reaction proceeds (literature).
Workup: quench residual isocyanate with a trace alcohol/amine at low temp; then aqueous workup. Avoid prolonged exposure to moisture during isolation to prevent urea formation.
Reaction Conditions
General literature guidance for reactions of pentyl isocyanate. These are not product specifications; optimize for each substrate.
Urea formation (amine + isocyanate)
Solvent: DCM, THF, toluene, EtOAc (anhydrous)
Temperature: 0–25 °C (exothermic); cool during addition
Catalyst/base: typically none; tertiary amines can accelerate sluggish anilines
Stoichiometry: 1.0–1.1 equiv isocyanate to amine
Time/yield: 0.5–4 h; often 80–95% isolated (literature)
Urethane (alcohol + isocyanate)
Solvent: toluene, 2-MeTHF, MTBE, DCM (dry)
Temperature: 25–80 °C; employ Dean–Stark for azeotropic drying when using higher-boiling solvents
Catalyst: DBU (1–10 mol%), DABCO, DMAP; dibutyltin dilaurate (0.01–0.5 mol%) in polymer model reactions
Time/yield: 2–24 h; commonly 70–90% (literature), slower for phenols
Thiocarbamate/thiourea formation
Solvent: toluene or acetonitrile (dry)
Catalyst: base (e.g., Et3N) may assist
Temperature: 25–60 °C
Monitoring and workup
IR: NCO stretch at ~2265–2275 cm−1 disappears as reaction completes
Quench residual NCO at low temp with a small aliquot of alcohol/amine before aqueous workup
Purification: silica gel chromatography (avoid wet solvents), or crystallization if product permits
Compatibility notes
Avoid strong nucleophiles not intended as substrates (water, excess alcohols) and strong bases that can induce side reactions (e.g., allophanate/biuret formation).
All conditions are representative literature values and should be validated for your system.
Safety and Handling
Item-specific GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
General safety guidance for aliphatic isocyanates (literature/industry practice):
Hazards
Respiratory sensitizer; skin sensitizer (commonly associated with H334/H317 for isocyanates in general)
Irritating to skin, eyes, and respiratory tract; harmful if inhaled; moisture contact can release CO2 and amines
PPE and engineering controls
Use in a certified chemical fume hood
Wear nitrile gloves (change regularly), lab coat, chemical splash goggles; consider respiratory protection per risk assessment
Handling
Keep strictly dry; exclude moisture (use desiccant and inert gas blanket)
Avoid contact with alcohols, amines, acids, bases, and water unless intended for reaction; these rapidly consume isocyanates
Purge lines and syringes with dry inert gas before transfer; use dry glassware
First aid (overview; defer to SDS)
Inhalation: move to fresh air; seek medical attention
Skin/eye contact: rinse with water for 15+ minutes; remove contaminated clothing; obtain medical advice
Ingestion: rinse mouth; do not induce vomiting; seek medical attention
Storage incompatibilities
Avoid moisture, strong nucleophiles (amines, alcohols), strong bases/acids, oxidizers; avoid heat and direct sunlight
Special risks
Can polymerize/oligomerize upon exposure to moisture or nucleophiles; pressure build-up possible in sealed wet containers; open cautiously if moisture ingress is suspected
Always consult the product-specific SDS for authoritative safety information.
Solvent Selection
Pentyl isocyanate is a moisture-sensitive electrophile; solvent choice should prioritize dryness, compatibility with the nucleophile, and control of exotherm.
