626-95-9

Basic information

• Product Name: 1,4-Pentanediol
• Synonyms: 1,4-Dihydroxy-1-methylbutane;1,4-Dihydroxypentane; 2,5-Pentanediol; 4-Hydroxy-1-pentanol
• CAS NO: 626-95-9
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.1476
• EINECS: 210-973-5
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 626-95-9.mol
• Article Data: 152

Chemical Properties

• Melting Point: 50.86°C (estimate)
• Boiling Point: 72-73 °C0.03 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.986 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00029mmHg at 25°C
• Refractive Index: 1.443
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol (Sparingly)
• PKA: 15.09±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 1,4-Pentanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Pentanediol(626-95-9)
• EPA Substance Registry System: 1,4-Pentanediol(626-95-9)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 626-95-9(Hazardous Substances Data)

Usage

Description

1,4-Pentanediol, also known as pentylidene glycol or tetramethylene glycol, is a diol compound with the chemical formula C5H12O2. It is a colorless, hygroscopic liquid with a sweet taste and a mild odor. The molecule consists of a five-carbon chain with two hydroxyl groups (-OH) attached to the first and fourth carbon atoms, respectively. 1,4-Pentanediol is a versatile chemical intermediate with various applications in different industries.

Uses

Used in Chemical Synthesis:
1,4-Pentanediol is used as a synthetic intermediate for the production of various chemicals and polymers. Its ability to form five-membered ethers upon dehydration makes it a valuable building block in organic synthesis.
Used in Polymer Industry:
1,4-Pentanediol is used as a monomer in the preparation of poly(ortho ester). Poly(ortho esters) are a class of biodegradable polymers with potential applications in drug delivery systems, medical devices, and other fields.
Used in Pharmaceutical Industry:
1,4-Pentanediol is used as a starting material for the synthesis of pharmaceutical compounds, such as antibiotics, antifungal agents, and other therapeutic drugs. Its presence in the molecular structure of these compounds can influence their solubility, stability, and bioavailability.
Used in Cosmetics and Personal Care Industry:
1,4-Pentanediol is used as a humectant and solvent in cosmetics and personal care products. Its hygroscopic nature helps to retain moisture in the skin, making it suitable for use in moisturizers, creams, and lotions.
Used in Food and Beverage Industry:
1,4-Pentanediol is used as a flavoring agent and humectant in the food and beverage industry. Its sweet taste and ability to retain moisture make it suitable for use in various food products, such as candies, chewing gum, and beverages.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 1961, 1947 DOI: 10.1021/ja01200a036

InChI:InChI=1/C5H12O2/c1-5(7)3-2-4-6/h5-7H,2-4H2,1H3

Upstream product

• 534-22-5 2-methylfuran 
• 591-11-7 5-methyl-5H-furan-2-one 
• 626-92-6 1,4-dichloropentane 
• 123-76-2 levulinic acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 110-87-2 3,4-dihydro-2H-pyran 
• 87935-64-6 (-)-agelasidine A hydrogen chloride salt 
• 111957-98-3 Pent-4-en-2-ol 
• 123-91-1 1,4-dioxane 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 626-87-9 1,4-dibromopentane 
• 1119-38-6 (S)-(+)-nerolidol 
• 96-47-9 2-methyltetrahydrofuran 

Downstream Products

• 1071-73-4 5-Hydroxy-2-pentanone 
• 74500-57-5 (S)-4-t-butyldimethylsilyloxy-1-trityloxypentane 
• 19041-15-7 (S)-γ-valerolactone 
• 26903-61-7 1,4-Pentadiolbisbenzoat 
• 128733-37-9 Benzoic acid 4-(dimethyl-phenyl-silanyloxy)-pentyl ester 
• 128733-36-8 1,4-Pentanediol 4-O-benzoyl ester 1-dimethylphenylsilyl ether 
• 123-76-2 levulinic acid 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 5412-69-1 5-diethylaminopentan-2-ol 
• 1679-47-6 3-methyltetrahydro-2-furanone 
• 626-96-0 4-oxopentanal 
• 74500-59-7 (4S)-4-[tert-butyl(dimethyl)silyl]oxypentyl 4-methylbenzenesulfonate 
• 155853-18-2 {(S)-6-[(1R,2R,4S)-2-[(S)-2-Benzyloxy-1-(2-methoxy-ethoxymethoxy)-ethyl]-4-(2-methoxy-ethoxymethoxy)-cyclopentyl]-1-methyl-hex-5-ynyloxy}-tert-butyl-dimethyl-silane 
• 1003-38-9 2,5-dimethyltetrahydrofuran 

Relevant articles and documents

Partially biobased polymers: The synthesis of polysilylethers via dehydrocoupling catalyzed by an anionic iridium complex

