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2,5-Hexanedione

2,5-Hexanedione Structure
2,5-Hexanedione structure
CAS No.
110-13-4
Chemical Name:
2,5-Hexanedione
Synonyms
2,5-HEXANEDIONE;Hexane-2,5-dione;Hexanedione;acan;2,5-Hexadione;2,5-dione;2,5-HEXANDIONE;NSC 7621;Diacetonyl;hexane-2,5-
CBNumber:
CB2455570
Molecular Formula:
C6H10O2
Molecular Weight:
114.14
MDL Number:
MFCD00008792
MOL File:
110-13-4.mol
MSDS File:
SDS
Last updated:2023-11-30 12:57:55
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2,5-Hexanedione Properties

Melting point -6--5 °C (lit.)
Boiling point 191 °C (lit.)
Density 0.973 g/mL at 25 °C (lit.)
vapor pressure 0.43 mm Hg ( 20 °C)
refractive index n20/D 1.425(lit.)
Flash point 174 °F
storage temp. Store below +30°C.
solubility alcohol: miscible
form Liquid
color Clear yellow to brown
PH 6.1 (10g/l, H2O, 20℃)
explosive limit 1.5%(V)
Water Solubility miscible
Merck 14,71
BRN 506525
Stability Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents. Flammable.
InChIKey OJVAMHKKJGICOG-UHFFFAOYSA-N
LogP -0.270
CAS DataBase Reference 110-13-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII C0Z8884J3P
Proposition 65 List 2,5-Hexanedione
NIST Chemistry Reference CH3COCH2CH2COCH3(110-13-4)
EPA Substance Registry System 2,5-Hexanedione (110-13-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H315-H319-H361f-H373
Precautionary statements  P202-P260-P301+P312-P302+P352-P305+P351+P338-P308+P313
Hazard Codes  Xn,Xi
Risk Statements  36/38-48/20/21/22-36/37/38
Safety Statements  23-26-36/37-37/39
WGK Germany  2
RTECS  MO3150000
F  8
Autoignition Temperature 400 °C
TSCA  Yes
HS Code  29141990
Toxicity LD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)
NFPA 704
2
1 0

2,5-Hexanedione price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.00105 2,5-Hexanedione for synthesis 110-13-4 100mL $116 2024-03-01 Buy
Sigma-Aldrich 8.00105 2,5-Hexanedione for synthesis 110-13-4 250ML $168 2024-03-01 Buy
Sigma-Aldrich 15972 2,5-Hexanedione analytical standard 110-13-4 5ml $121 2022-05-15 Buy
TCI Chemical H0101 Acetonylacetone >97.0%(GC) 110-13-4 25mL $38 2024-03-01 Buy
TCI Chemical H0101 Acetonylacetone >97.0%(GC) 110-13-4 100mL $90 2024-03-01 Buy
Product number Packaging Price Buy
8.00105 100mL $116 Buy
8.00105 250ML $168 Buy
15972 5ml $121 Buy
H0101 25mL $38 Buy
H0101 100mL $90 Buy

2,5-Hexanedione Chemical Properties,Uses,Production

Synthesis

2,5-Hexanedione has been prepared in several ways. A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle.

Mechanism of Toxicity

Identification of 2,5-hexanedione as the major neurotoxic metabolite of n-hexane proceeded rapidly after its discovery as a urinary metabolite. 2,5-Hexanedione has been found to produce a polyneuropathy indistinguishable from n-hexane. 2,5-Hexanedione is many times more potent than n-hexane, the parent compound, in causing neurotoxicity in experimental animals. It appears that the neurotoxicity of 2,5-hexanedione resides in its γ-diketone structure since 2,3-, 2,4-hexanedione and 2,6-heptanedione are not neurotoxic, while 2,5-heptanedione and 3,6-octanedione and other γ-diketones are neurotoxic.

Description

2, 5-hexadione (2,5HD) 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].

Chemical Properties

colourless to pale yellow liquid

Uses

It was used as reference standard for the determination of 2,5HD in human urine using gas chromatography-electron capture detection and gas chromatography-mass selective detection.

Uses

2,5-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.

Uses

It is the metabolite implicated in n-hexane neurotoxicity.

Application

2,5-Hexanedione is a neurotoxic metabolite of n-hexanes and methyl n-butyl ketone. It is also used as the starting material for diels-alder cycloaddition reactions, such as a reactions with amines to form 2,5-dimethylpyrroles.

Preparation

Preparation of 2,5-hexanedione.jpg
20 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.

