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Hexan-2,5-dion

2,5-Hexanedione

HCID 8035
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Grundinformationen

CAS
110-13-4
Standard-SMILES
CC(=O)CCC(C)=O
InChIKey
OJVAMHKKJGICOG-UHFFFAOYSA-N
Summenformel
C6H10O2
Durchschnittliche Molmasse
114,14 g/mol
Monoisotopische Masse
114,06807956

Überblick

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

Namen und Bezeichner

Bevorzugter Name
2,5-Hexanedione
IUPAC
hexane-2,5-dione
Lokaler Name
Hexan-2,5-dion
Englischer Name
2,5-Hexanedione
Summenformel
C6H10O2
Molmasse
114.14

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-0,3
Polarare Oberfläche (TPSA)
34,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
8
Formalladung
0
Komplexität
91,1

Experimentelle und physikochemische Eigenschaften

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)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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]

Gefahrenhinweise

Regulatory Information · 5 Einträge

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 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 3 Einträge

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.

Verwendung und Herstellung

Uses · 2 Einträge

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 Einträge

All Other Basic Organic Chemical Manufacturing

2,5-Hexanedione: ACTIVE

Anwendungen · 3 Einträge

2, 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].

Zugehörige Reaktionen

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Vapor Pressure · 2 Einträge

0.43 mmHg at 68 °F ; 1.6 mmHg at 77 °F (NTP, 1992)

2.93 [mmHg]

Physikochemische Eigenschaften

Schmelzpunkt
-6 · -6--5 °C (lit.)
Siedepunkt
191 °C · 191 °C (lit.)
Dichte
0.973 g/mL · 0.973 g/mL at 25 °C (lit.)
Dampfdruck
0.43 mm · 0.43 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.425(lit.)
Flammpunkt
174 °F · 174 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
alcohol: miscible; Miscible with water, ethylalcohol and ether,ess. oils and perfume materials.
Aggregatzustand
Liquid
Farbe
Clear yellow to brown
Geruch (Odor)
Pleasant, sweet-ethereal odor.
PH
6.1 · 6.1 (10g/l, H2O, 20℃)
Explosionsgrenze
1.5 % · 1.5%(V)
Wasserlöslichkeit
miscible
Merck
14 · 14,71
BRN
506525 · 506525
Stabilität
Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents. Flammable.
Kosmetik-Inhaltsstoffe Funktionen
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 Datenbank
110 · 110-13-4(CAS DataBase Reference)
NIST chemische Informationen
3 COCH2CH2COCH3 · CH3COCH2CH2COCH3(110-13-4)
EPA chemische Informationen
2 · 2,5-Hexanedione (110-13-4)
Hazards Summary · 1 Eintrag

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
Reactivity AlertsHighly Flammable
Reactivity Profile2,5-HEXANEDIONE is incompatible with oxidizing agents. It is also incompatible with strong bases and strong reducing agents. (NTP, 1992)
Air and Water ReactionsHighly flammable. Water soluble.
Hazard Classes and Categories · 2 Einträge

Skin Irrit. 2 (97.9%)

Flammable liquids - Category 4

Sicherheit und Schutzausrüstung

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 Eintrag

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 Eintrag

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 Eintrag

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)

Toxikologische Informationen

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

Sicherheitsdaten

F
8
wgk
2
tsca
TSCA listed
hs_code
29141990
RTECS-Nr.
MO3150000
risk_code
36/38-48/20/21/22-36/37/38
Toxizität
LD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)
hazard_code
Xn,Xi
safety_code
23-26-36/37-37/39
Speicherklasse
10 - Combustible liquids
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 2
Selbstentzündungstemperatur
400 °C
Beschreibung

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

VerwendenIt is the metabolite implicated in n-hexane neurotoxicity.

Darstellung · 1 Eintrag

synthetische20 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2,5-DimethylfuranIODINE PUREDiacetylKaliumcarbonatETHYL ACETOACETATE SODIUM SALT3-HEXENE-2,5-DIONE(2R,3S,4S,5R)-2,5-Bis(hydroxymethyl)-oxolane-2,3,4-triol5-(Chlormethyl)-2-furaldehyd5-MethylfurfuralHexan-2,5-diol

Nachgelagerte Produkte

2,5-Dimethyl-1H-pyrrol5-Methylisoxazol-3-carboxylsure1-[2,6-DICHLORO-4-(TRIFLUOROMETHYL)PHENYL]-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE2,5-DimethylthiophenAscorbinsureMethyl-3-methyl-2-butenoatTetrahydropyran2,5-Dimethyl-1-phenyl-1H-pyrrol1-(4-CYANOPHENYL)-2,5-DIMETHYLPYRROLE
Ergänzende Hinweise · 1 Eintrag

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.