4-Methyl-2-Pentanol

HCID 7910CAS 108-11-2

Basic information

Standard SMILES
CC(C)CC(C)O
InChIKey
WVYWICLMDOOCFB-UHFFFAOYSA-N
Molecular formula
C6H14O
Average molar mass
102.17 g/mol
Monoisotopic mass
102.10446507

Overview

Methyl isobutyl carbinol appears as a clear colorless liquid. Flash point 120 °F. Less dense than water. Vapors heavier than air.

Names & identifiers

Preferred name
4-Methyl-2-Pentanol
IUPAC
4-methylpentan-2-ol
English name
4-Methyl-2-pentanol
Molecular formula
C6H14O
Molecular weight
102.17

Names & synonyms

4-METHYL-2-PENTANOL4-Methylpentan-2-ol108-11-2Isobutylmethylcarbinol2-Pentanol, 4-methyl-Methyl isobutyl carbinol2-Methyl-4-pentanolMethylisobutylcarbinolMIBCIsobutylmethylmethanol1,3-Dimethylbutanol3-MIC
Show more names
4-methyl-2-pentanoFEMA 3351METHYL AMYL ALCOHOL1,3-Dimethyl-1-butanolISOBUTYL METHYL CARBINOL
4-Methylpentanol-2MAOHMetilamil alcoholMethylisobutyl carbinoldl-Methylisobutylcarbinol4-Methyl-2-amyl alcoholAlcool methyl amylique4-Methyl-2-pentyl alcohol

Database identifiers

CAS
108-11-2
PubChem CID
7910
DTXSID
DTXSID2026781
ChEMBL
CHEMBL448896
UNII
8U34XJK0R0
EC Number
203-551-7
Nikkaji
J2.414G

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
7

Experimental & physicochemical properties

Chemical Classes · 2 items

Flammable agents - 2nd degree

Volatile Organic Compound (VOC)

SolventsSolvents -> Alcohols (<C12)
FragrancesFragrance Ingredient (4-Methyl-2-pentanol) -> IFRA transparency List
LogP · 2 items

log Kow= 1.43

1.43

OdorMild odor.
Density · 6 items

0.807 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8075 @ 20 °C/4 °C

% IN SATURATED AIR: 0.46 @ 20 °C; DENSITY OF SATURATED AIR: 1.01 (AIR= 1)

Relative density (water = 1): 0.82

0.81

0.81

Physicochemical properties

Melting point
-90 °C · -90 °C
Boiling point
134 · 134-135 °C(lit.)
Density
0.802 g/mL · 0.802 g/mL at 25 °C(lit.)
vapor density
3.5 · 3.5 (vs air)
vapor pressure
3.7 mm · 3.7 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.415(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: 2-Pentanol, 4-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Pentanol, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Pentanol, 4-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: 03-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/16189

2-Pentanol, 4-methyl-: HSNO Approval: HSR001193 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 2-Pentanol, 4-methyl-: Environment tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 41 °C explosive vapour/air mixtures may be formed.

Fire PotentialMODERATE FIRE RISK.
Health Hazards · 2 items

Vapor irritates eyes and nose; may cause anesthesia. Prolonged contact with liquid causes irritation and cracking of skin; also irritates eyes. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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

Rinse mouth. Rest. Refer for medical attention .

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 items

Excerpt from NIOSH Pocket Guide for Methyl isobutyl carbinol:

General First Aid:

(General first aid procedures)

Safe StorageFireproof if in building. Separated from strong oxidants. Cool.
Exposure Control and Personal Protection · 2 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

20.0 [ppm]

Toxicology

Target OrgansEyes, skin, central nervous system
Ecotoxicity ValuesLD50 Goldfish 360 mg/l/24 hr (modified ASTM D 1345)
Environmental Fate · 3 items

TERRESTRIAL FATE: If 4-methyl-2-pentanol is released to soil, it will be expected to exhibit high to very high mobility in soil(1,SRC) based upon estimated Koc of 143 and 21 estimated from log Kow(2) and water solubility(3), respectively, using a recommended regression equations(4,SRC). It may, therefore, leach through soil(SRC). It will not hydrolyze in moist soil(4), but it may be subject to volatilization from near surface soil based upon estimated rates for its volatilization from water(4-6). It may be subject to biodegradation in soil based upon the rapid biodegradation observed in laboratory aqueous screening tests using sewage and activated sludge inoculum(7,8).

