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4-Methyl-2-Pentanol

HCID 7910
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Basic information

CAS
108-11-2
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-ol108-11-2IsobutylmethylcarbinolMethyl isobutyl carbinol2-Pentanol, 4-methyl-2-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
Formal charge
0
Complexity
41.4

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 · 3 items

log Kow= 1.43

1.43

1.67

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

Flavoring AgentsEU Flavoring substances
Color/Form · 2 items

COLORLESS LIQ

Colorless liquid.

Solubility · 6 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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)

REACH registered substance: 4-methylpentan-2-ol (EC: 203-551-7)

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.

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
Use ClassificationFragrance Ingredients
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Related reactions

96 records
New reaction record
HRID 4870 reaction equation
HRID 4870As reactantuspto-grants-1993_09
HRID 92523 reaction equation
HRID 92523As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 92588 reaction equation
HRID 92588As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 134601 reaction equation
HRID 134601As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 134616 reaction equation
HRID 134616As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 135404 reaction equation
HRID 135404As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 147932 reaction equation
HRID 147932As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 148974 reaction equation
HRID 148974As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Page 1 of 12

Compound notes

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2 % (NIOSH, 2024)

SOL IN ALC & ETHER.

MISCIBLE WITH MOST COMMON ORG SOLVENTS.

Water solubility of 1.64X10+4 mg/kg (experimental).

Solubility in water, g/100ml: 2

2%

Flash Point · 6 items

106 °F (USCG, 1999)

105 °F

105 °F (OPEN CUP)

41 °C

106 °F

106 °F

Boiling Point · 5 items

269.2 °F at 760 mmHg (USCG, 1999)

133 °C @ 760 MM HG

132 °C

271 °F

271 °F

Melting Point · 5 items

less than -130 °F (USCG, 1999)

-90 °C

-90 °C

-130 °F

-130 °F

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.)
FLAVIS Number
2.183 · 02.183 | 4-Methylpentan-2-ol
Flash point
107 °F · 107 °F
storage temp.
30 °C · Store below +30°C.
solubility
16.4 g/l · 16.4g/l
form
Liquid
pka
15.31 · 15.31±0.20(Predicted)
color
Clear colorless
Odor
Sharp; mild and nonresidual.
Odor Type
pungent
explosive limit
1 · 1-5.5%(V)
Water Solubility
2 g/100 · 2 g/100 mL
Specific Heat Capacity
2.67 J/ · Cp(liquid): 2.67 J/(g·K), at 25℃
BRN
1098268 · 1098268
Henry's Law Constant
2.2 · 2.2×10-1 mol/(m3Pa) at 25℃, Brockbank (2013)
Exposure limits
20 ppm; · ACGIH:TLV-TWA 20 ppm; TLV-STEL 40 ppmOSHA:PEL-TWA 25 ppm (100 mg/m3)NIOSH:REL-TWA 25 ppm; REL-STEL 40 ppm
Stability
Stable. Flammable. Incompatible with oxidizing agents, acids, acid chlorides.
Cosmetics Ingredients Functions
PERFUMING
InChI
1S/C6H14O/c1-5(2)4-6(3)7/h5-7H,4H2,1-3H3
InChIKey
WVYWICLMDOOCFB-UHFFFAOYSA-N
SMILES
CC(C)CC(C)O
LogP
1.57 at · 1.57 at 20℃
CAS DataBase Reference
108 · 108-11-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
8 U34XJK0R0 · 8U34XJK0R0
NIST Chemistry Reference
2 · 2-Pentanol, 4-methyl-(108-11-2)
EPA Substance Registry System
4 · 4-Methyl-2-pentanol (108-11-2)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
2 · GHS02,GHS07
Signal word
Warning
Hazard statements
303 · H303+H313-H316-H319-H335-H336-H226
Precautionary statements
501 · P501-P261-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P312-P337+P313-P305+P351+P338-P303+P361+P353-P332+P313-P304+P340+P312-P403+P233-P403+P235-P405
target organs
Respiratory system
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xi
Risk Statements
10 · 10-37-36/37/38
Safety Statements
24 · 24/25-26
OEB
A
OEL
25 ppm · TWA: 25 ppm (100 mg/m3), STEL: 40 ppm (165 mg/m3) [skin]
RIDADR
2053 · UN 2053
WGK Germany
1 · 1
RTECS
7350000 · SA7350000
Autoignition Temperature
305 °C · 305 °C
TSCA
TSCA listed
HazardClass
3 · 3
PackingGroup
III
HS Code
29051900 · 29051900
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
2 Flam · Eye Irrit. 2Flam. Liq. 3STOT SE 3
Hazardous Substances Data
108 · 108-11-2(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 2590 mg/kg LD50 dermal Rabbit 2884 mg/kg
IDLA
400 ppm · 400 ppm
REACH Registrations
Active

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.

