HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methyl-1-butanol
2-methylbutan-1-ol · 2-METHYL BUTANOL · FEMA 3998 · 2-Methyl butanol-1 · 1-Butanol,2-methyl- · ACTIVE-AMYL ALCOHOL · 2-methyl-butan-1-ol · DL-2-METHYL-1-BUTANOL
Identifiers & Physical Properties
| CAS No. | 137-32-6 |
|---|---|
| Molecular formula | C5H12O |
| Average molar mass | 88.15 g/mol |
| Monoisotopic mass | 88.088815 g/mol |
| SMILES | CCC(C)CO |
| InChIKey | QPRQEDXDYOZYLA-UHFFFAOYSA-N |
| PubChem CID | 8723 |
| ChEMBL | CHEMBL451923 |
| ChEBI | CHEBI:48945 |
| EC No. | 205-289-9 |
| DTXSID | DTXSID5027069 |
Chemical & Physical Properties
| XLogP | 1.2 |
|---|---|
| Topological polar surface area | 20.2 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 2 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 27.1 |
| Lipids | Fatty Acyls [FA] -> Fatty alcohols [FA05] |
| Solvents | Solvents -> Alcohols (<C12) |
| Fragrances | Fragrance Ingredient (2-Methylbutanol) -> IFRA transparency List |
| LogP (partition coefficient) | log Kow= 1.29 (measured)1.2901.3/1.4 |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 0.816 @ 20 °C/4 °CRelative density (water = 1): 0.80.815-0.8200.819 g/mL at 20 °C(lit.) |
| Flavoring agents | EU Flavoring substances |
| Color/Form | COLORLESS LIQ |
| Solubility | MISCIBLE WITH ALC & ETHERSol in acetoneWater solubility: 30,000 mg/l : 25 °CSolubility in water, g/100ml at 25 °C: 3.0 (moderate)Very slightly soluble in water50% soluble in heptane, triacetinsoluble (in ethanol)water: slightly soluble3.6g/a00g at 30°C3.6 g/100 mL (30 ºC) |
| Flash point | 50 °C122 °F (50 °C) (OPEN CUP)50 °C o.c.110 °F |
| Boiling point | 128 °C @ 760 MM HG128.00 to 130.00 °C. @ 760.00 mm Hg130 °C130 °C mm Hg(lit.) |
| Melting point | FREEZING POINT: LESS THAN -70 °C−70 °C(lit.) |
| alpha | -0.1~+0.1°(20℃/D)(neat) |
| Vapor density | 3 (vs air) |
| Vapor pressure | 3 mm Hg ( 20 °C) |
| Refractive index | n20/D 1.411 |
| FEMA | 3998 | (+/-)-2-METHYL-1-BUTANOL |
| FLAVIS Number | 02.076 | 2-Methylbutan-1-ol |
| Storage conditions | Store below +30°C. |
| Physical state | Liquid |
| pKa (acidity coefficient) | 15.24±0.10(Predicted) |
| Color | Clear colorless to very slightly yellow |
| pH | 7 (H2O) |
| Odor | at 100.00 %. ethereal fusel alcoholic fatty greasy winey whiskey leathery cocoa |
| Odor type | ethereal |
| Biological source | synthetic |
| Explosive limits | 1.2-10.3%(V) |
| Merck | 14,6030 |
| JECFA Number | 1199 |
| BRN | 1718810 |
| Henry's law constant | 7.6×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Major applications | flavors and fragrances |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3 |
| InChIKey | QPRQEDXDYOZYLA-UHFFFAOYSA-N |
| SMILES | CCC(C)CO |
| LogP (partition coefficient) | 1.22 |
| Surface tension | 24.09mN/m at 293.15K |
| CAS DataBase Reference | 137-32-6(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | 2-METHYL-1-BUTANOL |
| FDA UNII | 7VTJ239ASU |
| NIST Chemistry Reference | 1-Butanol, 2-methyl-(137-32-6) |
| EPA Substance Registry System | 2-Methyl-1-butanol (137-32-6) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS02,GHS07 |
| Signal word | Warning |
| GHS hazard statements | H332-H313-H316-H335-H226 |
| GHS precautionary statements | P501-P240-P261-P210-P233-P243-P241-P242-P271-P280-P370+P378-P312-P303+P361+P353-P332+P313-P304+P340+P312-P403+P233-P403+P235-P405 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn |
| Risk statements (R) | 10-20-37-66 |
| Safety statements (S) | 46-24/25 |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 100.0 ppm360.0 mg/m3, STEL: 125.0 ppm450.0 mg/m3 |
| UN transport number | UN 1105 3/PG 3 |
| Water hazard class (WGK) | 3 |
| RTECS number | EL5250000 |
| Autoignition temperature | 725 °F |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Acute Tox. 4 InhalationEye Dam. 1Flam. Liq. 3Skin Irrit. 2STOT SE 3 |
| Packing group | III |
| Customs code | 29051500 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 137-32-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 4170 mg/kg LD50 dermal Rabbit 2900 mg/kg |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | DangerH226 (36.3%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2020 reports by companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H226 (100%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatory information | Chemical: 1-Butanol, 2-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)1-Butanol, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butanol, 2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 15-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/120402-Methyl-1-butanol: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Fire hazards | Flammable. Above 50 °C explosive vapour/air mixtures may be formed. |
| Hazards summary | A skin, eye, and respiratory tract irritantMay cause CNS effectsSwallowing the liquid may cause aspiration into the lungs with the risk of chemical pneumonitis. The liquid defats the skin. [ICSC] Safe when used as a flavoring agent[JECFA] In oral lethal dose studies, animals have ataxia and prostration[OECD SIDS] An irritantEffects in high-dose animal studies include spastic paralysis with/without sensory change[MSDSonline]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. |
