2,6-Dichloro-1,4-benzoquinone
Basic information
- CAS
697-91-6- Standard SMILES
O=C1C=C(Cl)C(=O)C(Cl)=C1- InChIKey
JCARTGJGWCGSSU-UHFFFAOYSA-N- Molecular formula
- C6H2Cl2O2
- Average molar mass
- 176.98 g/mol
- Monoisotopic mass
- 175.94318466
Overview
2,6-dichlorobenzoquinone is a member of the class of 1,4-benzoquinones that is p-benzoquinone in which the hydrogens at positions 2 and 6 have been replaced by chlorines. A highly toxic and carcinogenic disinfection by-product found in drinking water. It has a role as a carcinogenic agent and a poison. It is a member of 1,4-benzoquinones and an organochlorine compound.
Names & identifiers
- Preferred name
- 2,6-Dichloro-1,4-benzoquinone
- IUPAC
- 2,6-dichlorocyclohexa-2,5-diene-1,4-dione
- English name
- 2,6-Dichloro-1,4-benzoquinone
- Molecular formula
- C6H2Cl2O2
- Molecular weight
- 176.98
Names & synonyms
2,6-Dichloro-1,4-benzoquinone697-91-62,6-Dichloro-p-benzoquinone2,6-Dichlorobenzoquinone2,6-DichloquinoneNSC 6211DCBQ2,6-Dichloro-2,5-cyclohexadiene-1,4-dioneDTXSID7061019CHEBI:147298RefChem:445459DTXCID2046549
Show more names
2,6-dichloro-p-quinonLABOTEST-BB LT001593422,6-dichloro-p-benzoquinon2,6-Dichoro-p-benzoquinonebenzoquinone,2,6-dichloro-
211-810-02,6-dichlorocyclohexa-2,5-diene-1,4-dione2,6-Dichloroquinone2,5-Cyclohexadiene-1,4-dione, 2,6-dichloro-p-Quinone, 2,6-dichloro-MFCD00037159p-BENZOQUINONE, 2,6-DICHLORO-2,6-Dichloro-p-quinone
Database identifiers
- CAS
697-91-6- PubChem CID
- 12771
- DTXSID
DTXSID7061019- ChEBI
CHEBI:147298
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 239
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aromatic Ketones, Halogenated
SpringerMaterials PropertiesBoiling point
Physical DescriptionYellow powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 122 · 122-124 °C(lit.)
- Boiling point
- 251.81 °C · 251.81°C (rough estimate)
- Density
- 1.5138 · 1.5138 (rough estimate)
- refractive index
- 1.4595 · 1.4595 (estimate)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Dark Yellow
- Water Solubility
- Insoluble in water. Solubility in methanol (almost transparency).
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
H302 (17%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryA skin and strong eye irritant; Toxic by ingestion; [Alfa Aesar MSDS] See Quinone.
Hazard Classes and CategoriesAcute Tox. 4 (17%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DK4000000
- hs_code
- 2914698090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2,5-Cyclohexadiene-1,4-dione, 2,6-dichloro-: ACTIVE
Applications
Uses2,6-Dichloro-1,4-benzoquinone is the suitable reagent used to in a study to evaluate the diffusion coefficients (D) for a family of quinones, nitroaromatics, ferrocenes and aromatic hydrocarbon compounds, in acetonitrile by single potential step chronoamperometry.1 It may be used in the preparation of 2,3,5-Trichloro-1,4-dihydroquinone, 2,3,5-trichloro-1,4-benzoquinone and 2,6-Dichloro-1,4-dihydroquinone.
General Description2,6-Dichloro-1,4-benzoquinone (DCBQ, 2,6-DCBQ) is a halobenzoquinone. Halobenzoquinones are disinfection byproducts (DBPs) found in drinking water. They are capable of producing reactive oxygen species and causing oxidative damage to proteins and DNA in T24 human bladder carcinoma cells. UV-induced transformation of DCBQ in drinking water has been reported. Detection of DCBQ in drinking water by liquid chromatography-ESI tandem mass spectrometry has been reported.
Upstream & downstream products
Upstream raw materials
Related reactions
5 records
Compound notes
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