Basic information
- CAS
504-02-9- Standard SMILES
O=C1CCCC(=O)C1- InChIKey
HJSLFCCWAKVHIW-UHFFFAOYSA-N- Molecular formula
- C6H8O2
- Average molar mass
- 112.13 g/mol
- Monoisotopic mass
- 112.0524295
Overview
Cyclohexane-1,3-dione is a cyclohexanedione carrying oxo substituents at positions 1 and 3. It is a cyclohexanedione and a beta-diketone.
Names & identifiers
- Preferred name
- 1,3-Cyclohexanedione
- IUPAC
- cyclohexane-1,3-dione
- English name
- 1,3-Cyclohexanedione
- Molecular formula
- C6H8O2
- Molecular weight
- 112.13
Names & synonyms
1,3-Cyclohexanedione504-02-9CYCLOHEXANE-1,3-DIONEDihydroresorcinolHydroresorcinolResorcinol, dihydro-6UK3D2BXJTDTXSID1044433NSC-57477DTXCID9024433CHEBI:17766RefChem:72549
Show more names
CHDTECO-013NSC 57477ohexanedioneDihydroresorcin
207-980-01,3-Cyclohexandione1,3 Cyclohexanedione1,3-CyclohexanoneMFCD00001585UNII-6UK3D2BXJT1,3-Benzenediol, dihydro-cyclohexan- 1,3-dione
Database identifiers
- CAS
504-02-9- PubChem CID
- 10434
- DTXSID
DTXSID1044433- ChEMBL
CHEMBL363919- ChEBI
CHEBI:17766- UNII
- 6UK3D2BXJT
- EC Number
- 207-980-0
- Nikkaji
- J6.214F
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 112
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aliphatic Ketones, Other
Physical Description
Dry Powder
Solid; [Merck Index] Light brown powder; [Alfa Aesar MSDS]
Collision Cross Section122.6 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1044433]
Physicochemical properties
- Melting point
- 101 · 101-105 °C (lit.)
- Boiling point
- 170.05 °C · 170.05°C (rough estimate)
- Density
- 1 · 1,1 g/cm3
- vapor pressure
- 0.018 Pa · 0.018Pa at 25℃
- refractive index
- 1.4576 · 1.4576 (estimate)
- storage temp.
- 2 °C · Store at +2°C to +8°C.
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Powder
- pka
- 5.26 · 5.26(at 25℃)
- color
- Pale yellow to beige
- Water Solubility
- soluble
- Merck
- 14 · 14,3178
- BRN
- 385888 · 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
- 0.461 at · 0.461 at 21.4℃ and pH3.2
- Surface tension
- 69.9 mN/m · 69.9mN/m at 1.01g/L and 22℃
- CAS DataBase Reference
- 504 · 504-02-9(CAS DataBase Reference)
- FDA UNII
- 6 UK3D2BXJT · 6UK3D2BXJT
- NIST Chemistry Reference
- 1 · 1,3-Cyclohexanedione(504-02-9)
- EPA Substance Registry System
- 1 · 1,3-Cyclohexanedione (504-02-9)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H318-H412
- Precautionary statements
- 273 · P273-P280-P301+P312+P330-P305+P351+P338+P310
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- RTECS
- 350000 · GV0350000
- F
- 8 · 8-21
- TSCA
- TSCA listed
- HS Code
- 29142900 · 29142900
- Storage Class
- 13 · 13 - Non Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.6% (1 of 168) of reports.
Danger
H302 (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.
Hazard information
Regulatory Information
Chemical: 1,3-Cyclohexanedione
1,3-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/13587
1,3-Cyclohexanedione: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Hazards SummaryMay cause irritation; Oral LD50 (rat) = 1,600-2,500 mg/kg; Harmful by ingestion; [Alfa Aesar MSDS] See Cyclohexanone.
Hazard Classes and CategoriesAcute Tox. 4 (98.2%)
Toxicology
Adverse EffectsNeurotoxin - Acute solvent syndrome
Safety data
- F
- 8-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GV0350000
- hs_code
- 29142900
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- safety_code
- 24/25
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H302-H318-H412
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1
- Precautionary statements
- P273-P280-P301+P312+P330-P305+P351+P338+P310
Chemistry & industry
Uses & manufacturing
U.S. Production2023: 550,000 - <1,000,000 lb
Industry UsesIntermediate
General Manufacturing Information
Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
1,3-Cyclohexanedione: ACTIVE
Applications
Uses1,3-Cyclohexanedione is used in organic synthesis and pharmaceutical intermediates. It is the intermediate of herbicides sulcotrione and nitrosulfonone. It is also nitisinone intermediate.
Uses1,3-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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 1,3-Cyclohexanedione is a cyclohexanedione carrying oxo substituents at positions 1 and 3. It is a beta-diketone and a cyclohexanedione.
Related reactions
501 records
Compound notes
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