584-02-1

Basic information

• Product Name: 3-Pentanol
• Synonyms: 3-pentylalcohol;alcool3-pentylique;diethylcarbinol(3-pentanol);Pentan-3-ol;pentanol(non-specificname);Pentanol-3;so-Amylalcohol;DIETHYL CARBINOL
• CAS NO: 584-02-1
• Molecular Formula: C₅H₁₂O
• Molecular Weight: 88.15
• EINECS: 209-526-7
• Product Categories: Industrial/Fine Chemicals;Alcohols;Building Blocks;C2 to C6;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 584-02-1.mol
• Article Data: 162

Chemical Properties

• Melting Point: -75 °C
• Boiling Point: 114-115 °C749 mm Hg(lit.)
• Flash Point: 105 °F
• Appearance: Clear colorless/Liquid
• Density: 0.815 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.95mmHg at 25°C
• Refractive Index: n20/D 1.410(lit.)
• Storage Temp.: Flammables area
• Solubility: Soluble in acetone, benzene, ethanol and diethyl ether.
• PKA: 15.31±0.20(Predicted)
• Relative Polarity: 0.463
• Explosive Limit: 1.2-8%(V)
• Water Solubility: 5.5 g/100 mL (30 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,7120
• BRN: 1730964
• CAS DataBase Reference: 3-Pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pentanol(584-02-1)
• EPA Substance Registry System: 3-Pentanol(584-02-1)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20-37-66-37/38
• Safety Statements: 46-36/37
• RIDADR: UN 1105 3/PG 3
• WGK Germany: 1
• RTECS: SA5075000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 584-02-1(Hazardous Substances Data)

Usage

Description

3-Pentanol, also known as a secondary alcohol, is a colorless liquid with the chemical formula C5H12O. It is a biogenic oxygenated volatile organic compound (BOVOC) and is characterized by a hydroxy group substitution at the 3rd position of a pentane molecule.

Uses

Used in Flavoring Industry:
3-Pentanol is used as a flavoring agent due to its distinctive aroma and taste, enhancing the sensory experience of various food and beverage products.
Used in Chemical Synthesis:
3-Pentanol serves as a starting material for the preparation of liquid crystals, such as 1-ethylpropyl (R)-2-[4-(4′-alkoxybiphenylcarbonyloxy)-phenoxy]propionates, by reacting with chiral (S)-lactic acid. This application is crucial in the development of advanced display technologies.
Used in Organic Chemistry:
3-Pentanol acts as a solvent and reductant in the catalytic deoxydehydration reaction of C4-C6 sugar alcohols into linear polyene using methyltrioxorhenium as a catalyst. This process is essential for the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
3-Pentanol is employed in the synthesis of 3-(4-bromophenyloxy)pentane by reacting with 4-bromophenol via a base-catalyzed Mitsunobu reaction. 3-Pentanol has potential applications in the development of pharmaceuticals and other bioactive molecules.
Additionally, 3-Pentanol is used as a reagent in the synthesis of pure bromopentanes for infrared standards, which are vital for the calibration and performance evaluation of analytical instruments in various scientific and industrial applications.

Purification Methods

Reflux the alcohol with CaO, distil, then reflux it with magnesium and again fractionally distil it. [Beilstein 1 IV 1662.]

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C4H10.CH4O/c1-3-4-2;1-2/h3-4H2,1-2H3;2H,1H3

Upstream product

• 71-23-8 propan-1-ol 
• 616-20-6 3-chloropentane 
• 107-31-3 Methyl formate 
• 925-90-6 ethylmagnesium bromide 
• 1191-96-4 ethylcyclopropane 
• 98-88-4 benzoyl chloride 
• 75-03-6 ethyl iodide 
• 109-94-4 formic acid ethyl ester 
• 2386-64-3 ethylmagnesium chloride 
• 123-38-6 propionaldehyde 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 96-22-0 pentan-3-one 
• 60-29-7 diethyl ether 

