10485-09-3

Basic information

• Product Name: 2-Bromoindene
• Synonyms: 2-BROMOINDENE;1H-INDENE, 2-BROMO-;2-Bromoindene,99%;2-bromo-1H-indene;2-BroMoindene, 95+%
• CAS NO: 10485-09-3
• Molecular Formula: C₉H₇Br
• Molecular Weight: 195.06
• EINECS: 1312995-182-4
• Product Categories: Indoles and derivatives;NULL
• Mol File: 10485-09-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 35-37°C
• Boiling Point: 127 °C / 23mmHg
• Flash Point: 113 °C
• Appearance: Yellow to pale brown low melting solid
• Density: 1.57 g/cm³
• Vapor Pressure: 0.0241mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 2-Bromoindene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoindene(10485-09-3)
• EPA Substance Registry System: 2-Bromoindene(10485-09-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 10485-09-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to pale brown low melting solid

Uses

2-Bromoindene is used as pharmaceutical intermediate.

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

Synthetic route

(1H-inden-2-yl)triisopropylsilane (1352210-71-9) → 2-bromoindene (10485-09-3)

Conditions	Yield
With N-Bromosuccinimide; 1,1,1,3',3',3'-hexafluoro-propanol In dichloromethane for 0.166667h;	91%
With N-Bromosuccinimide; 1,1,1,3',3',3'-hexafluoro-propanol In dichloromethane	91%

trans-2-bromo-1-indanol (10368-44-2) → 2-bromoindene (10485-09-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 4h; Heating;	90%
With PTA In toluene at 140℃; for 6h;	40%
at 155 - 160℃;

2-bromo-1-indanol (5400-80-6) → 2-bromoindene (10485-09-3)

Conditions	Yield
With H-β-zeolite In chlorobenzene at 120℃; for 6h;	77%
With toluene-4-sulfonic acid In toluene at 90℃; for 20h;	70%
With sulfuric acid In toluene for 1h; Heating;	65%

1H-inden-2-yl trifluoromethanesulfonate (256637-49-7) → 2-bromoindene (10485-09-3)

Conditions	Yield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; potassium bromide In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;	73%
With bis(1,5-cyclooctadiene)nickel (0); lithium bromide In tetrahydrofuran; N,N-dimethyl acetamide at 23℃; Inert atmosphere; Sealed tube;	47 %Spectr.

trans-1.2-Dibrom-indan (19598-04-0, 19598-15-3, 20357-79-3) → 2-bromoindene (10485-09-3) + 1-indene (95-13-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 66℃; for 24h;	A 66% B 9%

trans-1,2-bromoindane (19598-15-3) → 2-bromoindene (10485-09-3)

Conditions	Yield
at 200 - 210℃;
With tetralin
Destillation;

1,2-dibromoindane (20357-79-3) → 2-bromoindene (10485-09-3)

Conditions	Yield
In tetralin for 8h; Heating; Yield given;

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

(+-)-trans-2-bromo-1-hydroxy-indan → 2-bromoindene (10485-09-3)

Conditions	Yield
at 155 - 160℃;
With bromobenzene Destillation;
With tetrachloromethane; phosphorus pentoxide

(+-)-trans-2-bromo-1-hydroxy-indan → 2-bromoindene (10485-09-3) + trans-1,2-bromoindane (19598-15-3)

Conditions	Yield
With hydrogen bromide

tetrachloromethane (56-23-5) + trans-2-bromo-1-indanol (10368-44-2) + P2O5 → 2-bromoindene (10485-09-3)

trans-2-bromo-1-indanol (10368-44-2) + hydrogen bromide (10035-10-6, 12258-64-9) → 2-bromoindene (10485-09-3) + trans-1.2-dibromo-indan

1-indene (95-13-6) + 2-methylsulfanyl-3-methyl-benzothiazolium-p-toluenesulfonate → 2-bromoindene (10485-09-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / H2O, N-bromosuccinimide (NBS) / dimethylsulfoxide / 0.25 h / 22 °C 2: 90 percent / p-toluenesulfonic acid (PTS) / toluene / 4 h / Heating View Scheme

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

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / bromine / diethyl ether / -5 - 0 °C 2: 1,2,3,4-tetrahydro-naphthalene / 8 h / Heating View Scheme

1-phenyl-2-(triisopropylsilyl)prop-2-en-1-ol (1352210-24-2) → 2-bromoindene (10485-09-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: N-Bromosuccinimide; 1,1,1,3',3',3'-hexafluoro-propanol / dichloromethane / 0.17 h View Scheme
Multi-step reaction with 2 steps 1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate / dichloromethane / 2 h / 20 °C 2: 1,1,1,3',3',3'-hexafluoro-propanol; N-Bromosuccinimide / dichloromethane View Scheme

benzaldehyde (100-52-7) → 2-bromoindene (10485-09-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate / dichloromethane / 2 h / 20 °C / Inert atmosphere 3.1: N-Bromosuccinimide; 1,1,1,3',3',3'-hexafluoro-propanol / dichloromethane / 0.17 h View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 1.2: 1 h / -78 °C 2.1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate / dichloromethane / 2 h / 20 °C 3.1: 1,1,1,3',3',3'-hexafluoro-propanol; N-Bromosuccinimide / dichloromethane View Scheme

trans-1.2-Dibrom-indan (19598-04-0, 19598-15-3, 20357-79-3) → 2-bromoindene (10485-09-3) + 3-bromo-1H-indene (103028-42-8)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 90℃; for 24h; Overall yield = 74 %;

