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Neopentyl alcohol

HCID 6404
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Basic information

CAS
75-84-3
Standard SMILES
CC(C)(C)CO
InChIKey
KPSSIOMAKSHJJG-UHFFFAOYSA-N
Molecular formula
C5H12O
Average molar mass
88.15 g/mol
Monoisotopic mass
88.088815

Names & identifiers

Preferred name
Neopentyl alcohol
IUPAC
2,2-dimethylpropan-1-ol
English name
2,2-Dimethyl-1-propanol
Molecular formula
C5H12O
Molecular weight
88.14818

Names & synonyms

NEOPENTYL ALCOHOL75-84-32,2-dimethylpropan-1-ol2,2-Dimethyl-1-propanol2,2-Dimethylpropanoltert-ButylcarbinolNeoamyl alcoholNeopentanol1-Propanol, 2,2-dimethyl-tert-Butyl carbinol2,2-Dimethylpropyl alcohol5I067PJD7S
Show more names
DTXSID9052501RefChem:832324DTXCID3031074200-907-3NeopentylalcoholMFCD000046822,2,2-Trimethylethanol2,2-dimethyl-propan-1-ol

Database identifiers

CAS
75-84-3
PubChem CID
6404
DTXSID
DTXSID9052501
ChEMBL
CHEMBL458630
UNII
5I067PJD7S
EC Number
200-907-3
Nikkaji
J4.163G

Properties

Computed structural propertiesFilling in

XLogP
1.3
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
6
Formal charge
0
Complexity
33.7

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Alcohols (<C12)
SpringerMaterials PropertiesBoiling point
LogP · 2 items

log Kow = 1.31

1.29

OdorPEPPERMINT ODOR
Density · 2 items

0.812 @ 20 °C/4 °C

Liquid density = 851.5 kg/cu m

Viscosity2.5 mPa.S @ 20 °C (liquid viscosity)
Color/FormCRYSTALS
Solubility · 2 items

MISCIBLE WITH ALC, ETHER; IN WATER: ABOUT 3.5% @ 25 °C

Water solubility = 3.5X10+4 mg/L at 25 °C.

Flash Point98 °F (37 °C) (CLOSED CUP)

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 · 5 items

This chemical does not meet GHS hazard criteria for 15.7% (29 of 185) of reports.

Danger

H226 (23.8%): 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, P317, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 185 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: 1-Propanol, 2,2-dimethyl-

2,2-Dimethyl-1-propanol: Does not have an individual approval but may be used under an appropriate group standard

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.)

Fire PotentialDANGEROUS, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS. /AMYL ALCOHOL/
Hazards Summary · 1 item

Higher alcohols are not highly toxic in the industrial setting; Can cause liver injury, somnolence, and respiratory depression in experimental animals; Related compounds can cause irritation of eye, nose, and throat and CNS depression in high concentrations; [HSDB] Related compounds cause nose, throat, and respiratory tract irritation; Inhalation of high concentrations can cause CNS depression; Aqueous solutions cause severe eye irritation, based on animal studies; [CHEMINFO] An irritant; [MSDSonline]

NFPA Hazard Classification · 3 items

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThe primary alcohols are rapidly metabolized largely via the ADH route ... . /Primary amyl alcohols/
Absorption, Distribution and Excretion · 3 items

...BECAUSE OF THEIR LOW VOLATILITY &...LOW SOLUBILITY IN BODY FLUIDS, THEY ARE ABSORBED SLOWLY & ONLY TO SMALL EXTENT. /AMYL ALCOHOL/

RATE OF ELIMINATION...OF AMYL ALCOHOLS FROM BODY DECREASES IN FOLLOWING ORDER: PRIMARY, SECONDARY, TERTIARY. /AMYL ALC/

Small amounts of the primary and secondary alcohols, and appreciable amts of the tertiary isomer, are excreted unchanged in the respired air and urine. /Amyl alcohols/

Uses & manufacturing

Uses · 2 items

No specific uses were located for 2,2-dimethyl-1-propanol. In general, pentanols are used in the manufacture of lacquers, chemicals, pharmaceuticals and plastics; and used as flavouring agents and in fragrances. [CHEMINFO]

USED IN PHARMACEUTICAL PREPARATIONS; FLOTATION AGENT; ORGANIC SYNTHESIS /AMYL ALCOHOLS/

U.S. Imports(1984) 1.89X10+8 g/AMYL ALCOHOLS/
Methods of ManufacturingReview of manuf (by fractionation of fusel oil & via chlorination of pentanes) and properties: Industrial Chemicals, 2nd ed. W.L. Faith et al., Eds. NY,NY: Wiley & Sonspp. 107-14 (1957).
General Manufacturing Information · 3 items

