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1,6-Hexanediol

Catalog Number
MTL629118
CAS
629-11-8
Structure
IUPAC Name
hexane-1,6-diol
Synonyms
Hexamethylene glycol
Molecular Weight
118.17
Molecular Formula
HO(CH2)6OH
Canonical SMILES
OCCCCCCO
InChI
1S/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2
InChI Key
XXMIOPMDWAUFGU-UHFFFAOYSA-N
Boiling Point
250 °C (lit.)
Melting Point
38-42 °C (lit.)
Flash Point
215 °F
Purity
≥ 97%
Density
0.96
Appearance
White to Almost white powder to lump
Application
1,6-Hexanediol can be used for a variety of s such as:
a structure-directing agent for the synthesis of ZSM-5 zeolite
a solvent for titanium tetraisopropoxide to form titanium oxide (TiO2) nanocrystals
a phase change material in combination with lauric acid for thermal energy storage s
Storage
2-8°C
Active Content
95%
Physical State
Solid
Typical Applications
Use as solvent.
Use as intermediate in organic synthesis.
For example, used in synthesis of polyester, polyurethane, nylon.
Spec Sheet
Case Study

1,6-Hexanediol as an Inhibitor of Phase Separation in Viral Replication Factory Assembly

1,6-Hexanediol as an Inhibitor of Phase Separation in Viral Replication Factory Assembly Finoshin, Alexander D., et al. Journal of Virological Methods 335 (2025): 115147.

1,6-Hexanediol (HD), a hydrophobic aliphatic diol, has gained significant attention as a chemical probe for studying biomolecular condensation and liquid-liquid phase separation (LLPS). Recent investigations into the infection cycle of Autographa californica multiple nucleopolyhedrovirus (AcMNPV) in Spodoptera frugiperda Sf9 cells revealed its critical role in modulating viral replication dynamics.
During the early infection stage, the viral DNA-binding protein (DBP) transitions from cytoplasmic localization to nuclear foci, which act as replication factories. These structures are membrane-less compartments, presumably assembled through LLPS. The introduction of HD (1-2%) at 4 h post-infection did not prevent DBP nuclear transport but effectively blocked its accumulation into replication foci. Instead, DBP exhibited a diffuse nuclear distribution, predominantly near perinuclear regions. Importantly, fluorescence quantification confirmed that DBP concentrations remained comparable to untreated controls, suggesting that HD interferes directly with phase separation rather than protein expression levels.
Further experiments demonstrated that while short-term exposure to 1% HD inhibited DBP assembly without reducing protein levels, prolonged incubation (4-24 h) led to decreased DBP expression, indicating compromised viral protein synthesis. At 2% HD, DBP production was strongly suppressed, highlighting concentration-dependent effects.
These findings underscore the application of 1,6-hexanediol as a selective tool to disrupt LLPS-driven processes in viral replication. Beyond virology, HD is broadly applied in cell biology to interrogate phase separation phenomena, making it indispensable for dissecting the molecular mechanisms underlying membrane-less organelle assembly.

1,6-Hexanediol as a Key Precursor for the Synthesis of N,N,N',N'-Tetramethyl-1,6-hexanediamine via Catalytic Amination

1,6-Hexanediol as a Key Precursor for the Synthesis of N,N,N',N'-Tetramethyl-1,6-hexanediamine via Catalytic Amination Wang, Zhifei, et al. Molecular Catalysis 569 (2024): 114601.