Definition

ChEBI: 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

Synthesis Reference(s)

Canadian Journal of Chemistry, 59, p. 945, 1981 DOI: 10.1139/v81-137
Journal of the American Chemical Society, 105, p. 7200, 1983 DOI: 10.1021/ja00362a047
Tetrahedron Letters, 15, p. 4149, 1974

General Description

Clear colorless to amber liquid with a sweet aromatic odor.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

Acetonylacetone is incompatible with oxidizing agents. Acetonylacetone is also incompatible with strong bases and strong reducing agents.

Fire Hazard

Acetonylacetone is combustible.

Purification Methods

Purify it by dissolving in Et2O, stiring with K2CO3 (a quarter of the weight of dione), filtering, drying over anhydrous Na2SO4 (not CaCl2), filtering again, evaporating the filtrate and distilling it in a vacuum. It is then redistilled through a 30cm Vigreux column (p 11, oil bath temperature 150o). It is miscible with H2O and EtOH. The dioxime has m 137o (plates from *C6H6), the mono-oxime has b 130o/11mm, and the 2,4-dinitrophenylhydrazone has m 210-212o (red needles from EtOH). It forms complexes with many metals. [Werner et al. Chem Ber 22 2100 1989, for enol content see Gero J Org Chem 19 1960 1954, Beilstein 1 IV 3688.]

References

[1] KAIXUAN ZHOU, Xin L, Chenggong Sun. Directed glycerol conversion to 2,5-hexanedione and more advanced poly-oxygenates as platform chemicals and high energy–density fuel additives[J]. Chemical Engineering Journal, 2022, 430: Article 132981. DOI:10.1016/j.cej.2021.132981.
[2] XUEMING XU. The Wnt/β-catenin pathway is involved in 2,5-hexanedione-induced ovarian granulosa cell cycle arrest[J]. Ecotoxicology and Environmental Safety, 2023, 268: Article 115720. DOI:10.1016/j.ecoenv.2023.115720.

2,5-Hexanedione synthesis

625-86-5
110-13-4
Synthesis of 2,5-Hexanedione from 2,5-Dimethylfuran

2,5-Hexanedione Preparation Products And Raw materials

Raw materials

2,5-Dimethylfuran IODINE PURE 2,3-Butanedione Potassium carbonate ETHYL ACETOACETATE SODIUM SALT
3-HEXENE-2,5-DIONE (2R,3S,4S,5R)-2,5-Bis(hydroxymethyl)-oxolane-2,3,4-triol 5-Chloromethylfurfural 5-Methyl furfural 2,5-Hexanediol

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Preparation Products

2,5-Dimethyl-1H-pyrrole 5-Methylisoxazole-3-carboxylic acid 1-[2,6-DICHLORO-4-(TRIFLUOROMETHYL)PHENYL]-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE 2,5-Dimethylthiophene Ascorbic Acid
Methyl 3-methyl-2-butenoate Tetrahydropyran 2,5-DIMETHYL-1-PHENYLPYRROLE 1-(4-CYANOPHENYL)-2,5-DIMETHYLPYRROLE

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2,5-Hexanedione Suppliers

Global( 435)Suppliers
Supplier Tel Email Country ProdList Advantage
Wuhan Bright Chemical Co., Ltd
+86-02785804899 +86-15071395570 alice@brightchemical.com.cn China 93 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Shanghai Daken Advanced Materials Co.,Ltd 		+86-371-66670886 info@dakenam.com China 15371 58
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21695 55
Shanghai Time Chemicals CO., Ltd. 		+86-021-57951555 +8617317452075 jack.li@time-chemicals.com China 1807 55
Zjartschem 		+86-571-8723 8903 jocelynpan@zjarts.com jocelynpan@zjarts.com CHINA 993 58
career henan chemical co 		+86-0371-86658258 sales@coreychem.com China 29914 58
Zhejiang ZETian Fine Chemicals Co. LTD 		18957127338 stella@zetchem.com China 2141 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD 		+86 18953170293 sales@sdzschem.com China 2931 58
Jinan Carbotang Biotech Co.,Ltd. 		+8615866703830 figo.gao@foxmail.com China 6992 58
Supplier Advantage
Wuhan Bright Chemical Co., Ltd
58
Capot Chemical Co.,Ltd. 		60
Shanghai Daken Advanced Materials Co.,Ltd 		58
Henan Tianfu Chemical Co.,Ltd. 		55
Shanghai Time Chemicals CO., Ltd. 		55
Zjartschem 		58
career henan chemical co 		58
Zhejiang ZETian Fine Chemicals Co. LTD 		58
SHANDONG ZHI SHANG CHEMICAL CO.LTD 		58
Jinan Carbotang Biotech Co.,Ltd. 		58

