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
Show more names
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
- Formal charge
- 0
- Complexity
- 91.1
Experimental & physicochemical properties
Vapor Pressure
0.43 mmHg at 68 °F ; 1.6 mmHg at 77 °F (NTP, 1992)
2.93 [mmHg]
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
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- alcohol: miscible; Miscible with water, ethylalcohol and ether,ess. oils and perfume materials.
- form
- Liquid
- color
- Clear yellow to brown
- Odor
- Pleasant, sweet-ethereal odor.
- PH
- 6.1 · 6.1 (10g/l, H2O, 20℃)
- explosive limit
- 1.5 % · 1.5%(V)
- Water Solubility
- miscible
- Merck
- 14 · 14,71
- BRN
- 506525 · 506525
- Stability
- Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents. Flammable.
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
- InChIKey
- OJVAMHKKJGICOG-UHFFFAOYSA-N
- SMILES
- CC(=O)CCC(C)=O
- LogP
- -0.27 · -0.270
- CAS DataBase Reference
- 110 · 110-13-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 Z8884J3P · C0Z8884J3P
- Proposition 65 List
- 2 · 2,5-Hexanedione
- NIST Chemistry Reference
- 3 COCH2CH2COCH3 · CH3COCH2CH2COCH3(110-13-4)
- EPA Substance Registry System
- 2 · 2,5-Hexanedione (110-13-4)
- UNSPSC Code
- 12352115 · 12352115
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H361f-H373
- Precautionary statements
- 202 · P202-P260-P301+P312-P302+P352-P305+P351+P338-P308+P313
- target organs
- Nervous system
- Hazard Codes
- Xn,Xi
- Risk Statements
- 36 · 36/38-48/20/21/22-36/37/38
- Safety Statements
- 23 · 23-26-36/37-37/39
- WGK Germany
- 2 · 2
- RTECS
- 3150000 · MO3150000
- F
- 8 · 8
- Autoignition Temperature
- 400 °C · 400 °C
- TSCA
- TSCA listed
- HS Code
- 29141990 · 29141990
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 2
- Toxicity
- 50 orally · LD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)
- REACH Registrations
- Active
Safety & regulation
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
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.
Hazards Summary
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]
Hazard Classes and Categories
Skin Irrit. 2 (97.9%)
Flammable liquids - Category 4
Safety & protection
First Aid
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
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.
Personal Protective Equipment (PPE)
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
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)
- risk_code
- 36/38-48/20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn,Xi
- safety_code
- 23-26-36/37-37/39
- Storage Class
- 10 - Combustible liquids
- target organs
- Nervous system
- Hazard statements
- H302-H315-H319-H361f-H373
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 2
- Autoignition Temperature
- 400 °C
- Precautionary statements
- P202-P260-P301+P312-P302+P352-P305+P351+P338-P308+P313
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]
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].
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
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
Linked notes
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