Cyclohexan-1,3-dion
CYCLOHEXANE-1,3-DIONE · CHD · DIHYDRORESORCINOL · 1,3-Cyclohexandione · TECO-013 · NSC 57477 · ohexanedione · Dihydroresorcin
Identifikatoren & physikalische Daten
| CAS No. | 504-02-9 |
|---|---|
| Summenformel | C6H8O2 |
| Durchschnittliche Molmasse | 112,13 g/mol |
| Monoisotopische Masse | 112,0524295 g/mol |
| SMILES | O=C1CCCC(=O)C1 |
| InChIKey | HJSLFCCWAKVHIW-UHFFFAOYSA-N |
| PubChem CID | 10434 |
| ChEMBL | CHEMBL363919 |
| ChEBI | CHEBI:17766 |
| EC No. | 207-980-0 |
| DTXSID | DTXSID1044433 |
| Lokaler Name | Cyclohexan-1,3-dion |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 34,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 112 |
| Stoffklassen | Other Classes -> Aliphatic Ketones, Other |
| Physical Description | Dry PowderSolid[Merck Index] Light brown powder[Alfa Aesar MSDS] |
| Collision Cross Section | 122.6 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID1044433] |
| Schmelzpunkt | 101-105 °C (lit.) |
| Siedepunkt | 170.05°C (rough estimate) |
| Dichte | 1,1 g/cm3 |
| Dampfdruck | 0.018Pa at 25℃ |
| Brechungsindex | 1.4576 (estimate) |
| Lagerbedingungen | Store at +2°C to +8°C. |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly)soluble |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 5.26(at 25℃) |
| Farbe | Pale yellow to beige |
| Merck | 14,3178 |
| BRN | 385888 |
| InChI | 1S/C6H8O2/c7-5-2-1-3-6(8)4-5/h1-4H2 |
| InChIKey | HJSLFCCWAKVHIW-UHFFFAOYSA-N |
| SMILES | O=C1CCCC(=O)C1 |
| LogP (Verteilungskoeffizient) | 0.461 at 21.4℃ and pH3.2 |
| Oberflächenspannung | 69.9mN/m at 1.01g/L and 22℃ |
| CAS Datenbank | 504-02-9(CAS DataBase Reference) |
| NIST chemische Informationen | 1,3-Cyclohexanedione(504-02-9) |
| EPA chemische Informationen | 1,3-Cyclohexanedione (504-02-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.6% (1 of 168) of reports.DangerH302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 168 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1,3-Cyclohexanedione1,3-Cyclohexanedione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Cyclohexanedione 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: 14-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/135871,3-Cyclohexanedione: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| Gefahrenübersicht | May cause irritationOral LD50 (rat) = 1,600-2,500 mg/kgHarmful by ingestion[Alfa Aesar MSDS] See Cyclohexanone. |
| Hazard Classes and Categories | Acute Tox. 4 (98.2%) |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| F | 8-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29142900 |
| RTECS-Nr. | GV0350000 |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 13 - Non Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1 |
Anwendungen & Verwendung
Verwenden
1,3-Cyclohexanedione is used in organic synthesis and pharmaceutical intermediates. It is the intermediate of herbicides sulcotrione and nitrosulfonone. It is also nitisinone intermediate.
Verwenden
1,3-Cyclohexanedione can be used as a building block in the synthesis of:9-substituted 1,8-dioxo-xanthenes by reacting with unactivated aldehydes via aldol condensation/ Michael addition reaction.[(1,2,3-triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives by treating with phthalhydrazide, aromatic propargyloxy aldehydes, and azides via a four-component condensation reaction.It can be also used to prepare 2-substituted adducts, which are important intermediates for the synthesis of -enaminones , polyhydroquinoline derivatives , 1,8-dioxo-dodecahydroxanthenes , spirocyclopentanols , oxathioles , and triquinanes.