AQUATIC FATE: If 4-methyl-2-pentanol is released to water, it will not be expected to adsorb to sediment and suspended particulate matter or to bioconcentrate in aquatic organisms based upon estimated Koc and BCF, respectively, estimated(2,SRC) from the measured log Kow (1) and water solubility(3). It will not be expected to hydrolyze(2) or directly photolyze(4,SRC). It may be subject to biodegradation in natural waters based upon the rapid biodegradation observed in laboratory aqueous screening tests using sewage and activated sludge inoculum(5,6). It will be subject to volatilization from surface waters based upon half-lives of 23 hr for volatilization from a model river one meter deep flowing 1 m/sec with a wind velocity of 3 m/sec(2,SRC) and 10.6 days for volatilization from a model pond(7,SRC), respectively, estimated using a measured Henry's Law constant(8).

ATMOSPHERIC FATE: If 4-methyl-2-pentanol is released to the atmosphere, it can be expected to exist mainly in the vapor-phase in the ambient atmosphere(1,SRC) based upon an experimental vapor pressure of 5.3 mm Hg at 25 °C(2,SRC). The measured rate constant for vapor-phase reaction with photochemically produced hydroxyl radicals of 7.1X10-12 cu cm/molecule-sec at 25 °C(3) corresponds to an atmospheric half-life of 2.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). 4-Methyl-2-pentanol has been rated a moderately reactive (Class III) compound(4) with respect to ozone formation as observed in smog chamber tests(5). 4-Methyl-2-pentanol will not be expected to directly photolyze in the atmosphere(6,SRC).

Food Survey Values4-Methyl-2-pentanol was qualitatively detected in the mixture of volatiles from mountain Beaufort cheese(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 items

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

inhalation, skin absorption, ingestion, skin and/or eye contact

Regulatory information

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Methyl isobutyl carbinol is produced, as an intermediate or final product, by process units covered under this subpart.

Safety data

OEB
A
OEL
TWA: 25 ppm (100 mg/m3), STEL: 40 ppm (165 mg/m3) [skin]
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
IDLA
400 ppm
tsca
TSCA listed

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

... UNDERGOES IN RABBIT SOME GLUCURONIC ACID CONJUGATION. AVG AMT GLUCURONIDE EXCRETED FOLLOWING DOSE ADMIN BY STOMACH TUBE WAS 33.7% OF DOSE. URINE CONTAINED ALSO A SMALL AMT METHYL KETONE (PRESUMABLY ISOBUTYL METHYL KETONE) & AFTER EXTRACTION WITH 1:4 ETHANOL ETHER A GLUCURONIDE (TRIACETYL METHYL ESTER) GUM.

Uses & manufacturing

Uses · 3 items

Used primarily in the production of additives for anti-wear and corrosion inhibitors; Used secondarily as a flotation agent (copper ores, coal and tar sand mining); Also used as an additive to surface coatings and solvent to improve binder softness; Usually used in closed systems except as a floating agent; [ACGIH, 2020]

Solvent for dyestuffs, oils, gums, resins, waxes, nitrocellulose, and ethylcellulose; organic synthesis; froth flotation; brake fluids.

In the manufacture of lubricant additives, solvents, plasticizers, lacquers.

U.S. Production · 2 items

2023: 70,000,000 - <85,000,000 lb

(1972) 1.81X10+10 GRAMS

Consumer UsesSolvent
Industry UsesSurfactant (surface active agent)
Methods of Manufacturing... PREPARED COMMERCIALLY BY REDN OF MESITYL OXIDE IN ACETIC ACID SOLN WITH PLATINUM, OR OVER REDUCED COPPER ON ASBESTOS @ 120 °C.
Formulations/PreparationsGRADE: TECHNICAL
Applications · 5 items

DescriptionMIBC is a colorless liquid with a mild odor.The odor threshold is 0.52 ppm. Molecularweight 5 102.20; Specific gravity (H2O:1) 5 0.81; Boilingpoint 5 132.8℃; Freezing/Melting point 5 2 90℃; Vaporpressure 5 3 mmHg at 20℃; Flash point = 41℃. Theexplosive limits are LEL 5 1.0%; UEL 5 5.5%. HazardIdentification (based on NFPA-704 M Rating System):Health 2, Flammability 2, Reactivity 0. Slightly soluble inwater; solubility 5 2%.

UsesSolvent for dyestuffs, oils, gums, resins, waxes, nitrocellulose, and ethylcellulose; organic synthesis; froth flotation; brake fluids.

UsesSolvent; organic syntheses; brake fluids

Uses(^+)-4-Methyl-2-pentanol is employed as a solvent in organic synthesis, dyes and stains, natural resins and waxes. It is an additive to surface coatings. It finds applications in the manufacture of lube oil additives, zinc dialkyldithiophosphate, brake fluids. It is the precursor to some plasticizers and frother in mineral flotation. It acts as a corrosion inhibitor and also utilized in the characterization of volatile fraction of mono varietal wines and tar sand mining processes.

General DescriptionA clear colorless liquid. Flash point 120°F. Less dense than water. Vapors heavier than air.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北鑫杰成化工科技有限公司13554075426 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

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