1,6-Hexanediol (HDO) is an industrially valuable diol that serves as a versatile precursor for the synthesis of functional amines and polymers. A recent study demonstrated its efficient transformation into N,N,N',N'-tetramethyl-1,6-hexanediamine (TMHDA) through catalytic amination with dimethylamine (DMA) under mild conditions. Using a Cu/Ni/Zn catalyst supported on γ-Al2O3 (molar ratio Cu:Ni:Zn = 28:7:12), the process achieved nearly complete conversion of HDO and up to 85% selectivity toward TMHDA at 200 °C under normal pressure.
The amination of HDO involves two hydrogenation and two dehydrogenation steps, requiring careful balance of catalytic activity. Characterization analyses, including TEM, BET, XRD, H2-TPR, and XPS, revealed that zinc addition effectively suppressed Cu/Ni particle agglomeration and optimized the Cu valence state, thereby enhancing catalytic performance.
Experimentally, HDO and the catalyst were loaded into a round-bottom flask, with the catalyst pre-reduced in flowing hydrogen at 170 °C for 40 min. A DMA/H2 gas mixture was introduced continuously while a reflux condenser collected reaction water to minimize product loss. Reaction mixtures were sampled at 4, 6, and 8 h, followed by gas chromatography analysis using an Agilent GC8860A with flame ionization detection. Conversion and selectivity were calculated to quantify catalytic efficiency.
This work highlights 1,6-hexanediol as a promising substrate for green and efficient synthesis of tertiary diamines, offering sustainable routes for fine chemical and polymer applications.

1,6-Hexanediol as a Sustainable Precursor for the Reductive Amination to 1,6-Hexamethylenediamine

1,6-Hexanediol as a Sustainable Precursor for the Reductive Amination to 1,6-Hexamethylenediamine Zhang, Liyan, et al. Applied Catalysis A: General 669 (2024): 119509.

1,6-Hexanediol (HDO) has emerged as a versatile and sustainable feedstock for the synthesis of industrially relevant diamines. Recent studies have highlighted its application in the reductive amination process to produce 1,6-hexamethylenediamine (HMDA), an essential intermediate for nylon and polyamide production. Traditional HMDA synthesis relies on energy-intensive and less environmentally friendly methods, whereas HDO provides a green alternative.
A Ru/PRL(x)-Al2O3 catalyst, in which highly dispersed Ru species are anchored by CNx moieties derived from 1,10-phenanthroline, was developed for this transformation. The catalyst's enhanced acid-base properties, electron-deficient Ru centers, and small nanoparticle size contributed to remarkable performance, achieving a 54% yield of HMDA-one of the best reported to date.
The experimental procedure involved charging a stainless-steel reactor with HDO (5 mmol), Ru/PRL-Al2O3 catalyst (100 mg), and tert-butanol (5 mL). After nitrogen purging, the system was heated to 220 °C, pressurized with 1 MPa H2, and then charged with ammonia to 16 MPa. Stirring at 800 rpm ensured efficient mass transfer throughout the reaction. Post-reaction, the mixture was cooled and analyzed via GC (Shimadzu GC-2014C) using hexadecane as an internal standard, allowing precise calculation of conversion and selectivity.
This catalytic system not only demonstrates the feasibility of producing HMDA via a cleaner, greener pathway but also underscores the role of 1,6-hexanediol as a critical renewable platform molecule for industrial amine synthesis.

Custom Q&A

What is the IUPAC name for the compound with the chemical formula HO(CH2)6OH?

The IUPAC name for the compound HO(CH2)6OH is hexane-1,6-diol.

How is 1,6-Hexanediol usually prepared in the laboratory?

1,6-Hexanediol is usually prepared in the laboratory by the reduction of adipic acid with lithium aluminum hydride.

What is the appearance of 1,6-Hexanediol?

1,6-Hexanediol appears as a white to almost white powder or lump.

What is the boiling point of 1,6-Hexanediol?

The boiling point of 1,6-Hexanediol is 250 °C.

What are some synonyms for 1,6-Hexanediol?

Some synonyms for 1,6-Hexanediol are Hexamethylene glycol.

What are some applications of 1,6-Hexanediol?

1,6-Hexanediol can be used as a structure-directing agent for the synthesis of ZSM-5 zeolite, a solvent for titanium tetraisopropoxide to form titanium oxide (TiO2) nanocrystals, and a phase change material in combination with lauric acid for thermal energy storage.

What is the purity of 1,6-Hexanediol?

The purity of 1,6-Hexanediol is ≥ 97%.

How is 1,6-Hexanediol stored?

1,6-Hexanediol should be stored at 2-8°C.

What is the density of 1,6-Hexanediol?

The density of 1,6-Hexanediol is 0.96.

What is the Beilstein REAXYS Number for 1,6-Hexanediol?

The Beilstein REAXYS Number for 1,6-Hexanediol is 1633461.

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