1-indene
Conditions | Yield |
---|---|
With t-butyl bromide In acetonitrile for 1h; Reflux; | 100% |
Conditions | Yield |
---|---|
at 290℃; for 3h; | A 99% B 60% C 75% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; magnesium sulfate In tetrahydrofuran; methanol | A 96% B n/a |
2-bromoindene
1-indene
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
1-indene
Conditions | Yield |
---|---|
at 20℃; for 0.0833333h; chemoselective reaction; | 92% |
1-indene
Conditions | Yield |
---|---|
With molybdenum hexacarbonyl In toluene for 1.5h; Reflux; chemoselective reaction; | 91% |
2-bromoindene
A
2-Methylindene
B
1,2-dimethylindene
C
1-indene
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 |
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% |
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
1-indene
Conditions | Yield |
---|---|
With Grubbs catalyst first generation In 1,2-dichloro-ethane at 20℃; for 17h; Inert atmosphere; Sealed tube; | 86% |
cis,syn-cyclobutadiindene
1-indene
Conditions | Yield |
---|---|
With DCNB Irradiation; | 85% |
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
1-indene
Conditions | Yield |
---|---|
With m-Anisidine In N,N-dimethyl-formamide at 80℃; for 48h; stereospecific reaction; | 85% |
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
indan-2-ol
A
2,3-dihydro-1H-inden-2-yl benzoate
B
1-indene
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; sodium carbonate In n-heptane at 105℃; for 12h; Inert atmosphere; | A 83% B 11% |
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidinyl-lithium In hexane at 60℃; for 18h; | 81% |
1-indene
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
A
INDANE
B
1-indene
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 45℃; for 1h; | A 80% B 20% |
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
1-indene
Conditions | Yield |
---|---|
With phenanthrene Irradiation; | 80% |
With phenanthrene Rate constant; Irradiation; | 80% |
Conditions | Yield |
---|---|
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 0.666667h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 80% B 71% |
Conditions | Yield |
---|---|
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 3.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 79% B 65% |
Conditions | Yield |
---|---|
With iodophenylbis(triphenylphosphine)palladium In 1,2-dichloro-ethane at 120 - 130℃; for 2h; | A 78% B 22% |
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 120 - 130℃; for 2h; | A 78% B 22% |
1-indene
Conditions | Yield |
---|---|
With indium(III) chloride; indium; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 20℃; for 8h; | 78% |
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
1-indene
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% |
Conditions | Yield |
---|---|
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 0.25h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 74% B 60% |
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% |
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% |
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 0.5h; Irradiation; | 100% |
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% |
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% |
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 3h; ultrasound excitation; | 100% |
1-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. |
Conditions | Yield |
---|---|
With oxygen at 340 - 360℃; | 100% |
With oxygen at 340 - 360℃; | 100% |
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% |
Conditions | Yield |
---|---|
With indium(III) triflate In acetonitrile at 70℃; diastereoselective reaction; | 100% |
1-indene
trans-2-bromo-1-indanol
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% |
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
trans-1,2-bromoindane
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% |
Conditions | Yield |
---|---|
In dichloromethane 1.) -30 deg C, 1 h, 2.) -30 deg C to 15 deg C, overnight; | 99% |
diiodomethane
1-indene
benzo[2,3]bicyclo[3.1.0]hexane
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% |
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
(1aR,6aS)-6,6a-dihydro-1aH-indeno[1,2-b]oxirene
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% |
Conditions | Yield |
---|---|
palladium on activated carbon at 250℃; for 2h; | A 96% B 99% |
Conditions | Yield |
---|---|
A n/a B 99% | |
A n/a B 97% | |
A n/a B 95% |
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
1-indene
(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
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
1-indene
ethyl endo-3-tricyclo<4.4.0.02,4>deca-1(6),7,9-trienecarboxylate
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
1-indene
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% |
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% |
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
1-indene
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% |
Conditions | Yield |
---|---|
With urea; zinc(II) chloride at 110℃; for 1h; Green chemistry; | 99% |
1-indene
Conditions | Yield |
---|---|
With dirhodium tetraacetate In dichloromethane at 20℃; for 21h; Inert atmosphere; Sealed tube; diastereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In toluene at 25℃; for 24h; Reagent/catalyst; | 99% |
Reported in EPA TSCA Inventory.
OSHA PEL: TWA 10 ppm
ACGIH TLV: TWA 10 ppm
NIOSH REL: (Indene) TWA 10 ppm
1. Introduction of Indene
Indene ,with its CAS NO 95-13-6, is a kind of colorless or light yellow transparent liquid. It has synonyms of 1H-Indene ; HSDB 5286 ; Inden ; Indonaphthene and NSC 9270. Indene should be stored in shady and cool warehouse and mainly used in the production of indene/cumarone thermoplastic resins.
2.Properties of Indene
(1) Melting point: -5- -3 °C (2) Boiling point: 181-182 °C (3) Density: 0.996 g/mL at 25 °C(4) Refractive index: n20/D 1.595
(5) Flash point: 138 °F (6) Storage temp.: 2-8°C (7) Water Solubility: INSOLUBLE
3.Sturcture descriptors of Indene
IUPAC Name: 1H-indene
InChI: InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
InChIKey: YBYIRNPNPLQARY-UHFFFAOYSA-N
Canonical SMILES : C1C=CC2=CC=CC=C21
4.Safety information of Indene
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
5.Toxity data of Indene
ihl-rat LC50:14 g/m3 unr-rat LD50:2300 mg/kg unr-mus LD50:1800 mg/kg orl-uns LD50:>5 g/kg
1. GISAAA Gigiena i Sanitariya. 41 (4)(1976),104. 2. GISAAA Gigiena i Sanitariya. 41 (4)(1976),104. 3. GISAAA Gigiena i Sanitariya. 41 (4)(1976),104. 4. GISAAA Gigiena i Sanitariya. 39 (4)(1974),86.
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