1-Propanol, 2,2-dimethyl-: ACTIVE

...USED IN MFR OF LACQUERS, CHEMICALS, RUBBER, PLASTICS, FRUIT ESSENCES, & EXPLOSIVES, THEY ARE USED AS COMPONENT OF PAINT STRIPPERS & HYDRAULIC FLUIDS & AS INTERMEDIATE OF ORE-FLOTATION AGENTS & OTHER AMYL DERIVATIVES. /AMYL ALC/

...SOLVENTS FOR CAMPHOR, ALKALOIDS, SOFT COPALS, ESTER GUMS, RESINS, IODINE, PHOSPHORUS & SULFUR. /PENTANOLS/

Related reactions

159 records
New reaction record
HRID 4506 reaction equation
HRID 4506As reactantuspto-grants-1988_02
HRID 20400 reaction equation
HRID 20400As reactantuspto-grants-2010_06
HRID 20411 reaction equation
HRID 20411As reactantuspto-grants-2010_06
HRID 20415 reaction equation
HRID 20415As reactantuspto-grants-2010_06
HRID 24169 reaction equation
HRID 24169As reactantuspto-grants-2005_02
HRID 45249 reaction equation
HRID 45249As reactantuspto-grants-2013_09
HRID 51735 reaction equation
HRID 51735As reactantuspto-grants-2004_03
HRID 91307 reaction equation
HRID 91307As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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Compound notes

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Boiling Point
114 °C
Melting Point53 °C

Physicochemical properties

Melting point
53 °C · 53 °C
Boiling point
114 °C · 114 °C
Density
0.812 g/cm3 · 0.812 g/cm3
pka
15.24 · 15.24±0.10(Predicted)
Symbol(GHS)
2 · GHS02,GHS07
Signal word
Danger
Hazard statements
228 · H228-H332-H335
Precautionary statements
210 · P210-P240-P241-P261-P271-P304+P340+P312

3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and Categories · 2 items

Flam. Liq. 3 (23.8%)

Flammable agents - 3rd degree

Explosive Limits and PotentialMODERATE, WHEN EXPOSED TO FLAME. HYDROGEN TRISULFIDE (H2S3) CAN EXPLODE IT. /AMYL ALCOHOL/
Critical Temperature and PressureCritical temperature: 276.85 °C; Critical pressure 29,100 mm Hg

Safety & protection

Exposure Control and Personal Protection20.0 [ppm]
Fire Fighting ProceduresSEE AMYL ALCOHOL. ALCOHOL FOAM. DRY CHEMICAL. /AMYL ALCOHOL/
Storage ConditionsSTORAGE REQUIREMENTS: EVEN SLIGHTLY FLAMMABLE MATERIALS SHOULD BE ISOLATED FROM OXIDIZERS. ...STORAGE AREA SHOULD BE KEPT COOL & VENTILATED & SHOULD BE FIREPROOF.
Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal Protective Equipment (PPE) · 1 item

...USE OF BARRIER CREAMS & PERSONAL PROTECTIVE CLOTHING TO PREVENT SKIN CONTACT. CANISTER-TYPE RESPIRATORS CAPABLE OF ABSORBING ORG VAPOR WILL PROTECT AGAINST PULMONARY ABSORPTION IN...LOW LEVELS OF AIR CONTAMINATION. AIRLINE RESPIRATORS OR SELF-CONTAINED AIR...WHERE THERE IS HIGH-LEVEL... /PENTYL ALCOHOL/

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 123(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that neopentyl alcohol will have high mobility in soil(SRC). Volatilization of neopentyl alcohol may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 5.3X10-5 atm-cu m/mole(SRC), calculated from experimental values of vapor pressure(4) and water solubility(5) and from dry soil surfaces(SRC) based on an experimental vapor pressure of 16 mm Hg(4). Insufficient data are available to determine the rate or importance of biodegradation of neopentyl alcohol in soil(SRC) but the quarternary carbon structure would suggest that biodegradation may be slow(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 123(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that neopentyl alcohol may not adsorb to suspended solids and sediment(SRC) in the water. Neopentyl alcohol may volatilize from water surfaces based on an estimated Henry's Law constant of 5.3X10-5 atm-cu m/mole(SRC), calculated using an experimental vapor pressure(3) and an experimental water solubility(4). Estimated half-lives for a model river and model lake are 18.3 hours and 8.4 days, respectively(5,SRC). An estimated BCF value of 5.8(5,SRC), from an experimental log Kow(2), suggests that neopentyl alcohol will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(6). Insufficient data are available to determine the rate or importance of biodegradation of neopentyl alcohol in water(SRC) but the quarternary carbon structure would suggest that biodegradation may be slow(7).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 16 mm Hg at 25 °C(2) indicates that neopentyl alcohol will exist in the vapor-phase in the ambient atmosphere. Vapor-phase neopentyl 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 about 3.4 days(3,SRC). Neopentyl alcohol may be physically removed from the air by wet deposition(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Soil Adsorption/Mobility · 1 item

The Koc of neopentyl alcohol is estimated as approximately 123(SRC), using an experimental log Kow of 1.31(1) and a regression-derived equation(2). According to a recommended classification scheme(3), this estimated Koc value suggests that neopentyl alcohol has high mobility in soil(SRC).

