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Home > Encyclopedia > 2-Methyl-1-butanol

2-Methyl-1-butanol

2-Methyl-1-butanol structure

2-Methyl-1-butanol 

structure
  • CAS No:

    137-32-6

  • Formula:

    C5H12O

  • Chemical Name:

    2-Methyl-1-butanol

  • Synonyms:

    1-Butanol,2-methyl-;2-Methyl-1-butanol;sec-Butylcarbinol;Primary active amyl alcohol;Active amyl alcohol;Active primary amyl alcohol;2-Methyl-n-butanol;2-Methylbutyl alcohol;(±)-2-Methyl-1-butanol;NSC 8431;34713-94-5

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Clear colourless liquid; cooked roasted aroma with fruity or alcoholic undertones


2-methylbutan-1-ol is a primary alcohol that is isopentane substituted by a hydroxy group at position 1. It has a role as a Saccharomyces cerevisiae metabolite. It is an alkyl alcohol and a primary alcohol. It derives from a hydride of an isopentane.

2-Methyl-1-butanol Basic Attributes

88.15

88.15

1718810

205-289-9

0506

8431

1105

DTXSID5027069

COLORLESS LIQ

29051500

Characteristics

20.2

1.3/1.4

Clear colorless to very slightly yellow Liquid

0.816 g/cm3 @ Temp: 20 °C

-70 °C

128 °C @ Press: 760 Torr

110 °F

1.405

H2O: 3.6 g/100 mL (30 ºC)

Flammables area

3 mm Hg ( 20 °C)

3 (vs air)

Oral-rat LD50: 1000 mg/kg

Flammable; spicy and irritating smoke is emitted from the fire

1.2-10.3%(V)

1.41e-05 atm-m3/mole

SPECIFIC OPTICAL ROTATION: +3.75 DEG @ 18 °C/D /1-Butanol, 2-methyl (l)/

725 °F (385 °C).|385 °C

Safety Information

III

3

UN 1105 3/PG 3

3

10-20-37-66

46-24/25

EL5250000

Xn

Treasury is ventilated, low temperature and dry; stored and transported separately from oxidant

Steam and air can be explosive when mixed

P210-P261-P280-P304 + P340 + P312-P337 + P313-P403 + P235

H226-H315-H319-H332-H335

Amyl alcohols or pentanols, Cahiers de Notes Documentaires S'ecurit'e et Hygi'ene du Travail 1st Quarter 1987.

Flammable. Above 50 °C explosive vapour/air mixtures may be formed.

|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P305+P351+P338, P310, P321, P332+P313, P362, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226 (36.71%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 2032 companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P403+P235, and P501

Use alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Explosive limits , vol% in air: 1.4-9.0

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

... Severely irritating to the eyes, minimally irritating to the skin.

Collect leaking and spilled liquid in sealable metal or glass containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Fireproof. Cool.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the central nervous system.

The substance defats the skin, which may cause dryness or cracking.

NO open flames, NO sparks and NO smoking. Above 50 °C use a closed system, ventilation and explosion-proof electrical equipment.

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

The major hazards encountered in the use and handling of 2-methyl-1-butanol stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this colorless liquid may occur from its use as a solvent, as a frothing agent in ore flotation, in lubricants, plasticizers, oils, and paints, and as a chemical intermediate for diamyldithiophosphates, 2-methyl-1-butylamine, esters, and ethers. Effects from exposure may include irritation of the eyes, skin, and mucous membranes, headache, dizziness, giddiness, nausea, cardiac arrhythmias, or pulmonary edema. In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. This substance must be moderately heated before ignition will occur. If this substance should be involved in a fire, use water to cool the material to below its flash point.

2-Methyl-1-butanol was identified as one of the odorous compounds emitted to the air from a sedimentation tank at a German water treatment facility(1).

2-Methyl-1-butanol was qualitatively detected in indoor air samples from a residential dwelling that had received an oil floor finish known as "Glitsa"(1).

Toxicity

moderately toxic

LD50 Rat oral 4.92 ml/kg|LD50 Rabbit dermal 2.89 g/kg

2-Methyl-1-butanol has been identified as a volatile component of blue cheese aroma(1), Concord grape juice essence(2), nectarines(3), apples(4,5), papaya fruit(6), oranges(7), and tomatoes(8). 2-Methyl-1-butanol is released in the volatile emissions from poultry manure(9).

2-Methyl-1-butanol was identified as one of the odorous compounds emitted to the air from a sedimentation tank at a German water treatment facility(1). Various solvent uses of 2-methyl-1-butanol will release 2-methyl-1-butanol to air through evaporation(SRC).