2-bromoindene (10485-09-3) + (diisopropylamino)dichloroborane (44873-49-6) → bis(2-indenyl)(diisopropylamino)borane (862126-28-1)

Conditions	Yield
Stage #1: 2-bromoindene With magnesium In tetrahydrofuran; ethylene dibromide at 20℃; for 1.5h; Schlenk technique; Inert atmosphere; Glovebox; Stage #2: (diisopropylamino)dichloroborane In tetrahydrofuran at -78 - 20℃; Schlenk technique; Inert atmosphere; Glovebox;	100%

2-ethynylpyridine (1945-84-2) + 2-bromoindene (10485-09-3) → 2-((1H-inden-2-yl)ethynyl)pyridine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 60℃;	100%

2-bromoindene (10485-09-3) + n-C3H7MgX → 2-n-propyl-1H-indene (92013-11-1)

Conditions	Yield
With [nickel(II)dichloride(1,3-bis(diphenylphosphino)propane)] In diethyl ether Heating;	99%

2-bromoindene (10485-09-3) + (1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-yl)(difluoromethyl)silver → 2-(difluoromethyl)-1H-indene

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [Pd(π-cinnamyl)Cl]2 In 1,4-dioxane at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;	99%

2-bromoindene (10485-09-3) + 4-methoxyphenylacetylen (768-60-5) → 2-((4-methoxyphenyl)ethynyl)-1H-indene

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 60℃;	99%

2-bromoindene (10485-09-3) → 2-iodo-1H-indene (1301604-87-4)

Conditions	Yield
With copper(l) iodide; rac-diaminocyclohexane; sodium iodide In 1,4-dioxane at 110℃; Inert atmosphere;	98%

2-bromoindene (10485-09-3) + n-BuMgX → 2-n-butylindene (92013-12-2)

Conditions	Yield
With [nickel(II)dichloride(1,3-bis(diphenylphosphino)propane)] In diethyl ether Heating;	97%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 2-bromoindene (10485-09-3) → C9H7Br(1-)*2C6H16N2*Li(1+)

Conditions	Yield
Stage #1: 2-bromoindene With n-butyllithium In diethyl ether; hexane at 20℃; for 4h; Stage #2: N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; diethyl ether; hexane	97%

2-bromoindene (10485-09-3) + 1-trimethylsilylvinylboronic acid MIDA ester → [1-(1H-inden-2-yl)vinyl]trimethylsilane

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 60℃; Suzuki-Miyaura Coupling; Inert atmosphere;	97%

1-(3,5-dimethylphenyl)acetylene (6366-06-9) + 2-bromoindene (10485-09-3) → 2-((3,5-dimethylphenyl)ethynyl)-1H-indene

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 60℃;	97%

2-bromoindene (10485-09-3) + phenylmagnesium bromide (100-58-3) → 2-phenylindene (4505-48-0)

Conditions	Yield
With sarcosine; cobalt(II) bromide In tetrahydrofuran at -20℃; Inert atmosphere;	95%
With iron(II) acetylacetonate; D-glucosamine hydrochloride; triethylamine In tetrahydrofuran at -20℃; for 1h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;	83%

2-bromoindene (10485-09-3) + S-Methylisothiourea sulfate (867-44-7) → (1H-inden-2-yl)(methyl)sulfane (90474-74-1)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 2h;	95%

tetraacetyl thioglucose (19879-84-6) + 2-bromoindene (10485-09-3) → (2S,3R,4S,5R,6R)-2-((1H-inden-2-yl)thio)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1467023-93-3)

Conditions	Yield
With 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide; nickel dibromide In N,N-dimethyl-formamide at 20℃; for 3h; Electrochemical reaction; Inert atmosphere;	95%

4-cyanophenylacetylene (3032-92-6) + 2-bromoindene (10485-09-3) → 4-((1H-inden-2-yl)ethynyl)benzonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 60℃;	95%

2-bromoindene (10485-09-3) + ethylene dibromide (106-93-4) + dimethylsilicon dichloride (75-78-5) → 2-chloromethylsilylindene

Conditions	Yield
In tetrahydrofuran	94%

2-bromoindene (10485-09-3) + dimethylsilicon dichloride (75-78-5) → bis(inden-1-yl)dimethylsilane (18666-26-7)

Conditions	Yield
With magnesium In tetrahydrofuran; ethylene dibromide Cooling with ice;	94%

2-bromoindene (10485-09-3) + C27H34O + dimethylsilicon dichloride (75-78-5) → C38H46OSi

