3-Buten-1-ol
[CAS# 627-27-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Acyclic hydrocarbon
• Name: 3-Buten-1-ol
• Synonyms: 3-Butene-1-ol; Allyl carbinol
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.11
• CAS Registry Number: 627-27-0
• EC Number: 210-991-3
• SMILES: C=CCCO

Properties

• Density: 0.842 g/mL (20 °C) (Expl.)
• Boiling point: 112-114 °C (Expl.)
• Refractive index: 1.42-1.422 (Expl.)
• Flash point: 32 °C (Expl.)
• Water solubility: soluble (Expl.)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07;GHS09 Danger
• Risk Statements: H226-H315-H318-H319-H335-H411
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P273-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

• Transport Information: UN 1987

Discovery and Applications

3-Buten-1-ol is an unsaturated alcohol with the molecular formula C4H8O. It consists of a hydroxyl group (-OH) attached to the terminal carbon of a butene chain, making it both an alcohol and an alkene. The compound’s unique combination of functional groups provides versatility in synthetic organic chemistry, enabling its use in various industrial applications and research contexts.

The discovery of 3-buten-1-ol can be attributed to early studies of unsaturated hydrocarbons and alcohols, particularly those derived from the catalytic hydration or hydroformylation of alkenes. Advances in catalytic processes in the mid-20th century allowed for the efficient synthesis of unsaturated alcohols, including 3-buten-1-ol, from readily available petroleum-derived feedstocks. Researchers explored its potential as a precursor for more complex molecules, recognizing its reactivity at both the hydroxyl and alkene sites.

One of the primary applications of 3-buten-1-ol is in the synthesis of polymers and resins. The compound is used as a monomer or comonomer in polymerization reactions to produce materials with desirable mechanical and thermal properties. Its unsaturated bond can participate in addition reactions, while the hydroxyl group can undergo esterification or etherification, enabling the creation of crosslinked networks or functionalized polymers.

In the pharmaceutical industry, 3-buten-1-ol serves as a versatile building block for the synthesis of active pharmaceutical ingredients (APIs). Its reactive alkene moiety facilitates the introduction of functional groups through hydroboration, epoxidation, or halogenation, while the hydroxyl group allows for further functionalization. These properties have been utilized in the development of intermediates for drugs targeting a range of therapeutic areas.

The agrochemical sector also benefits from the chemical’s reactivity, using it in the production of pesticides, herbicides, and plant growth regulators. Its dual functionality allows for the design of molecules tailored to specific biological pathways, optimizing activity and environmental stability. Derivatives of 3-buten-1-ol have been explored for their efficacy in controlling pests and enhancing crop yields.

In addition, 3-buten-1-ol is employed as a flavor and fragrance precursor in the food and cosmetic industries. Its structure enables the formation of esters and other derivatives with fruity or floral aromas, which are highly valued in product formulations. Its reactivity ensures that it can be readily transformed into a variety of scent and flavor molecules, contributing to its commercial significance.

Ongoing research focuses on optimizing sustainable production methods for 3-buten-1-ol, particularly through biomass-derived feedstocks and green chemistry approaches. These efforts aim to reduce the environmental impact associated with its synthesis while expanding its applications in emerging fields such as renewable materials and advanced pharmaceuticals.

References

1950. Qualitative analysis of certain polyatomic alcohols, with special reference to 1,3-butylene glycol. Zeitschrift fur Lebensmittel-Untersuchung und -Forschung, 91(5).
DOI: 10.1007/bf01453501

2021. Catalytic production of hexamethylenediamine from renewable feedstocks. Korean Journal of Chemical Engineering, 38(4).
DOI: 10.1007/s11814-020-0725-9

2024. Ring opening of epoxides: a facile approach towards the synthesis of polyketides and related stereoenriched natural products: a review. Molecular Diversity, 28(6).
DOI: 10.1007/s11030-024-11057-7