Durene is an important aromatic hydrocarbon mainly used as a precursor for pyromellitic dianhydride and high-performance polyimide materials.
Durene's highly methyl-substituted benzene structure makes it valuable in oxidation chemistry, specialty synthesis, and aromatic reaction studies.
Durene-derived products are widely applied in heat-resistant polymers, coatings, electrical insulation materials, and advanced industrial formulations.

CAS Number: 95-93-2
EC Number: 202-465-7
Molecular Formula: C12H18O2
Molecular Weight: 194.27 g/mol

Synonyms: 1,2,4,5-TETRAMETHYLBENZENE, Durene, 95-93-2, Durol, Benzene, 1,2,4,5-tetramethyl-, p-Xylene, 2,5-dimethyl-, DTXSID1029124, 181426CFYB, NSC-6770, DTXCID309124, CHEBI:38978, RefChem:590468, 202-465-7, MFCD00008528, 1,2,4,5-tetramethyl-benzene, CAS-95-93-2, NSC 6770, EINECS 202-465-7, Duren, UNII-181426CFYB, AI3-25182, CCRIS 8660, 2,5-dimethyl-p-xylene, DURENE [MI], NCIMech_000514, SCHEMBL39444, BIDD:ER0685, SCHEMBL375363, SCHEMBL395548, SCHEMBL1871392, SCHEMBL2813641, SCHEMBL2813643, CHEMBL1797134, SCHEMBL10718639, NSC6770, WLN: 1R B1 D1 E1, Tox21_201920, Tox21_303511, 1,2,4,5-TETRAMETHLYBENZENE, EBC-80269, SBB058376, 1,2,4,5-Tetramethylbenzene, 98%, AKOS000119934, FT00689, NCGC00249135-01, NCGC00257264-01, NCGC00259469-01, LS-13806, DB-038211, NS00078869, ST50188811, 1,2,4,5-TETRAMETHYLBENZENE (DURENE), EN300-19396, G77316, F448616, Q907919, 1,2,4,5-Tetramethylbenzene 10 microg/mL in Cyclohexane, F0001-2285, Z104473710, 1,2,4,5-Tetramethylbenzene, Standard for quantitative NMR, TraceCERT(R), InChI=1/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H, 1,2,4,5-Tetramethylbenzene; p-Xylene, 2,5-dimethyl- (7CI); 1,2,4,5-Tetramethylbenzene; Durene; Durol; NSC 6770, (2,4,5-Trimethylphenyl)methyl, 1,2,4,5-Tetramethylbenzene, 1,2,4,5-Tétraméthylbenzène, 1,2,4,5-Tetramethylbenzol, 15220-27-6, 1903393, 202-465-7, 95-93-2, Benzene, 1,2,4,5-tetramethyl-, Durene, 1,2,4,5-Tetramethyl Benzene, 1,2,4,5-Tetramethylbenzene (Durene), 1,2,4,5-Tetramethylbenzene Zone Refined (number of passes:23), 1,2,4,5-Tetramethylbenzene-3,6-d2, 1,2,4,5-Tetramethylbenzene-d14, 12408-10-5, 15502-50-8, 1859-01-4, 1R B1 D1 E1, 2,5-dimethyl-p-xylene, 202-466-2, 4,5-DIMETHYLBENZENE-1,2-DIMETHANOL, 4-05-00-00668, 60070-05-5, 63697-22-3, 95-94-3, 97%, Durol, Durol, Durene, EINECS 202-465-7, p-Xylene, 2,5-dimethyl-, p-Xylene, 2,5-dimethyl- (7CI), デュレン

Durene is an organic compound with the formula C6H2(CH3)4.
Durene is a colourless solid with a sweet odor.

Durene is classified as an alkylbenzene.
Durene is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene).

Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.
Durene is an aromatic hydrocarbon consisting of a benzene ring substituted with four methyl groups.

Durene is typically a colorless to white crystalline solid with a characteristic aromatic odor and is used as an intermediate in organic synthesis.
Durene is particularly important as a precursor for pyromellitic dianhydride and other specialty chemicals used in polymers, resins, coatings, and advanced materials.

Durene appears as colorless crystals with a camphor-like odor.
Durene is a tetramethylbenzene carrying methyl groups at positions 1, 2, 4 and 5.

Durene is an aromatic hydrocarbon characterized by its four methyl groups attached to a benzene ring.
Durene is a colorless liquid at room temperature and has a distinctive sweet odor.

Durene is insoluble in water but soluble in organic solvents such as ethanol and ether.
Durene's molecular formula is C10H14, and it has a relatively high boiling point compared to other simple hydrocarbons, reflecting its stable aromatic structure.

Durene is primarily used in the production of various chemicals and as a solvent in organic synthesis.
Durene can also serve as a precursor for the synthesis of certain polymers and resins.
Due to its aromatic nature, durene can participate in electrophilic substitution reactions, making it a valuable compound in organic chemistry.

Uses of Durene:
Durene is mainly used as an intermediate in the production of pyromellitic dianhydride (PMDA), an important raw material for high-performance polyimides, heat-resistant polymers, electrical insulation materials, and specialty resins.
Durene is also employed in organic synthesis as a starting material for preparing substituted aromatic compounds, oxidation products, and functional intermediates.

In the polymer industry, durene-derived chemicals are used in advanced coatings, adhesives, films, and engineering materials requiring good thermal and chemical resistance.
Durene can also serve as a model aromatic hydrocarbon in catalytic oxidation, alkylation, and hydrocarbon conversion studies.

Durene's highly substituted benzene structure makes it useful in research involving steric effects, aromatic reactivity, and molecular structure.
In addition, durene is used in specialty chemical manufacturing and in the synthesis of fine chemicals and functional aromatic derivatives.

