PROPYLOXIRANE

Propyloxirane is a colorless, highly flammable liquid epoxide available as the racemate (CAS 1003-14-1) and in enantiopure (R)- and (S)-forms, widely used as a reactive building block and intermediate in organic synthesis and fine chemical production.
Propyloxirane serves as a versatile building block and reactive intermediate in organic synthesis, used as a gelation agent for the sol-gel synthesis of transition and main-group metal oxide aerogels, as a reaction component in ring-opening reactions with nucleophiles to produce diols, amino alcohols, and thioethers, and as an intermediate in the production of fine chemicals, specialty chemicals, and polymers for the chemical, pharmaceutical, and diagnostic industries.
Propyloxirane is classified under GHS as a Danger substance (H225 highly flammable liquid and vapour; H302+H312+H332 harmful if swallowed, in contact with skin, or if inhaled; H319 causes serious eye irritation; H351 suspected of causing cancer) and requires careful handling with appropriate protective equipment and ventilation in laboratory and industrial settings.

CAS Number: 1003-14-1
EC Number: 213-701-3
Molecular Formula: C₅H₁₀O
Molecular Weight: 86.13 g/mol

Synonyms: 1,2-Epoxypentane, 2-Propyloxirane, Propyloxirane, Propylethylene oxide, 1-Pentene oxide, Pentene 1,2-oxide, Pentane 1,2-epoxy-, Pentylene oxide, Oxirane 2-propyl-, Oxirane propyl-, 1,2-Pentylene oxide, 1,2-epoxy-pentan, n-Propyloxirane, n-Propyloxiran, 2-Propyl-oxirane, (±)-1,2-Epoxypentane, S-1,2-Epoxypentane, 1-n-Pentenoxid, n-Pentenoxid, n-Pentenoxid-1,2, Penten-1,2-oxid, 1-Pentenoxid, 1,2-Epoxypentan, NSC 46349, NSC834, MFCD00192124, CAS 1003-14-1

Propyloxirane is a colorless liquid epoxide available as a racemate and in enantiopure (R)- and (S)-forms.
Propyloxirane is widely used as a reactive building block and intermediate in organic synthesis and fine chemical production.

Propyloxirane is used as a gelation agent in the sol-gel synthesis of transition-metal and main-group metal oxide aerogels.
Propyloxirane undergoes ring-opening reactions with nucleophiles to produce diols, amino alcohols, thioethers, and other functional intermediates.

Propyloxirane functions as a reactive intermediate in the production of polymers and specialty chemicals.
Propyloxirane is used as a research reagent in the chemical, diagnostic, and pharmaceutical industries.

Propyloxirane participates in asymmetric synthesis when used in enantiopure (R)- or (S)-forms, enabling the preparation of chiral intermediates with defined stereocenters.
Propyloxirane is a useful model substrate in studies of epoxide hydrolase activity, glutathione S-transferase substrate recognition, and cytochrome P450-mediated metabolism.

Propyloxirane has a strained three-membered epoxide ring that provides high reactivity toward a broad range of nucleophiles under mild conditions.
Propyloxirane is a colorless liquid with a melting point of −90°C and a boiling point of 89–90°C.

Uses of Propyloxirane:
Propyloxirane is used as a gelation agent in the sol-gel synthesis of various transition metal oxide and main-group metal oxide aerogels, where the epoxide ring acts as a proton scavenger that drives hydrolysis and condensation of inorganic salts to form monolithic aerogel networks.
The strained epoxide ring undergoes regioselective nucleophilic ring opening with amines, thiols, alcohols, and carboxylic acids to produce β-amino alcohols, β-thioethers, diols, and ester intermediates that serve as building blocks for fine chemicals and active pharmaceutical ingredients.
Propyloxirane functions as a reactive intermediate in the production of polymers and specialty chemicals, and is used as a research reagent in the chemical, diagnostic, and pharmaceutical industries.
Propyloxirane participates in asymmetric synthesis routes when used in its enantiopure (R)- or (S)-forms, enabling the preparation of chiral intermediates with defined stereocenters for medicinal chemistry and SAR studies.
Propyloxirane is a useful model substrate in studies of epoxide hydrolase enzyme activity, glutathione S-transferase substrate recognition, and cytochrome P450-mediated oxidative metabolism pathways.

