1-Pentanol

HCID 6276CAS 30899-19-5

Basic information

Standard SMILES
CCCCCO
InChIKey
AMQJEAYHLZJPGS-UHFFFAOYSA-N
Molecular formula
C5H12O
Average molar mass
88.15 g/mol
Monoisotopic mass
88.088815

Overview

N-pentanol appears as a colorless liquid with a mild to moderately strong odor. Less dense than water. Flash point 91 °F. Boiling point 280 °F. Vapors heavier than air. Moderately toxic by ingestion. Vapors may irritate skin and eyes. Used as a solvent and to make other chemicals.

Names & identifiers

Preferred name
1-Pentanol
IUPAC
pentan-1-ol
English name
ISOAMYL ALCOHOL
Molecular formula
C5H12O
Molecular weight
88.15

Names & synonyms

1-PentanolPentan-1-ol71-41-0Amyl alcoholN-Amyl alcoholn-PentanolPentyl alcoholButylcarbinolAmylol1-Pentyl alcoholButyl carbinoln-Butylcarbinol
Show more names
3-METHYLBUTAN-1-OLISOPENTANOLFUSEL OIL3-METHYL BUTANOLFEMA 2057METHYL-BUTANOLISOBUTYLCARBINOL2-METHYL-4-BUTANOL3-METHYLBUTYL ALCOHOLAMYL ALCOHOL, PRIMARY
n-Pentan-1-olN-PENTYL ALCOHOLPentanol-1PentasolAlcool amyliquen-AmylalkoholPrimary amyl alcoholAmyl alcohol, normal

Database identifiers

CAS
30899-19-5、71-41-0
PubChem CID
6276
DTXSID
DTXSID6021741
ChEMBL
CHEMBL14568
ChEBI
CHEBI:44884
UNII
M9L931X26Y
EC Number
200-752-1、250-378-8
Nikkaji
J1.423K

Properties

Computed structural properties

XLogP
1.6
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
3
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
LipidsFatty Acyls [FA] -> Fatty alcohols [FA05]
SolventsSolvents -> Alcohols (<C12)
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Amyl alcohol) -> IFRA transparency List
LogP · 3 items

low Kow= 1.51

1.51

1.51

Physicochemical properties

Melting point
117 °C · −117 °C(lit.)
Boiling point
131 · 131-132 °C
Density
0.809 g/mL · 0.809 g/mL at 25 °C(lit.)
vapor density
3 · 3 (vs air)
vapor pressure
2 mm · 2 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.407

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P317, P319, P321, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

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

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P321, P332+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: 1-Pentanol

Chemical: Pentanol

Regulation (EC) No 1831/2003 (amended)

1-Pentanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Pentanol 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: 14-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2115

Pentanol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

DOT LabelFlammable Liquid
Fire Hazards · 2 items

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

Flammable. Heating will cause rise in pressure with risk of bursting. Above 43 °C explosive vapour/air mixtures may be formed.

Fire PotentialExtremely flammable if exposed to heat or flame.
Health Hazards · 1 item

Irritation of skin, eyes, and respiratory tract; headache and vertigo; dyspnea and cough; nausea, vomiting, and diarrhea. Double vision, deafness, delirium, and occasionally fatal poisoning, preceded by severe nervous symptoms, have been reported. Coma, glycosuria, and methemoglobinemia can occur. (USCG, 1999)

Hazards SummaryA skin, eye, and respiratory tract irritant; Inhalation of high concentrations can cause CNS depression; [ICSC] Vapor can cause lacrimation, but no significant corneal injury; [HSDB]

Safety & protection

Fire Fighting · 2 items

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

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

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Seek medical attention if you feel unwell.

Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageFireproof. Separated from strong oxidants.
Firefighting HazardsThe vapor is heavier than air and may travel along the ground; distant ignition possible.
Exposure Control and Personal Protection20.0 [ppm]

Toxicology

Body Burden · 1 item

n-Pentyl alcohol was detected in the expired air in 4 of 8 male subjects (smoking and nonsmoking) at a concn range 0.007-0.60 ug/hr(1). It was also detected in the expired air of non-smoking healthy subjects(2) and the mean concn was 0.505 ng/L in 54 subjects with a percent occurrence of 22%(3). n-Pentyl alcohol was found in 4 of 12 mother's milk collected from NJ, PA and LA(4). It was also detected in 29 of 46 adipose tissues collected during the 1982 National Human Adipose Tissue Survey(5).

