4876-10-2

Basic information

• Product Name: 4-Bromomethyl-1,2-dihydroquinoline-2-one
• Synonyms: 4-Bromomethyl-2-quinolinol;4-(BROMOMETHYL)-2(1H)-QUINOLINONE;4-BROMOMETHYLQUINOLINONE;4-BROMOMETHYL-1,2-DIHYDROQUINOLIN-2-ONE;4-BROMOMETHYL-1,2-DIHYDROQUINOLINE-2-ONE;2(1H)-QUINOLINONE, 4-(BROMOMETHYL)-;4-Bromomethyl Carbostyril;4-(bromomethyl)-2-hydroxyquinoline
• CAS NO: 4876-10-2
• Molecular Formula: C10H8BrNO
• Molecular Weight: 238.08
• EINECS: 1312995-182-4
• Product Categories: Quinolines, Quinazolines and derivatives;API intermediates;(intermediate of Rebamipide);Isoquinolines ,Others ,Quinolines ,Quinaldines
• Mol File: 4876-10-2.mol
• Article Data: 43

Chemical Properties

• Melting Point: 255-258°C
• Boiling Point: 391.8 °C at 760 mmHg
• Flash Point: 190.8 °C
• Appearance: White-like powder
• Density: 1.542 g/cm³
• Vapor Pressure: 2.4E-06mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 11.17±0.70(Predicted)
• CAS DataBase Reference: 4-Bromomethyl-1,2-dihydroquinoline-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromomethyl-1,2-dihydroquinoline-2-one(4876-10-2)
• EPA Substance Registry System: 4-Bromomethyl-1,2-dihydroquinoline-2-one(4876-10-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-34
• Safety Statements: 26-36/37/39-45
• HazardClass: 8
• Hazardous Substances Data: 4876-10-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to light reddish yellow solid

Uses

4-Bromomethyl-2(1H)-quinolinone is a reagent used in the preparation of coumarins and 1-aza coumarins which has nti-microbial, anti-inflammatory, and analgesic activities.

InChI:InChI=1/C10H8BrNO/c11-6-7-5-10(13)12-9-4-2-1-3-8(7)9/h1-5H,6H2,(H,12,13)

Synthetic route

4-bromo-3-oxo-N-phenylbutanamide (1205-74-9) → 4-bromomethyl-2(1H)-quinolinone (4876-10-2)

Conditions	Yield
With phosphorus pentoxide at 83℃; for 13h; Solvent; Flow reactor; Large scale;	95.08%
With sulfuric acid at 40℃; for 1.5h;	64%
With sulfuric acid Heating;

N-phenylacetoacetamide (102-01-2) → 4-bromomethyl-2(1H)-quinolinone (4876-10-2)

Conditions	Yield
With sulfuric acid; bromine In chloroform
Multi-step reaction with 2 steps 1: bromine; acetic acid 2: sulfuric acid / 4 h View Scheme
Multi-step reaction with 2 steps 1: bromine / chloroform 2: sulfuric acid / 4 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: bromine / chloroform / 2 h / Heating / reflux 2: sulfuric acid / 1.5 h / 40 °C View Scheme

aniline (62-53-3) → 4-bromomethyl-2(1H)-quinolinone (4876-10-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridine / xylene / 0.5 h / Heating / reflux 1.2: 3.07 h / Heating / reflux 2.1: bromine / chloroform / 2 h / Heating / reflux 3.1: sulfuric acid / 1.5 h / 40 °C View Scheme

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → 2-acetylamino-2-(ethoxycarbonyl)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic acid ethyl ester (4900-38-3)

Conditions	Yield
With sodium ethanolate; tetra-(n-butyl)ammonium iodide In ethanol at 60℃; for 8h; Reagent/catalyst; Temperature;	98.44%
With sodium In ethanol for 2h;	69%
With sodium hydroxide In water; dimethyl sulfoxide at 20 - 30℃; for 2h; Reagent/catalyst; Solvent; Large scale;

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + N-(pyridin-4-yl)furan-2-carboxamide (35218-42-9) → N-[(2-Oxo-1,2-dihydroquinolin-4-yl)methyl]-N-pyridin-4-yl-2-furamide (953065-10-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 2h;	95%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-(aminomethyl)quinolin-2(1H)-one

Conditions	Yield
With ammonia In isopropyl alcohol at 60℃; for 4h;	95%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-methyl-1,2-dihydroquinolin-2-one (607-66-9)

Conditions	Yield
With tetraethylammonium perchlorate; triethylamine In ethanol; dimethyl sulfoxide at 20℃; for 4h; Electrolysis; Green chemistry;	95%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + allyl alcohol (107-18-6) → 4-[(allyloxy)methyl]quinol-2(1H)-one (1627597-87-8)

Conditions	Yield
Stage #1: allyl alcohol With sodium hydride In tetrahydrofuran at 0℃; for 4h; Reflux; Stage #2: 4-bromomethyl-2(1H)-quinolinone In tetrahydrofuran at 0 - 20℃; for 6h;	91%

C10H9Cl2NO2 + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → C20H16Cl2N2O3

Conditions	Yield
With triethylamine In toluene at 70 - 80℃; for 5h; Solvent; Temperature;	90%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + 2-(2-propynylsulfanyl)-1H-1,3-benzimidazole (24786-40-1) → 4-((4-((1H-benzo[d]imidazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)methyl)quinolin-2(1H)-one

Conditions	Yield
With sodium azide; copper(II) sulfate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 20℃; for 12h;	89%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid (70458-96-7) → 1-ethyl-6-fluoro-7-(4-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
Stage #1: 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid With potassium carbonate In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: 4-bromomethyl-2(1H)-quinolinone In water; acetonitrile at 20℃; for 25h;	88.9%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + N-(4-chloro-2-mercapto-5-methylbenzenesulfonyl)cyanamide dipotassium salt → N-[4-chloro-2-(1,2-dihydro-2-oxoquinolin-4-ylmethylthio)-5-methylphenylsulfonyl]cyanamide potassium

Conditions	Yield
In ethanol at 20℃; for 4h;	88%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + diethyl (((4-chlorophenyl)carbonyl)amino)propanedioate (81918-01-6) → ethyl 2-(4-chlorobenzamido)-2-ethoxyoxo-3-[2-(1H)-quinolin-4-yl]propionate (1028268-32-7)

Conditions	Yield
Stage #1: diethyl (((4-chlorophenyl)carbonyl)amino)propanedioate With sodium ethanolate; sodium In ethanol at 20℃; for 1.5h; Stage #2: 4-bromomethyl-2(1H)-quinolinone In ethanol at 20℃;	88%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + 4-hydroxy-benzaldehyde (123-08-0) → 4-[(1,2-dihydro-2-oxoquinolin-4-yl)methoxy]-benzaldehyde (1041095-99-1)

Conditions	Yield
With potassium carbonate In ethanol for 8h; Reflux;	87%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + 3-methyl-2-buten-1-ol (556-82-1) → 4-{[(3-methyl-2-buten-1-yl)oxy]methyl}quinol-2(1H)-one (1627597-92-5)

Conditions	Yield
Stage #1: 3-methyl-2-buten-1-ol In tetrahydrofuran at 0℃; for 4h; Reflux; Stage #2: 4-bromomethyl-2(1H)-quinolinone With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at -78 - 20℃; for 2h;	83%

N'-benzylidene-2-hydroxybenzohydrazide (59395-02-7, 18269-02-8) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 2-(2-Oxo-1,2-dihydro-quinolin-4-ylmethoxy)-benzoic acid [1-phenyl-meth-(E)-ylidene]-hydrazide (137156-69-5)

Conditions	Yield
	80%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + Benzimidazol-2-thiol (134469-07-1) → 4-(2'-S-benzimidazolyl)mercaptomethylcarbostyril (132657-24-0)

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Heating;	80%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + methyl salicylate (119-36-8) → 4-(o-carbomethoxyphenoxymethyl)carbostyril

Conditions	Yield
With potassium carbonate In ethanol for 5h; Heating;	80%

(2-hydroxyphenyl)mercury chloride (90-03-9) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-(2-chloromercury-phenoxymethyl)-azachromene-2-one (1252026-32-6)

Conditions	Yield
With potassium carbonate In butanone under N2; mixt. of 4-bromomethyl-1-azacoumarin, o-(chloromercury)phenol,anhyd. K2CO3 and dry butanone heated under reflux for 20 h; cooling to room temp., concn., soln. poured onto crushed ice, recrystn. from warm acetic acid; elem. anal.;	80%

4,5-dimethyl-7-hydroxycoumarin (51786-56-2) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-[(4,5-dimethyl-2-oxo-2H-chromen-7-yloxy)methyl]quinolin-2(1H)-one (1299366-49-6)

Conditions	Yield
With potassium carbonate In ethanol for 8h; Reflux;	80%

salicylonitrile (611-20-1) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-(3-aminobenzofuran-2-yl)quinoline-2(H)-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 5h;	80%

7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-[(4-methyl-2-oxo-2H-chromen-7-yloxy)methyl]quinolin-2(1H)-one (1299366-41-8)

Conditions	Yield
With potassium carbonate In ethanol for 8h; Reflux;	78%

(E)-4-bromo-3-methyl-3-buten-1-ol (74723-02-7) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → (E)-4-(((4-bromo-3-methylbut-3-en-1-yl)oxy)methyl)quinolin-2(1H)-one

Conditions	Yield
Stage #1: (E)-4-bromo-3-methyl-3-buten-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: 4-bromomethyl-2(1H)-quinolinone In tetrahydrofuran; mineral oil at 0 - 20℃; for 22h; Inert atmosphere;	78%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + vanillin (121-33-5) → 4-[(1,2-dihydro-2-oxoquinolin-4-yl)methoxy]-3-methoxybenzaldehyde (1384968-50-6)

Conditions	Yield
With potassium carbonate In ethanol for 8h; Reflux;	77%

ciprofloxacin (85721-33-1) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 1-cyclopropyl-6-fluoro-7-(4-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
Stage #1: ciprofloxacin With potassium carbonate In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: 4-bromomethyl-2(1H)-quinolinone In water; acetonitrile at 20℃; for 25h;	75.7%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-(mercaptomethyl)quinolin-2(1H)-one (132657-26-2)

