3-Chloro-1-propanol: Properties, Safety & Lab Use Guide

3-Chloro-1-propanol is a bifunctional haloalcohol intermediate widely employed in organic synthesis for the introduction of three-carbon tethers bearing both a nucleophilic hydroxyl and an electrophilic chloride leaving group.

CAS Number

627-30-5

Molecular Formula

C₃H₇ClO

Molecular Weight

94.54 g/mol

Appearance

Colorless to pale yellow liquid

Boiling Point

~160 °C (literature)

Functional Groups

Primary alcohol (–OH) and primary alkyl chloride (–Cl)

Key Application

Organic synthesis intermediate and bifunctional linker

Chemical Identity and Physical Properties

3-Chloro-1-propanol (CAS 627-30-5), also known as trimethylene chlorohydrin or 3-chloropropan-1-ol, is a short-chain haloalcohol with the molecular formula C₃H₇ClO and a molecular weight of 94.54 g/mol. The molecule contains two reactive functional groups separated by a propylene bridge: a primary hydroxyl group at C-1 and a primary chloride at C-3. This arrangement makes it a versatile bifunctional building block in synthetic chemistry.

The compound is a colorless to pale yellow liquid with a faint characteristic odor. Its boiling point is approximately 160 °C under atmospheric pressure. It is miscible with common organic solvents such as ethanol, diethyl ether, and acetone, and shows moderate miscibility with water. The presence of the hydroxyl group confers hydrogen-bonding capability, contributing to a higher boiling point than simple propyl chloride analogs.

Synthetic Applications and Reactivity

The dual functionality of 3-Chloro-1-propanol makes it an important building block across multiple areas of synthetic organic chemistry. The primary alkyl chloride end participates readily in S_N2 nucleophilic substitution reactions with a broad range of nucleophiles including amines, thiols, alkoxides, and carboxylates, enabling efficient C–N, C–S, C–O, and C–C bond-forming reactions. The hydroxyl group, meanwhile, can be selectively protected, oxidized, or converted to other leaving groups depending on the target transformation.

Common uses include: (1) introduction of three-carbon spacers in the synthesis of heterocycles, crown ethers, and macrocycles; (2) preparation of oxetane (trimethylene oxide) via intramolecular cyclization under basic conditions; (3) synthesis of 1,3-propanediol derivatives after halide displacement; (4) alkylation of heteroatom nucleophiles in pharmaceutical and agrochemical intermediate synthesis; and (5) use as a tethering linker in surface functionalization and polymer chemistry. Selective mono-functionalization is achievable because the chloride is inherently more electrophilic toward external nucleophiles, while the hydroxyl can be temporarily protected as a silyl or acyl ether.

Safety, Handling, and Storage

Hazard profile: 3-Chloro-1-propanol is a harmful liquid and vapour. It is classified as an irritant to the skin, eyes, and respiratory tract. Prolonged or repeated exposure may cause sensitization. The compound should be treated as a potential lachrymator. Consult the current Safety Data Sheet (SDS) before use.

Personal protective equipment (PPE): Always work with 3-Chloro-1-propanol in a well-ventilated fume hood. Wear chemical-resistant gloves (e.g., nitrile or neoprene), safety goggles with side shields, and a laboratory coat. Avoid inhalation of vapors and contact with skin or eyes.

Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area, away from heat sources, ignition sources, and incompatible materials such as strong bases, strong oxidizing agents, and reactive metals. Recommended storage temperature is typically 2–25 °C. Keep away from moisture to prevent slow hydrolysis of the C–Cl bond.

Disposal: Dispose of waste material and containers in accordance with local environmental regulations governing halogenated organic solvents. Do not pour down the drain.

Quality, Purity, and Analytical Characterization

For research applications, purity is a critical parameter because trace impurities such as 1,3-dichloropropane, 3-chloropropanal, or water can interfere with sensitive synthetic steps or biological assays. Aladdin Scientific's 3-Chloro-1-propanol (SKU C109471) should be verified by standard analytical methods prior to use in demanding applications.