Polarity/miscibility (literature/general)
Miscible with common aprotic organics: hexanes, heptane, toluene, diethyl ether, MTBE, THF, DCM, acetonitrile
Avoid protic solvents (MeOH, EtOH, water) unless deliberately conducting urethane formation, as these consume the isocyanate
Typical choices by transformation
Urea formation (amine + isocyanate): DCM, toluene, THF, EtOAc; often run at 0–25 °C; base usually unnecessary
Urethane formation (alcohol + isocyanate): toluene, xylene, 2-MeTHF, MTBE; catalytic DBU, DABCO, or tin catalysts; azeotropic drying useful
Surface derivatization/analytical tagging: acetonitrile or DCM under anhydrous conditions
Practical tips
Dry solvents thoroughly (molecular sieves 3Å/4Å, or freshly distilled)
For polar substrates, THF or acetonitrile can improve solubility; for hydrophobic systems, toluene/hexanes limit side reactions
Where removal is critical, use volatile solvents (DCM, Et2O). For scale-up, toluene/2-MeTHF offer higher boiling points to manage rate and heat
Comparison (general)
DCM: excellent control and low temperature, easy removal; environmental concerns
Toluene/2-MeTHF: greener profile; good for urethane catalysis and Dean–Stark drying
Hexanes/heptane: inert medium for highly reactive amines; may need cosolvent for substrate solubility
Storage and Reconstitution
Item-specific storage and shipping (from Product Data)
Storage Conditions: Room temperature
Shipped In: Normal
General handling/storage guidance for isocyanates (literature)
Store under inert gas (N2/Ar) in tightly sealed containers to exclude moisture.
Keep in a cool, dry, well-ventilated place away from heat and sunlight.
Use dry septa and anhydrous techniques for withdrawals; recap promptly.
If available, include desiccant in secondary containment; consider amber bottles to limit light exposure.
Reconstitution
Not applicable; supplied neat as a liquid reagent. If dilution is desired, prepare anhydrous stock solutions in a dry, compatible solvent (e.g., toluene, DCM, THF) and store short-term at low temperature in sealed vials.
Stability notes (general)
Sensitive to moisture; gradual formation of ureas/biurets may occur if exposed to traces of water.
Monitor by IR (NCO band ~2265–2275 cm−1) or GC to assess integrity during extended storage.
Always consult the product’s CoA/SDS for item-specific stability and handling details.
Structure and Identity
Pentyl isocyanate is a linear aliphatic isocyanate (R–N=C=O) bearing a normal pentyl substituent on nitrogen. The isocyanate functional group is cumulene-like (–N=C=O) and highly electrophilic at the carbon atom.
Item-specific identifiers (from Product Data)
SKU: P352487
CAS: 3954-13-0
CID: 206036
InChIKey: 386773 (as provided)
Storage Conditions: Room temperature; Shipped: Normal
2D depiction: a five-carbon straight chain terminating at nitrogen which is double-bonded to carbon (N=C) and that carbon is double-bonded to oxygen (=O).
Synthetic Utility
Functional group and reactivity profile (literature/general):
Electrophilic carbon in –N=C=O undergoes nucleophilic addition with amines (→ ureas), alcohols (→ carbamates/urethanes), and thiols (→ thiocarbamates). Reaction is typically high yielding and atom-economical.
Compatible with a broad range of protecting groups when moisture is excluded; reactions are often catalyst-free with amines.
Named/typical transformations:
Urea linkages in medicinal chemistry: coupling of anilines or aliphatic amines with pentyl isocyanate for structure–property tuning (lipophilicity modulation via C5 chain).
Polyurethane model reactions: with diols as small-molecule surrogates for polyurethane segment studies.
Surface modification: formation of carbamates on hydroxylated surfaces/polymers (e.g., cellulose, silica) via isocyanate grafting.
Retrosynthetic value:
Provides a direct route to N-pentyl ureas and O-pentyl carbamates without separate activation of the nucleophile.
Orthogonal to acid chloride/amidation pathways; avoids base and HCl salts, minimizing salt waste.
Selectivity and control:
Primary vs. secondary amines: both reactive; secondary often faster but can give viscous products—dilution helps.
Phenols vs. aliphatic alcohols: phenols typically slower; employ catalysts (DBU, DMAP, tin) or heat.
Avoid competitive hydrolysis by maintaining low water activity (dry solvents, inert atmosphere, molecular sieves).
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting reagent (e.g., antibody, probe). No antigen/epitope, clone, isotype, or species reactivity data apply.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
C2311449