INDENE

Indene is a versatile bicyclic aromatic hydrocarbon widely used as an intermediate in resin, polymer, and specialty chemical production.
Indene is particularly important in the manufacture of indene-coumarone resins used in coatings, adhesives, rubber compounding, and industrial formulations.
Indene's reactive fused-ring structure also makes indene valuable in organic synthesis and the preparation of fine chemical derivatives.

CAS Number: 95-13-6
EC Number: 202-393-6
Molecular Formula: C9H8
Molecular Weight: 116.16 g/mol

Synonyms, INDENE, 1H-Indene, 95-13-6, Indonaphthene, Inden, DTXSID8042052, NSC 9270, 67H8Y6LB8A, NSC-9270, DTXCID6022052, CHEBI:41921, RefChem:790898, CHEBI:37910, 202-393-6, MFCD00003777, CHEMBL192812, 9003-64-9, Indenyl radical, HSDB 5286, EINECS 202-393-6, UNII-67H8Y6LB8A, indene, (1H-indene), Indene, 98%, INDENE [HSDB], INDENE [MI], Indene, >=99%, Indene, analytical standard, SCHEMBL8617, SCHEMBL29246, SCHEMBL29539, WLN: L56 BHJ, SCHEMBL157900, SCHEMBL277639, SCHEMBL277806, SCHEMBL441664, SCHEMBL742019, SCHEMBL745001, orb3025452, orb3026152, SCHEMBL1423172, SCHEMBL1423878, SCHEMBL3210567, SCHEMBL4121654, SCHEMBL6526220, SCHEMBL8024727, SCHEMBL8036370, Indene 10 |Ig/mL in Methanol, SCHEMBL17633524, SCHEMBL23805024, SCHEMBL28039313, SCHEMBL29350094, MSK9078, NSC9270, Indene 10 microg/mL in Methanol, NSC62567, Tox21_301215, BDBM50167941, NSC-62567, SBB040862, TD1704, AKOS000269048, AKOS025243274, EBC-618167, CAS-95-13-6, NCGC00255989-01, 71551-80-9, BS-22312, CS-0015092, CS-0198083, I0016, I0354, NS00001084, ST50214452, EN300-19944, D72500, F358247, Q421008, Q27115417, F0001-2266, Z104476162, InChI=1/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H, Indene, contains 50-100 ppm tert-butylcatechol as stabilizer, technical grade, >=90%, 1H-Inden, 1H-Inden-1-yl, 1H-Indene, 1H-Indène, 202-393-6, 635873, 95-13-6, Indene, L56 BHJ, 1H-INDEN, 1H-Inden-1-ylidene, 2237858, 2515168, 7420867, 770-96-7, 82539-36-4, 90%, 97%, benzocyclopentene, EINECS 202-393-6, INDEN, Inden, indene(rs20000613), Indene, stab. withmissing, indene-1,1-diyl, Indene-[d3], Indene;1H-indene, Indenyl, indenylidene, indonaphthene, NK8225000 [RTECS], 茚

Indene is a flammable polycyclic hydrocarbon.
Indene is a colorless and aromatic smelling liquid.

Indene is used in the synthesis of new C60 derivative (indene-C60 Bisadduct) and to prepare polyindene by the controlled cationic polymerization initiated with cumyl methyl ether/TiCl4 in CH2Cl2.
Polyindene is further used to synthesize polyolefins.

Indene is also used in the synthesis of istatins, in the production of indene/cumarone thermoplastic resins, and in the production of hydrocarbon resins.
Indene is mainly consumed by the paints & coatings, rubber, and construction industries.

Indene should be stored in a cool place.
The container should be kept tightly closed in a dry and well-ventilated place.

Containers which areopened must be carefully resealed and kept upright to prevent leakage.
Indene is incompatible with strong oxidizing agents.

Recommended storage temperature is 2 - 8°C.
Indene is sensitive to light.

Indene is an aromatic, polycyclic hydrocarbon with chemical formula C9H8.
Indene is composed of a benzene ring fused with a cyclopentene ring.

Indene is colorless although samples often are pale yellow.
The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins.
Substituted indenes and their closely related indane derivatives are important structural motifs found in many natural products and biologically active molecules, such as sulindac.[4]

Indene appears as a colorless liquid derived from coal tar. Fp: -2 °C; bp:182 °C.
Indene's density 0.997 g cm-3.
Indene is insoluble in water but soluble in organic solvents.

Indene is an ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.
Indene is an ortho-fused bicyclic arene and an indene.

Indene is a flammable polycyclic hydrocarbon.
Indene is composed of a benzene ring fused with a cyclopentene ring.

Indene is colorless although samples often are pale yellow.
The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins.

Indene is oxidized to mixtures of cis- and trans-indandiols and related metabolites by Pseudomonas putida and Rhodococcus sp.

Indene is a colorless to faint yellow liquid with an aromatic odor.
Indene is a polycyclic hydrocarbon, C9H8, consisting of an indane and styrene type.

Derived from coal tar or petroleum distillates, indene is a chemical intermediate regularly needed for the manufacture of resins, polymers, and fine chemicals.
Indene's reactivity and versatility make it a useful key raw material in the manufacture of synthetic resins, coatings, and fragrance intermediates.
Indene's derivatives are often used in laboratory, industrial, and polymer-related applications.

Indene is defined as a vinyl aromatic compound that can be polymerized cationically to produce commercial low molecular weight resins.

Indene is used in the synthesis of new C60 derivative, indene-C60 bisadduct1.
Indene was used in preparing polyindene by the controlled cationic polymerization initiated with cumyl methyl ether/TiCl4 in CH2Cl2.
Indene is also used in the synthesis of istatins and in the production of indene/cumarone thermoplastic resins.

Indene is an organic building block that has been used in the synthesis of isatins as selective inhibitors of carboxylesterases.

Indene is a bicyclic aromatic hydrocarbon consisting of a benzene ring fused with a five-membered cyclopentene ring.
Indene is typically a colorless to pale yellow liquid with a characteristic aromatic odor and is commonly obtained from coal tar fractions or petroleum-derived streams.

Indene is used as an intermediate in organic synthesis and in the production of indene-coumarone resins, specialty polymers, coatings, adhesives, and fine chemicals.
Indene is a flammable polycyclic hydrocarbon with chemical formula C9H8.

Indene is composed of a benzene ring fused with a cyclopentene ring.
Indene is colorless although samples often are pale yellow.

Applications of Indene:
Indene can also be used directly to synthesize 2-Aminoindan & NM-2-AI.
Indene is used as a starting material to make 2-indanone [615-13-4].
2-indanone in-turn is used to synthesize the following drugs: Aprindine, Delapril, Indanorex, Indantadol, Pip-AI [23928-93-0], Pyr-AI, S-15535 & BChE-IN-7 [2416910-85-3], 2-aminoindane analog of fentanyl: O=C(CC)N(C1=CC=CC=C1)C2CCN(C3CC(C=CC=C4)=C4C3)CC2.

Indene is used in the synthesis of new C60 derivative, indene-C60 bisadduct.
Indene was used in preparing polyindene by the controlled cationic polymerization initiated with cumyl methyl ether/TiCl4 in CH2Cl2.
Indene is also used in the synthesis of istatins and in the production of indene/cumarone thermoplastic resins.

Chemical & Industrial Applications:
Indene is primarily used in the production of indene-coumarone resins, which are applied in paints, coatings, varnishes, and adhesives.
These resins enhance durability, gloss, and adhesion in industrial coatings.

Indene is also used as a monomer and polymer additive in the manufacturing of plastics and synthetic rubbers.
Explore related fine chemicals like Phytol and Vinyl Sulfurol.

Fragrance & Perfumery uses:
Indene and its derivatives are commonly employed in aroma chemical synthesis as intermediates and contribute to woody, amber, and balsamic aspects of perfumery molecules.
Indene is often utilised in synthetic musk bases, resinous fragrance compositions, and can lend depth and fixative qualities to a fragrance.
Related fragrance ingredients include Rosalva and Linalyl Formate.

Research & Laboratory Use:
In research and academic chemistry, Indene is used as a starting material in organic synthesis, catalysis studies, and polymer research.
Indene's conjugated structure makes it helpful in studying aromatic reactivity and polymerization mechanisms.
You may also like Fenchyl Alcohol and Octyl Palmitate.

Speciality & Intermediate Applications:
Indene is an important building block in the production of fine chemicals, dyes, and pharmaceuticals.
Indene's structure allows for easy functionalization, leading to compounds used in pharmaceutical intermediates and advanced materials.
Explore other intermediates such as Ethyl Isovalerate and Pentanoic Acid.

Uses of Indene:
Indene is used to prepare coumarone-indene resins.
Indene is used as a comonomer in coumarone and petroleum-derived aromatic hydrocarbon resins.