Human Toxicity Excerpts · 5 items

PENTYL ALCOHOL IS IRRITATING TO THE MUCOUS MEMBRANES OF THE EYES, NOSE, AND THROAT... THE COMPLAINTS FROM SYSTEMIC ILLNESS INCLUDE HEADACHE, DIZZINESS, NAUSEA, VOMITING, DIARRHEA, DELIRIUM, &.../CNS DEPRESSION/. /PENTYL ALCOHOL/

NO EFFECTS UPON NERVES OF SKIN OF MEN & NO LOCAL WHEAL FORMATION, ERYTHEMA, OR HYPEREMIA WERE OBSERVED...FOLLOWING APPLICATION OF ALL ISOMERS EXCEPT 1-PENTANOL. /AMYL ALCOHOL/

ACCORDING TO ANIMAL EXPERIMENTS, AMYL ALCOHOLS ARE ABOUT FOUR TIMES AS TOXIC AS ETHYL ALCOHOL. HOWEVER, BECAUSE OF THEIR LOW VOLATILITY &...LOW SOLUBILITY IN BODY FLUIDS, THEY ARE ABSORBED SLOWLY & ONLY TO SMALL EXTENT. /AMYL ALCOHOL/

The exposure of 2,2-dimethyl-1-propanol for 5 min induced erythema in only 17% of the 12 human subjects over the subsequent 60 min.

For more Human Toxicity Excerpts (Complete) data for NEOPENTYL ALCOHOL (8 total), please visit the HSDB record page.

Artificial Pollution Sources · 1 item

Amyl alcohols, such as neopentyl alcohol, are used as pharmaceutical preparations, flotation agents, and in organic synthesis(1). Therefore, neopentyl alcohol's production and use in these areas may result in its release to the environment through various waste streams(SRC).

Environmental BiodegradationAlthough no biodegradation data are available for neopentyl alcohol, the quarternary carbon structure would suggest that biodegradation may be slow(1).
Environmental Bioconcentration · 1 item

An estimated BCF value of 5.8 was calculated for neopentyl alcohol(SRC), using an experimental log Kow of 1.31(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for neopentyl alcohol is estimated as 5.3X10-5 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 16 mm Hg(1), and water solubility, 3.5X10+4 mg/l(2). This Henry's Law constant value indicates that neopentyl alcohol will volatilize from water surfaces(3,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 18.3 hours(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 8.4 days(3,SRC). Neopentyl alcohol's vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil may occur(SRC).

Non-Human Toxicity Excerpts · 5 items

ALL ISOMERS OF AMYL ALCOHOL ARE.../CNS DEPRESSANTS/, & IN HIGH DOSAGE LETHAL TO ANIMALS... /PENTANOLS/

2,2-Dimethyl-1-propanol (at concn of 50 mM) stimulates in vitro the peptidase activity (by 160%) but inhibits the esterase activity (by 76%) of carboxypeptidase A.

2,2-Dimethyl-1-propanol inhibits the cytochrome p450 dependent mixed function oxidases, specificaly aniline hydroxylase, in suspensions of rat liver microsomes.

The concn (H50) which caused 50% hemolysis of rabbit erythrocytes in isotonic saline, 1 hr at 37 °C, is 2,2-dimethyl-1-propanol, 128 mM. The concn (ID50) required to produce 50% inhibition of cell growth of mouse fibroblast L cells is 2,2-dimethyl-1-propanol, 10.8 mM.

All /amyl alcohols/ are appreciably irritating to the eyes and capable of causing transient corneal opacity. All are somewhat irritating to the uncovered skin when exposures are repeated and severely irritating when confined to the skin. All can be absorbed through the skin of animals in toxic amts when exposures are severe. High conc of vapor are irritating to the mucous membranes and typically cause central nervous system effects and death by respiratory failure. /Amyl alcohols/

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of neopentyl alcohol with photochemically produced hydroxyl radicals has been estimated as 4.66X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 3.4 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

Probable Routes of Human ExposureOccupational exposure to pentyl alcohols, such as neopentyl alcohol, can occur through dermal contact, inhalation, and ingestion(1).
Environmental Water ConcentrationsDRINKING WATER: Neopentyl alcohol was reported in advanced treatment water in Orange County, CA(1).

Safety data

Signal word
Danger
Symbol(GHS)
GHS02,GHS07
Hazard statements
H228-H332-H335
Precautionary statements
P210-P240-P241-P261-P271-P304+P340+P312