75476-78-7

Basic information

• Product Name: 1H-INDENE, 5-BROMO-
• Synonyms: 5-BROMO-1H-INDENE;1H-INDENE, 5-BROMO-
• CAS NO: 75476-78-7
• Molecular Formula: C₉H₇Br
• Molecular Weight: 195.06
• Mol File: 75476-78-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 245 °C at 760 mmHg
• Flash Point: 105.5 °C
• Appearance: Colourless
• Density: 1.523 g/cm³
• Vapor Pressure: 0.0459mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 1H-INDENE, 5-BROMO-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDENE, 5-BROMO-(75476-78-7)
• EPA Substance Registry System: 1H-INDENE, 5-BROMO-(75476-78-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 75476-78-7(Hazardous Substances Data)

Usage

General Description

5-bromo-1H-indene is a chemical compound with the molecular formula C9H7Br. It is a brominated derivative of 1H-indene and is commonly used in organic synthesis and medicinal chemistry. 5-bromo-1H-indene is a versatile building block for the synthesis of various biologically active compounds and is used as an intermediate in the production of pharmaceuticals and agrochemicals. It is also utilized in the preparation of dyes, pigments, and other organic materials. The compound has potential applications in the fields of pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C9H7Br/c10-9-5-4-7-2-1-3-8(7)6-9/h1,3-6H,2H2

Synthetic route

6-Bromo-2,3-dihydro-1H-inden-1-ol (75476-86-7) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	97%
With toluene-4-sulfonic acid In benzene for 3h; Reflux;	95%
With toluene-4-sulfonic acid In benzene at 65℃; for 14h;	88%

5-Bromo-1-indanone (34598-49-7) → 6-bromo-1H-indene (33065-61-1) + 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Stage #1: 5-Bromo-1-indanone With lithium aluminium tetrahydride at 0℃; for 2h; Stage #2: With toluene-4-sulfonic acid In benzene at 75℃; for 2h;	A 90% B n/a

5-bromo-2,3-dihydro-1H-inden-2-ol (862135-61-3) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
With toluene-4-sulfonic acid In benzene

5-bromo-1H-inden-2(3H)-one (174349-93-0) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: p-TsOH / benzene View Scheme

6-bromoindan-1-one (14548-39-1) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / sodium borohydride / methanol / 2 h / 20 °C 2: 87 percent / p-TsOH / benzene / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 89 percent / NaBH4 / ethanol / 25 °C 2: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating View Scheme
Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 1 h / Ambient temperature 2: 77 percent / H2SO4 (20percent), ethylene glycol / 20 h / 75 °C View Scheme

6-bromo-1H-indene (33065-61-1) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 28 percent / Pseudomonas putida UV4 / 7 h 2: 88 percent / sodium borohydride / methanol / 2 h / 20 °C 3: 87 percent / p-TsOH / benzene / 2 h / Heating View Scheme

5-Bromo-1-indanone (34598-49-7) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / sodium borohydride / methanol / 2 h / 20 °C 2: 92 percent / p-TsOH / benzene / 2 h / Heating 3: 28 percent / Pseudomonas putida UV4 / 7 h 4: 88 percent / sodium borohydride / methanol / 2 h / 20 °C 5: 87 percent / p-TsOH / benzene / 2 h / Heating View Scheme

5-bromo-1-indanol (34598-50-0) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / p-TsOH / benzene / 2 h / Heating 2: 28 percent / Pseudomonas putida UV4 / 7 h 3: 88 percent / sodium borohydride / methanol / 2 h / 20 °C 4: 87 percent / p-TsOH / benzene / 2 h / Heating View Scheme

6-bromoindan-1-one (14548-39-1) → 5-bromo-1H-indene (75476-78-7) + n-PrMgX

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / ethanol 2: p-TsOH / toluene / 80 °C View Scheme