Downstream Products

• 58368-67-5 pentan-3-yl formate 
• 18980-15-9 6-Diethylmethyl-3-methyl-p-Chlorophenol 
• 101-81-5 Diphenylmethane 
• 617-80-1 2-ethyl-butyronitrile 
• 109-68-2 2-pentene 
• 64002-68-2 4-(1-ethyl-propyl)-[1]naphthol 
• 18980-18-2 2-Diethylmethyl-3,5-dimethyl-p-Chlorophenol 
• 504-60-9 penta-1,3-diene 
• 600-14-6 2,3-Pentanedione 
• 600-40-8 1,1-dinitroethane 
• 625-29-6 2-methyl-1-chlorobutane 
• 616-20-6 3-chloropentane 
• 107-81-3 2-bromopentane 
• 1809-10-5 3-bromopentane 

Relevant articles and documents

REACTION OF DIALKYLMAGNESIUM WITH CARBON MONOXIDE AND NITROSODURENE

Reaction between diethylmagnesium and carbon monoxide gives rise to the formation of pentanone-3, pentanol-3, 3-ethylpentanol-3, 3-ethyl-3-hydroxyhexanone-4 and 3-ethylhexanone-4.The use of CO and application of C NMR spectroscopy revealed that C2H5COCH(C2H5)2 arose after hydrolysis of C2H5COC(C2H5)2MgC2H5.Reaction between (C2H5)2Mg and nitrosodurene proceeds according to the nitrene-radical mechanism and the EPR spectrum presents a signal derived from Me4PhN(radical)-N(PhMe4)OMgC2H5.Upon this basis a carbene-radical mechanism is proposed for the reaction between carbon monoxide and diethylmagnesium.

Manganese-Catalyzed Hydrogenation of Ketones under Mild and Base-free Conditions

In this paper, several Mn(I) complexes were applied as catalysts for the homogeneous hydrogenation of ketones. The most active precatalyst is the bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dippe) (CO)3(CH2CH2CH3)]. The reaction proceeds at room temperature under base-free conditions with a catalyst loading of 3 mol % and a hydrogen pressure of 10 bar. A temperature-dependent selectivity for the reduction of α,β-unsaturated carbonyls was observed. At room temperature, the carbonyl group was selectively hydrogenated, while the C=C bond stayed intact. At 60 °C, fully saturated systems were obtained. A plausible mechanism based on DFT calculations which involves an inner-sphere hydride transfer is proposed.

Hydrodeoxygenation of C4-C6 sugar alcohols to diols or mono-alcohols with the retention of the carbon chain over a silica-supported tungsten oxide-modified platinum catalyst

The hydrodeoxygenation of erythritol, xylitol, and sorbitol was investigated over a Pt-WOx/SiO2 (4 wt% Pt, W/Pt = 0.25, molar ratio) catalyst. 1,4-Butanediol can be selectively produced with 51% yield (carbon based) by erythritol hydrodeoxygenation at 413 K, based on the selectivity over this catalyst toward the regioselective removal of the C-O bond in the -O-C-CH2OH structure. Because the catalyst is also active in the hydrodeoxygenation of other polyols to some extent but much less active in that of mono-alcohols, at higher temperature (453 K), mono-alcohols can be produced from sugar alcohols. A good total yield (59%) of pentanols can be obtained from xylitol, which is mainly converted to C2 + C3 products in the literature hydrogenolysis systems. It can be applied to the hydrodeoxygenation of other sugar alcohols to mono-alcohols with high yields as well, such as erythritol to butanols (74%) and sorbitol to hexanols (59%) with very small amounts of C-C bond cleavage products. The active site is suggested to be the Pt-WOx interfacial site, which is supported by the reaction and characterization results (TEM and XAFS). WOx/SiO2 selectively catalyzed the dehydration of xylitol to 1,4-anhydroxylitol, whereas Pt-WOx/SiO2 promoted the transformation of xylitol to pentanols with 1,3,5-pentanetriol as the main intermediate. Pre-calcination of the reused catalyst at 573 K is important to prevent coke formation and to improve the reusability.

Chromium-Catalyzed Production of Diols From Olefins

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.