Typical analytical methods:

• GC purity: Gas chromatography with FID detection is the primary method to assess chemical purity and detect volatile organic impurities such as residual starting materials or by-products.
• ¹H NMR: Proton NMR in CDCl₃ provides characteristic signals: –CH₂Cl protons near δ 3.6 ppm, –CH₂OH protons near δ 3.7 ppm, and the central –CH₂– near δ 2.1 ppm. The hydroxyl proton appears as a broad singlet whose chemical shift varies with concentration and solvent.
• Karl Fischer titration: Determines water content, important since moisture promotes hydrolysis.
• Refractive index: Can be used as a quick identity check against literature values.

Researchers should verify the current certificate of analysis (CoA) available from Aladdin Scientific for lot-specific purity data.

Regulatory and Shipping Considerations

3-Chloro-1-propanol is a regulated chemical under transportation guidelines due to its flammable and harmful properties. It is generally classified as a flammable liquid for shipping purposes (consult current IATA, IMDG, and DOT classifications). Proper UN number assignment, hazard labels, and packaging requirements must be fulfilled before international or domestic shipment.

Researchers and procurement teams should confirm current import/export regulations in their jurisdiction, as haloalcohol compounds may be subject to specific controls. Aladdin Scientific ships products in compliance with applicable regulations; customers should provide accurate end-use information during ordering to facilitate smooth customs clearance. Always request an up-to-date SDS and CoA at the time of purchase.

Frequently asked questions

What is 3-Chloro-1-propanol primarily used for in the laboratory?

3-Chloro-1-propanol is primarily used as a bifunctional organic synthesis intermediate. Its primary alkyl chloride undergoes efficient SN2 reactions with nucleophiles such as amines, thiols, and alkoxides, while the hydroxyl group can be selectively protected or further functionalized, making it valuable for preparing heterocycles, linkers, and pharmaceutical intermediates.

How should 3-Chloro-1-propanol be stored to maintain stability?

Store 3-Chloro-1-propanol in a tightly sealed container at 2–25 °C in a cool, dry, well-ventilated location away from moisture, strong bases, oxidizing agents, and ignition sources. Moisture should be excluded to prevent hydrolysis of the C–Cl bond, which can generate HCl and degrade purity over time.

Can 3-Chloro-1-propanol undergo intramolecular cyclization, and what product forms?

Yes. Under basic conditions, the hydroxyl group of 3-Chloro-1-propanol can act as an intramolecular nucleophile to displace the adjacent chloride via an SN2 mechanism, forming oxetane (1,3-propylene oxide, a four-membered cyclic ether). This reaction requires careful control of base concentration and temperature to minimize competing intermolecular reactions.

What personal protective equipment (PPE) is recommended when handling 3-Chloro-1-propanol?

Researchers should wear chemical-resistant gloves (nitrile or neoprene), safety goggles with side shields, and a laboratory coat when handling 3-Chloro-1-propanol. All work should be conducted in a well-ventilated fume hood to prevent inhalation of vapors. The current SDS should be reviewed prior to use.

How can I confirm the identity and purity of 3-Chloro-1-propanol before use?

Identity and purity can be confirmed using GC-FID for overall purity and detection of volatile impurities, ¹H NMR for structural confirmation (characteristic signals at approximately δ 3.6–3.7 ppm for the methylene groups adjacent to Cl and OH), and Karl Fischer titration for water content. Request the lot-specific Certificate of Analysis (CoA) from Aladdin Scientific for reference values.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General SN2 reactivity of primary alkyl halides and haloalcohols.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Haloalcohol chemistry, intramolecular cyclization to oxetanes.)
3. PubChem Compound Summary for CID 12218: 3-Chloro-1-propanol. National Center for Biotechnology Information. https://pubchem.ncbi.nlm.nih.gov/compound/3-Chloro-1-propanol
4. Sigma-Aldrich / MilliporeSigma Material Safety Data Sheet: 3-Chloro-1-propanol, CAS 627-30-5. (Physical property reference and hazard classification.)

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