Benefits and Advantages of Propyloxirane:
The strained three-membered epoxide ring of propyloxirane confers exceptional chemical reactivity toward a broad range of nucleophiles under mild conditions, enabling selective ring-opening transformations without requiring harsh reagents or elevated temperatures.
Propyloxirane provides a short propyl chain that imparts moderate lipophilicity (XLogP3 1.4, LogP 1.34) compared to lower alkyl epoxides, making ring-opened products suitable for applications where balanced water/lipid solubility is required.
Propyloxirane is commercially available in both racemic and enantiopure (R)- and (S)-forms with high purity (≥98% GC), offering flexibility for racemic library synthesis and for stereospecific chiral synthesis in a single commercially available compound family.
The low molecular weight (86.13 g/mol) and straightforward structure of propyloxirane make it an atom-efficient building block that introduces minimal molecular weight overhead when incorporated as a two-carbon epoxide unit in target molecules.

Features of Propyloxirane:
Propyloxirane is a colorless liquid at room temperature with a melting point of −90°C and a boiling point of 89–90°C (750 mmHg); density is 0.83 g/cm³ at 25°C and refractive index n20/D is 1.396.
The flash point of 8.5°C classifies propyloxirane as a highly flammable liquid (Flammable Liquid Category 2, GHS H225); vapour pressure is significant at ambient temperature, and vapours are heavier than air and may accumulate in low areas.
Propyloxirane is soluble in common organic solvents including dichloromethane, THF, ethyl acetate, hexane, ethanol, and acetone; water solubility is limited due to the moderate logP of approximately 1.34.
The compound possesses one rotatable bond, one hydrogen bond acceptor (the epoxide oxygen), zero hydrogen bond donors, and a topological polar surface area of 12.5–13 Ų; defined atom stereocenter count is 1 for the enantiopure forms.

Chemical Properties of Propyloxirane:
Propyloxirane has IUPAC name 2-propyloxirane, SMILES CCCC1CO1, InChI=1S/C5H10O/c1-2-3-5-4-6-5/h5H,2-4H2,1H3, and InChIKey SYURNNNQIFDVCA-UHFFFAOYSA-N (racemate); PubChem CID 13253 (racemate), ChemSpider 13253, MDL number MFCD00192124, EC number 213-701-3.
The epoxide functional group of propyloxirane is susceptible to acid-catalysed and base-catalysed ring-opening reactions; under acidic conditions, nucleophilic attack occurs preferentially at the more substituted carbon (C-2, Markovnikov selectivity), while under basic conditions attack occurs at the less hindered terminal carbon (C-1, anti-Markovnikov selectivity).
Propyloxirane undergoes ring-opening polymerisation with appropriate initiators to produce poly(propylene oxide)-type polyethers; it also participates in cycloaddition reactions and serves as an electrophilic building block in transition-metal-catalysed asymmetric desymmetrisations.
Propyloxirane is relatively stable under neutral conditions but hydrolyses to 1,2-pentanediol in the presence of acid or base; incompatible with strong acids, strong bases, strong oxidising agents, and strong reducing agents.

Production of Propyloxirane:
Propyloxirane is produced industrially by the epoxidation of 1-pentene using peracids such as meta-chloroperoxybenzoic acid (mCPBA), or via the Sharpless asymmetric epoxidation using titanium tartrate catalysts for enantioselective synthesis of the (R)- or (S)-enantiomers.
Alternative synthetic routes include the Weiss-Cook synthesis from 1,2-pentanediol via mesylation and ring closure under basic conditions, and the halohydrin cyclisation route from 1-pentene and hypochlorous acid followed by base-mediated ring closure.
Propyloxirane is commercially available at ≥98% purity (GC) as a colorless liquid; the enantiopure (R)- and (S)-forms are also commercially available.

Propyloxirane Material Safety Data Sheet (MSDS):

Handling of Propyloxirane:
Propyloxirane must be handled with strict precautions due to its high flammability (flash point 8.5°C) and suspected carcinogenicity (H351); all ignition sources including open flames, sparks, and hot surfaces must be eliminated in handling areas, and appropriate exhaust ventilation must be maintained.
Work must be carried out in a well-ventilated area or fume hood; avoid contact with skin and eyes, avoid breathing vapours or mist, and do not eat, drink, or smoke during use.

Propyloxirane SDS:

Stability and Reactivity of Propyloxirane:

Chemical stability:
Propyloxirane is stable under recommended storage conditions. Propyloxirane is sensitive to heat, strong acids, and strong bases, which promote ring opening or polymerisation.

Reactivity:
Propyloxirane undergoes exothermic ring-opening reactions with amines, thiols, alcohols, and water. Contact with strong acids or strong bases causes rapid hydrolysis or polymerisation.

Conditions to avoid:
Ignition sources — open flames, sparks, hot surfaces (flash point 8.5°C).
Excessive heat.
Contact with strong oxidising agents, strong acids, and strong bases.
Static discharge during transfer.

Incompatible materials:
Strong oxidising agents.
Strong acids and strong bases.
Strong reducing agents.

Hazardous decomposition products:
Carbon monoxide (CO) and carbon dioxide (CO₂).
Irritating organic vapours and fumes upon combustion.

Handling and Storage of Propyloxirane:

Handling:
Handle only in well-ventilated areas or under local exhaust ventilation.
Eliminate all ignition sources; use explosion-proof electrical equipment.
Avoid contact with skin, eyes, and clothing; avoid breathing vapours.
Use appropriate personal protective equipment at all times.
Do not eat, drink, or smoke in work areas.
Wash hands thoroughly after handling.

Storage:
Store at 2–8°C in a tightly closed container in a cool, dry, well-ventilated area away from ignition sources.
Keep away from heat, sparks, open flames, and oxidising agents.
Store under inert atmosphere (nitrogen or argon) where long-term stability is required.
UN number: UN 1993 (flammable liquid, n.o.s.); Packing Group II; Hazard Class 3.

First Aid Measures for Propyloxirane:

Inhalation:
Move the affected person to fresh air immediately.
If breathing has stopped, apply artificial respiration; consult a physician.

Skin contact:
Remove contaminated clothing immediately and wash the affected skin with soap and plenty of water.
Consult a physician if irritation develops or persists.

Eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes, occasionally lifting eyelids.
Consult a physician immediately.

Ingestion:
Never give anything by mouth to an unconscious person; rinse the mouth with water.
Consult a physician immediately.

Firefighting Measures for Propyloxirane:

Suitable extinguishing media:
Water spray, alcohol-resistant foam, dry chemical powder, or carbon dioxide.

Specific hazards:
Propyloxirane is a highly flammable liquid with a flash point of 8.5°C; vapours may form explosive mixtures with air and can travel to ignition sources and flash back. Combustion produces carbon monoxide, carbon dioxide, and irritating organic fumes.

Protective equipment for firefighters:
Self-contained breathing apparatus (SCBA) and full chemical-protective clothing must be used.

Firefighting procedures:
Evacuate non-essential personnel; fight the fire from an upwind position using appropriate extinguishing media.
Cool containers exposed to fire with water spray to prevent pressure build-up and rupture.

Accidental Release Measures for Propyloxirane:

Personal precautions:
Eliminate all ignition sources immediately; ensure adequate ventilation.
Avoid breathing vapours and prevent contact with skin and eyes; wear full PPE.

Environmental precautions:
Do not allow propyloxirane to enter drains, surface water, or groundwater.

Clean-up methods:
Absorb the spill with inert absorbent material such as sand or vermiculite; collect in sealed, labelled containers.
Ventilate the area thoroughly after clean-up and dispose of waste in accordance with applicable regulations.

Exposure Controls / Personal Protective Equipment for Propyloxirane:

Engineering controls:
Use local exhaust ventilation or work in a fume hood to control vapour concentrations.
No specific occupational exposure limit has been established; maintain concentrations as low as reasonably achievable.