Related articles

View Lastest Price from 2,5-Hexanedione manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Acetonylacetone pictures 2024-04-19 Acetonylacetone
110-13-4
 US $5.00 / kg 1kg ≥99% 100mt/year Jinan Finer Chemical Co., Ltd
2,5-Hexanedione pictures 2023-06-17 2,5-Hexanedione
110-13-4
 US $5.00-2.00 / KG 1KG 99% 10000kg Hebei Guanlang Biotechnology Co,.LTD
Acetonylacetone pictures 2022-09-21 Acetonylacetone
110-13-4
 US $0.00-0.00 / kg 1kg 98% 1Ton Henan Aochuang Chemical Co.,Ltd.
  • 2,5-Hexanedione pictures
  • 2,5-Hexanedione
    110-13-4
  • US $5.00-2.00 / KG
  • 99%
  • Hebei Guanlang Biotechnology Co,.LTD
  • Acetonylacetone pictures
  • Acetonylacetone
    110-13-4
  • US $0.00-0.00 / kg
  • 98%
  • Henan Aochuang Chemical Co.,Ltd.

2,5-Hexanedione Spectrum

Acetonylacetone(110-13-4)MSAcetonylacetone(110-13-4)1HNMRAcetonylacetone(110-13-4)13CNMRAcetonylacetone(110-13-4)IR1Acetonylacetone(110-13-4)IR2Acetonylacetone(110-13-4)Raman

110-13-4(2,5-Hexanedione)Related Search:

RHODIZONIC ACID DIPOTASSIUM SALT 3,4-DIACETYL-2,5-HEXANEDIONE RHODIZONIC ACID DIHYDRATE 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester HYDRINDANTIN
QUASSIN Sodium rhodizonate Diethyl succinosuccinate Adrenosterone 1,4-Cyclohexanedione
2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE 5-PHENYLCYCLOHEXANE-1,3-DIONE 1,4-Cyclohexanedione mono(2,2-dimethyltrimethylene ketal) 4,4,5,5,6,6,6-HEPTAFLUORO-1-PHENYL-1,3-HEXANEDIONE Dimedone
2-ACETYL-1,3-CYCLOHEXANEDIONE 1,1,1-TRIFLUORO-5,5-DIMETHYL-2,4-HEXANEDIONE 1,3-Cyclohexanedione

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2,5-Diketohexane Acetone, acetonyl- Acetonyl acetone 2,5-hexanedione 2,5-Dioxohexane 2,5-Hexanedione, Standard f GC Acetonylacetone,97% NSC 7621 1,2-Diacetylethane 2,5-Hexanedione HEXANEDIONE, 2,5-(SG) 2,5-Hexanedione ,97% Hexane-2,5-dione 99+% Acetonylacetone, 97% 250ML Acetonylacetone, 97% 5ML 2,5-HEXANEDIONE FOR SYNTHESIS 4-Acetylbutan-2-one, 2,5-Dioxohexane 2,5-Hexanedione puriss. p.a., >=99.0% 2,5-Hexanedione >=98% 2,5-Hexanedione Vetec(TM) reagent grade, 98% Acetonylacetone/2,5-Diketohexane Acetonylacetone 1,2-Diacetylethane acetonyl-aceton alpha,beta-Diacetylethane Diacetonyl hexane-2,5- Hexanedione-(2,5) 1,2-DIACETYLETHANE ACETONYLACETONE AKOS BBS-00004255 ACETONYLACETONE, 98+% 2,5-Hexanedione, Wacker Quaility α,β-Diacetylethane sym-diacetylethane Hexan-2,5-Dion Acetonylacetone 110-13-4 Acetonylacetone> Hexane-2,5-dione 96% ACETONYL ACETONE, 97%ACETONYL ACETONE, 97%ACETONYL ACETONE, 97%ACETONYL ACETONE, 97% 2,5-Hexadione Hexanedione 2,5-dione Hexane-2,5-dione 2,5-HEXANEDIONE 2,5-HEXANDIONE acan 2,5-Hexanedione (8CI, 9CI, ACI) 110-13-4 990014-46-9 CH3COCH22COCH3 CH3COCH2CH2COCH3 Carbonyl Compounds C3 to C6 Analytical Chromatography Product Catalog Building Blocks Analytical Standards Analytical Reagents Alphabetic General Use HA -HT