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3-Methyl-1-butanol

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3-Methyl-1-butanol Basic information
3-Methyl-1-butanol Chemical Properties
  • Melting point:-117 °C
  • Boiling point:131-132 °C
  • Density 0.809 g/mL at 25 °C(lit.)
  • vapor density 3 (vs air)
  • vapor pressure 2 mm Hg ( 20 °C)
  • refractive index n20/D 1.407
  • FEMA 2057 | ISOAMYL ALCOHOL
  • Flash point:109.4 °F
  • storage temp. Flammables area
  • solubility 25g/l
  • pka>14 (Schwarzenbach et al., 1993)
  • form Liquid
  • color <20(APHA)
  • Specific Gravity0.813 (15/4℃)
  • PH7 (25g/l, H2O, 20℃)
  • PH Range5.6 at 25 g/l at 20 °C
  • OdorMild odor; alcoholic, non-residual.
  • Odor Threshold0.0017ppm
  • explosive limit1.2-9%, 100°F
  • Water Solubility 25 g/L (20 ºC)
  • λmaxλ: 260 nm Amax: 0.06
    λ: 280 nm Amax: 0.06
  • Merck 14,5195
  • JECFA Number52
  • BRN 1718835
  • Henry's Law Constant33.1 at 37 °C (Bylaite et al., 2004)
  • Exposure limitsNIOSH REL: TWA 100 ppm (360 mg/m3), IDLH 500 ppm; OSHA PEL: TWA 100 ppm; ACGIH TLV: TWA 100 ppm, STEL 125 ppm (adopted).
  • Stability:Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides.
  • CAS DataBase Reference123-51-3(CAS DataBase Reference)
  • NIST Chemistry Reference1-Butanol, 3-methyl-(123-51-3)
  • EPA Substance Registry System3-Methyl-1-butanol (123-51-3)
Safety Information
MSDS
3-Methyl-1-butanol Usage And Synthesis
  • Chemical propertiesColorless to pale yellow clear oily liquid. Apple brandy aroma and spicy flavor. Melting point:-117.2 °C. Boiling point: 130 °C. Relative density (d2525): 0.813. Refractive index (nD20): 1.4075. Vapors are toxic. Miscible in ethanol and ether. Slightly soluble in water.
    Natural products present in the form of esters in strawberries, peppermint, lemongrass, eucalyptus oil and rum and so on.
  • content analysisdetermined through non-polar column method of gas chromatography(GT-10-4).
    Toxicity  GRAS (FEMA).
    Use limits
    FEMA (mg/kg): soft drinks 17; cold drinks 7.6; candy 52; baked goods 24; pudding 46; gum 300; alcohol 100. Modest limit (FDA § 172.515, 2000).
  • Uses(1) Used as food flavors according to GB 2760-96. Mainly used for the preparation of apple and banana flavor.
    (2) Used as chromatographic reagent and extractant, and also used in the pharmaceutical industry
    (3) Used in the manufacture of spices, pharmaceuticals and mineral processing agents, and also used as solvents
    (4) This goods have apple brandy aroma and spicy flavor. China's GB 2760-86 provides for its allowable use as food spices, mainly for the preparation of apple and banana flavor. Isoamyl alcohol and sodium nitrite can perform esterification to form isoamyl nitrite, which is the fastest nitrous esters short-acting vasodilator. Isoamyl alcohol can be used to synthesize sedatives and hypnotics, such as bromural and amytal. Isoamyl alcohol can also be used as solvents and the reagents for chemical analysis. It is also used as the raw materials to produce plasticizers and photographic pharmaceutical. In addition, it is one component of the fuel oil.
    (5) Used for the manufacture of spices, pharmaceuticals and photographic drugs, and also used as solvents.
    (6) Used as the solvents of fat, resin and alkaloid. Used for the determination of fat in milk and the determination of iron, silicon, thorium and fusel oil. Also used for the complexation extraction of iron, cobalt, copper salt and diphenylcarbazide. Used for the separation of lithium Chloride from other alkali metal chlorides.
  • Production methods(1) This product naturally presents in the form of esters in strawberries, peppermint, lemongrass, eucalyptus oil and rum and so on. It can be synthesized by acid method or the hydroformylation of C4 alkenes. 3-methyl-1-butanol (85% in the fusel oil) can be obtained by chemical treatment and distillation separation of the fusel oil that is the side products form the alcohol fermentation of starch and sugar.
