Indene

Iupac Name：1H-indene

CAS No.: 95-13-6

Molecular Weight：116.16

Modify Date.: 2022-10-26 09:06

Introduction: Indene (also called 1H-Indene, C9H8) is a flammable polycyclic hydrocarbon. It is a colorless and aromatic smelling liquid. It 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. These industrial resins, also called indene-coumarone resins, are mainly consumed by the paints & coatings, rubber, and construction industries.It 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. View more+

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1. Names and Identifiers

1.1 Name: Indene
1.2 Synonyms: (+)-xylitol (1H)-indene 1H-INDENE EINECS 202-393-6 eutrit inden INDENE OEKANAL, 250 MG INDONAPHTHENE kannit Klinit Kylit L56 BHJ Meso-X MFCD00003777 newtol Technicalindene Xilite XYLIT XYLITE

1.3 CAS No.: 95-13-6

1.4 CID: 7219

1.5 EINECS(EC#): 202-393-6

1.6 Molecular Formula: C9H8 (isomer)

1.7 Inchi: InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2

1.8 InChkey: YBYIRNPNPLQARY-UHFFFAOYSA-N

1.9 Canonical Smiles: C1C=CC2=CC=CC=C21

1.10 Isomers Smiles: C1C=CC2=CC=CC=C21

2. Properties

2.1 Density: 0.996

2.1 Melting point: -5--3℃

2.1 Boiling point: 181℃

2.1 Refractive index: 1.567-1.572

2.1 Flash Point: 58℃

2.1 Precise Quality: 116.06300

2.1 PSA: 0.00000

2.1 logP: 2.25590

2.1 Solubility: organic solvents: miscible

2.2 Appearance: pale yellow to orange liquid

2.3 Atmospheric OH Rate Constant: 5.10e-11 cm3/molecule*sec

2.4 Storage: Keep Cold. Light Sensitive.

2.5 Chemical Properties: Yellow green clear liquid

2.6 Color/Form: White to pale yellow

2.7 Heat of Combustion: 4.13X10+7 J/Kg at 25 °C

2.8 Ionization Potential: 8.81 eV

2.9 Odor Threshold: 0.0038ppm

2.10 pKa: 20(at 25℃)

2.11 Water Solubility: INSOLUBLE

2.12 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.

2.13 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Purification Methods: Shake indene with 6M HCl for 24hours (to remove basic nitrogenous material), then reflux it with 40% NaOH for 2hours (to remove benzonitrile). Fractionally distil, then fractionally crystallise it by partial freezing. The higher-melting portion is converted to its sodium salt by adding a quarter of its weight of sodamide under nitrogen and stirring for 3hours at 120o. Unreacted organic material is distilled off at 120o/1mm. The sodium salts are hydrolysed with water, and the organic fraction is separated by steam disillation, followed by fractional distillation. Before use, the distillate is passed, under nitrogen, through a column of activated silica gel. It turns yellow in air as it readily oxidizes and polymerises. [Russell J Am Chem Soc 78 1041 1956, Beilstein 5 IV 1532.] Indene Preparation Products And Raw materials Preparation Products

3.2 Usage: Preparation of coumarone-indene resins, intermediate.

4. Safety and Handling

4.1 Symbol: GHS02, GHS08

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R10;R65

4.1 Safety Statements: S23;S24/25;S62

4.1 Packing Group: III

4.1 Hazard Class: 3

4.1 Hazard Declaration: H226-H304

4.1 RIDADR: UN 3295

4.1 Caution Statement: P301 + P310-P331

4.1 WGK Germany: 1

4.1 RTECS: NK8225000

4.1 Report: Reported in EPA TSCA Inventory.

4.2 Safety: Safety Information of Indene (CAS NO.95-13-6):
Hazard Codes: Xn
Risk Statements: 10-65
10: Flammable
65: Harmful: May cause lung damage if swallowed
Safety Statements: 23-24/25-62
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24: Avoid contact with skin
25: Avoid contact with eyes
62: If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label
RIDADR: UN 3295 3/PG 3
WGK Germany: 1
RTECS: NK8225000
F: 8
HazardClass: 3
PackingGroup: III

4.3 Sensitive: Light Sensitive

4.4 Specification: Indene , its CAS NO. is 95-13-6, the synonyms are 1H-Indene ; HSDB 5286 ; Inden ; Indonaphthene ; NSC 9270 .

