2,5-Hexanedione

HCID 8035CAS 110-13-4

Basic information

Standard SMILES
CC(=O)CCC(C)=O
InChIKey
OJVAMHKKJGICOG-UHFFFAOYSA-N
Molecular formula
C6H10O2
Average molar mass
114.14 g/mol
Monoisotopic mass
114.06807956

Overview

2,5-Hexanedione can cause male reproductive toxicity according to an independent committee of scientific and health experts.

Names & identifiers

Preferred name
2,5-Hexanedione
IUPAC
hexane-2,5-dione
English name
2,5-Hexanedione
Molecular formula
C6H10O2
Molecular weight
114.14

Names & synonyms

2,5-HEXANEDIONEHexane-2,5-dioneAcetonylacetone110-13-41,2-Diacetylethane2,5-DiketohexaneDiacetonyl2,5-HexadioneAcetonyl acetone2,5-Dioxohexanealpha,beta-DiacetylethaneNSC 7621
Show more names
acanHexanedione2,5-dione2,5-HEXANDIONE
hexanedione, 2,5-DTXSID8030138NSC-7621C0Z8884J3PDTXCID6010138CHEBI:85014acetone, acetonylalpha, beta-diacetylethane

Database identifiers

CAS
110-13-4
PubChem CID
8035
DTXSID
DTXSID8030138
ChEMBL
CHEMBL1564795
ChEBI
CHEBI:85014
UNII
C0Z8884J3P
EC Number
203-738-3
Nikkaji
J5.518B

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
34.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
8

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SolventsSolvents -> Ketones (<C12)
SpringerMaterials PropertiesBoiling point
LogP-0.27
Density0.9737 at 68 °F (NTP, 1992) - Less dense than water; will float
Solubilitygreater than or equal to 100 mg/mL at 72 °F (NTP, 1992)

Physicochemical properties

Melting point
-6 · -6--5 °C (lit.)
Boiling point
191 °C · 191 °C (lit.)
Density
0.973 g/mL · 0.973 g/mL at 25 °C (lit.)
vapor pressure
0.43 mm · 0.43 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.425(lit.)
Flash point
174 °F · 174 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (97.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P260, P264, P264+P265, P280, P302+P352, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 143 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Hazard information

Regulatory Information · 5 items

Chemical: 2,5-Hexanedione

Hazard Traits - Reproductive Toxicity

2,5-Hexanedione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Hexanedione 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: 24-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/17623

2,5-Hexanedione: HSNO Approval: HSR002760 Approved with controls

DOT LabelFlammable Liquid
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health Hazards · 1 item

SYMPTOMS: This compound may cause irritation of the skin and eyes. It may also cause irritation of the mucous membranes and upper respiratory tract. Exposure to high concentrations of this compound may cause narcosis. It is neurotoxic. It may cause peripheral neuropathy. Discoloration of the skin has been reported. Chronic exposure may produce severe neurologic damage and testicular germinal cell damage. It may affect formed elements of blood after prolonged exposure. Chronic exposure may also cause severe impairment of the central and peripheral nervous systems, the testes and circulating elements in the blood.

Hazards Summary · 1 item

A mild irritant; High concentrations may cause narcosis; [Merck Index] Causes degenerative changes to brain and nerves in 15-week intermittent dermal studies of rats; Causes neurotoxicity and male reproductive changes in repeated dose studies; [RTECS] A skin and strong eye irritant; Prolonged or repeated exposure may cause serious organ injury; May cause impaired fertility; Harmful by ingestion and inhalation; [Alfa Aesar MSDS]

Reactive GroupKetones

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
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.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity DataLC50 (rat) = 2,000 ppm/4hr

Safety data

F
8
wgk
2
tsca
TSCA listed
rtecs
MO3150000
hs_code
29141990
Toxicity
LD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 3 items

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.

Toxic substances from microorganisms, plants or animals that interfere with the functions of the nervous system. Most venoms contain neurotoxic substances. Myotoxins are included in this concept.

Uses & manufacturing

Uses · 2 items

Used as a solvent for cellulose acetate, roll-coating inks, lacquers, and stains; as an intermediate for pharmaceuticals and photographic chemicals; and in electroplating; [NTP]

Electroplating [Category: Plate]

U.S. Production2023: 75,000 - <500,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

2,5-Hexanedione: ACTIVE

Applications · 5 items

Description2, 5-hexadione (2,5-HD) is a flammable, transparent colorless to amber water-soluble liquid that is a multifunctional platform chemical, a major metabolite of n-hexane, and a key intermediate for the production of high energy density aviation fuels from biomass resources. It has a sweet aromatic smell and neurotoxic effects. It can be used as a high energy density fuel additive of platform chemicals, and can induce ovarian granulosa cell cycle arrest to establish ovarian injury model. It can also be used for biological monitoring of 2, 5-hexanedione exposure to n-hexane[1-2].

UsesIt is the metabolite implicated in n-hexane neurotoxicity.

Uses2,5-Hexanedione is used as a reagent in the preparation of trans-2,5-dimethylpyrrolidine. It is also used in the synthesis of 2,5-dimethylpyrroles. Further, it plays an important role as a reagent used for the protection of amino groups in amino sugars and nucleosides. In addition to this, it is used in the preparation of five-membered heterocycles like indane-type and benzannulated systems. It is also employed as a precursor in Diels-alder cycloaddition reactions.

UsesUrinary 2,5-hexanedione (2,5-HD) is used as a biomarker for biological monitoring of workers exposed to n-hexane.[6]

General DescriptionClear colorless to amber liquid with a sweet aromatic odor.

Preparation methods · 1 item

Preparation20 g of diethyl 2,3-diacetylbutanedioate are mechanically shaken for several days with 250 ml (excess) of 5% aqueous sodium hydroxide, and until no diethyl 2,3-diacetylbutanedioate separates on acidification of a sample with dilute hydrochloric acid. The solution is then saturated with potassium carbonate and extracted with ether, the extract is washed with brine to remove alcohol, dried over calcium chloride, and distilled, the fraction 192-198° C being retained. You can get 2,5-Hexanedione with a yield of 70%. Colourless liquid; agreeable odour; miscible with water, alcohol and ether; m.p. 9° C; b.p. 194° C; d=0.973 g/ml at 20° C.

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]
枣庄九星生物科技有限公司0632-3759569 13589608009
Additional notes · 1 item

DefinitionChEBI: 2,5-hexanedione is a diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone It has a role as a human xenobiotic metabolite and a neurotoxin. It is a diketone and a methyl ketone. It derives from a hydride of a hexane.

Related reactions

232 records

Linked notes

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