Basic information
- 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
Show more names
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 properties
- 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
LogP
log Kow = 1.31
1.29
Density
0.812 @ 20 °C/4 °C
Liquid density = 851.5 kg/cu m
Solubility
MISCIBLE WITH ALC, ETHER; IN WATER: ABOUT 3.5% @ 25 °C
Water solubility = 3.5X10+4 mg/L at 25 °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
Safety & regulation
GHS classification
GHS Classification
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
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.)
Hazards Summary
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
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
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
Flam. Liq. 3 (23.8%)
Flammable agents - 3rd degree
Safety & protection
Disposal Methods
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)
...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
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).
Soil Adsorption/Mobility
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
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
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 Bioconcentration
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
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
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
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).
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Hazard statements
- H228-H332-H335
- Precautionary statements
- P210-P240-P241-P261-P271-P304+P340+P312
Chemistry & industry
Pharmacology
Absorption, Distribution and Excretion
...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
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/
General Manufacturing Information
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/
Suppliers50 total
Related reactions
Linked notes
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