Neopentyl glycol

HCID 31344CAS 126-30-7

Basic information

Standard SMILES
CC(C)(CO)CO
InChIKey
SLCVBVWXLSEKPL-UHFFFAOYSA-N
Molecular formula
C5H12O2
Average molar mass
104.15 g/mol
Monoisotopic mass
104.08372962

Overview

2,2-dimethylpropane-1,3-diol is a white crystalline solid. Melting point 130 °C.

Names & identifiers

Preferred name
Neopentyl glycol
IUPAC
2,2-dimethylpropane-1,3-diol
English name
neopentyl glycol
Molecular formula
C5H12O2
Molecular weight
104.15

Names & synonyms

Neopentyl glycol126-30-72,2-Dimethylpropane-1,3-diol2,2-DIMETHYL-1,3-PROPANEDIOLDimethylolpropaneNeopentanediolNeopentylene glycol1,3-Propanediol, 2,2-dimethyl-NeopentylglycolNeolDimethyltrimethylene glycolHydroxypivalyl alcohol
Show more names
NEOPENTYL GLYCONPG Glycol2,2-Dimethyl-1
2,2-Dimethyltrimethylene glycolNexcoat 6002,2-Dimethyl-1,3 propanediolDTXSID8027036QI80HXD6S5ORISTAR NPGNSC-63661,3-Dihydroxy-2,2-dimethylpropane

Database identifiers

CAS
126-30-7
PubChem CID
31344
DTXSID
DTXSID8027036
ChEMBL
CHEMBL3184801
ChEBI
CHEBI:143768
UNII
QI80HXD6S5
EC Number
204-781-0
Nikkaji
J2.511I

Properties

Computed structural properties

XLogP
0
Topological polar surface area
40.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
7

Experimental & physicochemical properties

PolymersOther Classes -> Alcohols and Polyols, Other
SpringerMaterials PropertiesBoiling point
LogP · 2 items

log Kow = 0.12

-0.84

OdorSweetish
Density · 4 items

1.1 g/cu cm

1.1 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

1.06 @25 °C

Color/Form · 2 items

Needles from benzene

Crystalline solid

Physicochemical properties

Melting point
126 · 126-128 °C
Boiling point
208 °C · 208 °C
Density
1.06 · 1.06
vapor density
3.6 · 3.6 (vs air)
vapor pressure
0.8 mm · <0.8 mm Hg ( 20 °C)
refractive index
1.4406 · 1.4406 (estimate)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1.9% (19 of 1013) of reports.

Danger

H315 (21.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 1013 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 4 items

Chemical: 1,3-Propanediol, 2,2-dimethyl-

1,3-Propanediol, 2,2-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanediol, 2,2-dimethyl- 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: 28-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15079

1,3-Propanediol, 2,2-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1,3-Propanediol, 2,2-dimethyl-: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 2 items

Special Hazards of Combustion Products: Emits toxic fumes under fire condition. (USCG, 1999)

Combustible. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible when exposed to heat or flame.
Health Hazards · 1 item

May be harmful by ingestion or skin absorption. Causes eye and skin irritation. Material is irritating to mucous membrane and upper respiratory tract. INHALATION: Call for medical aid. Remove to fresh air. If breathing has stopped, give artificial respiration. If breathing is difficult, give oxygen. (USCG, 1999)

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents: Water sprays, dry chemical powder, alcohol or polymer foam. (USCG, 1999)

Use water spray, powder.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Rinse mouth.

First AidEYES: Flush with copious amounts of water.
Safe StorageSeparated from oxidants. Dry.
Fire Fighting Procedures · 2 items

Water or foam may cause frothing.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Hygroscopic.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that neopentyl glycol is expected to have very high mobility in soil(SRC). Volatilization of neopentyl glycol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X1-07 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Neopentyl glycol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.27X10-2 mm Hg at 25 °C(3). Utilizing the Japanese MITI test, 1.2% of the Theoretical BOD was reached in 2 weeks(4) indicating that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that neopentyl glycol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.1X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 122 and 890 days, respectively(SRC). According to a classification scheme(4), a BCF range of 0.3-0.5(5) suggests bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 1.2% of the Theoretical BOD was reached in 2 weeks(5) indicating that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), neopentyl glycol, which has a estimated vapor pressure of 1.27X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase neopentyl glycol 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 44 hrs(SRC), calculated from its rate constant of 8.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Neopentyl glycol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Toxicity Summary · 1 item

IDENTIFICATION AND USE: Neopentyl glycol (NPG) is a solid. It is used in chemical synthesis, and in polyester manufacture. An insect repellent. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: NPG was not irriating to skin in rabbits, and non sensitizing to the skin in the Murine Local Lymph Node Assay. NPG was practically non-toxic in acute studies in rats and guinea pigs. No treatment-related, adverse findings were observed at clinical examinations, clinical pathology and pathology up to a dose level of 1000 mg/kg bw/d in 90 day oral gavage studies in rats. In other rat study reproductive performance of the parent generation and development of the F1 generation were not affected after oral application of dose levels up to 1000 mg/kg bw/day. In male rats single i.p. injection of 2000 mg/kg bw resulted in a mid level of ataxia but no loss of righting reflex. NPG had no mutagenic activity in Salmonella typhimurium TA 100, TA 1535, TA 98, TA 1537, or in Escherichia coli WP2 uvrA tested with and without metabolic activation at dose levels up to 5000 ug/plate. NPG was not mutagenic in the HPRT locus assay under in vitro conditions in CHO cells in the absence and the presence of metabolic activation.

Signs and Symptoms · 4 items

Cough.

Redness.

Redness. Pain.

Burning sensation.

Ongoing Test Status · 1 item

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of August 9, 2018: http://actor.epa.gov/dashboard/]

Effluent Concentrations · 1 item

Neopentyl glycol was detected at a concentraiton of 14.7 ug/L in an industrial landfill leachate sampled Decemeber 1996. It was not detected in in an industrial effluent from a petrochemical plant taken in July 1996, January 1997, or March 1997 (landfill leachate); detection limit = 1.0 ug/L(1).

Safety data

F
3
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
TY5775000
hs_code
29053990

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

4 rabbits were gavaged with 1000 -1500 mg/kg bw unlabelled neopentyl glycol and excretion of the test substance and their metabolites via urine was determined the following 24 hr (pooled data). After oral application 62% (range 53-67%) of the applied dose was found in the 24-hr urine as the conjugate of glucuronic acid indicating rapid absorption. Only 1.9% of the applied dose was excreted as 3-hydroxy-2,2-dimethylpropionic acid and 0.7% as unchanged neopentyl glycol. Conclusion: Rapid absorption of the test substance after oral exposure followed by conjugation with glucuronic acid and excretion via urine.

Absorption, Distribution and Excretion · 1 item

4 rabbits were gavaged with 1000 -1500 mg/kg bw unlabelled neopentyl glycol and excretion of the test substance and their metabolites via urine was determined the following 24 hr (pooled data). After oral application 62% (range 53-67%) of the applied dose was found in the 24-hr urine as the conjugate of glucuronic acid indicating rapid absorption. Only 1.9% of the applied dose was excreted as 3-hydroxy-2,2-dimethylpropionic acid and 0.7% as unchanged neopentyl glycol. Conclusion: Rapid absorption of the test substance after oral exposure followed by conjugation with glucuronic acid and excretion via urine.

Uses & manufacturing

Uses · 6 items

Used to make plasticizers and polyesters and as modifier of alkyd resins; [Merck Index] Used in chemical synthesis and in the polymers industry; [IUCLID] Used to make large scale and fine chemicals, rubber products, plastic products, textiles, leather, fur, wood and wood products, pulp-paper and paper products, non-metallic mineral products (i.e. plasters and cement), in printing and reproduction of recorded media, building and construction work, scientific research and development, and consumer construction chemicals; [ECHA REACH Registrations]

Pulp and Paper Processing [Category: Industry]

In the manufacture of plasticizers, polyesters, as modifier of alkyd resins.

Used in polyester manufacture. An insect repellent.

Application: 2,2-Dimethyl-1,3-propanediol may be used in the synthesis of: 2,2-dimethyl-1,3-propanediol cyclic phosphorochloridate; 2,2-dimethyl-1,3-propanediol cyclic phenylphosphonate; [1',3'-(2',2'-dimethylpropylene)]-2-iodo-3-octyl-5-thienylboronate; cyclic carbonate; 2,2-dimethyl-1,3-propanediol bis(cyclic-2,2-dimethyltrimethylene phosphite)

Synthetic lubricants.

ImpuritiesImpurities may include neopentyl glycol monoformate, neopentyl glycol monoisobutyrate, 2,2,4-trimethyl-1,3-pentanediol, and the cyclic acetal from the reaction of hydroxypivaldehyde and neopentyl glycol.
U.S. Production · 2 items

2023: 100,000,000 - <250,000,000 lb

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,3-Propanediol, 2,2-dimethyl-:

Consumer UsesPlasticizer
Industry UsesIntermediate
Methods of Manufacturing · 1 item

The aldol addition of isobutyraldehyde (2-methylpropanal) and formaldehyde gives hydroxypivaldehyde (3-hydroxy-2,2- dimethylpropanal), which is then reduced to neopentyl glycol. ... Both aldol addition and subsequent reduction are exothermic. Hydroxypivaldehyde can be reduced either by a crossed Cannizzaro reaction with equimolar amounts of formaldehyde and a base, or by catalytic hydrogenation.

Applications · 4 items

UsesNPG Glycol is used in the synthesis of tetraphenylporphyrins. Also used in the synthesis of Bryostatin 2, a protein kinase modulator.

UsesIn the manufacture of plasticizers, polyesters, as modifier of alkyd resins.

Uses2,2-Dimethyl-1,3-propanediol may be used in the synthesis of:2,2-dimethyl-1,3-propanediol cyclic phosphorochloridate2,2-dimethyl-1,3-propanediol cyclic phenylphosphonate[1′,3′-(2′,2′-dimethylpropylene)]-2-iodo-3-octyl-5-thienylboronatecyclic carbonate2,2-dimethyl-1,3-propanediol bis(cyclic-2,2-dimethyltrimethylene phosphite)

General DescriptionWhite crystalline solid. Melting point 130°C.

Preparation methods · 1 item

Preparation3-hydroxy-2,2-dimethylpropanal) could be reduced to neopentyl glyco. Hydroxypivaldehyde can be reduced either by a crossed Cannizzaro reaction with equimolar amounts of formaldehyde and a base, or by catalytic hydrogenation. If inorganic bases such as potassium carbonate or sodium hydroxide are used as catalysts, satisfactory yields (ca. 80 %) of neopentyl glycol can be obtained only with an excess of isobutyraldehyde. Tertiary amines are also used as catalysts for the aldol addition. Catalytic transfer hydrogenation of the aldol intermediate is also possible using formate salts as hydrogen source. After fractional distillation a very good yield of high-purity neopentyl glycol is obtained.

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]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东飞扬化工有限公司18954855616 · [email protected]

Additional notes

DefinitionChEBI: Neopentyl glycol is a propane-1,3-diol carrying two methyl groups at position 2.

Related reactions

251 records

Linked notes

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