95-13-6

Basic information

• Product Name: Indene
• Synonyms: inden;Technicalindene;INDENE;INDONAPHTHENE;1H-INDENE;AKOS BBS-00004330;INDENE, 99+%;INDENE, TECH., 90+%
• CAS NO: 95-13-6
• Molecular Formula: C₉H₈
• Molecular Weight: 116.16
• EINECS: 202-393-6
• Product Categories: Arenes;Building Blocks;Organic Building Blocks;Alpha Sort;Alphabetic;Analytical Standards;AromaticsVolatiles/ Semivolatiles;Chemical Class;E-LAnalytical Standards;Hydrocarbons;IChemical Class;Neats;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 95-13-6.mol
• Article Data: 170

Chemical Properties

• Melting Point: −5-−3 °C(lit.)
• Boiling Point: 181-182 °C(lit.)
• Flash Point: 138 °F
• Appearance: White to pale yellow/Crystalline Powder
• Density: 0.996 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.15mmHg at 25°C
• Refractive Index: n20/D 1.595(lit.)
• Storage Temp.: 2-8°C
• Solubility: organic solvents: miscible
• PKA: 20(at 25℃)
• Water Solubility: INSOLUBLE
• Sensitive: Light Sensitive
• Stability: Stable, but air and light sensitive; may polymerize upon exposure to light. Typically contains aroung 80 - 100 ppm of p-tert-but
• Merck: 14,4939
• BRN: 635873
• CAS DataBase Reference: Indene(CAS DataBase Reference)
• NIST Chemistry Reference: Indene(95-13-6)
• EPA Substance Registry System: Indene(95-13-6)

Safety Data

• Hazard Codes: Xn
• Statements: 10-65-36/37/38-20
• Safety Statements: 23-24/25-62-37/39-26
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 1
• RTECS: NK8225000
• F: 8
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 95-13-6(Hazardous Substances Data)

Usage

Chemical Description

Indene is a bicyclic aromatic hydrocarbon with the chemical formula C9H8.

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.

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.

Chemical Properties

Yellow green clear liquid

Uses

Different sources of media describe the Uses of 95-13-6 differently. You can refer to the following data:
1. Preparation of coumarone-indene resins, intermediate.
2. Preparation of coumarone-indene resins
3. 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.

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.

Synthesis Reference(s)

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

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.

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.

Health Hazard

Indene is expected to be an irritant of the mucous membranes.

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.]

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

Synthetic route

C17H18O2 → 1-indene (95-13-6)

Conditions	Yield
With t-butyl bromide In acetonitrile for 1h; Reflux;	100%

trans-1,2-bis(hydroxydiphenylmethyl)indan → benzophenone (119-61-9) + 1,1-Diphenylmethanol (91-01-0) + 1-indene (95-13-6)

Conditions	Yield
at 290℃; for 3h;	A 99% B 60% C 75%

2,5,7-trimethyl-indan-1-one (65001-59-4) → 1-indene (95-13-6) + 2,4,6-trimethyl-indene (150096-40-5)

Conditions	Yield
With sodium tetrahydroborate; magnesium sulfate In tetrahydrofuran; methanol	A 96% B n/a

2-bromoindene (10485-09-3) → 1-indene (95-13-6)

Conditions	Yield
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile) In toluene at 90℃; for 5h;	93%

trans-1.2-Dibrom-indan (19598-04-0, 19598-15-3, 20357-79-3) → 1-indene (95-13-6)

Conditions	Yield
at 20℃; for 0.0833333h; chemoselective reaction;	92%

6,6a-dihydro-1aH-1-thia-cyclopropa[a]indene → 1-indene (95-13-6)

Conditions	Yield
With molybdenum hexacarbonyl In toluene for 1.5h; Reflux; chemoselective reaction;	91%

2-bromoindene (10485-09-3) + [3-(dimethylamino)propyl]dimethyl aluminium(III) → 2-Methylindene (2177-47-1) + 1,2-dimethylindene (70063-93-3) + 1-indene (95-13-6)

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 2h; Yields of byproduct given;	A 88% B n/a C n/a

2-(3-phenyl-2-propenyl)benzaldehyde → benzaldehyde (100-52-7) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;	A 86% B 71%

(E)-2-(3-(4-fluorophenyl)allyl)benzaldehyde → 4-fluorobenzaldehyde (459-57-4) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 1.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 86% B 22%