Ecotoxicity Values · 5 items

LC50 Brachydanio rerio (Zebra fish) 530 mg/L/96 hr; static

LC50 Leuciscus idus (Golden orfe) 479 mg/L/48 hr; static

LC50 Pimephales promelas (Fathead minnow, fry <24 hr old) 606 mg/L/96 hr; flow through

LC50 Alburnus alburnus (Bleak) 470 mg/L/96 hr; static

For more Ecotoxicity Values (Complete) data for N-PENTYL ALCOHOL (20 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), determined from a log Kow of 1.51(2)and a regression-derived equation(3), indicates that n-pentyl alcohol is expected to have moderate mobility in soil(SRC). Volatilization of n-pentyl alcohol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.3X10-5 atm-cu m/mole(4). The potential for volatilization of n-pentyl alcohol from dry soil surfaces may exist (SRC) based upon a vapor pressure of 2.2 mm Hg(5). Screening studies using sewage inoculum(6-9) suggest that n-pentyl alcohol will readily degrade in soils under aerobic and anaerobic conditions(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), determined from a log Kow of 1.51(2) and a regression-derived equation(3), indicates that n-pentyl alcohol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.3X10-5 atm-cu m/mole(4) Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 43 hours and 23 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The rate constant for the reaction of n-pentyl alcohol with hydroxyl radicals in aqueous solution has a maximum value of 4.8X10+9/M-sec at a pH of 5(7,8). Based on this rate constant and a value of 10-17 M for the concentration of hydroxyl radical in eutrophic water(9), the half-life of n-pentyl alcohol due to this reaction can be estimated to be 56 days. Therefore, this reaction should not be important in water(SRC). Biodegradation tests of n-pentyl alcohol with sewage and activated sludge(10-13) indicate that aerobic biodegradation will occur in natural water. Biodegradation tests under anaerobic conditions(14,15) suggests that biodegradation of the compound should occur in anaerobic water and sediment(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-pentyl alcohol , which has a vapor pressure of 2.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-pentyl alcohol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(3).

Food Survey Values · 1 item

n-Pentyl alcohol has been detected in volatile components of nectarine(1), fried bacon(3) and roasted filberts(4), Chickpea (Cocer arietimum)(5), kiwi fruit flower(7), Japanese apples(8), Cassava products(10) and Dalieb (Borassus aethiopum), an edible fruit of deciduous palm grown in Sudan(9). Unspecified isomer(s) of pentyl alcohol were detected in volatile components of fried chicken(6). n-Pentyl alcohol was detected at a mean concn 0.008 mg/kg in dry beans, at 0.019 mg/kg in dry split peas and at 0.095 mg/kg in dry lentils(2). n-Pentyl alcohol was detected at concns of 454-1267 ug/kg in commercial soybean curds(11). n-Pentyl alcohol was identified, not quantified, in blue cheese(12).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Regulatory information

FDA Requirements · 1 item

Amyl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

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. Amyl alcohol is produced, as an intermediate or a final product, by process units covered under this subpart.

Safety data

OEB
A
OEL
TWA: 100.0 ppm; 360.0 mg/m3, STEL: 125.0 ppm; 450.0 mg/m3
wgk
1
rtecs
EL5425000
ridadr
UN 1201 3/PG II/III (FUSEL OIL)
hs_code
2905 19 00

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

1-Pentanol is oxidized by alcohol dehydrogenase to /the aldehyde, and the aldehyde is then oxidized by aldehyde dehydrogenase to/ valeric acid in rats, and it can undergo further oxidation or be excreted in the urine.

Pentanol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-pentoxyoxane-2-carboxylic acid.

Absorption, Distribution and Excretion · 5 items

...It is absorbed by GI tract, lung, and through the skin.

When rats were exposed by inhalation to 100, 300, or 600 ppm 6 hr/day, 5 days/week for 7 weeks, 1-pentanol was found in the brain at 0.2, 1.4, and 3.2 ppm, respectively. Similar but smaller values were found in rats exposed to the same concentrations for 14 weeks. 1-Pentanol is oxidized by alcohol dehydrogenase to /the aldehyde, and the aldehyde is then oxidized by aldehyde dehydrogenase to/ valeric acid in rats, and it can undergo further oxidation or be excreted in the urine.

