4-Bromomethyl-1,2-dihydroquinoline-2-one supplier

Name
4-Bromomethyl-1,2-dihydroquinoline-2-one
EINECS 679-473-6
CAS No. 4876-10-2
Article Data136
CAS DataBase
Density 1.542 g/cm³
Solubility
Melting Point 255-258 °C
Formula C₁₀H₈BrNO
Boiling Point 391.8 °C at 760 mmHg
Molecular Weight 238.084
Flash Point 190.8 °C
Transport Information
Appearance White-like powder
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Quinolinol,4-(bromomethyl)- (8CI);Carbostyril, 4-(bromomethyl)- (6CI,7CI);4-(Bromomethyl)carbostyril;4-(Bromomethyl)quinolin-2(1H)-one;NSC 108455;4-Bromomethyl-2(1H)-quinolinone;
PSA 33.12000
LogP 2.83530

Synthetic route

: 1205-74-9
4-bromo-3-oxo-N-phenylbutanamide

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

Conditions

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;

: 102-01-2
N-phenylacetoacetamide

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

Conditions

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

: 62-53-3
aniline

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 1068-90-2
2-acetylaminomalonic acid diethyl ester

: 4900-38-3
2-acetylamino-2-(ethoxycarbonyl)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic acid ethyl ester

Conditions

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;

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 35218-42-9
N-(pyridin-4-yl)furan-2-carboxamide

: 953065-10-6
N-[(2-Oxo-1,2-dihydroquinolin-4-yl)methyl]-N-pyridin-4-yl-2-furamide

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 4-(aminomethyl)quinolin-2(1H)-one

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 607-66-9
4-methyl-1,2-dihydroquinolin-2-one

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 107-18-6
allyl alcohol

: 1627597-87-8
4-[(allyloxy)methyl]quinol-2(1H)-one

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: C20H16Cl2N2O3

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 24786-40-1
2-(2-propynylsulfanyl)-1H-1,3-benzimidazole

: 4-((4-((1H-benzo[d]imidazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)methyl)quinolin-2(1H)-one

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

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: 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

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%

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 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

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 81918-01-6
diethyl (((4-chlorophenyl)carbonyl)amino)propanedioate

: 1028268-32-7
ethyl 2-(4-chlorobenzamido)-2-ethoxyoxo-3-[2-(1H)-quinolin-4-yl]propionate

Conditions

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%

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 123-08-0
4-hydroxy-benzaldehyde

: 1041095-99-1
4-[(1,2-dihydro-2-oxoquinolin-4-yl)methoxy]-benzaldehyde

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 556-82-1
3-methyl-2-buten-1-ol

: 1627597-92-5
4-{[(3-methyl-2-buten-1-yl)oxy]methyl}quinol-2(1H)-one

Conditions

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%

: 59395-02-7, 18269-02-8
N'-benzylidene-2-hydroxybenzohydrazide

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 137156-69-5
2-(2-Oxo-1,2-dihydro-quinolin-4-ylmethoxy)-benzoic acid [1-phenyl-meth-(E)-ylidene]-hydrazide

Conditions

Conditions	Yield
	80%

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 134469-07-1
Benzimidazol-2-thiol

: 132657-24-0
4-(2'-S-benzimidazolyl)mercaptomethylcarbostyril

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 119-36-8
methyl salicylate

: 4-(o-carbomethoxyphenoxymethyl)carbostyril

Conditions

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

: 90-03-9
(2-hydroxyphenyl)mercury chloride

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 1252026-32-6
4-(2-chloromercury-phenoxymethyl)-azachromene-2-one

Conditions

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%

: 51786-56-2
4,5-dimethyl-7-hydroxycoumarin

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 1299366-49-6
4-[(4,5-dimethyl-2-oxo-2H-chromen-7-yloxy)methyl]quinolin-2(1H)-one

Conditions

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

: 611-20-1
salicylonitrile

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 4-(3-aminobenzofuran-2-yl)quinoline-2(H)-one