1-allyl-2-vinylbenzene (21919-44-8) → 1-indene (95-13-6)

Conditions	Yield
With Grubbs catalyst first generation In 1,2-dichloro-ethane at 20℃; for 17h; Inert atmosphere; Sealed tube;	86%

cis,syn-cyclobutadiindene (25456-57-9) → 1-indene (95-13-6)

Conditions	Yield
With DCNB Irradiation;	85%

inden-1-one (83-33-0) → 1-indene (95-13-6)

Conditions	Yield
With toluene-4-sulfonic acid; 2,2-Dimethyl-1,3-propanediol In benzene at 80℃; for 24h;	85%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tributylphosphine; sodium 2,2,2-trifluoroacetate; bis(pinacol)diborane In tetrahydrofuran at 70℃; for 10h; Glovebox; Sealed tube; Inert atmosphere;	46%
Multi-step reaction with 3 steps 1: LiAlH4 2: 41 percent / n-BuLi / hexamethylphosphoric acid triamide 3: 81 percent / LTMP / hexane / 18 h / 60 °C View Scheme
Stage #1: inden-1-one With sodium tetrahydroborate In methanol Stage #2: In benzene Acidic conditions;

trans-1,2-bromoindane (19598-15-3) → 1-indene (95-13-6)

Conditions	Yield
With m-Anisidine In N,N-dimethyl-formamide at 80℃; for 48h; stereospecific reaction;	85%

C17H16O → 2-methylphenyl aldehyde (529-20-4) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 0.666667h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 84% B 75%

benzoic acid methyl ester (93-58-3) + indan-2-ol (4254-29-9) → 2,3-dihydro-1H-inden-2-yl benzoate (71482-23-0) + 1-indene (95-13-6)

Conditions	Yield
With iron(III)-acetylacetonate; sodium carbonate In n-heptane at 105℃; for 12h; Inert atmosphere;	A 83% B 11%

1-methoxyindane (1006-27-5) → 1-indene (95-13-6)

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In hexane at 60℃; for 18h;	81%

(E)-2-(3-(o-tolyl)allyl)benzaldehyde → 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 8h; Schlenk technique; Inert atmosphere;	81%

2-(6,6a-dihydro-1aH-1-aza-cyclopropa[a]inden-1-yl)-isoindole-1,3-dione (70381-08-7) → INDANE (496-11-7) + 1-indene (95-13-6)

Conditions	Yield
With hydrazine hydrate In ethanol at 45℃; for 1h;	A 80% B 20%

1-Indanol (6351-10-6) → 1-chloroindane (35275-62-8) + 1-indene (95-13-6)

Conditions	Yield
With pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran Ambient temperature;	A 80% B 6%
Stage #1: 1-Indanol With N,N-dimethylthiourea In dichloromethane at 20℃; Stage #2: With N-chloro-succinimide In dichloromethane at 20℃; for 1h; Irradiation;	A 79 %Chromat. B 20.961 %Chromat.

(4bR*,4cR*,9aR*,9bR*)-4b,4c,9,9a,9b,10-hexahydrocyclobuta[1,2-a:4,3-a']diindene (7099-25-4, 23358-17-0, 25456-57-9, 112246-68-1) → 1-indene (95-13-6)

Conditions	Yield
With phenanthrene Irradiation;	80%
With phenanthrene Rate constant; Irradiation;	80%

(E)-2-(3-([1,1'-biphenyl]-2-yl)allyl)benzaldehyde → 2-Phenylbenzaldehyde (1203-68-5) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 0.666667h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 80% B 71%

(E)-2-(3-mesitylallyl)benzaldehyde → mesytaldehyde (487-68-3) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 3.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 79% B 65%

(1H-inden-1-yl)trimethylstannane (23022-40-4) → 1-(1-indenyl)-indene (2177-49-3) + 1-indene (95-13-6)

Conditions	Yield
With iodophenylbis(triphenylphosphine)palladium In 1,2-dichloro-ethane at 120 - 130℃; for 2h;	A 78% B 22%

(1H-inden-1-yl)trimethylstannane (23022-40-4) + C6H5PdI(P(C6H5)3)2 → 1-(1-indenyl)-indene (2177-49-3) + 1-indene (95-13-6)