After an oral dose of 0.5, 1, or 2 g/kg of 1-pentanol, the maximal blood levels in mice occurred at 10 min and were nonlinear. The blood levels were 7, 11, and 16 mg/dL, respectively. No 1-pentanol could be found in the blood after 4 hr.

Rats given 1g/kg of 1-pentanol (0.25 g at 15-min intervals) by intraperitoneal injection showed a peak blood concentration of about 21 mg% 1 hr after dosing started and disappearance from the blood after 3.5 hr. Only 0.88% and 0.29% were excreted in the expired air and urine, respectively. Rats given a 2-g/kg oral dose of 1-pentanol had a peak blood concentration of 20 to 25 mg% in 1 hour and essentially none after 4 hr. No alcohol was detected in the urine.

For more Absorption, Distribution and Excretion (Complete) data for N-PENTYL ALCOHOL (6 total), please visit the HSDB record page.

Uses & manufacturing

Uses · 6 items

Used as a solvent (resins, gums, petroleum additives, synthetic flavors, hydraulic fluids), intermediate, lubricant, ore-flotation agent, plasticizer, corrosion inhibitor, and antioxidant; [HSDB] Occurs naturally in many foods; [CHEMINFO]

Metal Extraction and Refining [Category: Industry]

In organic synthesis; as solvent.

Synthetic flavor

Solvent for resins; diluent for hydraulic fluids; intermediate for n-pentyl acetate and other esters; intermediate for dithiophosphate esters (lubricating oil additive and hydraulic fluid additive).

Solvent in the manufacturing of petroleum additives, urea-formaldehyde plastics processing, organic chemical manufacturing and raw material for pharmaceutical preparations

U.S. Production · 6 items

2023: 10,000,000 - <50,000,000 lb

1-Pentanol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1962) 5.5-6.8X10+9 GRAMS (ALL AMYL ALCOHOLS)

(1984) 8.52X10+11 g /ALLYL ALCOHOL, N-PENTYL ALCOHOL, 2-METHYL-1-BUTANOL/

(1986) >10 million - 50 million pounds

For more U.S. Production (Complete) data for N-PENTYL ALCOHOL (8 total), please visit the HSDB record page.

Consumer UsesDispersing agent
Industry UsesIntermediate
Methods of Manufacturing · 3 items

BY HYDROGENATION OF VALERIC ALDEHYDE WITH SODIUM AMALGAM; FROM AMYL CHLORIDE.

Fractional distillation of mixed alcohols resulting from the chlorination and alkaline hydrolysis of pentane

... Commercial processes for the production of amyl alcohols include separation from fusel oils, chlorination of C-5 alkanes with subsequent hydrolysis to produce a mixture of seven of the eight isomers ... and a low pressure oxo process, or hydroformylation, of C-4 olefins followed by hydrogenation of the resultant C-5 aldehydes. /Amyl Alcohols/

Formulations/Preparations · 2 items

Grade: Technical; CP; 98%.

In commerce, however, amyl alcohol is generally a mixture of several isomers, typically 74% (by weight) 1-pentanol, 25% 2-methyl-1-butanol, and 1% 3-methyl-1-butanol.

Applications · 2 items

UsesPentyl alcohol can be used in organic synthesis, as a solvent for coatings, a raw material for pharmaceuticals, a flotation agent for non-ferrous metals, and an antifoaming agent for boiler water. It can also be used to manufacture amyl acetate. Mixtures of pentyl alcohol with other solvents can be used as co-solvents for nitrocellulose lacquer and for extracting resin from wood.

UsesIsoamyl alcohol is a clear, colorless alcohol. It is one of several isomers of amyl alcohol. It is commonly used as a solvent in various applications, such as inks, coatings, and pharmaceutical preparations.

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]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
聊城作之杭化工有限公司19163518031; 19163518031
Additional notes · 1 item

DefinitionChEBI: Pentan-1-ol is an alkyl alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia. It has a role as a plant metabolite. It is an alkyl alcohol, a primary alcohol, a pentanol and a short-chain primary fatty alcohol.

Related reactions

435 records

Linked notes

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