4.5 Toxicity

1.	ihl-rat LC50:14 g/m3	GISAAA Gigiena i Sanitariya. 41 (4)(1976),104.
2.	unr-rat LD50:2300 mg/kg	GISAAA Gigiena i Sanitariya. 41 (4)(1976),104.
3.	unr-mus LD50:1800 mg/kg	GISAAA Gigiena i Sanitariya. 41 (4)(1976),104.
4.	orl-uns LD50:>5 g/kg	GISAAA Gigiena i Sanitariya. 39 (4)(1974),86.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Aspiration hazard, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H226 Flammable liquid and vapour H304 May be fatal if swallowed and enters airways
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P331 Do NOT induce vomiting.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : CCl4 solution

IR : liquid film

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

95-13-6Total: 66 Synthesis Route

83-33-0 247 Suppliers

6351-10-6 40 Suppliers

95-13-6 135 Suppliers

Literatures:
Chidara, Vamshi K.; Du, Guodong Organometallics, 2013 , vol. 32, # 18 p. 5034 - 5037
Yield: ~64%

71-43-2 200 Suppliers

673-32-5 24 Suppliers

92-52-4 147 Suppliers

13703-52-1

4794-05-2 1 Suppliers

95-13-6 135 Suppliers

74-86-2 65 Suppliers

Literatures:
Zeitschrift fuer Physikalische Chemie (Muenchen, Germany), , vol. 153, p. 109 - 128
Yield: null

611-14-3 56 Suppliers

611-15-4 13 Suppliers

95-13-6 135 Suppliers

Literatures:
The Standard Oil Company Patent: US4613711 A1, 1986 ;
Yield: ~55%

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8. Other Information

8.0 Merck: 14,4939

8.1 BRN: 635873

8.2 Description: Indene (also called 1H-Indene, C9H8) is a flammable polycyclic hydrocarbon. It is a colorless and aromatic smelling liquid. It 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. These industrial resins, also called indene-coumarone resins, are mainly consumed by the paints & coatings, rubber, and construction industries.
It 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.

8.3 References: [1] https://en.wikipedia.org/wiki/Indene
[2] https://www.alfa.com/de/catalog/L12665/
[3] Stephen F. Hahn, Marc A. Hillmyer (2003) High glass transition temperature polyolefins obtained by the catalytic hydrogenation of polyindene, 36, 71-76.

8.4 Chemical Properties: Yellow green clear liquid

8.5 Uses: Preparation of coumarone-indene resins, intermediate.

8.6 Uses: Preparation of coumarone-indene resins

8.7 Definition: indene: A colourless flammable hydrocarbon,C₉H₈; r.d. 0.996; m.p.–1.8°C; b.p. 182.6°C. Indene is anaromatic hydrocarbon with a five-memberedring fused to a benzenering. It is present in coal tar and isused as a solvent and raw materialfor making other organic compounds.

8.8 Synthesis Reference(s): Tetrahedron Letters, 18, p. 49, 1977 DOI: 10.1016/S0040-4039(01)92547-X

8.9 General Description: A colorless liquid derived from coal tar. Fp: -2°C; bp:182°C. Density 0.997 g cm-3. Insoluble in water but soluble in organic solvents.

8.10 Reactivity Profile: Indene is combustible (flash point between 140°F and 200°F). Polymerizes and oxidizes on standing in the air. This reaction is accelerated by heating, acids, and catalysts, including peroxides. Has exploded during nitration with a mixture of H2SO4 and HNO3.

8.11 Hazard: Toxic by inhalation.

8.12 Health Hazard: Indene is expected to be an irritant of the mucous membranes.

8.13 Purification Methods: Shake indene with 6M HCl for 24hours (to remove basic nitrogenous material), then reflux it with 40% NaOH for 2hours (to remove benzonitrile). Fractionally distil, then fractionally crystallise it by partial freezing. The higher-melting portion is converted to its sodium salt by adding a quarter of its weight of sodamide under nitrogen and stirring for 3hours at 120o. Unreacted organic material is distilled off at 120o/1mm. The sodium salts are hydrolysed with water, and the organic fraction is separated by steam disillation, followed by fractional distillation. Before use, the distillate is passed, under nitrogen, through a column of activated silica gel. It turns yellow in air as it readily oxidizes and polymerises. [Russell J Am Chem Soc 78 1041 1956, Beilstein 5 IV 1532.]

8.14 Usage: 1H-Indene is a building block that has been used in the synthesis of isatins. It was used in the synthesis of new C60 derivative, indene-C60 bisadduct. It was used in preparing polyindene by the controlled cationic polymerization initiated with cumyl methyl ether/TiCl4 in CH2Cl2.

8.15 Usage: 1H-Indene is used in the synthesis of new C60 derivative, indene-C60 bisadduct1. It was used in preparing polyindene by the controlled cationic polymerization initiated with cumyl methyl ether/TiCl4 in CH2Cl2. It is also used in the synthesis of istatins and in the production of indene/cumarone thermoplastic resins.

9. Computational chemical data

Molecular Weight: 116.16g/mol
Molecular Formula: C₉H₈
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 116.062600255
Monoisotopic Mass: 116.062600255
Complexity: 124
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 0
Heavy Atom Count: 9
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwAAAAAAAAAAAAAAAAAAAAAQAAAAAwAAAAAAAAAEABAAAAGAAAAAAADACAGAAwAIAAAACAAiBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAgIAOgAAAAAAQAAAAAAAAACAAAAAAAAAAAA==

10. Question & Answer

Basic sites on Indene ion Aug 08 2021
Answer key says that A is the most basic site but I don’t understand the concept behind that. To assess the basic site, I’d normally look at the molecule as is and assess the current stability of the atom in question. The least stable would be my strongest base. Looking at this question both the ...

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