Conditions	Yield
In 1,2-dichloro-ethane at 120 - 130℃; for 2h;	A 78% B 22%

Acetic acid (1S,2S)-1-bromo-indan-2-yl ester → 1-indene (95-13-6)

Conditions	Yield
With indium(III) chloride; indium; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 20℃; for 8h;	78%

(E)-2-(3-(naphthalen-1-yl)allyl)benzaldehyde → 1-naphthaldehyde (66-77-3) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 2h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 78% B 58%

7-ethynyl-cyclohepta-1.3.5-triene (25928-15-8) → 1-indene (95-13-6)

Conditions	Yield
With acetonitrile[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I) hexafluoroantimonate In dichloromethane at 25℃; for 1.5h; Reagent/catalyst; Inert atmosphere;	77%

(E)-2-(3-(p-tolyl)allyl)benzaldehyde → 4-methyl-benzaldehyde (104-87-0) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 0.25h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 74% B 60%

1-bromoindene 1,2-oxide → 1-(1-indenyl)-indene (2177-49-3) + inden-1-one (83-33-0) + 1-indene (95-13-6)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; phosphorous acid trimethyl ester In benzene for 4h; Heating;	A 8% B 3% C 73%

1-indene (95-13-6) → inden-1-one (83-33-0)

Conditions	Yield
With dihydrogen peroxide In water at 75℃; for 12h;	100%
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 70℃; for 24h; Temperature; Wacker Oxidation;	95%
With iron(II) chloride In ethanol at 80℃; for 6h;	93%

1-bromo-octane (111-83-1) + 1-indene (95-13-6) → 3-octylindene (43130-63-8)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 0.5h; Irradiation;	100%

1-indene (95-13-6) → 2,3-epoxyindene (768-22-9)

Conditions	Yield
With dihydrogen peroxide In ethanol; water at 50℃; for 1h; Catalytic behavior; Green chemistry;	100%
With Amberlite IRC-50; dihydrogen peroxide; dicyclohexyl-carbodiimide In ethanol; water for 24h; Ambient temperature; other reagents: H2O2/KHCO3/dicyclohexylcarbodiimide, H2O2/Na3PO4*12H2O/dicyclohexylcarbodiimide, H2O2/KHCO3/benzonitrile, hydrogen peroxide-sodium carbonate/dicyclohexylcarbodiimide;	98%
With 3,3-dimethyldioxirane In acetone at 20℃; for 1h;	96%

methanol (67-56-1) + 1-indene (95-13-6) → 1-methoxy-2,3-dihydro-1H-inden-2-ol (71720-52-0)

Conditions	Yield
With dihydrogen peroxide; methyltrioxorhenium(VII) at 25℃; for 3h;	100%
With boron trifluoride diethyl etherate; dihydrogen peroxide In diethyl ether at 50 - 55℃; for 12h;	69%

1-indene (95-13-6) + octyl halide → 3-octylindene (113416-62-9)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 3h; ultrasound excitation;	100%

1-indene (95-13-6) → 6,6a-dihydro-1aH-1-oxa-cyclopropa[a]indene

Conditions	Yield
With N-methyl-2-indolinone; 3-chloro-benzenecarboperoxoic acid; Merrifield resin-supported sulfonato-Mn(salen) In acetonitrile at -20℃;	100%
With sodium hypochlorite; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) In aq. phosphate buffer at 15℃; for 2h; pH=11.3; Reagent/catalyst; Ionic liquid; enantioselective reaction;	95%
With dihydrogen peroxide; chiral di-μ-oxotitanium(salen) In water; ethyl acetate at 20℃; for 24h;	87 % Spectr.

1-indene (95-13-6) → phthalic anhydride (85-44-9)

Conditions	Yield
With oxygen at 340 - 360℃;	100%
With oxygen at 340 - 360℃;	100%

5-tert-butyl-1,3,2-benzodioxaborolane (188707-78-0) + 1-indene (95-13-6) → 2-ethylindenyl-Bcat' (256234-74-9)

Conditions	Yield
Cp2Ti(HBcat')2 In benzene-d6 react. indene, HBcat', and 10 mol % Cp2Ti(HBcat')2 in benzene-d6 at 25°C for 10 min;	100%
dimethyltitanocene In benzene-d6 react. indene, HBcat', and 10 mol % Cp2TiMe2 in benzene-d6 at 25°C for 10 h;	96%