Conditions

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

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 1299366-41-8
4-[(4-methyl-2-oxo-2H-chromen-7-yloxy)methyl]quinolin-2(1H)-one

Conditions

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

: 74723-02-7
(E)-4-bromo-3-methyl-3-buten-1-ol

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: (E)-4-(((4-bromo-3-methylbut-3-en-1-yl)oxy)methyl)quinolin-2(1H)-one

Conditions

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%

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 121-33-5
vanillin

: 1384968-50-6
4-[(1,2-dihydro-2-oxoquinolin-4-yl)methoxy]-3-methoxybenzaldehyde

Conditions

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

: 85721-33-1
ciprofloxacin

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 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

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%

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 132657-26-2
4-(mercaptomethyl)quinolin-2(1H)-one

Conditions

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

: 667-27-6
Ethyl bromodifluoroacetate

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: ethyl 2-(4-(bromomethyl)-2-oxo-1,2-dihydroquinolin-3-yl)-2,2-difluoroacetate

Conditions

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%

: 2373-31-1
6-hydroxy-4-methyl-chromen-2-one

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 1299366-34-9
4-[(4-methyl-2-oxo-2H-chromen-6-yloxy)methyl]quinolin-2(1H)-one

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 513-42-8
3-hydroxy-2-methyl-1-propene

: 1627597-90-3
4-{[(2-methylallyl)oxy]methyl}quinolin-2(1H)-one

Conditions

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%

: 371-41-5
4-Fluorophenol

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 1091595-24-2
4-[4'-fluorophenoxymethyl]-1-aza-coumarin

Conditions

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

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 1432579-06-0
4-(azidomethyl)quinolin-2(1H)-one

Conditions

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;

: 4876-10-2
4-bromomethyl-2(1H)-quinolinone

: 371-40-4
4-fluoroaniline

: 333984-71-7
4-[4'-fluoroanilinomethyl]-1-aza-coumarin

Conditions

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

4-Bromomethyl-1,2-dihydroquinoline-2-one Chemical Properties

IUPAC Name: 4-(Bromomethyl)-1H-quinolin-2-one
Synonyms of 2(1H)-Quinolinone,4-(bromomethyl)- (CAS NO.4876-10-2): 4-Bromomethyl-2-quinolinol ; 4-(Bromomethyl)-2(1h)-quinolinone ; 4-Bromomethylquinolinone ; 4-Bromomethyl-1,2-dihydroquinolin-2-one ; 4-Bromomethyl Carbostyril ; 4-(Bromomethyl)-2-hydroxyquinoline
CAS NO: 4876-10-2
Molecular Formula of 2(1H)-Quinolinone,4-(bromomethyl)- (CAS NO.4876-10-2): C₁₀H₈BrNO
Molecular Weight: 238.0806
Molecular Structure:

Melting Point: 255-258 °C
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 20.31 Å²
Index of Refraction: 1.616
Molar Refractivity: 53.93 cm³
Molar Volume: 154.3 cm³
Surface Tension: 46.3 dyne/cm
Density of 2(1H)-Quinolinone,4-(bromomethyl)- (CAS NO.4876-10-2): 1.542 g/cm³
Flash Point: 190.8 °C
Enthalpy of Vaporization: 64.15 kJ/mol
Boiling Point: 391.8 °C at 760 mmHg
Vapour Pressure: 2.4E-06 mmHg at 25°C

4-Bromomethyl-1,2-dihydroquinoline-2-one Uses

2(1H)-Quinolinone,4-(bromomethyl)- (CAS NO.4876-10-2) is used as pharmaceutical Intermediates and rebamipide intermediate R-2.

4-Bromomethyl-1,2-dihydroquinoline-2-one Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
Hazard Note: Irritant

Product Name

4-Bromomethyl-1,2-dihydroquinoline-2-one

Synthetic route

4-Bromomethyl-1,2-dihydroquinoline-2-one Chemical Properties

4-Bromomethyl-1,2-dihydroquinoline-2-one Uses

4-Bromomethyl-1,2-dihydroquinoline-2-one Safety Profile

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