Conditions	Yield
With thiourea In diethyl ether; ethanol 1.) room temperature, 2 h, 2.) reflux, 4 h, 3.) room temperature, overnight;	75%
Stage #1: 4-bromomethyl-2(1H)-quinolinone With thiourea In ethanol Reflux; Inert atmosphere; Stage #2: With water; sodium hydroxide In ethanol Reflux; Inert atmosphere;
With thiourea In diethyl ether; ethanol at 20℃; for 6h; Reflux;
Multi-step reaction with 2 steps 1: acetone / 20 °C 2: sulfuric acid; ethanol / Reflux View Scheme

Ethyl bromodifluoroacetate (667-27-6) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → ethyl 2-(4-(bromomethyl)-2-oxo-1,2-dihydroquinolin-3-yl)-2,2-difluoroacetate

Conditions	Yield
With dipotassium hydrogenphosphate; copper(l) iodide; 1,10-Phenanthroline In acetonitrile at 110℃; for 36h; Inert atmosphere;	75%
With copper(l) iodide; N,N,N',N'',N'''-pentamethyldiethylenetriamine In acetonitrile at 80℃; for 12h; Schlenk technique; Inert atmosphere; regioselective reaction;	68%

6-hydroxy-4-methyl-chromen-2-one (2373-31-1) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-[(4-methyl-2-oxo-2H-chromen-6-yloxy)methyl]quinolin-2(1H)-one (1299366-34-9)

Conditions	Yield
With potassium carbonate In ethanol for 8h; Reflux;	74%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + 3-hydroxy-2-methyl-1-propene (513-42-8) → 4-{[(2-methylallyl)oxy]methyl}quinolin-2(1H)-one (1627597-90-3)

Conditions	Yield
Stage #1: 3-hydroxy-2-methyl-1-propene With sodium hydride In tetrahydrofuran at 0℃; for 4h; Reflux; Stage #2: 4-bromomethyl-2(1H)-quinolinone In tetrahydrofuran at 0 - 20℃; for 6h;	74%

4-Fluorophenol (371-41-5) + 4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-[4'-fluorophenoxymethyl]-1-aza-coumarin (1091595-24-2)

Conditions	Yield
With potassium carbonate for 10h; Reflux;	70%

4-bromomethyl-2(1H)-quinolinone (4876-10-2) → 4-(azidomethyl)quinolin-2(1H)-one (1432579-06-0)

Conditions	Yield
With sodium azide In water; acetone at 20℃;	70%
With sodium azide In water; N,N-dimethyl-formamide for 8h;
With sodium azide In water; acetone at 20℃; for 0.25h;
With sodium azide In water; N,N-dimethyl-formamide; acetone for 10h;

4-bromomethyl-2(1H)-quinolinone (4876-10-2) + 4-fluoroaniline (371-40-4) → 4-[4'-fluoroanilinomethyl]-1-aza-coumarin (333984-71-7)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 135 - 148℃; for 10h;	68%

Upstream product

• 102-01-2 N-phenylacetoacetamide 
• 1205-74-9 4-bromo-3-oxo-N-phenylbutanamide 
• 634-47-9 2-chloro-4-methylquinoline 
• 81704-80-5 isocyanomethide anion 
• 624-83-9 methyl isocyanate 
• 74-90-8 hydrogen cyanide 
• 7732-18-5 water 
• 57-13-6 urea 
• 773837-37-9 sodium cyanide 
• 7722-84-1 dihydrogen peroxide 
• 1310-73-2 sodium hydroxide 
• 201230-82-2 carbon monoxide 
• 7664-41-7 ammonia 
• 7440-44-0 pyrographite 

Downstream Products

• 63791-98-0 4-acetoxymethyl-quinolin-2-ol 
• 134480-61-8 2-hydroxy-4-quinoline 
• 134480-63-0 2-hydroxy-4-quinoline 
• 6281-32-9 4-quinolylmethanol 
• 5632-17-7 4-(chloromethyl)quinoline 
• 5632-16-6 4-(bromomethyl)quinoline 
• 90098-04-7 rebamipide 
• 1028268-32-7 ethyl 2-(4-chlorobenzamido)-2-ethoxyoxo-3-[2-(1H)-quinolin-4-yl]propionate 
• 333983-01-0 4-((phenylamino)methyl)quinolin-2(1H)-one 
• 953065-14-0 4-[(methyl-phenyl-amino)-methyl]-1H-quinolin-2-one 
• 953066-94-9 4-((4-(2-fluorophenyl)piperazin-1-yl)methyl)quinolin-2(1H)-one 
• 885951-26-8 4-[(isopropylamino)methyl]quinolin-2(1H)-one 
• 953065-28-6 4-(((furan-2-ylmethyl)(phenyl)amino)methyl)quinolin-2(1H)-one 
• 953065-30-0 4-(((2-(Furan-2-yl)ethyl)(phenyl)amino) methyl)quinolin-2(1H)-one 

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