3-(4-bromophenyl)propionic acid (1643-30-7) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride 2: 91 percent / AlCl3 / CS2 3: 89 percent / NaBH4 / ethanol / 25 °C 4: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 3 h / Reflux 2: sodium tetrahydroborate / ethanol / 3 h / 10 - 20 °C 3: toluene-4-sulfonic acid / benzene / 3 h / Reflux View Scheme

diethyl 2-(4-bromobenzyl)malonate (70146-78-0) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: 95 percent / KOH / acetic acid; H2O; tetrahydrofuran 2: 85 percent / 165 °C 3: thionyl chloride 4: 91 percent / AlCl3 / CS2 5: 89 percent / NaBH4 / ethanol / 25 °C 6: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating View Scheme

2-[(4-bromophenyl)methyl]propanedioic acid (92013-18-8) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / 165 °C 2: thionyl chloride 3: 91 percent / AlCl3 / CS2 4: 89 percent / NaBH4 / ethanol / 25 °C 5: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating View Scheme

3-(4-bromophenyl)propanoyl chloride (55394-81-5) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / AlCl3 / CS2 2: 89 percent / NaBH4 / ethanol / 25 °C 3: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating View Scheme

1-bromomethyl-4-bromobenzene (589-15-1) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
Multi-step reaction with 7 steps 1: 74 percent / NaOEt / Heating 2: 95 percent / KOH / acetic acid; H2O; tetrahydrofuran 3: 85 percent / 165 °C 4: thionyl chloride 5: 91 percent / AlCl3 / CS2 6: 89 percent / NaBH4 / ethanol / 25 °C 7: 97 percent / p-toluenesulfonic acid * H2O / benzene / Heating View Scheme

5-bromo-1-indanol (34598-50-0) + p-toluenesulfonyl chloride (98-59-9) → 5-bromo-1H-indene (75476-78-7)

Conditions	Yield
With pyridine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether; toluene

5-bromo-1H-indene (75476-78-7) + n-PrMgX → 5-n-propyl-1H-indene (92013-19-9)

Conditions	Yield
With [nickel(II)dichloride(1,3-bis(diphenylphosphino)propane)] In diethyl ether Heating;	98%

5-bromo-1H-indene (75476-78-7) + n-BuMgX → 5-n-butyl-1H-indene (92013-20-2)

Conditions	Yield
With [nickel(II)dichloride(1,3-bis(diphenylphosphino)propane)] In diethyl ether Heating;	98%

5-bromo-1H-indene (75476-78-7) + EtMgX → 5-ethyl-1H-indene (66256-31-3)

Conditions	Yield
With [nickel(II)dichloride(1,3-bis(diphenylphosphino)propane)] In diethyl ether Heating;	96%

methylmagnesium bromide (75-16-1) + 5-bromo-1H-indene (75476-78-7) → 5-methyl-1H-indene (7480-80-0)

Conditions	Yield
With [nickel(II)dichloride(1,3-bis(diphenylphosphino)propane)] In diethyl ether Heating;	93%

5-bromo-1H-indene (75476-78-7) + 3-(2'-iodoethyl)-1H-indene (852295-56-8) → 3-[2'-(1H-inden-3''-yl)-ethyl]-5-bromo-1H-indene (852295-58-0)

Conditions	Yield
Stage #1: 3-(2'-iodoethyl)-1H-indene With n-butyllithium In tetrahydrofuran Stage #2: 5-bromo-1H-indene In tetrahydrofuran	79%

3-diazo-indolin-2-one (3265-29-0) + 5-bromo-1H-indene (75476-78-7) → C17H12BrNO (1439478-57-5)

Conditions	Yield
Stage #1: 5-bromo-1H-indene With silver tetrafluoroborate; C44H38Au2Cl2O2P2 In fluorobenzene at 0 - 25℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 3-diazo-indolin-2-one In fluorobenzene at 0℃; for 0.2h; Schlenk technique; Inert atmosphere; enantioselective reaction;	72%

5-bromo-1H-indene (75476-78-7) → 6-bromoindan-1-one (14548-39-1) + 5-bromo-1,2-dihydroxyindane

Conditions	Yield
With Pseudomonas putida UV4 for 7h;	A 4% B n/a

2,3-epoxy-1,2,3,4-tetrahydronaphthalene (2461-35-0) + 5-bromo-1H-indene (75476-78-7) + N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine (118753-70-1) → 1'-(2-hydroxy-1,2,3,4-tetrahydronaphth-3-yl)spiro<6-bromo-1H-indene-1,4'-piperidine> + 1'-(2-hydroxy-1,2,3,4-tetrahydronaphth-3-yl)spiro<5-bromo-1H-indene-1,4'-piperidine>

