2,5-Hexanedione
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Basic information
- CAS
110-13-4- 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 propertiesFilling in
- XLogP
- -0.3
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 91.1
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)
Flash Point174 °F (NTP, 1992)
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point376 °F at 760 mmHg (NTP, 1992)
Melting Point22.1 °F (NTP, 1992)
Vapor Density3.94 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
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
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
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
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.
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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
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
All Other Basic Organic Chemical Manufacturing
2,5-Hexanedione: ACTIVE
Applications
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].
Related reactions
232 records
Compound notes
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