Hazards SummaryIn acute animal studies, high concentrations induce narcosis and anesthesia. [ACGIH] Inhalation of high concentrations can cause CNS depression; A skin, eye, and respiratory tract irritant; [ICSC]
DOT ID and Guide · 2 items

2053 129

2053 129

Reactive GroupAlcohols and Polyols
EC ClassificationSymbol: Xi; R: 10-37; S: (2)-24/25
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
OSHA Standards · 2 items

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 25 ppm (100 mg/cu m). Skin Designation.

Vacated 1989 OSHA PEL TWA 25 ppm (100 mg/cu m); STEL 40 ppm (165 mg/cu m), skin designation, is still enforced in some states.

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]

Fire Fighting ProceduresALCOHOL FOAM.
Nonfire Spill ResponseExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Spillage Disposal · 1 item

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Preventive Measures · 3 items

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

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.

Isolation and Evacuation · 2 items

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

Immediate precautionary measure

Eye PreventionWear safety goggles.

Toxicology

Toxicological InformationRanking: 548 (total points: 244.7)
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

Signs and Symptoms · 4 items

Cough. Sore throat. Unconsciousness.

Dry skin. Redness. Pain.

Redness. Pain.

irritation eyes, skin; headache, drowsiness; dermatitis; In Animals: narcosis

Effluent Concentrations · 1 item

4-Methyl-2-pentanol was detected at a concn of 136 ppb in a sample of influent water from an unspecified municipal wastewater treatment plant(1). It was not indicated whether the compound was detected in final effluent from the plant(1). It was detected at a concn of 45 ppb in effluent samples taken from the Los Angeles County wastewater treatment plant discharge, Palos Verdes, CA between Nov 1980 and Aug 1981(2). A concn of 140 ppm was found in samples of leachate or samples of groundwater plume taken at an unspecified industrial landfill at an unspecified time(3). 4-Methyl-2-pentanol was qualitatively detected in 4 of 16 samples of concentrate derived from large volume (>400 gallons) samples of advanced treatment concentrate from 4 of 6 cities (Lake Tahoe, CA, Oct 1974; Pomona, CA, 1975; Orange County, CA, Feb 1976; Blue Plains, Washington, DC, May 1975)(4).

Soil Adsorption/Mobility · 1 item

Based upon an experimental log Kow of 1.43(1), a Koc of 143 has been estimated using a recommended regression equation(2). Based upon an experimental water solubility of 1.64X10+4 mg/kg(3), a Koc of 21 has been estimated using a recommended regression equation(2). Based upon these estimated Koc, 4-methyl-2-pentanol will be expected to exhibit high to very high mobility in soil(4). 4-Methyl-2-pentanol, therefore, may leach through soil to groundwater if it does not volatilize or biodegrade first(SRC).

Natural Pollution Sources4-Methyl-2-pentanol was qualitatively detected in the mixture of volatiles from mountain Beaufort cheese(1) which indicates that the compound may be formed naturally(SRC).
Atmospheric Concentrations · 1 item

4-Methyl-2-pentanol was qualitatively detected in ambient air samples taken Nov 20, 1979 at the BFI Landfill in New Jersey(1). It was detected in ambient air during an air pollution peak at concn ranging from 0.9 to 7.0 ppb; date and location not specified(2).

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
rtecs
SA7350000
ridadr
UN 2053
hs_code
29051900
Toxicity
LD50 orally in Rabbit: 2590 mg/kg LD50 dermal Rabbit 2884 mg/kg
risk_code
10-37-36/37/38
Signal word
Warning
Symbol(GHS)
GHS02,GHS07
hazard_code
Xi
safety_code
24/25-26
hazard_class
3
Storage Class
3 - Flammable liquids
packing_group
III
target organs
Respiratory system
Hazard statements
H303+H313-H316-H319-H335-H336-H226
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2Flam. Liq. 3STOT SE 3
Autoignition Temperature
305 °C
Precautionary statements
P501-P261-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P312-P337+P313-P305+P351+P338-P303+P361+P353-P332+P313-P304+P340+P312-P403+P233-P403+P235-P405
Hazardous Substances Data
108-11-2(Hazardous Substances Data)

2-Pentanol, 4-methyl-: ACTIVE

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.

Upstream & downstream products

Upstream raw materials

Barium hydroxideDiacetone Alcohol2-Methyl-4-heptanol

Downstream products

4-Methyl-2-pentanonetrans-4-Methyl-2-pentene4-Methyl-1-pentene