    (2) Derived from fusel oil fractionation.
    Pentane performs chlorination and hydrolysis reaction to form mixed alcohol, and then isoamyl alcohol can be derived from the mixed alcohol.
  • Hazards & Safety InformationCategory     Flammable liquids
    Toxic classification   moderate toxic
    Acute Toxicity   Oral-rat LD50: 1300 mg/kg; celiac-mouse LD50: 233 mg/kg
    Stimulation Data   Skin-Rabbit 20mg/24hours Moderate; Eye-Rabbit 20mg/24hours Moderate
    Explosives hazardous characteristics   Mix with air to be explosive
    Flammability hazard characteristics   In case of fire, high temperature and oxidant flammable; combustion to release excitive smoke
    Storage and transportation characteristics   Ventilation; Low temperature; dry; Separate storage with oxidizing agent
    Extinguishing agent  dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent
    Occupational Standard  TLV-TWA 100 PPM (360 mg /m3); STEL 125 PPM (450 mg/m3)
  • DescriptionIsoamyl alcohol has a characteristic pungent odor and repulsive taste. Industrially prepared by rectification of fusel oil.
  • Chemical PropertiesIsoamyl alcohol has a fusel oil, whiskey-characteristic, pungent odor and repulsive taste.
  • Chemical PropertiesAmyl alcohols (pentanols) have eight isomers. All are flammable, colorless liquids, except the isomer 2,2- dimethyl-1-propanol, which is a crystalline solid.
  • Chemical Propertiescolourless liquid
  • Chemical PropertiesThe air odor threshold for 3-methyl-1-butanol was reported as 0.042 ppm , which provides some acute warning for exposure to this chemical.
  • Physical propertiesClear, colorless liquid with a pungent odor. An odor threshold concentration of 1.7 ppbv was reported by Nagata and Takeuchi (1990).
  • OccurrenceConstitutes the major portion of fusel oil; also known as fermentation of amyl alcohol; it has been identified as an ester among the constituents of Roman chamomile oil; French peppermint, Java citronella, Réunion geranium, tea, Teucrium chamaedrys, Eucalyptus amigdalina, Achillea ageratum and Artemisia camphorata. It is reported present in the aromas of strawberry and raspberry. It is also reported found in over 230 natural sources including apple, apricot, banana, sweet and sour cherry, citrus peel oils and juices, berries, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, asparagus, cabbage, kohlrabi, celery stalk and seed, leek, peas, potato, sauerkraut, tomato, ginger, mint oils, vinegar, mustard, bread, cheeses, butter, milk, fish,meats, cognac, rum, whiskies, cider, sherry, grape wines, tea, filberts, pecans, walnuts, oats, honey, soybean, avocado, Arctic bramble, olive, passion fruit, rose and Malay apple, mushroom, mango, tamarind, pear brandy, port, cardamom, gin, quince, radish, sukiyaki, sake, buckwheat, corn oil, sweet corn, laurel, malt, wort, cherimoya, loquat, Bourbon vanilla, shrimp, oysters, crayfish, mussels and scallops
  • Uses3-Methyl-1-butanol and 2-methyl-1-butanol are normally used as apple or banana flavoring agents for wine. They can also be used as chemical intermediates and solvents in pharmaceutical products.
  • UsesIsoamylol is one of the several isomers of amyl alcohol and the main ingredient in the production of banana oil.
  • UsesSolvent for fats, resins, alkaloids, etc.; manufacture of isoamyl (amyl) Compounds, isovaleric acid, mercury fulminate, pyroxylin, artificial silk, lacquers, smokeless powders; in microscopy; for dehydrating celloidin solutions; for determining fat in milk.
  • DefinitionChEBI: An alkyl alcohol that is butan-1-ol substituted by a methyl group at position 3.
  • Production Methods3-Methyl-1-butanol is used as solvents for oils, fats, resins, and waxes; in the plastics industry in spinning polyacrylonitrile; and in manufacturing lacquers, chemicals, and pharmaceuticals. It is also used as flavoring agents and in fragrances. Industrial exposure is principally by the dermal contact and inhalation.
  • PreparationIndustrially prepared by rectification of fusel oil.