TERRESTRIAL FATE: The only identifiable degradation process in soil is biodegradation. Although biodegradation data specific to 2-methyl-1-butanol are unavailable, analogy to similar aliphatic alcohols suggests that 2-methyl-1-butanol will readily biodegrade. Based upon an estimated Koc values of 15 and 120, 2-methyl-1-butanol is expected to leach readily in soil(2,SRC); however, the importance of leaching may be lessened by relatively rapid, concurrent biodegradation(SRC).|AQUATIC FATE: The only important identifiable degradation process in water is biodegradation. Although biodegradation data specific to 2-methyl-1-butanol are unavailable, analogy to similar aliphatic alcohols suggests that 2-methyl-1-butanol will be readily biodegradable. The volatilization half-lives of 2-methyl-1-butanol from a model environmental river (1 meter deep) and model pond have been estimated to be 61 hr and 28 days, respectively(1,2,SRC). Aquatic bioconcentration, hydrolysis, photodegradation and adsorption to sediment are not expected to be important(SRC).|ATMOSPHERIC FATE: Based upon a vapor pressure of 3.13 mm Hg at 25 °C(1), 2-methyl-1-butanol is expected to exist almost entirely in the vapor-phase in the ambient atmosphere(2,SRC). It will degrade in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals (estimated half-life of 47 hr)(3,SRC). Physical removal from air via wet deposition is possible since 2-methyl-1-butanol is relatively soluble in water(SRC).

The rate constant for the vapor-phase reaction of 2-methyl-1-butanol with photochemically produced hydroxyl radicals has been estimated to be 8.21X10-12 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 47 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Alcohols are generally resistant to aqueous environmental hydrolysis(2); therefore, 2-methyl-1-butanol is not expected to hydrolyze in the environment(SRC).

Based upon a water solubility of 30,000 mg/l at 25 °C(1), the BCF for 2-methyl-1-butanol can be estimated to be 1.8 from a regression-derived equation(2,SRC). Based upon a measured log Kow of 1.29(3), the BCF for 2-methyl-1-butanol can be estimated to be 5.6 from a regression-derived equation(2,SRC). These BCF values suggest that 2-methyl-1-butanol will not bioconcentrate significantly in aquatic organisms(SRC).

Based upon a water solubility of 30,000 mg/l at 25 °C(1), the Koc for 2-methyl-1-butanol can be estimated to be 15 from a regression-derived equation(2,SRC). Based upon a measured log Kow of 1.29(3), the Koc for 2-methyl-1-butanol can be estimated to be 120 from a regression-derived equation(2,SRC). These BCF values suggest that 2-methyl-1-butanol has high to very high soil mobility(4).

2-Methyl-1-butanol has an experimentally measured Henry's Law constant of 1.41X10-5 atm-cu m/mole at 25 °C(1). This value of Henry's Law constant indicates that volatilization from environmental waters is slow, but may be significant from shallow rivers(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 61 hr(2,SRC). Volatilization half-life from an model environmental pond can be estimated to be about 28 days(3,SRC).

2-Methyl-1-butanol has been identified as a volatile component of blue cheese aroma(1), Concord grape juice essence(2), nectarines(3), apples(4,6), roasted filbert nuts(5), papaya fruit(7), oranges(8), tomatoes(9), beer(10), and wine(11).

The general population is exposed to 2-methyl-1-butanol through inhalation of aromas and ingestion of various foods, particularly fruits and fermented beverages. (SRC)

2-Methyl-1-butanol was detected in 5.4% of 387 expired air samples collected from 54 human volunteers that were classified as healthy urban non-smokers(1); the 2-methyl-1-butanol concn ranged from 3.63 to 41.8 ng/l(1).

Drug Information

Fresh air, rest.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

TOXIC BY INGESTION, INHALATION & SKIN ABSORPTION.|2-Methyl-1-butanol ... /is/ low in single dose oral toxicity. ... Severely irritating to the eyes, minimally irritating to the skin, & can be absorbed through the skin. ...

2-methylbutanol

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.

Cough. Dizziness. Drowsiness. Sore throat.


Dry skin. Redness.


Redness. Pain.

2-Methyl-1-butanol Use and Manufacturing

Methods of Manufacturing

BY FRACTIONATION OF FUSEL OIL AND VIA CHLORINATION OF PENTANES.|REACTION OF N-BUTENES WITH CARBON MONOXIDE & HYDROGEN IN THE PRESENCE OF COBALT HYDROCARBONYL (OXO PROCESS) FOLLOWED BY HYDROGENATION OF THE RESULTING C5 ALDEHYDES TO A MIXT OF AMYL ALCOHOLS WHICH CAN BE SEPARATED BY DISTILLATION

Uses

Useful synthetic raw materials.


Intermediates

Production

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1981) 1.36-2.72X10+9 GRAMS (ESTIMATED PRODN)

EXISTS IN COMMERCE LARGELY AS D-AMYL ALCOHOL.

All other basic organic chemical manufacturing|1-Butanol, 2-methyl-: ACTIVE|SYNTHETIC PRODUCT IS RACEMIC MIXTURE OF BOTH DEXTRO- & LEVOROTATORY CMPD &, THEREFORE, NOT OPTICALLY ACTIVE.

NIOSH Method 1402. Analyte: 3-Methyl-1-butanol. Matrix: Air. Procedure: Gas Chromatography, Flame Ionization Detection. For 3-methyl-1-butanol this method has an estimated detection limit of 0.01 mg for a 10-l sample. The precision/RSD is 0.077 and the recovery is 107.6%. Applicability: The working range is 15 to 150 mg/cu m for a 10-l sample. This method may be used to determine two or more analytes simultaneously by varying GC conditions (eg, temperature programming). Interferences: Less volatile compounds may displace more volatile compounds on the charcoal. /3-Methyl-1-butanol/

Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty alcohols [FA05]

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:88.15
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:88.088815002
Monoisotopic Mass:88.088815002
Topological Polar Surface Area:20.2
Heavy Atom Count:6
Complexity:27.1
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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