Technical pure indene is used for the production of indan and its derivatives.
Esters of indene-1-carboxylic acid, which are effective as acaricides, can be synthesized from indene for use in, eg, collars

Indene was used in the synthesis of new C60 derivative, indene-C60 bisadduct.
Indene was used in preparing polyindene by the controlled cationic polymerization initiated with cumyl methyl ether/TiCl4 in CH2Cl2.

Industry Uses:
Monomers

Reactivity of Indene:
Indene readily polymerises.
Oxidation of indene with acid dichromate yields homophthalic acid (o-carboxylphenylacetic acid).
Indene condenses with diethyl oxalate in the presence of sodium ethoxide to form indene–oxalic ester, and with aldehydes or ketones in the presence of alkali to form benzofulvenes, which are highly coloured.

Treatment of indene with organolithium reagents gives lithium indenyl compounds:
C9H8 + RLi → LiC9H7 + RH

Indenyl is a ligand in organometallic chemistry, giving rise to many transition metal indenyl complexes.

At temperatures ranging from 30-75 Kelvin (the temperature range of most dark molecular clouds and photodissociation regions), Indene undergoes a process called superhydrogenation.
Indene begins with saturation of carbon atoms in the pentagonal ring which is then followed by the hydrogenation of the benzene unit.
Quantum tunneling also plays a role is this.

Isolation of Indene:
Indene occurs naturally in coal-tar fractions boiling around 175–185 °C.
Indene can be obtained by heating this fraction with sodium to precipitate solid "sodio-indene".

This step exploits indene's weak acidity evidenced by its deprotonation by sodium to give the indenyl derivative.
The sodio-indene is converted back to indene by steam distillation.

Stability and Reactivity of Indene:

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

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

Conditions to Avoid:
Heat, sparks, open flames, hot surfaces, and static discharge.

Incompatible Materials:
Strong oxidizing agents.

Hazardous Decomposition Products:
Combustion may produce carbon monoxide and carbon dioxide.

Handling and Storage of Indene:

Safe Handling:
Use with adequate ventilation and avoid breathing vapors or contact with skin and eyes.
Keep away from ignition sources and use non-sparking tools where appropriate.

Storage Conditions:
Keep the container tightly closed in a dry, cool, and well-ventilated area.
Refrigerated storage may be recommended to maintain product quality, and the material should be kept away from strong oxidizing agents.

First Aid Measures of Indene:

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 water.

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

Ingestion:
Do not induce vomiting and obtain immediate medical attention because aspiration may occur.

Firefighting Measures of Indene:

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

Specific Hazards:
Indene is a flammable liquid, and its vapors may travel to an ignition source and flash back.

Protective Equipment:
Firefighters should wear full protective equipment and self-contained breathing apparatus.

Accidental Release Measures of Indene:

Personal Precautions:
Remove ignition sources, provide adequate ventilation, and take precautions against static discharge.

Environmental Precautions:
Prevent the material from entering surface water, drains, or sewer systems.

Cleanup Methods:
Absorb spilled liquid with inert material and transfer it to suitable closed containers using non-sparking tools.

Exposure Controls/Personal Protection of Indene:

Engineering Controls:
Provide adequate general or local exhaust ventilation.

Eye Protection:
Wear suitable safety glasses, goggles, or face protection.

Hand Protection:
Wear appropriate chemical-resistant gloves.

Skin Protection:
Wear suitable protective clothing.

Respiratory Protection:
Use suitable respiratory protection with an organic vapor filter when ventilation is inadequate or vapor exposure may become elevated.

Identifiers of Indene:
CAS Number: 95-13-6
Beilstein Reference: 635873
ChEBI: CHEBI:41921
ChEMBL: ChEMBL192812
ChemSpider: 6949
DrugBank: DB02815
ECHA InfoCard: 100.002.176
EC Number: 202-393-6
Gmelin Reference: 27265
KEGG: C11565
PubChem CID: 7219
UNII: 67H8Y6LB8A
CompTox Dashboard (EPA): DTXSID8042052
InChI: InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
Key: YBYIRNPNPLQARY-UHFFFAOYSA-N
InChI=1/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
Key: YBYIRNPNPLQARY-UHFFFAOYAJ
SMILES: c1ccc2c(c1)CC=C2

Name: 1H-indene
CAS Number: 95-13-6
ECHA EINECS - REACH Pre-Reg: 202-393-6
FDA UNII: 67H8Y6LB8A
Nikkaji Web: J4.708B
Beilstein Number: 635873
MDL: MFCD00003777
XlogP3: 2.90 (est)
Molecular Weight: 116.16276000
Formula: C9 H8