Partially biobased polysilylethers (PSEs) are synthesized via dehydrocoupling polymerization catalyzed by an anionic iridium complex. Different types (AB type or AA and BB type) of monomers are suitable. Levulinic acid (LA) and succinic acid (SA) have been ranked within the top 10 chemicals derived from biomass. BB type monomers (diols) derived from LA and SA have been applied to the synthesis of PSEs. The polymerization reactions employ an air-stable anionic iridium complex bearing a functional bipyridonate ligand as catalyst. Moderate to high yields of polymers with number-average molecular weights (Mn) up to 4.38 × 104 were obtained. A possible catalytic cycle via an Ir-H species is presented. Based on the results of kinetic experiments, apparent activation energy of polymerization in the temperature range of 0–10 °C is about 38.6 kJ/mol. The PSEs synthesized from AA and BB type monomers possess good thermal stability (T5 = 418 °C to 437 °C) and low glass-transition temperature (Tg = ?49.6 °C).

Transformation of γ-valerolactone into 1,4-pentanediol and 2-methyltetrahydrofuran over Zn-promoted Cu/Al2O3catalysts

The transformation of γ-valerolactone (GVL) into 1,4-pentanediol (1,4-PDO) and 2-methyltetra-hydrofuran (2-MTHF) in the presence of H2, one of the useful biomass conversion and utilization processes, was investigated with monometallic Cu/Al2O3 and bimetallic ZnCu/Al2O3 catalysts. A 10 wt% Cu-loaded monometallic catalyst produced 1,4-PDO and 2-MTHF in comparable quantities at a medium conversion (～50%). When Zn was added in a range of Zn/Cu molar ratios of up to 2, in contrast, the catalysts yielded 1,4-PDO in a high selectivity of about 97% at low and high conversion levels. In addition, the 1,4-PDO selectivity over the ZnCu/Al2O3 catalysts remained almost unchanged during recycled runs. That is, the addition of Zn to Cu/Al2O3 switched the product selectivity and improved the catalyst stability and reusability. Furthermore, the physicochemical properties of the catalysts were characterized by several methods including XRD, TEM, TPR, XPS, FTIR of adsorbed pyridine, and so on. On the basis of those results, the relationships between the catalytic performance (activity, selectivity, and reusability) and the catalyst structural features were discussed.

Manganese-Catalyzed Hydrogenation of Sclareolide to Ambradiol

The hydrogenation of (+)-Sclareolide to (?)-ambradiol catalyzed by a manganese pincer complex is reported. The hydrogenation reaction is performed with an air- and moisture-stable manganese catalyst and proceeds under relatively mild reaction conditions at low manganese and base loadings. A range of other esters could be successfully hydrogenated leading to the corresponding alcohols in good to quantitative yields using this easy-to-make catalyst. A scale-up experiment was performed leading to 99.3 % of the isolated yield of (?)-Ambradiol.

Chemoselective and Site-Selective Reductions Catalyzed by a Supramolecular Host and a Pyridine-Borane Cofactor

Supramolecular catalysts emulate the mechanism of enzymes to achieve large rate accelerations and precise selectivity under mild and aqueous conditions. While significant strides have been made in the supramolecular host-promoted synthesis of small molecules, applications of this reactivity to chemoselective and site-selective modification of complex biomolecules remain virtually unexplored. We report here a supramolecular system where coencapsulation of pyridine-borane with a variety of molecules including enones, ketones, aldehydes, oximes, hydrazones, and imines effects efficient reductions under basic aqueous conditions. Upon subjecting unprotected lysine to the host-mediated reductive amination conditions, we observed excellent ?-selectivity, indicating that differential guest binding within the same molecule is possible without sacrificing reactivity. Inspired by the post-translational modification of complex biomolecules by enzymatic systems, we then applied this supramolecular reaction to the site-selective labeling of a single lysine residue in an 11-amino acid peptide chain and human insulin.

Synthesis method of pentanediol, and synthesis method for preparing biomass-based pentadiene through conversion of levulinic acid and derivatives of levulinic acid

The invention provides a synthesis method of pentanediol, and the method comprises the following steps: carrying out conversion reaction on a mixed solution obtained by mixing levulinic acid and/or levulinic acid derivatives, a catalyst and an organic solvent in a hydrogen-containing atmosphere to obtain the pentanediol. According to the method, a large amount of cheap and easily available bio-based chemical levulinic acid or derivatives thereof can be utilized, pentanediol is obtained through catalytic conversion, and m-pentadiene is further obtained. The raw materials are derived from renewable resources, the m-pentadiene is prepared through hydrogenation and dehydration, and particularly, a green and sustainable process route for synthesizing the m-pentadiene is finally obtained through a dehydration reaction route and construction of a dehydration catalyst. The invention provides a method for green and sustainable synthesis of linear pentadiene based on bio-based chemical conversion, and the method has the advantages of simple operation, short flow, no need of harsh experimental conditions, easy preparation of raw materials and catalysts, and large-scale synthesis prospect.