Eye protection:
Face shield and safety glasses; use equipment tested and approved under NIOSH (US) or EN 166 (EU).

Hand protection:
Chemically resistant gloves; inspect gloves before use and replace contaminated gloves immediately.

Skin and body protection:
Complete chemical-protective suit; the type of protective equipment must be selected according to concentration and amount at the specific workplace.

Respiratory protection:
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.
For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.

Hygiene measures:
Wash hands before breaks and at the end of the workday; do not eat, drink, or smoke in work areas; remove contaminated clothing before leaving the work area.

Propyloxirane Identifiers:
CAS Number: 1003-14-1
EC Number: 213-701-3
MDL Number: MFCD00192124
PubChem CID: 13253 (racemate); 1201472 ((S)-form, CAS 123731-68-0); 1201473 ((R)-form)
ChemSpider ID: 13253
IUPAC Name: 2-propyloxirane
Molecular Formula: C₅H₁₀O
Molecular Weight: 86.13 g/mol
Exact Mass: 86.073165 Da
SMILES: CCCC1CO1
InChI: InChI=1S/C5H10O/c1-2-3-5-4-6-5/h5H,2-4H2,1H3
InChIKey: SYURNNNQIFDVCA-UHFFFAOYSA-N
XLogP3: 1.4
LogP: 1.34
Hydrogen Bond Acceptors: 1
Hydrogen Bond Donors: 0
Rotatable Bond Count: 2
Topological Polar Surface Area: 12.5–13 Ų
Heavy Atom Count: 6
Defined Stereocenter Count: 1 (enantiopure forms)
GHS Signal Word: Danger
GHS Hazard Statements: H225, H302, H312, H319, H332, H351
GHS Precautionary Statements: P201, P210, P280, P302+P352, P304+P340, P305+P351+P338, P308+P313, P370+P378, P403+P235
Hazard Class: 3 (Flammable liquids)
Packing Group: II
UN Number: UN 1993
NACRES: NA.23
UNSPSC: 12162002
Nikkaji: J941.217D (S-form)
Beilstein: 5-17-01-00087

Properties of Propyloxirane:
Physical state: Liquid
Appearance: Colorless liquid
Odour: Characteristic ethereal epoxide odour
Molecular formula: C₅H₁₀O
Molecular weight: 86.13 g/mol
Melting point: −90°C
Boiling point: 89–90°C (750 mmHg)
Flash point: 8.5°C (highly flammable)
Density: 0.83 g/cm³ (25°C)
Refractive index: n20/D 1.396
LogP: 1.34 (XLogP3: 1.4)
Topological polar surface area: 12.5–13 Ų
Hydrogen bond acceptors: 1
Hydrogen bond donors: 0
GHS Classification: Danger — H225, H302, H312, H319, H332, H351
Storage temperature: 2–8°C

Propyloxirane Properties — Specifications:
Product name: Propyloxirane (1,2-Epoxypentane)
CAS Number: 1003-14-1
EC Number: 213-701-3
Molecular Formula: C₅H₁₀O
Molecular Weight: 86.13 g/mol
Purity (GC): ≥98%
Appearance: Colorless liquid
Boiling point: 89–90°C
Density: 0.83 g/cm³ (25°C)
Refractive index: n20/D 1.396
Storage: 2–8°C; tightly closed; away from ignition sources
Format: Liquid
Documents: CoA (Certificate of Analysis), MSDS/SDS available

Names of Propyloxirane:
Propyloxirane
1,2-Epoxypentane
2-Propyloxirane
Propylethylene oxide
1-Pentene oxide
Pentene 1,2-oxide
Pentane, 1,2-epoxy-
Pentylene oxide
Oxirane, 2-propyl-
Oxirane, propyl-
1,2-Pentylene oxide
n-Propyloxirane
n-Propyloxiran
2-Propyl-oxirane
(±)-1,2-Epoxypentane
S-1,2-Epoxypentane
1-n-Pentenoxid
n-Pentenoxid
Penten-1,2-oxid
1,2-Epoxypentan
NSC 46349
NSC834
MFCD00192124
CAS 1003-14-1
UN 1993