Conditions	Yield
With hydrogenchloride; triethylamine; lithium hexamethyldisilazane Yield given. Multistep reaction. Yields of byproduct given;

5-bromo-1H-indene (75476-78-7) + N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine (118753-70-1) → 5-bromo-1'-(tert-butoxycarbonyl)spiro<1H-indene-1,4'-piperidine> + 6-bromo-1'-(tert-butoxycarbonyl)spiro<1H-indene-1,4'-piperidine> (158628-80-9)

Conditions	Yield
With lithium hexamethyldisilazane 1.) THF, 4 deg C, 45 min, 2.) THf, from 4 deg C, 2h to RT, 18 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

5-bromo-1H-indene (75476-78-7) + N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine (118753-70-1) → C13H14BrN*ClH + C13H14BrN*ClH

Conditions	Yield
With hydrogenchloride; lithium hexamethyldisilazane Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

5-bromo-1H-indene (75476-78-7) → 7-bromoisoquinoline (58794-09-5)

Conditions	Yield
Yield given. Multistep reaction;

5-bromo-1H-indene (75476-78-7) + C12H15Cl2NO2 → ((1S,2S)-6-Bromo-1-chloro-indan-2-yl)-carbamic acid 5-phenyl-pentyl ester

Conditions	Yield
With sodium hydrogen sulfate 1.) toluene; Multistep reaction;

5-bromo-1H-indene (75476-78-7) + dimethyl amine (124-40-3) → (1S,2S)-6-Bromo-1-dimethylamino-indan-2-ol

Conditions	Yield
Stage #1: 5-bromo-1H-indene With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Stage #2: dimethyl amine In ethanol at 100℃;

5-bromo-1H-indene (75476-78-7) → 3-[2'-(1H-inden-3''-yl)ethyl]-5-(4'''-vinylphenyl)-1H-indene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: BuLi / tetrahydrofuran 1.2: 79 percent / tetrahydrofuran 2.1: 83 percent / aq. K2CO3 / Pd(PPh3)4 / various solvent(s) / Heating View Scheme

5-bromo-1H-indene (75476-78-7) → ((1S,2S)-6-Bromo-2-methoxy-indan-1-yl)-dimethyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: m-CPBA / CH2Cl2 / 20 °C 1.2: ethanol / 100 °C 2.1: NaH / tetrahydrofuran / 20 °C View Scheme

5-bromo-1H-indene (75476-78-7) → ((1S,2S)-6-Ethynyl-2-methoxy-indan-1-yl)-dimethyl-amine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: m-CPBA / CH2Cl2 / 20 °C 1.2: ethanol / 100 °C 2.1: NaH / tetrahydrofuran / 20 °C 3.1: Et3N; CuI; PdCl2(PPh3)2 / 80 °C 4.1: Bu4NF / tetrahydrofuran / 20 °C View Scheme

5-bromo-1H-indene (75476-78-7) → ((1S,2S)-2-Methoxy-6-trimethylsilanylethynyl-indan-1-yl)-dimethyl-amine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: m-CPBA / CH2Cl2 / 20 °C 1.2: ethanol / 100 °C 2.1: NaH / tetrahydrofuran / 20 °C 3.1: Et3N; CuI; PdCl2(PPh3)2 / 80 °C View Scheme

5-bromo-1H-indene (75476-78-7) → 2-((2S,3S)-3-Dimethylamino-2-methoxy-indan-5-yl)-7-methoxy-6-oxazol-5-yl-1H-quinolin-4-one

Conditions	Yield
Multi-step reaction with 5 steps 1.1: m-CPBA / CH2Cl2 / 20 °C 1.2: ethanol / 100 °C 2.1: NaH / tetrahydrofuran / 20 °C 3.1: Et3N; CuI; PdCl2(PPh3)2 / 80 °C 4.1: Bu4NF / tetrahydrofuran / 20 °C 5.1: Et2NH; PdCl2(PPh3)2 / 120 °C / 1551.44 Torr View Scheme

