Dichlone

C10H4Cl2O2, 227.046 g/mol. Its structure, the values that were measured, the values that were calculated, and where each one came from.

Organic — aromatic ketone4 measured properties

Drawn from the SMILES. It shows how the atoms are connected — not a photograph of a molecule, and not its shape in space.

Identifiers

Molecular formula: C₁₀H₄Cl₂O₂
Molecular weight: 227.046 g/mol
Exact mass: 225.958835 g/mol
SMILES: O=C1C(Cl)=C(Cl)C(=O)c2ccccc21
InChI: InChI=1S/C10H4Cl2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H
InChIKey: SVPKNMBRVBMTLB-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Both are open without an account.

Measured properties

Values somebody obtained from a sample and published. Where two sources report the same property they are both shown, in the units each used — a disagreement between them is information, and averaging it away would be inventing a number neither one gave.

Boiling Point: Sublimes 527 °F (USCG, 1999)measured · U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.; 275 °C at 2 mm Hgmeasured · Golden yellow needles or leaflets from alcohol.
Melting Point: 379.4 °F (USCG, 1999)measured · U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.; 195 °Cmeasured · Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. C-156; Melting Point: greater than or equal to 188 °C /Technical Grade/measured · Tomlin CDS, ed. Dichlone (117-80-6). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council
Solubility: Slightly sol in alcohol, ether, benzenemeasured · Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-156; About 4% in xylene, o-dichlorobenzene. Moderately soluble in acetone, dioxanemeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 536; In water, 8.0 mg/L; water buffered to pH 7.4. /Temp not specified/measured · PMID:6834390; Hodnett EM et al; J Med Chem 26: 570-4 (1983); 0.1 mg/L water at 25 °C; 1.0 mg/L and 7 mg/L (temp not specified)measured · Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 624; Moderately soluble in ethyl acetate, acetic acid, dimethylformamide; sparingly soluble in alcoholsmeasured · Tomlin CDS, ed. Dichlone (117-80-6). In: The e-Pesticide Manual, 13th Edition Version 3.1 (2004-05). Surrey UK, British Crop Protection Council
Vapor Pressure: 0.0000011 [mmHg]measured · reference compound database; 1.1X10-6 mm Hg at 25 °Cmeasured · Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 1811

Calculated properties

Derived from the structure rather than from a sample. These are reproducible and they are not measurements: a calculated partition coefficient and a measured one can differ by a long way, and where both exist they are listed apart on purpose.

logP: 2.7548calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 34.14 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 0calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 2calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 53.835 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.6823calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon10 atoms · 52.9% by mass
Cl Chlorine2 atoms · 31.2% by mass
O Oxygen2 atoms · 14.1% by mass
H Hydrogen4 atoms · 1.8% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 14
Total atoms, hydrogen included: 18
Rings: 2
Aromatic rings: 1
Stereocentres: 0
Formal charge: 0

Functional groups

Ketone
A carbonyl bonded to two carbons.
Halide (C–X)
A halogen atom attached to carbon.
Alkene
A carbon–carbon double bond.
Aromatic ring
A flat six-membered ring with delocalised electrons.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Dichlone yet.

Other names for it

No systematic name is recorded.

The sources also call it 2,3-Dichloro-1,4-naphthoquinone, Phygon, Diclone, 2,3-Dichloronaphthoquinone, Phygon XL, Algistat, Sanquinon, Uniroyal, Phygon paste, Dichloronaphthoquinone, Quintar, 1,4-Naphthalenedione, 2,3-dichloro-.

Structurally related

Molecules sharing this formula, or whose fingerprint is at least 40% similar to this one. Similarity is Tanimoto on Morgan fingerprints over this library only — it is a measure of structural overlap, not of how alike they behave.

1,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-

C22H18Cl2O2

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Dichlone. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

(Pyrazin-2-yl)methanamine

used as a reactant

C₅H₇N₃, 109.132 g/mol.

Where these values came from

chemistry engine
structure perception

No matching record was found in the currently indexed sources (reference compound database)..

What this page does not claim

The identifiers are what the source record holds, copied rather than recomputed. Measured values are reported as their source gave them, units and all; calculated values are marked as calculated and are not measurements. Where a field is absent the page says so, because a blank cell reads as a zero and a guessed value reads as a fact.

Nothing here is a hazard assessment, a purity statement or advice about handling a sample. A flash point quoted from a safety database is a number somebody published, not a judgement by us about whether this molecule is safe for what you intend.