C17H13BrN2O3 + 1-indene (95-13-6) → C26H21BrN2O3

Conditions	Yield
With indium(III) triflate In acetonitrile at 70℃; diastereoselective reaction;	100%

1-indene (95-13-6) → trans-2-bromo-1-indanol (10368-44-2)

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran; water at 20℃; for 24h;	99.6%
With N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide); ammonium acetate; water In acetone at 20℃; for 0.05h;	94%
With N-Bromosuccinimide In tetrahydrofuran; water at 20℃; for 12h;	94%

1-indene (95-13-6) → INDANE (496-11-7)

Conditions	Yield
With hydrogen; lithium aluminium tetrahydride; nickelocene In tetrahydrofuran Ambient temperature; atmospheric pressure;	99%
With fac-[Mn(1,2-bis(di-isopropylphosphino)ethane)(CO)3(CH2CH2CH3)]; hydrogen In diethyl ether at 60℃; under 37503.8 Torr; for 24h;	99%
With chloro-trimethyl-silane; benzoic acid; sodium iodide In acetonitrile at 75℃; for 16h; Heating;	98%

1-indene (95-13-6) → trans-1,2-bromoindane (19598-15-3)

Conditions	Yield
With iodic acid; potassium bromide In dichloromethane; water at 20℃; for 0.166667h;	99%
With bromine In dichloromethane at 0℃; for 0.5h;	96%
With periodic acid; potassium bromide In dichloromethane; water at 20℃; for 0.166667h;	90%

propargyl alcohol (107-19-7) + 1-indene (95-13-6) → 2-Bromo-1-(2-propynyloxy)indane (127773-49-3)

Conditions	Yield
In dichloromethane 1.) -30 deg C, 1 h, 2.) -30 deg C to 15 deg C, overnight;	99%

diiodomethane (75-11-6) + 1-indene (95-13-6) → benzo[2,3]bicyclo[3.1.0]hexane (15677-15-3, 148323-54-0, 148323-57-3)

Conditions	Yield
Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane for 0.333333h; cooling; Stage #2: 1-indene In hexane; dichloromethane at 20℃; for 2h;	99%
With tetradecafluorohexane; triethylaluminum In hexane at 20℃; for 58h; Darkness;	92%
With copper(l) chloride; zinc In diethyl ether Heating;	44%

1-indene (95-13-6) → 1,1,3-trideuterioindene (770-96-7)

Conditions	Yield
With water-d2; N-benzyl-trimethylammonium hydroxide In pyridine; methanol for 12h;	99%
With water-d2; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane Sealed tube;	85%
With water-d2; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;	68%
With water-d2; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane Heating; Yield given;
With chloroform-d1; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 20℃; for 12h;

1-indene (95-13-6) → (1aR,6aS)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene (768-22-9, 67528-26-1, 71214-81-8, 85354-35-4)

Conditions	Yield
With pyridine N-oxide; sodium hypochlorite In dichloromethane; water at 0℃; for 9h; pH=11.3; optical yield given as %ee; enantioselective reaction;	99%
With sodium hypochlorite; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese; ammonium acetate In dichloromethane at 0℃; for 4.5h; pH=11.3; aq. phosphate buffer; optical yield given as %ee; enantioselective reaction;	95%
With titanium(IV) isopropylate; dihydrogen peroxide In dichloromethane at 20℃; for 18h;	88%

methyltetrahydrofluorene + 1-indene (95-13-6) → methylfluorene + INDANE (496-11-7)

Conditions	Yield
palladium on activated carbon at 250℃; for 2h;	A 96% B 99%

1,2,3,4-tetrahydro-9H-fluorene (17057-95-3) + 1-indene (95-13-6) → 9H-fluorene (86-73-7) + INDANE (496-11-7)

Conditions	Yield
	A n/a B 99%
	A n/a B 97%
	A n/a B 95%

[Zr(N(CH3)2)3(μ-N(CH3)2)]2 + 1-indene (95-13-6) → π-C9H7Zr(N(CH3)2)3

Conditions	Yield
In toluene under N2 using Schlenk techniques; mixt. stirred at 90°C overnight under stream of N2; filtered; solvent evapd. to dryness; as oil; elem. anal.;	99%

