基本情報
- 標準SMILES
CC(=O)CCC(C)=O- InChIKey
OJVAMHKKJGICOG-UHFFFAOYSA-N- 分子式
- C6H10O2
- 平均分子量
- 114.14 g/mol
- 単同位体質量
- 114.06807956
概要
2,5-Hexanedione can cause male reproductive toxicity according to an independent committee of scientific and health experts.
名称と識別子
- 優先名称
- 2,5-Hexanedione
- IUPAC
- hexane-2,5-dione
- 現地名
- アセトニルアセトン
- 英語名
- 2,5-Hexanedione
- 分子式
- C6H10O2
- 分子量
- 114.14
名称と別名
名称をさらに表示
データベース識別子
- CAS
110-13-4- PubChem CID
- 8035
- DTXSID
DTXSID8030138- ChEMBL
CHEMBL1564795- ChEBI
CHEBI:85014- UNII
- C0Z8884J3P
- EC Number
- 203-738-3
- Nikkaji
- J5.518B
物性
構造計算による物性
- XLogP
- -0.3
- 極性表面積
- 34.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 3
- 重原子数
- 8
- 形式電荷
- 0
- 複雑度
- 91.1
実験および物理化学的性質
Vapor Pressure
0.43 mmHg at 68 °F ; 1.6 mmHg at 77 °F (NTP, 1992)
2.93 [mmHg]
物理化学的性質
- 融点
- -6 · -6--5 °C (lit.)
- 沸点
- 191 °C · 191 °C (lit.)
- 比重(密度)
- 0.973 g/mL · 0.973 g/mL at 25 °C (lit.)
- 蒸気圧
- 0.43 mm · 0.43 mm Hg ( 20 °C)
- 屈折率
- 20 · n20/D 1.425(lit.)
- 闪点
- 174 °F · 174 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- アルコール:混和性
- 外見
- 液体
- 色
- クリアイエロー~ブラウン
- 臭い (Odor)
- Pleasant, sweet-ethereal odor.
- PH
- 6.1 · 6.1 (10g/l, H2O, 20℃)
- 爆発限界(explosive limit)
- 1.5 % · 1.5%(V)
- 水溶解度
- 混和性
- Merck
- 14 · 14,71
- BRN
- 506525 · 506525
- 安定性
- 安定。強塩基、強還元剤、強酸化剤とは相容れない。可燃性。
- 化粧品成分の機能
- 香料
- 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 データベース
- 110 · 110-13-4(CAS DataBase Reference)
- NISTの化学物質情報
- 3 COCH2CH2COCH3 · CH3COCH2CH2COCH3(110-13-4)
- EPAの化学物質情報
- 2 · 2,5-Hexanedione (110-13-4)
化学的性質
化学的特性colourless to pale yellow liquid
安全と法規制
GHS分類
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]
危険有害性情報
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
安全と保護具
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)
毒性情報
安全データ
- F
- 8
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- MO3150000
- 毒性
- LD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)
- hs_code
- 29141990
- risk_code
- 36/38-48/20/21/22-36/37/38
- 化審法
- (2)-563
- 消防法
- 危険物第4類第三石油類(水溶性)
- hazard_code
- Xn,Xi
- safety_code
- 23-26-36/37-37/39
- 自然発火温度
- 400 °C
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 2
- ストレージクラス
- 10 - Combustible liquids
化学と産業
薬理情報
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.
用途と製造
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
応用分野
用途有機合成中間体 (NITE CHRIP)
用途有機合成原料。
説明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].
使用Urinary 2,5-hexanedione (2,5-HD) is used as a biomarker for biological monitoring of workers exposed to n-hexane.[6]
使用It is the metabolite implicated in n-hexane neurotoxicity.
一般的な説明Clear colorless to amber liquid with a sweet aromatic odor.
調製方法
製造方法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.
純化方法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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: 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.
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