1,2-Tetradecanediol
[CAS 21129-09-9]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives
• Name: 1,2-Tetradecanediol
• Synonyms: 1,2-Tetradecylene glycol; NSC 71507; n-Tetradecane-1,2-diol
• Molecular Formula: C₁₄H₃₀O₂
• Molecular Weight: 230.39
• CAS Registry Number: 21129-09-9
• EC Number: 244-228-0
• SMILES: CCCCCCCCCCCCC(CO)O

Properties

• Solubility: Insoluble (1.4E^-3 g/L) (25 °C), Calc.^*
• Density: 0.903±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 68-68.5 °C^**
• Boiling point: 331.1$+/-$10.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 143.8$+/-$13.6 $degree$C (Calc.)^*
• Index of refraction: 1.461 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Swern, Daniel

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

1,2-Tetradecanediol is a long-chain aliphatic diol with the molecular formula C₁₄H₃₀O₂. It consists of a straight fourteen-carbon hydrocarbon chain bearing two hydroxyl groups located on adjacent carbon atoms at positions 1 and 2. The compound belongs to the class of vicinal diols, also known as glycols, in which two hydroxyl groups are attached to neighboring carbon atoms.

Structurally, the molecule contains both a primary alcohol group at the terminal carbon (position 1) and a secondary alcohol group at the adjacent carbon (position 2). This arrangement gives the compound amphiphilic characteristics, combining a long hydrophobic alkyl chain with a polar diol functionality. The hydroxyl groups can participate in hydrogen bonding, while the hydrocarbon chain contributes hydrophobic and lipophilic properties.

The vicinal diol structure significantly influences the chemical behavior of 1,2-tetradecanediol. The hydroxyl groups are capable of undergoing typical alcohol reactions such as esterification, etherification, oxidation, and dehydration. Because the hydroxyl groups are adjacent, the compound may also participate in reactions characteristic of vicinal diols, including oxidative cleavage under strong oxidizing conditions.

1,2-Tetradecanediol can be synthesized through several organic synthetic routes. One common approach involves epoxidation of tetradecene followed by hydrolysis of the resulting epoxide to yield the vicinal diol. Alternatively, hydroxylation of unsaturated tetradecene derivatives using oxidizing agents such as osmium tetroxide or permanganate can produce the compound.

The long hydrocarbon chain gives the molecule surfactant-like characteristics, although it is less strongly surface-active than compounds containing ionic or polyoxyethylene groups. The balance between the hydrophobic alkyl segment and hydrophilic hydroxyl groups allows the compound to function as an intermediate in formulations, emulsifiers, or specialty chemical syntheses.

Long-chain vicinal diols such as 1,2-tetradecanediol are used in organic synthesis as intermediates for preparing esters, urethanes, polymers, and specialty surfactants. The presence of two reactive hydroxyl groups enables incorporation into polymeric materials through condensation or addition reactions. The long alkyl chain can impart hydrophobicity, flexibility, or lubricating properties to the resulting materials.

In materials and formulation chemistry, long-chain diols are sometimes used in cosmetics, coatings, lubricants, and personal care products. Their hydroxyl functionality can improve compatibility with other polar ingredients, while the alkyl chain contributes emollient and hydrophobic properties.

From a physicochemical perspective, 1,2-tetradecanediol has relatively low water solubility because the long C₁₄ hydrocarbon chain dominates the molecular character despite the presence of two hydroxyl groups. However, the hydroxyl groups increase polarity compared with hydrocarbons or monoalcohols of similar chain length. The compound is generally more soluble in organic solvents than in water.

The stereochemistry at the secondary alcohol carbon can give rise to chiral forms depending on the synthesis route. Hydroxylation of unsymmetrical alkenes may produce racemic mixtures unless stereoselective methods are employed.

Historically, long-chain diols have attracted attention as intermediates in industrial organic chemistry because they combine reactive alcohol functionality with hydrophobic alkyl chains. Their properties make them useful building blocks for specialty esters, surfactants, and polymer additives.

Overall, 1,2-tetradecanediol is a long-chain vicinal diol containing both primary and secondary hydroxyl groups attached to a fourteen-carbon aliphatic chain. Its combination of hydrophilic alcohol functionality and hydrophobic alkyl character makes it useful in synthetic chemistry, materials science, and formulation applications.

References

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DOI: 10.1007/s00709-025-02089-3

2024. Operando-informed precatalyst programming towards reliable high-current-density electrolysis. Nature Materials.
DOI: 10.1038/s41563-025-02128-7