Empirical Formula (Hill Notation): C9H8
CAS Number: 95-13-6
Molecular Weight: 116.16
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24851616
EC Number: 202-393-6
Beilstein/REAXYS Number: 635873
MDL number: MFCD00003777
eCl@ss: 39011614
Assay: ≥99%
Form: liquid

Product Name: Indene
CAS: 95-13-6
MF: C9H8
MW: 116.16
EINECS: 202-393-6

Product Number: I0016
Purity / Analysis Method : >93.0%(GC)
Molecular Formula / Molecular Weight: C9H8 = 116.16 
Physical State (20 deg.C): Liquid
Storage Temperature : Frozen (<0°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive,Heat Sensitive
CAS RN: 95-13-6
Reaxys Registry Number: 635873
PubChem Substance ID: 87571426
SDBS (AIST Spectral DB): 1357
Merck Index (14): 4939
MDL Number: MFCD00003777

Properties of Indene:
Chemical formula: C9H8
Molar mass: 116.16
Appearance: Colorless liquid
Density: 0.997 g/mL
Melting point: −1.8 °C (28.8 °F; 271.3 K)
Boiling point: 181.6 °C (358.9 °F; 454.8 K)
Solubility in water: Insoluble
Acidity (pKa): 20.1 (in DMSO)
Magnetic susceptibility (χ): −80.89×10−6 cm3/mol

Molecular Weight: 116.16 g/mol
XLogP3: 2.9
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 0
Exact Mass: 116.062600255 Da
Monoisotopic Mass: 116.062600255 Da
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 9
Complexity: 124
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

Quality Segment: 100
assay: ≥99%
form: liquid
refractive index: n20/D 1.595 (lit.)
bp: 181-182 °C (lit.)
mp: −5-−3 °C (lit.)
solubility: organic solvents: miscible, water: insoluble
density: 0.996 g/mL at 25 °C (lit.)
storage temp.: 2-8°C
SMILES string: C1C=Cc2ccccc12
InChI: 1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
InChI key: YBYIRNPNPLQARY-UHFFFAOYSA-N

Melting point : -5--3 °C (lit.)
Boiling point : 181-182 °C (lit.)
density : 0.996 g/mL at 25 °C (lit.)
vapor pressure : 1.7 hPa (20 °C)
refractive index : n20/D 1.595(lit.)
Fp : 138 °F
storage temp. : 2-8°C
solubility : organic solvents: miscible
pka: 20(at 25℃)
form : Crystalline Powder
color : White to pale yellow
Odor Threshold: 0.0038ppm
Water Solubility : INSOLUBLE
Specific Heat Capacity: Cp(liquid): 1.61 J/(g·K), at 25℃
Sensitive : Light Sensitive
Merck : 14,4939
BRN : 635873
Henry's Law Constant: 6.2×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
Exposure limits: PC-TWA:50 mg/m3
Stability: Stable, but air and light sensitive; may polymerize upon exposure to light. Typically contains aroung 80 - 100 ppm of p-tert-butylcatechol as inhibitor. Refrigerate. Flammable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions: PERFUMING
InChI: 1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
InChIKey: YBYIRNPNPLQARY-UHFFFAOYSA-N
SMILES: C1C=Cc2ccccc12
LogP: 3.02 at 25℃ and pH6.4
CAS DataBase Reference: 95-13-6(CAS DataBase Reference)
NIST Chemistry Reference: Indene(95-13-6)
EPA Substance Registry System: Indene (95-13-6)

Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity: 0.99000 to 0.99700 @ 20.00 °C.
Pounds per Gallon - (est).: 8.247 to 8.306
Refractive Index: 1.57000 to 1.57500 @ 20.00 °C.
Boiling Point: 182.00 °C. @ 760.00 mm Hg
Vapor Pressure: 1.200000 mmHg @ 25.00 °C. (est)
Flash Point: 120.00 °F. TCC ( 48.89 °C. )
logP (o/w): 2.920

Specifications of Indene:
Appearance: Colorless to Light yellow to Light orange clear liquid
Purity(GC): min. 93.0 %

Assay (GC): >96.0%
Refractive Index: 1.5720-1.5770 @ 20?C
Form: Liquid
Appearance (Color): Clear colorless to yellow

Related compounds of Indene:
Benzofuran, Benzothiophene, Indole

Names of Indene:

Preferred IUPAC name:
1H-Indene

Other names:
Benzocyclopentadiene
Indonaphthene
Bicyclo[4.3.0]nona-1,3,5,7-tetraene