Conditions	Yield
Stage #1: 2-bromoindene With iodine; magnesium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Reflux; Stage #2: dimethylsilicon dichloride In tetrahydrofuran; hexane at -78℃; for 19h; Stage #3: C27H34O With 1,3-dimethyl-2-imidazolidinone; n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 47h; Inert atmosphere;	94%
Stage #1: 2-bromoindene With iodine; magnesium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: dimethylsilicon dichloride In tetrahydrofuran; hexane at -78℃; for 19h; Inert atmosphere; Stage #3: C27H34O With 1,3-dimethyl-2-imidazolidinone; n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 47h; Inert atmosphere;	94%

2-bromoindene (10485-09-3) → 2-ethylindene (17059-50-6)

Conditions	Yield
Ni(dppp)Cl2 In diethyl ether	93.1%

2-bromoindene (10485-09-3) + (2,6-dimethoxyphenyl)boronic acid (23112-96-1) → 2-(2, 6-dimethoxyphenyl)-1H-indene

Conditions	Yield
Stage #1: 2-bromoindene; (2,6-dimethoxyphenyl)boronic acid With potassium carbonate In toluene at 20℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 90℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	93%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran; water at 100℃; for 24h; Inert atmosphere; Schlenk technique;	79%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 100℃; for 12h;

carbon dioxide (124-38-9) + 2-bromoindene (10485-09-3) → indene-2-carboxylic acid (41712-14-5)

Conditions	Yield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique; Stage #2: 2-bromoindene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 16h; Schlenk technique; Sealed tube;	93%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 60℃; for 0.416667h; Schlenk technique; Stage #2: 2-bromoindene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 6h; Schlenk technique;	93%

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%

1,2-dichlorotetramethylsilane (4342-61-4) + 2-bromoindene (10485-09-3) → 1,2-di(1H-inden-1-yl)-1,1,2,2-tetramethyldisilane (221392-72-9)

Conditions	Yield
With magnesium In tetrahydrofuran; ethylene dibromide Cooling with ice;	92%

2-bromoindene (10485-09-3) + trimethylsilylacetylene (1066-54-2) → C14H16Si

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;	92%
With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; diisopropylamine In toluene at 20℃; for 6h; Inert atmosphere;

2-methylfuran (534-22-5) + 2-bromoindene (10485-09-3) → 2-(5-methyl-2-furyl)-1H-indene (291773-42-7)

Conditions	Yield
Stage #1: 2-methylfuran With n-butyllithium In hexane at -78 - 20℃; for 2h; Stage #2: With Triisopropyl borate In hexane at -78 - 20℃; Stage #3: 2-bromoindene With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In hexane; water at 85℃; for 4h;	92%

2-bromoindene (10485-09-3) + C16H17N2O2S(1+)*CF3O3S(1-) → (1H-inden-2-yl)(p-tolyl)sulfane

Conditions	Yield
With nickel(II) triflate; triphenylphosphine; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In N,N-dimethyl acetamide at 60℃; Inert atmosphere;	92%

2-cyclohexylacetylene (931-48-6) + 2-bromoindene (10485-09-3) → 2-(cyclohexylethynyl)-1H-indene

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 60℃;	91%

2-bromoindene (10485-09-3) + diphenylsilyl chloride (1631-83-0) → 2-(diphenylsilyl)indene (720652-62-0)

Conditions	Yield
Stage #1: 2-bromoindene With iodine; magnesium In tetrahydrofuran for 0.666667h; Heating; Stage #2: diphenylsilyl chloride In tetrahydrofuran Heating; Further stages.;	90%

2-bromoindene (10485-09-3) + isopropenylmagnesium bromide (13291-18-4) → 2-isopropylidylene-indene (38740-43-1)

Conditions	Yield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether	90%

Upstream product

• 19598-04-0 trans-1.2-Dibrom-indan 
• 100-52-7 benzaldehyde 
• 1352210-71-9 (1H-inden-2-yl)triisopropylsilane 
• 1352210-24-2 1-phenyl-2-(triisopropylsilyl)prop-2-en-1-ol 
• 95-13-6 1-indene 
• 10368-44-2 trans-2-bromo-1-indanol 
• 10035-10-6 hydrogen bromide 
• 20357-79-3 1,2-dibromoindane 
• 5400-80-6 2-bromo-1-indanol 
• 19598-15-3 trans-1,2-bromoindane 
• 256637-49-7 1H-inden-2-yl trifluoromethanesulfonate 
• 56-23-5 tetrachloromethane 

Downstream Products

• 720652-62-0 2-(diphenylsilyl)indene 
• 41712-14-5 indene-2-carboxylic acid 
• 4505-48-0 2-phenylindene 
• 16274-93-4 2-benzyl-1H-indene 
• 749870-00-6 2-(2,4,6-trimethylphenyl)indene 
• 51220-31-6 (1H-inden-2-yl)dimethyl(phenyl)silane 
• 720652-64-2 2-(phenylsilyl)indene 
• 17059-50-6 2-ethylindene 
• 2177-47-1 2-Methylindene 
• 70063-93-3 1,2-dimethylindene 
• 95-13-6 1-indene 
• 615-13-4 2-indanone 
• 38740-43-1 2-(prop-1-en-2-yl)-1H-indene 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 

Relevant articles and documents

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