Reactions and Uses of Durene:
Durene is a relatively easily oxidized benzene derivative, with E1/2 of 2.03 V vs NHE.
Durene's nucleophilicity is comparable to that of phenol.

Durene is readily halogenated on the ring for example.
Nitration gives the dinitro derivative, a precursor to duroquinone.

In industry, Durene is the precursor to pyromellitic dianhydride, which is used for manufacturing curing agents, adhesives, coating materials.
Durene is used in the manufacture of some raw materials for engineering plastics (polyimides) and cross-linking agent for alkyd resins.
Durene is also a suitable starting material for the synthesis of hexamethylbenzene.

With a simple proton NMR spectrum comprising two signals due to the 2 aromatic hydrogens (2H) and four methyl groups (12H), durene is used as an internal standard.

Production of Durene:
Durene is a component of coal tar and was first prepared from pseudocumene in 1870.
Durene is produced by methylation of other methylated benzene compounds such as p-xylene and pseudocumene.

C6H4(CH3)2 + 2 CH3Cl → C6H2(CH3)4 + 2 HCl

In industry, a mixture of xylenes and trimethylbenzenes is alkylated with methanol.
Durene can be separated from its isomers by selective crystallization, exploiting its high melting point.
The original synthesis of durene involved a similar reaction starting from toluene.

Durene is a significant byproduct of the production of gasoline from methanol via the "MTG (Methanol to Gasoline) process".

Stability and Reactivity of Durene:

Chemical Stability:
Stable under normal recommended storage and handling conditions.

Reactivity:
No hazardous reactions are expected under normal conditions of use.

Conditions to Avoid:
Excessive heat, sparks, open flames, and other ignition sources.

Incompatible Materials:
Strong oxidizing agents.

Hazardous Decomposition Products:
Thermal decomposition or combustion may produce carbon monoxide, carbon dioxide, and irritating organic fumes.

Handling and Storage of Durene:

Safe Handling:
Avoid breathing dust or vapors and prevent unnecessary contact with skin and eyes.
Use adequate ventilation and appropriate personal protective equipment.

Storage Conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated area away from heat, ignition sources, and incompatible materials.

First Aid Measures of Durene:

Inhalation:
Move the affected person to fresh air and obtain medical attention if symptoms occur.

Skin Contact:
Remove contaminated clothing and wash the affected area thoroughly with soap and water.

Eye Contact:
Rinse cautiously with plenty of water for several minutes and seek medical attention if irritation persists.

Ingestion:
Rinse the mouth and obtain medical advice if discomfort or symptoms occur.

Firefighting Measures of Durene:

Suitable Extinguishing Media:
Use dry chemical powder, carbon dioxide, water spray, or suitable foam.

Specific Hazards:
Combustion may generate carbon oxides and irritating fumes.

Protective Equipment:
Firefighters should wear suitable protective clothing and self-contained breathing apparatus when necessary.

Accidental Release Measures of Durene:

Personal Precautions:
Remove ignition sources, provide adequate ventilation, and avoid generating dust.

Environmental Precautions:
Prevent the material from entering drains, waterways, or soil.

Cleanup Methods:
Carefully sweep or collect spilled material and place it in a suitable closed container for disposal.

Exposure Controls/Personal Protection of Durene:

Engineering Controls:
Provide adequate general ventilation or local exhaust ventilation.

Eye Protection:
Wear appropriate safety glasses or chemical goggles.

Hand Protection:
Wear suitable chemical-resistant gloves.

Skin Protection:
Wear appropriate protective clothing.

Respiratory Protection:
Use suitable respiratory protection if ventilation is inadequate or airborne dust or vapor concentrations become elevated.

Identifiers of Durene:
Product Number: B0493
Purity / Analysis Method : >99.0%(GC)
Molecular Formula / Molecular Weight: C12H18O2 = 194.27 
Physical State (20 deg.C): Solid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
Reaxys Registry Number: 1950294
PubChem Substance ID: 87563522
SDBS (AIST Spectral DB): 11008
MDL Number: MFCD00004623

Formula: C10H14
InChI: InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3
InChI key: InChIKey=SQNZJJAZBFDUTD-UHFFFAOYSA-N
SMILES: CC1=C(C)C=C(C)C(C)=C1

CAS Number: 95-93-2
ChEBI: CHEBI:38978
ChemSpider: 6999
ECHA InfoCard: 100.002.242
KEGG: C14534
PubChem CID: 7269
UNII: 181426CFYB
CompTox Dashboard (EPA): DTXSID1029124
InChI: InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3
Key: SQNZJJAZBFDUTD-UHFFFAOYSA-N
InChI=1/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3
Key: SQNZJJAZBFDUTD-UHFFFAOYAJ
SMILES: c1c(c(cc(c1C)C)C)C

Properties of Durene:
Chemical formula: C10H14
Molar mass: 134.21816
Density: 0.868 g/cm3
Melting point: 79.2 °C (174.6 °F; 352.3 K)
Boiling point: 192 °C (378 °F; 465 K) at 760mmHg
Magnetic susceptibility (χ): −101.2·10−6 cm3/mol

Molecular Weight: 134.22 g/mol
XLogP3: 4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 0
Exact Mass: 134.109550447 Da
Monoisotopic Mass: 134.109550447 Da
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 10
Complexity: 80.6
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Durene:
Appearance: White to Light yellow to Light orange powder to crystal
Purity(GC): min. 99.0 %
Melting point: 254.0 to 258.0 °C
Solubility in hot Pyridine: within almost transparency
NMR: confirm to structure

Names of Durene:

Preferred IUPAC name:
1,2,4,5-Tetramethylbenzene

Other name:
Durol