5-bromo-1H-indene (75476-78-7) + n-PrMgX → [(1S,2S)-6-Bromo-2-(5-phenyl-pentyloxycarbonylamino)-indan-1-yl]-acetic acid ethyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 2.) aq. NaHSO4 / 1.) toluene 2: NaH / dimethylformamide / 40 °C 3: aq. NaCl / dimethylsulfoxide / 160 °C View Scheme

5-bromo-1H-indene (75476-78-7) + n-PrMgX → 2-[(1S,2S)-6-Bromo-2-(5-phenyl-pentyloxycarbonylamino)-indan-1-yl]-malonic acid diethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) aq. NaHSO4 / 1.) toluene 2: NaH / dimethylformamide / 40 °C View Scheme

Upstream product

• 75476-86-7 6-Bromo-2,3-dihydro-1H-inden-1-ol 
• 34598-49-7 5-Bromo-1-indanone 
• 1643-30-7 3-(4-bromophenyl)propionic acid 
• 70146-78-0 diethyl 2-(4-bromobenzyl)malonate 
• 92013-18-8 2-[(4-bromophenyl)methyl]propanedioic acid 
• 34598-50-0 5-bromo-1-indanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 55394-81-5 3-(4-bromophenyl)propanoyl chloride 
• 14548-39-1 6-bromoindan-1-one 
• 33065-61-1 6-bromo-1H-indene 
• 174349-93-0 5-bromo-1H-inden-2(3H)-one 
• 862135-61-3 5-bromo-2,3-dihydro-1H-inden-2-ol 

Downstream Products

• 1160247-30-2 tert-butyl 5-bromo-3-oxo-2,3-dihydrospiro[indene-1,4’-piperidine]-1‘-carboxylate 
• 174349-93-0 5-bromo-1H-inden-2(3H)-one 
• 1255922-78-1 5-bromo-2-(2-oxoethyl)benzaldehyde 
• 52689-24-4 5-Ethylindan 
• 14548-39-1 6-bromoindan-1-one 
• 7480-80-0 5-methyl-1H-indene 

Relevant articles and documents

Use of oxirane ring-opening reactions for synthesis of ethylene- bis(indenyl) ligands containing alkene tethers

An efficient strategy is presented for the synthesis of novel bis-indenyl ligands containing alkene tethers for their further immobilization. The tether was attached to a bridge or aromatic ring of the ligand. The ligands were prepared using oxirane ring-opening reaction.

Total Synthesis of Anmindenol A and Its Application to the Design, Synthesis, and Biological Evaluation of Derivatives Thereof

The first total synthesis of anmindenol A is described in four steps. A notable feature of the synthetic route includes the efficient construction of the 3,10-dialkylsubstituted benzofulvene core via a stereoselective vinylogous Stork enamine aldol condensation. The strategy provided a blueprint for the practical preparation of derivatives with modifications in the C-10 alkyl substituents. The novel derivatives inhibited nitric oxide production in stimulated RAW 264.7 macrophage cells.

LIQUID CRYSTAL COMPOUND, LIQUID CRYSTAL COMPOSITION, AND LIQUID CRYSTAL DISPLAY DEVICE

PROBLEM TO BE SOLVED: To provide a liquid crystal compound, a liquid crystal composition, and a liquid crystal device using the compound or the composition. SOLUTION: The liquid crystal compound is represented by formula (I). In formula (I), R1 represents H, an alkyl having 1 to 10 carbon atoms, or the like; R2 represents an alkenyl having 2 to 10 carbon atoms or a fluoroalkenyl having 2 to 10 carbon atoms and one or two non-adjacent -CH2- in R2 is replaced by -O- or an ether having 2 to 10 carbon atoms; A1 to A4 each independently represent a formula below, where R3 independently represents H or a halogen; Z1 to Z3 each independently represents a sing bond, -CH2-, -CH2O-, -OCH2-, -CF=CF-, -COO-, -OCO-, -CF2O-, -OCF2-, -C≡C-, -CH=CH-, or the like; and n and m each independently represent 0 or 1. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT