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ChemicalBook--->CAS DataBase List--->123-51-3

123-51-3

123-51-3 Structure

123-51-3 Structure
IdentificationMore
[Name]

3-Methyl-1-butanol
[CAS]

123-51-3
[Synonyms]

1-Hydroxy-3-methylbutane
2-METHYL-4-BUTANOL
3-METHYL-1-BUTANOL
3-METHYLBUTAN-1-OL
3-METHYL BUTANOL
3-METHYLBUTYL ALCOHOL
FEMA 2057
FUSEL OIL
ISOAMYL ALCOHOL
ISOBUTYLCARBINOL
ISOPENTANOL
ISOPENTYL ALCOHOL
METHYL-BUTANOL
NATURAL ISO AMYL ALCOHOL
1-Butanol,3-methyl-
3-methyl-1-butano
3-methylbutan-
3-methylbutanoI
3-Metil-butanolo
Alcool amilico
[EINECS(EC#)]

204-633-5
[Molecular Formula]

C5H12O
[MDL Number]

MFCD00002934
[Molecular Weight]

88.15
[MOL File]

123-51-3.mol
Chemical PropertiesBack Directory
[Appearance]

Amyl alcohols (pentanols) have eight isomers. All are flammable, colorless liquids, except the isomer 2,2- dimethyl-1-propanol, which is a crystalline solid.
[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)
[FEMA ]

2057
[refractive index ]

n20/D 1.407
[Fp ]

109.4 °F
[storage temp. ]

Flammables area
[solubility ]

25g/l
[form ]

Liquid
[pka]

>14 (Schwarzenbach et al., 1993)
[color ]

<20(APHA)
[Specific Gravity]

0.813 (15/4℃)
[Odor]

Mild odor; alcoholic, non-residual.
[PH]

7 (25g/l, H2O, 20℃)
[PH Range]

5.6 at 25 g/l at 20 °C
[Stability:]

Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides.
[explosive limit]

1.2-9%, 100°F
[Odor Threshold]

0.0017ppm
[Odor Type]

fermented
[Water Solubility ]

25 g/L (20 ºC)
[λmax]

λ: 260 nm Amax: 0.06
λ: 280 nm Amax: 0.06
[JECFA Number]

52
[Merck ]

14,5195
[BRN ]

1718835
[Henry's Law Constant]

33.1 at 37 °C (Bylaite et al., 2004)
[Dielectric constant]

15.3(23℃)
[Exposure limits]

NIOSH REL: TWA 100 ppm (360 mg/m3), IDLH 500 ppm; OSHA PEL: TWA 100 ppm; ACGIH TLV: TWA 100 ppm, STEL 125 ppm (adopted).
[LogP]

1.35 at 20℃
[CAS DataBase Reference]

123-51-3(CAS DataBase Reference)
[NIST Chemistry Reference]

1-Butanol, 3-methyl-(123-51-3)
[EPA Substance Registry System]

123-51-3(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R10:Flammable.
R20:Harmful by inhalation.
R37:Irritating to the respiratory system.
R66:Repeated exposure may cause skin dryness or cracking.
R20/22:Harmful by inhalation and if swallowed .
[Safety Statements ]

S46:If swallowed, seek medical advice immediately and show this container or label .
S16:Keep away from sources of ignition-No smoking .
[RIDADR ]

UN 1105 3/PG 3
[WGK Germany ]

1
[RTECS ]

EL5425000
[Autoignition Temperature]

644 °F
[TSCA ]

Yes
[HazardClass ]

3
[PackingGroup ]

II
[HS Code ]

29335995
[Hazardous Substances Data]

123-51-3(Hazardous Substances Data)
[Toxicity]

LD50 orally in rats: 7.07 ml/kg (Smyth)
[IDLA]

500 ppm
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Pentane-->Vanillin-->D-(+)-Maltose monohydrate-->FUSEL OIL-->PEPPERMINT-->AlcoholMixture
[Preparation Products]

Pinacolone-->Norfloxacin-->Buprofezin-->Isoamyl nitrite-->pinacolone,tert-butyl methy1 ketone,3,3-dimethyl-2-butyl ketone-->(1-(4-(Hydroxymethyl)-6-(trifluoromethyl)pyrimidin-2-yl)piperidin-4-yl)methanol-->2-(4-Hydroxypiperidin-1-yl)-6-(trifluoromethyl)pyrimidine-4-carboxamide-->1-(4-(Hydroxymethyl)-6-(trifluoromethyl)pyrimidin-2-yl)piperidin-4-ol-->2-(4-(Hydroxymethyl)piperidin-1-yl)-6-(trifluoromethyl)pyrimidine-4-carboxamide-->Isovaleric acid-->Ethyl 2-(4-hydroxypiperidin-1-yl)-6-(trifluoromethyl)pyrimidine-4-carboxylate-->Ethyl 2-(4-(hydroxymethyl)piperidin-1-yl)-6-(trifluoromethyl)pyrimidine-4-carboxylate-->Ethyl 2-(4-(ethoxycarbonyl)piperidin-1-yl)-6-(trifluoromethyl)pyrimidine-4-carboxylate-->Isovaleraldehyde-->Diethyl ethyl(isoamyl)malonate-->3-Methylbutyl 3-methylbutanoate-->Calcitonin-->1,3-BENZODITHIOLYLIUM TETRAFLUOROBORATE-->Isoamyl acetate-->Diethyl isoamylmalonate-->1-Bromo-3-methylbutane-->Pimelic acid-->Bromisoval-->Isoamyl butyrate-->N,N-Diethyl-4-nitrosoaniline-->Isopentyl isobutyrate-->Lobenzarit-->Sodium isoamylxanthate-->FEMA 2080-->N,N'-DICYCLOHEXYLUREA-->Isopentyl phenylacetate-->Isopentyl formate-->Amyl salicylate-->2-Bromo-3-methylbutanoyl bromide-->Isoamyl benzoate-->ACETOACETIC ACID ISOAMYL ESTER-->Ethopabate-->GALLIC ACID ISOAMYL ESTER-->Isoamyl propionate-->Allyl (3-methylbutoxy)acetate
Hazard InformationBack Directory
[General Description]

Colorless liquid with a mild, choking alcohol odor. Less dense than water, soluble in water. Hence floats on water. Produces an irritating vapor.
[Reactivity Profile]

ISOAMYL ALCOHOL(123-51-3) 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].
[Air & Water Reactions]

Highly flammable. Water soluble.
[Hazard]

Moderate fire risk. Vapor is toxic and irritant. Explosive limits in air 1.2–9%.
[Health Hazard]

Very high vapor concentrations irritate eyes and upper respiratory tract. Continued contact with skin may cause irritation.
[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.
[First aid]

Skin contact contributes significantly to overall exposure. If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN2811 Pentanols, Hazard Class: 3; Labels: 3- Flammable liquid. UN1987 Alcohols, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid.
[Incompatibilities]

Forms 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.
[Description]

Isoamyl alcohol has a characteristic pungent odor and repulsive taste. Industrially prepared by rectification of fusel oil.
[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.
[Physical properties]

Clear, colorless liquid with a pungent odor. An odor threshold concentration of 1.7 ppbv was reported by Nagata and Takeuchi (1990).
[Occurrence]

Constitutes 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
[Characteristics]

Amyl alcohols (pentanols) have eight isomers. All are flammable, colorless liquids, except the isomer 2,2- dimethyl-1-propanol, which is a crystalline solid.
[Definition]

ChEBI: An alkyl alcohol that is butan-1-ol substituted by a methyl group at position 3.
[Preparation]

3-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.
[Preparation]

Industrially prepared by rectification of fusel oil.
[Aroma threshold values]

Detection: 250 ppb to 4.1 ppm
[Taste threshold values]

Taste characteristics at 50 ppm: fusel, fermented, fruity, banana, ethereal and cognac
[Flammability and Explosibility]

Flammable
[Chemical Reactivity]

Reactivity 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.
[Biochem/physiol Actions]

3-Methyl-1-butanol is a pentanol isomer useful in biofuels. It is used as a starting material for the production of isoamyl acetate, a flavoring agent applicable in the food industry. 3-Methyl-1-butanol shows anti-fungal action by inhibiting the hyphal formation and reducing biofilm formation in Candida albicans. It is also used in DNA extraction protocols.
[Environmental Fate]

Biological. 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).
[Purification Methods]

Dry 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.]
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

3-Methyl-1-butanol(123-51-3).msds
Questions And AnswerBack Directory
[Chemical properties]

3-Methyl-1-butanol, also called 3-methylbutanol or Isoamyl alcohol, is found in tea leaves, black tea, and green tea. It is a colorless to pale yellow liquid with a clear oily texture. It has a distinct apple brandy scent and a spicy taste. The vapors of this substance are poisonous. It can be mixed well with ethanol and ether, but only slightly dissolves in water. It is a natural component found as esters in various products such as strawberries, peppermint, lemongrass, eucalyptus oil, and rum, among others.
[Uses]

(1) 3-Methyl-1-butanol is 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 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.
Spectrum DetailBack Directory
[Spectrum Detail]

3-Methyl-1-butanol(123-51-3)MS
3-Methyl-1-butanol(123-51-3)1HNMR
3-Methyl-1-butanol(123-51-3)13CNMR
3-Methyl-1-butanol(123-51-3)IR1
3-Methyl-1-butanol(123-51-3)IR2
3-Methyl-1-butanol(123-51-3)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

3-Methyl-1-butanol, 98%(123-51-3)
[Alfa Aesar]

3-Methyl-1-butanol, mixture of isomers, 99%(123-51-3)
[Sigma Aldrich]

123-51-3(sigmaaldrich)
[TCI AMERICA]

3-Methyl-1-butanol,>98.0%(GC)(123-51-3)
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