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

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 584-02-1 differently. You can refer to the following data:
1. 3-Pentanol is widely used as a flavoring agent. It is biogenic oxygenated volatile organic compound (BOVOC) and is used as a reagent in the synthesis of pure bromopentanes for infrared standards.
2. 3-Pentanol can be used as: A starting material for the preparation of liquid crystals, 1-ethylpropyl (R)-2-[4-(4′-alkoxybiphenylcarbonyloxy)-phenoxy]propionates by reacting with chiral (S)-lactic acid.Solvent/reductant in the catalytic deoxydehydration reaction of C4?C6 sugar alcohols into linear polyene using methyltrioxorhenium as a catalyst.A reactant for the synthesis of 3-(4-bromophenyloxy)pentane by reacting with 4-bromophenol via base-catalyzed Mitsunobu reaction.

Definition

ChEBI: A secondary alcohol that is pentane substituted at position 3 by a hydroxy group.

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 
• 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 
• 109-94-4 formic acid ethyl ester 
• 109-68-2 2-pentene 

Downstream Products

• 58368-67-5 pentan-3-yl formate 
• 101434-25-7 adipic acid di(3-pentyl) ester 
• 18980-15-9 6-Diethylmethyl-3-methyl-p-Chlorophenol 
• 101-81-5 Diphenylmethane 
• 617-80-1 2-ethyl-butyronitrile 
• 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.

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.

Uranyl(VI) Triflate as Catalyst for the Meerwein-Ponndorf-Verley Reaction

Catalytic transformation of oxygenated compounds is challenging in f-element chemistry due to the high oxophilicity of the f-block metals. We report here the first Meerwein-Ponndorf-Verley (MPV) reduction of carbonyl substrates with uranium-based catalysts, in particular from a series of uranyl(VI) compounds where [UO2(OTf)2] (1) displays the greatest efficiency (OTf = trifluoromethanesulfonate). [UO2(OTf)2] reduces a series of aromatic and aliphatic aldehydes and ketones into their corresponding alcohols with moderate to excellent yields, using iPrOH as a solvent and a reductant. The reaction proceeds under mild conditions (80 °C) with an optimized catalytic charge of 2.3 mol % and KOiPr as a cocatalyst. The reduction of aldehydes (1-10 h) is faster than that of ketones (>15 h). NMR investigations clearly evidence the formation of hemiacetal intermediates with aldehydes, while they are not formed with ketones.

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.