(-)-3,10-dihydroxy-6,12-diisopropyl-3,10-dimethyltricyclo[6.2.2.02,7]dodeca-5,11-diene-4,9-dione (1012322-12-1) + 1-indene (95-13-6) → (1R,2R,10R,11S,12S)-12-hydroxy-12-methyl-14-(propan-2-yl)tetracyclo[9.2.2.0(2,10).0(3,8)]pentadeca-3,5,7,14-tetraen-13-one (1144084-76-3)

Conditions	Yield
In 1,3,5-trimethyl-benzene at 150℃; for 12h; retro-Diels-Alder/Diels-Alder cascade; Inert atmosphere; regioselective reaction;	99%
In 1,3,5-trimethyl-benzene at 180℃; for 0.25h; Microwave irradiation; Inert atmosphere; diastereoselective reaction;	99%

diazoacetic acid ethyl ester (623-73-4) + 1-indene (95-13-6) → ethyl endo-3-tricyclo<4.4.0.02,4>deca-1(6),7,9-trienecarboxylate (59875-31-9, 59905-91-8, 59905-96-3, 59953-45-6, 72258-13-0, 114180-54-0, 114182-19-3)

Conditions	Yield
With C20H19ClN3ORh; NaBArf In dichloromethane at 0℃; Inert atmosphere; optical yield given as %de;	99%
With dirhodium tetraacetate In dichloromethane at 20℃; for 18h; Inert atmosphere; stereoselective reaction;

bis(methoxycarbonyl)(phenyliodinio)methanide (145838-86-4) + 1-indene (95-13-6) → (1aS,6aS)-dimethyl 6,6a-dihydrocyclopropa[a]indene-1,1(1aH)-dicarboxylate

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; (4S,4's)-2,2'-(1,3-bis(4-(tert-butyl)phenyl)propane-2,2-diyl)bis(4-phenyl-4,5-dihydro-oxazole) In toluene at -40℃; for 92h; Molecular sieve; Inert atmosphere;	99%

ethenetetracarbonitrile (670-54-2) + 1-indene (95-13-6) + 2-(phenylethynyl)acetophenone (171258-08-5) → 10-benzoyl-5-methyl-5,10,10a,11-tetrahydro-4bH-5,10-ethanobenzo[b]fluorene-12,12,13,13-tetracarbonitrile

Conditions	Yield
With (1,3-dimesitylimidazol-2-ylidene)gold(I) chloride; Selectfluor In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; Schlenk technique;	99%

4-chlorobenzaldehyde (104-88-1) + 1-indene (95-13-6) → C23H16Cl2O

Conditions	Yield
With cesiumhydroxide monohydrate In ethanol at 25℃; for 0.166667h; Schlenk technique; regioselective reaction;	99%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2, 45842-10-2) + 1-indene (95-13-6) → 1-(((1S*,2S*)-2-azido-2,3-dihydro-1H-inden-1-yl)oxy)-2,2,6,6-tetramethylpiperidine

Conditions	Yield
With sodium azide In water; acetonitrile at 22℃; for 2h; Electrochemical reaction; Inert atmosphere;	99%
With Amberlyst A26 resin bound bis(azido)iodate(I) In tetrahydrofuran at 20℃; for 20h; Solvent; Irradiation; Inert atmosphere;	77%
With trimethylsilylazide; C7H15IO4S In dichloromethane at 35℃; for 12h; Sealed tube; Inert atmosphere; Irradiation; regioselective reaction;	75%

p-toluidine (106-49-0) + 4-methoxy-benzaldehyde (123-11-5) + 1-indene (95-13-6) + air → 6-(4-methoxyphenyl)-2-methyl-7H-indeno[2,1-c]quinoline

Conditions	Yield
With urea; zinc(II) chloride at 110℃; for 1h; Green chemistry;	99%

6-[(4-methylbenzene)sulfonyl]-6-azasipro[2.5]oct-1-ene + 1-indene (95-13-6) → 4-((1,1a,6,6a-tetrahydrocyclopropa[a]inden-1-yl)methylene)-1-tosylpiperidine

Conditions	Yield
With dirhodium tetraacetate In dichloromethane at 20℃; for 21h; Inert atmosphere; Sealed tube; diastereoselective reaction;	99%

1-tert-butoxy-6-iodohexane (81060-09-5) + 1-indene (95-13-6) → 3-(6-tert-butoxyhexyl)-1H-indene

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In toluene at 25℃; for 24h; Reagent/catalyst;	99%

