2,5-Hexanedione
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2,5-Hexanedione
structure -
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CAS No:
110-13-4
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Formula:
C6H10O2
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Chemical Name:
2,5-Hexanedione
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Synonyms:
2,5-Hexanedione;α,β-Diacetylethane;1,2-Diacetylethane;Acetonylacetone;Diacetonyl;2,5-Dioxohexane;2,5-Diketohexane;NSC 7621;4-Acetyl-2-butanone
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CAS No:
Description
colourless to pale yellow liquidChEBI: A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanoneClear colorless to amber liquid with a sweet aromatic odor.
2,5-hexanedione is a clear colorless to amber liquid with a sweet aromatic odor. (NTP, 1992)
2,5-hexanedione is a clear colorless to amber liquid with a sweet aromatic odor. (NTP, 1992)|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.
2,5-Hexanedione Basic Attributes
114.14
114.14
506525
203-738-3
C0Z8884J3P
7621
1224
DTXSID8030138
29141990
Characteristics
34.1
-0.3
Clear yellow to brown Liquid
0.971 g/cm3 @ Temp: 20 °C
-5.5 °C
194 °C
174 °F
n 20/D 1.425(lit.)
Micible with water.
Store below +30°C.
0.43 mm Hg ( 20 °C)
3.94 (NTP, 1992) (Relative to Air)
Oral-Rat LD50: 2076 mg/kg; Oral-Mouse LD50: 2386 mg/kg
Combustible in case of open flame, high temperature, strong oxidant; burning emits irritating smoke
1.5%(V)
7.13e-12 cm3/molecule*sec
Highly flammable. Water soluble.
Ketones
Highly Flammable
2,5-HEXANEDIONE is incompatible with oxidizing agents. It is also incompatible with strong bases and strong reducing agents. (NTP, 1992)
920 °F (NTP, 1992)
Safety Information
I; II; III
NONH for all modes of transport
2
36/38-48/20/21/22-36/37/38
23-26-36/37-37/39
MO3150000
Xn,Xi
Warehouse ventilated, low temperature and dry
Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents. Flammable.
P305 + P351 + P338
H315-H319-H373
This chemical is combustible. (NTP, 1992)
|Warning|H315 (97.87%): Causes skin irritation [Warning Skin corrosion/irritation]|P260, P264, P280, P302+P352, P305+P351+P338, P314, P321, P332+P313, P337+P313, P362, and P501|Aggregated GHS information provided by 141 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P280, P301+P312, P304+P340, P305+P351+P338, P312, P314, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
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. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)
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)
Drug Information
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. (See all compounds classified as Cholinesterase Inhibitors.)|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. (See all compounds classified as Neurotoxins.)|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. (See all compounds classified as Cross-Linking Reagents.)
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. ACUTE/CHRONIC HAZARDS: This compound is highly toxic by inhalation. It may be harmful by ingestion or skin absorption. The vapor or mist is irritating to the eyes, skin, mucous membranes and upper respiratory tract. High concentrations may cause narcosis. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
1,2-diacetylethane
2,5-Hexanedione Use and Manufacturing
Derived from 2, 5-dimethylfuran hydrolysis. Another synthetic method is the reaction of sodium acetoacetate with pure iodine to form diethyl diacetylsuccinate, which is then hydrolyzed with 10% sodium hydroxide solution. The reaction solution was saturated with anhydrous potassium carbonate to precipitate acetone acetone. It is extracted with ether. After distilling off the ether from the extract, the residue is distilled and the fractions at 192-194°C are collected to obtain a colorless product. A 97% purity commercial product sold abroad, has a melting point of -6-5°C, a boiling point of 191°C, a relative density of 0.973, and a flash point of 78°C.
It is the metabolite implicated in n-hexane neurotoxicity.
2,5-Hexanedione: ACTIVE
Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
Computed Properties
Molecular Weight:114.14
XLogP3:-0.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:114.068079557
Monoisotopic Mass:114.068079557
Topological Polar Surface Area:34.1
Heavy Atom Count:8
Complexity:91.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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