3-Methyl-1-butanol

ChemicalBook > CAS DataBase List > 3-Methyl-1-butanol

3-Methyl-1-butanol

Chemical properties Uses Production methods

Product Name: 3-Methyl-1-butanol
CAS No.: 123-51-3
Chemical Name: 3-Methyl-1-butanol
Synonyms: ISOAMYL ALCOHOL;3-METHYLBUTAN-1-OL;ISOPENTYL ALCOHOL;ISOPENTANOL;FUSEL OIL;3-METHYL BUTANOL;i-Amyl Alcohol;Isoamylol;3-methyl-1-butano;3-methylbutanoI
CBNumber: CB8852971
Molecular Formula: C5H12O
Formula Weight: 88.15
MOL File: 123-51-3.mol

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3-Methyl-1-butanol Property

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.: room temp
solubility: 25g/l
form: Liquid
pka: >14 (Schwarzenbach et al., 1993)
Specific Gravity: 0.813 (15/4℃)
color: <20(APHA)
PH: 7 (25g/l, H2O, 20℃)
Odor: Mild odor; alcoholic, non-residual.
PH Range: 5.6 at 25 g/l at 20 °C
Odor Type: fermented
Odor Threshold: 0.0017ppm
explosive limit: 1.2-9%, 100°F
Water Solubility: 25 g/L (20 ºC)
λmax: λ: 260 nm Amax: 0.06
λ: 280 nm Amax: 0.06
Merck: 14,5195
JECFA Number: 52
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).
Stability:: Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides.
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: 3-Methyl-1-butanol (123-51-3)

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Safety

Hazard Codes: Xn
Risk Statements: 10-20-37-66-20/22-R20/22-R10
Safety Statements: 46-16-S16
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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H318Causes serious eye damage

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: W205710
Product name: Isoamyl alcohol
Purity: natural, ≥98%, FG
Packaging: 1kg
Price: $81.9
Updated: 2024/03/01

Sigma-Aldrich

Product number: W205710
Product name: Isoamyl alcohol
Purity: natural, ≥98%, FG
Packaging: 4kg
Price: $174
Updated: 2024/03/01

Sigma-Aldrich

Product number: W205710
Product name: Isoamyl alcohol
Purity: natural, ≥98%, FG
Packaging: 8kg
Price: $444
Updated: 2024/03/01

Sigma-Aldrich

Product number: W205710
Product name: Isoamyl alcohol
Purity: natural, ≥98%, FG
Packaging: 20kg
Price: $565
Updated: 2024/03/01

Sigma-Aldrich

Product number: W205702
Product name: Isoamyl alcohol
Purity: ≥98%, FG
Packaging: 1kg
Price: $83
Updated: 2024/03/01

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3-Methyl-1-butanol Chemical Properties,Usage,Production

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.

Chemical Properties

Isoamyl alcohol has a fusel oil, whiskey-characteristic, pungent odor and repulsive taste. The 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 properties

Clear, colorless liquid with a pungent odor. An odor threshold concentration of 1.7 ppb_v 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.

Uses

3-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.

Uses

Isoamylol is one of the several isomers of amyl alcohol and the main ingredient in the production of banana oil.

Uses

3-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.

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.

Definition

ChEBI: Isoamylol is an primary alcohol that is butan-1-ol in which a hydrogen at position 3 has been replaced by a methyl group. It has a role as a xenobiotic metabolite, a Saccharomyces cerevisiae metabolite and an antifungal agent. It is a primary alcohol, a volatile organic compound and an alkyl alcohol. It derives from a hydride of an isopentane.

Production Methods

Isoamyl alcohol has a characteristic pungent odor and repulsive taste. 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

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.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

3-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].

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.

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.

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 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).

Shipping

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

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.]

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.

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.

