Chloranilic acid
Basic information
- CAS
87-88-7- Standard SMILES
O=C1C(O)=C(Cl)C(=O)C(O)=C1Cl- InChIKey
IPPWILKGXFOXHO-UHFFFAOYSA-N- Molecular formula
- C6H2Cl2O4
- Average molar mass
- 208.98 g/mol
- Monoisotopic mass
- 207.9330139
Overview
structure
Names & identifiers
- Preferred name
- Chloranilic acid
- IUPAC
- 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione
- English name
- Chloranilic acid
- Molecular formula
- C6H2Cl2O4
- Molecular weight
- 208.98
Names & synonyms
Chloranilic acid87-88-7p-Chloranilic acid2,5-Dichloro-3,6-dihydroxy-p-benzoquinone2,5-Cyclohexadiene-1,4-dione, 2,5-dichloro-3,6-dihydroxy-YJ8L3BB7Y4NSC-6108DTXSID3058959NSC-97383RefChem:125280DTXCID0048557201-780-7
Show more names
NSC 97383chloranilicp-chloranilicacidTIMTEC-BB SBB008913CHLORANILIC ACID AR
2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dioneCHLORANILICACIDNSC 61082,5-dichloro-3,6-dihydroxy-1,4-benzoquinone2,5-Dichloro-3,6-dihydroxybenzoquinone2,5-Dihydroxy-3,6-dichlorobenzoquinoneBRN 1875040p-Quinone, 2,5-dichloro-3,6-dihydroxy-
Database identifiers
- CAS
87-88-7- PubChem CID
- 66604
- DTXSID
DTXSID3058959- UNII
- YJ8L3BB7Y4
- EC Number
- 201-780-7
- Nikkaji
- J1.055.803D、J9.875B
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 305
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aromatic Ketones, Halogenated
SpringerMaterials PropertiesCrystal structure
Physical DescriptionRed solid; [Merck Index] Orange powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 300 °C · ≥300 °C (lit.)
- Boiling point
- 300.11 °C · 300.11°C (rough estimate)
- Density
- 1.93 · 1.93
- refractive index
- 1.457 · 1.4570 (estimate)
- storage temp.
- Amber Vial, Refrigerator
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 1 · pK1:1.09;pK2:2.42 (25°C)
- form
- Fine Powder
- color
- Orange to red
- Odor
- Odorless
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2,5-Cyclohexadiene-1,4-dione, 2,5-dichloro-3,6-dihydroxy-
Chloranilic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DK4005000
- hs_code
- 29147000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
Chemistry & industry
Uses & manufacturing
UsesReacts with metal cations forming stable salts; Used in spectrophotometry; [Merck Index]
General Manufacturing Information2,5-Cyclohexadiene-1,4-dione, 2,5-dichloro-3,6-dihydroxy-: ACTIVE
Applications
UsesChloranilic acid is the reactant involved in:Acting as a proton donor in reactions studying dimensionality controlSynthesis of dimethylbipyridyl complexesSynthesis of (nonylbenzimidazolylmethyl)benzene for preparation of neutral altitudinal rotor-shaped dirhenium metallacyclesCharge-transfer reactions with metoprolol tartrateSalt formation with organic basesSynthesis of osmium metalla-rectangles with anticancer activity
UsesChloranilic acid is a strong dibasic organic acid which exhibits electron-acceptor properties on one hand and acidic properties leading to formation of hydrogen bonds on the other hand.Chloranilic acid is used in spectrophotometry. It reacts with metal ions to form stable complexes. It is also used as a reactant in the preparation of dimethylbipyridyl complexes and (nonylbenzimidazolylmethyl)benzene. Further, it is used in charge-transfer reactions with metoprolol tartrate. It is also employed in the synthesis of osmium metalla-rectangles with anticancer activity. In addition to this, it has potential antibacterial activities against methicillin-resistant Staphylococcus aureus.
UsesReacts with metal cations to form stable salts. Used in spectrophotometry: Hart, organic. Chem. Bull. 33, no. 3 (1961).
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…