| EC classification | Symbol: XnR: 10-20-37-66S: (2)-46 |
| UN classification | UN Hazard Class: 3UN Pack Group: III |
| Special Reports | Amyl alcohols or pentanols, Cahiers de Notes Documentaires S'ecurit'e et Hygi'ene du Travail 1st Quarter 1987. |
| Packaging and Labelling | Note: C |
| NFPA Hazard Classification | 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. |
| Hazard Classes and Categories | Flam. Liq. 3 (100%)Flam. Liq. 3 (36.3%)Flammable liquids - Category 3 |
| Explosive Limits and Potential | Explosive limits , vol% in air: 1.4-9.0 |
| Skin, Eye, and Respiratory Irritations | ... Severely irritating to the eyes, minimally irritating to the skin. |
| Fire fighting | Use alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| First aid measures | 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.Rinse mouth. Do NOT induce vomiting. Rest. Refer for medical attention . |
| Safe storage | Fireproof. Cool. |
| Exposure control and personal protection | 20.0 [ppm] |
| Spillage disposal | 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. |
| Preventive Measures | 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. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames, NO sparks and NO smoking. Above 50 °C use a closed system, ventilation and explosion-proof electrical equipment. |
| Inhalation Risk | A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C. |
| Skin Prevention | Protective gloves. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Inhalation Prevention | Use ventilation, local exhaust or breathing protection. |
| Body burden | 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). |
| Environmental fate | 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). |
| Food survey values | 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). |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Exposure routes | The substance can be absorbed into the body by inhalation of its vapour and by ingestion. |
| Signs and Symptoms | Cough. Dizziness. Drowsiness. Sore throat.Dry skin. Redness.Redness. Pain. |
| Effluent Concentrations | 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). |
| Soil Adsorption/Mobility | 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). |
| Natural Pollution Sources | 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). |
| Atmospheric Concentrations | 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). |
| Human Toxicity Excerpts | 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. ... |
| Artificial Pollution Sources | 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). |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 100.0 ppm360.0 mg/m3, STEL: 125.0 ppm450.0 mg/m3 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | EL5250000 |
| UN transport number | UN 1105 3/PG 3 |
| Customs code | 29051500 |
| Toxicity | LD50 orally in Rabbit: 4170 mg/kg LD50 dermal Rabbit 2900 mg/kg |
| Risk statements (R) | 10-20-37-66 |
| Signal word | Warning |
| GHS pictogram | GHS02,GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 46-24/25 |
| Hazard class | 3Acute Tox. 4 InhalationEye Dam. 1Flam. Liq. 3Skin Irrit. 2STOT SE 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | III |
| Target organs | Respiratory system |
| GHS hazard statements | H332-H313-H316-H335-H226 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| Autoignition temperature | 725 °F |
| GHS precautionary statements | P501-P240-P261-P210-P233-P243-P241-P242-P271-P280-P370+P378-P312-P303+P361+P353-P332+P313-P304+P340+P312-P403+P233-P403+P235-P405 |
| Hazardous substances data | 137-32-6(Hazardous Substances Data) |
Applications & Uses
Occurrence
Reportedly present in over 120 natural food products, including apple, apricot, banana, orange, bilberry, black currant, cranberry, papaya, strawberry, tomato and alcoholic beverages
Uses
2-Methyl-1-butanol is a whiskey-scented amyl alcohol that is naturally present in all fruits wine and beer. 2-Methyl-1-butanol is commercially used as a solvent in paints and oils and as flavorant in many processed foods. 2-Methyl-1-butanol has a characteristic redolence, which is thought to account for its active properties as an attractant for hornets and certain wasps, such as yellowjackets, in traps. As a biochemical active ingredient, it has a non-toxic mode of action – targeted pests are killed through physical entrapment.
Uses
2-Methyl-1-butanol is a volatile metabolite produced by a number of different plant species. Used as a solvent in organic synthesis (introduction of active amyl group), in lubricants, plasticizers, additives for oils & paints. It is also employed as a perfuming agent.
Uses
Solvent, organic synthesis (introduction of active amyl group), lubricants, plasticizers, additives for oils and paints.
General Description
S-(-)-2-Methyl-1-butanol is a precursor for the synthesis of chiral liquid crystals. It is a potential new-biofuel.
Preparation & Synthesis
Preparation
Prepared from hydroboration of 2-methyl-1-butene. (–)2-Methyl-1-butanol is isolated by fractional distillation of fusel oil