  • Preparation3-Methyl-1-butanol and 2-methyl-1-butanol were first isolated from fusel oils, by-products of ethanol fermentation by yeast. These compounds can also be derived from the chlorination of pentane followed by hydrolysis. Another alternative process is the oxo process, a general strategy for the manufacture of C4 and higher alcohols. Both the chlorination process and the oxo process are current commercial processes for the production of 3-methyl-1-butanol and 2-methyl-1-butanol, but the oxo process via the hydroformylation reaction is the more popular. Two main technologies are used for the process. The first was brought on stream by Ruhrchemie in Germany and Exxon in USA in the 1940s and is generally referred to as "high-pressure cobalt catalyst technology." The active catalyst species is cobalt hydrocarbonyl, and a pressure of 200–300 atm is required to maintain the stability of the catalyst. In the early 1960s, Shell commercialized a modern version of the cobalt catalyst process. This technology uses organophosphine ligands, which allows a lower operating pressure of 30–100 atm but at the expense of the catalyst activity. The Shell technology is employed primarily in the production of linear primary alcohols, whereas the high-pressure cobalt technology is frequently used in the production of branched alcohols.
  • Aroma threshold valuesDetection: 250 ppb to 4.1 ppm
  • Taste threshold valuesTaste characteristics at 50 ppm: fusel, fermented, fruity, banana, ethereal and cognac
  • General DescriptionColorless liquid with a mild, choking alcohol odor. Less dense than water, soluble in water. Hence floats on water. Produces an irritating vapor.
  • Air & Water ReactionsHighly flammable. Water soluble.
  • Reactivity Profile3-Methyl-1-butanol attacks plastics [Handling Chemicals Safely, 1980. p. 236]. Mixtures with concentrated sulfuric acid and strong hydrogen peroxide may cause explosions. Mixing with hypochlorous acid in water or water/carbon tetrachloride solution can generate isoamyl hypochlorites, which may explode, particularly on exposure to sunlight or heat. Mixing with chlorine would also yield isoamyl hypochlorites [NFPA 491 M, 1991]. Base-catalysed reactions with isocyanates can occur with explosive violence [Wischmeyer,1969].
  • HazardModerate fire risk. Vapor is toxic and irritant. Explosive limits in air 1.2–9%.
  • Health HazardVery high vapor concentrations irritate eyes and upper respiratory tract. Continued contact with skin may cause irritation.
  • Chemical ReactivityReactivity with Water: No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
  • Potential Exposure(n-isomer); Suspected reprotoxic hazard, Primary irritant (w/o allergic reaction), (iso-, primary): Possible risk of forming tumors, Primary irritant (w/o allergic reaction), (sec-, active primary-, and other isomers) Primary irritant (w/o allergic reaction). Used as a solvent in organic synthesis and synthetic flavoring, pharmaceuticals, corrosion inhibitors; making plastics and other chemicals; as a flotation agent. The (n-isomer) is used in preparation of oil additives, plasticizers, synthetic lubricants, and as a solvent.
  • Environmental FateBiological. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM isoamyl alcohol) and ThOD were 4.46 and 59.5%, respectively (Vaishnav et al., 1987).
    Chemical/Physical. Isoamyl alcohol will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993).
  • ShippingUN2811 Pentanols, Hazard Class: 3; Labels: 3- Flammable liquid. UN1987 Alcohols, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid.
  • Purification MethodsDry the alcohol by heating with CaO and fractionally distilling, then heating with BaO and redistilling. Alternatively, boil it with concentrated KOH solution, wash it with dilute H3PO4, and dry it with K2CO3, then anhydrous CuSO4, before fractionally distilling it. If very dry alcohol is required, the distillate is refluxed with the appropriate alkyl phthalate or succinate as described for ethanol. It is separated from 2-methyl-1-butanol by fractional distillation, fractional crystallisation and preparative gas chromatography. [Beilstein 1 IV 1677.]
  • IncompatibilitiesForms an explosive mixture with air. Contact with strong oxidizers and hydrogen trisulfide may cause fire and explosions. Incompatible with strong acids. Violent reaction with alkaline earth metals forming hydrogen, a flammable gas.
  • Waste DisposalDissolve 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.
3-Methyl-1-butanol Preparation Products And Raw materials
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