Upstream product

• 35275-62-8 1-chloroindane 
• 7281-17-6 5,10,10a,11-tetrahydro-4bH-5,10-o-benzeno-benzo[b]fluorene 
• 6351-10-6 1-Indanol 
• 75-36-5 acetyl chloride 
• 90031-76-8 (+/-)-indan-1-yl-trimethyl-ammonium; iodide 
• 10277-82-4 (+)-indan-1-yl-trimethyl-ammonium; iodide 
• 447-53-0 1,2-Dihydronaphthalene 
• 496-11-7 INDANE 
• 127-09-3 sodium acetate 
• 827-52-1 1-phenyl-1-cyclohexane 
• 480-72-8 1,2,2a,3,4,5-hexahydro-acenaphthylene 
• 1572-46-9 9-benzylfluorene 
• 78926-41-7 2-formylstyrene p-toluenesulphonylhydrazone 
• 98652-53-0 2,2-dibromo-3'-methylenespirooxabicyclo<2.2.1>heptane> 

Downstream Products

• 97355-38-9 [1-(4-nitro-benzylidene)-inden-3-yl]-(4-nitro-phenyl)-methanol 
• 115145-51-2 diethyl-[2-(4-inden-1-ylidenemethyl-phenoxy)-ethyl]-amine 
• 16275-01-7 1-benzyl-1H-indene 
• 40241-58-5 1,3-dibenzyl-indene 
• 22495-71-2 3-benzyl-1H-indene 
• 13206-55-8 trans-2-phenylmercapto-1-indanol 
• 32785-03-8 (1RS)-trans-2-((RS)-benzenesulfinyl)-indan-1-ol 
• 32785-03-8 (1RS)-trans-2-((SR)-benzenesulfinyl)-indan-1-ol 
• 14585-67-2 3-(2-(N,N-diethylamino)ethyl)indene 
• 34472-48-5 1-(1-methylethylidene)-1H-indene 
• 2294-91-9 3-ethyl-1H-indene 
• 14091-22-6 S--mercaptoessigsaeure 
• 768-22-9 2,3-epoxyindene 
• 125349-04-4 N-(3-hydroxyindan-2-yloxy)phtalimide 

Relevant articles and documents

Spontaneous resolution versus formation of racemic crystals of indenylpotassium complexes

During a study of stereochemically labile organometallic reagents, we found that crystallisation of [K(ind)(pmdta)]n (ind = indenyl, pmdta = N,N,N',N'',N''-pentamethyldiethylenetriamine) from tetrahydrofuran (THF) gave rise to three different crystalline phases depending on the concentration. The more concentrated solutions gave racemic crystals of the previously known coordination polymer [K(ind)(pmdta)]n, a-1. More dilute solutions gave crystals of a new phase, b-1, which was found to undergo spontaneous resolution. From even more dilute solutions, we were able to isolate a chiral inclusion compound with THF, 2, which also undergoes spontaneous resolution. Crystals of b-1 and 2 were enantiomerically pure, and since b-1 is a reactive organometallic reagent, attempts were made to use the crystals in enantioselective synthesis. Reacting single crystals with N-chlorosuccinimide gave rise to chiral 1-chloroindene, but no enantiomeric excess was observed.

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The preparation of an aryl substitued diazetine and the kinetics for its thermal decomposition to nitrogen and alkene are reported.

Mehrfachbindungen zwischen Hauptgruppenelementen und Uebergangsmetallen. CXLIII. Indenyltrioxorhenium(VII): Organometalloxid mit dynamischer Struktur

Indenyltrioxorhenium(VII), (C9H7)ReO3, was synthesized from Re2O7 and (indenyl)tris(n-butyl)tin.It is a moisture- and temperature-sensitive compound (dec. -30 deg C), the structure of which adopts η1-coordination of the organic ligand.According to 1H NMR studies, a haptotropic structural rearrangement occurs at > -25 deg C in solution (1,3-shift mechanism).Decomposition studies show a concentration decay of the title compound in anhydrous solution, with formation of ReO3 and indene.Keywords: Rhenium; Indenyl; Dynamic structure; NMR

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Desulfurization of a variety of thiiranes to alkenes occurs chemoselectively in high yields upon treatment with MoCl5/Zn system under mild conditions. The new methodology demonstrates high functional group tolerance toward chloro, bromo, fluoro, methoxy, ester, ether and keto groups.

Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions

We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.