846032-36-8

Basic information

• Product Name: 4-Bromo-2-indanone
• Synonyms: 4-Bromo-2-indanone;4-Bromoindan-2-one;4-Bromo-1,3-dihydro-2H-inden-2-one;4-broMo-2,3-dihydro-1H-inden-2-one;2H-Inden-2-one, 4-broMo-1,3-dihydro-;4-BroMo-1H-inden-2(3H)-one;4-bromo-1,3-dihydroinden-2-one
• CAS NO: 846032-36-8
• Molecular Formula: C9H7BrO
• Molecular Weight: 211.05528
• Mol File: 846032-36-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 312℃
• Flash Point: 126℃
• Appearance: /
• Density: 1.608
• Vapor Pressure: 0.000536mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 4-Bromo-2-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-indanone(846032-36-8)
• EPA Substance Registry System: 4-Bromo-2-indanone(846032-36-8)

Safety Data

• Hazardous Substances Data: 846032-36-8(Hazardous Substances Data)

Usage

General Description

4-Bromo-2-Indanone, also known as 4-Bromo-2-hydroxy indan-1-one, is a chemical compound with the molecular formula C9H7BrO2. It is a pale yellow solid that is commonly used as a reagent in organic synthesis and pharmaceutical research. 4-Bromo-2-Indanone is versatile and has been found to participate in various reactions such as the Michael addition, Friedel-Crafts acylation, and the Pd-catalyzed cross-coupling reaction. It is also an important intermediate in the synthesis of biologically active compounds and can function as a building block in the preparation of complex molecules. Additionally, it is known to exhibit biological activities and has been studied for its potential in the development of new drugs.

InChI:InChI=1/C9H7BrO/c10-9-3-1-2-6-4-7(11)5-8(6)9/h1-3H,4-5H2

Synthetic route

4-bromo-3H-indene (16657-07-1) → 4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8)

Conditions	Yield
Stage #1: 4-bromo-3H-indene With 4-methylmorpholine N-oxide; osmium(VIII) oxide Stage #2: With toluene-4-sulfonic acid

C9H7BrO (125114-82-1) → 4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8)

Conditions	Yield
With zinc(II) iodide In benzene at 0 - 20℃; Product distribution / selectivity; Inert atmosphere;

7-bromo-2,3-dihydro-1H-inden-1-one (125114-77-4) → 4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / ethanol; dichloromethane / 3 h / 0 - 20 °C 2: toluene-4-sulfonic acid / toluene / 0.5 h / Reflux 3: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 4: zinc(II) iodide / toluene / 4 h / 0 - 20 °C View Scheme

rac-7-bromo-2,3-dihydro-1H-inden-1-ol → 4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 0.5 h / Reflux 2: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 3: zinc(II) iodide / toluene / 4 h / 0 - 20 °C View Scheme

4-bromo-indene (45738-35-0) → 4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 2: zinc(II) iodide / toluene / 4 h / 0 - 20 °C View Scheme

C9H7BrO → 4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8)

Conditions	Yield
With zinc(II) iodide In toluene at 0 - 20℃; for 4h;

4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8) → 8-bromo-1,4-dihydro-2H-isoquinolin-3-one (943749-58-4)

Conditions	Yield
With hydrogenchloride; sodium azide at 0 - 12℃; for 12.3333h;	33%

4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8) → 4-bromo-2,2-difluoro-indan (846032-40-4)

Conditions	Yield
With diethylamino-sulfur trifluoride

4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8) + 4-tert-butylphenylboronic acid (123324-71-0) → 4-(4-t-butylphenyl)-2-indanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 16h;

4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8) → 2-[2-(5-methylfuryl)]-4-(4-t-butylphenyl)indene + C24H24O

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 16 h / 80 °C 2.1: n-butyllithium / tetrahydrofuran / 4 h / -25 - 20 °C 2.2: 16 h / -25 - 20 °C 2.3: 0.17 h / Reflux View Scheme

4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8) → bis(2-[2-(5-methylfuryl)]-4-(4-t-butylphenyl)inden-1-yl)(6-t-butoxyhexyl)methylsilane

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 16 h / 80 °C 2.1: n-butyllithium / tetrahydrofuran / 4 h / -25 - 20 °C 2.2: 16 h / -25 - 20 °C 2.3: 0.17 h / Reflux 3.1: n-butyllithium / tetrahydrofuran / 3 h / -25 - 20 °C 3.2: 15 h / 0 - 20 °C View Scheme

4-bromo-1,3-dihydro-2H-inden-2-one (846032-36-8) → 3-oxo-1,2,3,4-tetrahydroisoquinoline-8-carbonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide; hydrogenchloride / 12.33 h / 0 - 12 °C 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 6 h / 150 °C / Inert atmosphere View Scheme

Upstream product

• 16657-10-6 (±)-4-bromo-2,3-dihydro-1H-inden-1-ol 
• 15115-60-3 4-bromo-2,3-dihydroinden-1-one 
• 45738-35-0 4-bromo-indene 
• 1196049-18-9 rac-7-bromo-2,3-dihydro-1H-inden-1-ol 
• 125114-77-4 7-bromo-2,3-dihydro-1H-inden-1-one 
• 125114-82-1 C₉H₇BrO 
• 16657-07-1 4-bromo-3H-indene 

Downstream Products

• 125141-73-3 4-bromo-2,3-dihydro-1H-inden-2-ol 
• 124067-30-7 4-Methoxy-indan-2-one 
• 943749-58-4 8-bromo-1,4-dihydro-2H-isoquinolin-3-one 

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