3-Methyl-1-butanol Preparation Products And Raw materials

Raw materials

PEPPERMINT AlcoholMixture D-(+)-Maltose monohydrate Pentane Vanillin FUSEL OIL

Preparation Products

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

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Hebei Duling International Trade Co. LTD

Product: 3-Methyl-1-butanol 123-51-3
Price: US $9.90/kg
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Release date: 2022-10-21

Hebei Kingfiner Technology Development Co.Ltd

Product: isoamyl alcohol 123-51-3
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Weijer International Trade (Hebei) Co., Ltd

Product: isoamylol 123-51-3
Price: US $1.00/KG
Min. Order: 1KG
Purity: >99%
Supply Ability: 20000T
Release date: 2023-03-10

123-51-3, 3-Methyl-1-butanolRelated Search:

Thiophanate-methyl Ethambutol Kresoxim-methyl Ethyl acetate Methyl salicylate 1-Butanol 2-Methyl-1-propanol tert-Butanol CHLOROPHOSPHONAZO III Tribenuron methyl Sodium tert-butoxide 3-Methyl-1-butene Potassium tert-butoxide Isosorbide (3aS)-4,8-Dimethyl-3-methylene-4β-ethenyl-3aβ,4,5,8bβ-tetrahydrobenzo[1,2-b:3,4-b']difuran-2(3H)-one Isotretinoin Methyl Isochroman

3-methyl-1-butano

3-methylbutan-

3-methylbutanoI

3-Metil-butanolo

Alcool amilico

Alcool isoamylique

alcoolamilico

alcoolisoamylique

isoamylalcohol,primary

isoamylalkohol

iso-amylalkohol

isoamylalkohol(czech)

Isoamylol

Isopentan-1-ol

isopentanol(non-specificname)

isopentylalcohol(non-specificname)

Methyl-3-butan-1-ol

methylbutanol(non-specificname)

ISOAMYL ALCOHOL (3-METHYLBUTANOL-1)

3-METHYL-1-BUTANOL, 98.5+%, A.C.S. REAGE NT

ISOAMYL ALCOHOL 98+% NATURAL

3-METHYL-1-BUTANOL CHROMASOLV FOR HP

ISOAMYL ALCOHOL ACS REAGENT

ISOAMYL ALCOHOL MOLECULAR*BIOLOGY REAGEN T

ISOAMYL ALCOHOL APPROX. 98%

3-METHYL-1-BUTANOL REAGENT GRADE 98%

3-METHYL-1-BUTANOL, ANHYDROUS, 99+%

3-METHYL-1-BUTANOL, REAGENTPLUS, >=99%

3-METHYL-1-BUTANOL 98.5+% A.C.S. REAG&

ISOAMYL ALCOHOL 98+%

ISO-AMYL ALCOHOL R. G., REAG. ACS, REAG. PH. EUR.

3-METHYL-1-BUTANOL, BIOTECH GRADE SOLVEN T,99+%

ISOAMYL ALCOHOL GC STANDARD

IsoamylAlcohol,Acs

ISO-AMYL ALCOHOL (3-METHYL-1-BUTANOL)

3-Methyl-1-butanol, reagent ACS

ISOAMYL ALCOHOL REAGENT (ACS)

ISOPENTYLALCOHOL,REAGENT,ACS

ISOAMYL ALCOHOL(3-METHYL-1-BUTANOL)(RG)

ios-Pentanol

ISOAMYL ALCOHOL WITH GC

3-Methyl-1-butanol, ACS, 98.5+%

3-Methyl-1-butanol, mixture of isomers, 99%

ISOAMYL ALCOHOL NATURAL 98% F&F GRADE

ISOAMYL ALCOHOL, NATURAL 99% PHARMACUTICAL GRADE

ISOAMYL ALCOHOL, SYNTHETIC

ISOAMYL ALCOHOL extrapure AR

Isoamyl Alcohol (isopentyl alcohol)

3-Methyl-1-butanol, Isoamyl alcohol, Isopentyl alcohol

Isopentyl Alcohol, Reagent

3-Methyl-1-butanol, 99%, for biocheMistry, AcroSeal

3-Methyl-1-butanol, 99%, anhydrous, AcroSeal

ISOAMYL ALCOHOL FOR ANALYSIS EMSURE

ISOAMYL ALCOHOL (MIXTURE OF ISOMERS) FOR

3-METHYLBUTANOL-1

ISOAMYLALKOHOL NATUERLICH

Methyl-1-buta

3-Methyl-1-butanol, SuperDry, J&KSeal