Conditions | Yield |
---|---|
With trichlorophosphate for 1h; Heating; | 94% |
With trichlorophosphate Reflux; | 89.5% |
With trichlorophosphate for 2h; Heating / reflux; | 88.5% |
7-chloro-4(1H)-oxoquinoline
4,7-dichloroquinoline
Conditions | Yield |
---|---|
With trichlorophosphate for 2h; Reflux; | 85% |
With trichlorophosphate for 2h; Reflux; | 85% |
With ((1,3,5-triazine-2,4,6-triyl)tris(oxy))tris(triphenylphosphonium) chloride at 140 - 150℃; for 2h; Solvent; Ionic liquid; | |
With trichlorophosphate Reflux; |
7-fluoro-1,4-dihydroquinolin-4-one
4,7-dichloroquinoline
Conditions | Yield |
---|---|
With trichlorophosphate for 1h; Reflux; | 85% |
Conditions | Yield |
---|---|
With Eosin Y; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 1h; Inert atmosphere; Irradiation; chemoselective reaction; | 78% |
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Irradiation; chemoselective reaction; | 73% |
4,7-dichloroquinoline
Conditions | Yield |
---|---|
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In n-heptane at 100℃; under 11251.1 Torr; for 12h; Autoclave; | 62% |
7-chloro-4-quinolinesulfonyl chloride
A
4,7-dichloroquinoline
B
7-chloro-4-quinolinesulfonamide
Conditions | Yield |
---|---|
With ammonia In water at 20℃; | A 31% B 56% |
5-[(3-chloro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diphenyl ether / 0.08 h / 300 °C / microwave irradiation 2: POCl3 / 3 h / Heating View Scheme |
2-acetyl-5-chloroaniline
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 75 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 95 percent / K2CO3 / dimethylformamide / 1 h / 80 °C 3: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 4: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 5: 81 percent / aq. NaOH / methanol / Heating 6: 94 percent / POCl3 / 1 h / Heating View Scheme |
N-(2-acetyl-5-chlorophenyl)-4-methylbenzenesulfonamide
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / K2CO3 / dimethylformamide / 1 h / 80 °C 2: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 3: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 4: 81 percent / aq. NaOH / methanol / Heating 5: 94 percent / POCl3 / 1 h / Heating View Scheme |
N-allyl-N-p-toluenesulfonyl-2-acetyl-5-chloroaniline
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 98 percent / NaI; Et3N / acetonitrile / 1 h / Heating 2: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 3: 81 percent / aq. NaOH / methanol / Heating 4: 94 percent / POCl3 / 1 h / Heating View Scheme |
N-p-toluenesulfonyl-4-(t-butyldimethylsilyloxy)-7-chloro-1,2-dihydroquinoline
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 81 percent / aq. NaOH / methanol / Heating 2: 94 percent / POCl3 / 1 h / Heating View Scheme |
N-allyl-N-p-toluenesulfonyl-2-[1-(tert-butyldimethylsilyloxy)vinyl]-5-chloroaniline
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-(Mes)2-imidazolidin-2-yl) / CH2Cl2 / 1 h / 50 °C 2: 81 percent / aq. NaOH / methanol / Heating 3: 94 percent / POCl3 / 1 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diphenyl ether / 1 h / Heating 2: POCl3 / 100 °C View Scheme |
7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester
A
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2 N aq. NaOH / 1 h / Heating 2: diphenyl ether / 1 h / Heating 3: POCl3 / 100 °C View Scheme |
2-(3-chlorophenylamino)methylenemalonic acid diethyl ester
A
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: diphenyl ether / 1 h / Heating 2: 2 N aq. NaOH / 1 h / Heating 3: diphenyl ether / 1 h / Heating 4: POCl3 / 100 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.5 h / 165 °C 2: diphenyl ether / 1 h / Heating 3: 2 N aq. NaOH / 1 h / Heating 4: diphenyl ether / 1 h / Heating 5: POCl3 / 100 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 2: phosphoryl chloride View Scheme |
7-chlorokynurenic acid
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: mineral oil / 270 °C 2: phosphoryl chloride View Scheme | |
Multi-step reaction with 2 steps 1: 1-chloro-naphthalene 2: phosphoryl chloride View Scheme |
7-chloro-4-hydroxy-quinoline-2-carboxylic acid ethyl ester
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous NaOH 2: mineral oil / 270 °C 3: phosphoryl chloride View Scheme | |
Multi-step reaction with 3 steps 1: aqueous NaOH 2: 1-chloro-naphthalene 3: phosphoryl chloride View Scheme |
7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous NaOH 2: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 3: phosphoryl chloride View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide; water / diphenylether / 0.5 h 2: paraffin oil / 0.83 h / 230 °C 3: trichlorophosphate / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: aqueous NaOH 3: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 4: phosphoryl chloride View Scheme | |
Multi-step reaction with 2 steps 1: dowtherm / 4 h 2: trichlorophosphate / 6 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1: diphenylether / Reflux 2: sodium hydroxide; ethanol / Reflux 3: diphenylether / Reflux 4: trichlorophosphate / 2 h / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid / Erhitzen des Reaktionsprodukts in Paraffinoel auf 250grad 2: aqueous NaOH 3: mineral oil / 270 °C 4: phosphoryl chloride View Scheme | |
Multi-step reaction with 5 steps 3: aqueous NaOH 4: 250 - 270 °C / oder in einem Gemisch von Diphenylaether und Biphenyl 5: phosphoryl chloride View Scheme | |
Multi-step reaction with 4 steps 1: acetic acid / Erhitzen des Reaktionsprodukts in Paraffinoel auf 250grad 2: aqueous NaOH 3: mineral oil / 270 °C 4: phosphoryl chloride View Scheme |
Conditions | Yield |
---|---|
Stage #1: 3-chloro-aniline; diethyl 2-ethoxymethylenemalonate Heating; Stage #2: With trichlorophosphate |
7-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid ethyl ester
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / 1 h / Reflux 2: diphenylether / 0.5 h / Reflux 3: trichlorophosphate / 1 h / Reflux View Scheme |
7-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diphenylether / 0.5 h / Reflux 2: trichlorophosphate / 1 h / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 2 h / 100 °C 2: diphenylether / 0.25 h / Reflux 3: sodium hydroxide / 1 h / Reflux 4: diphenylether / 0.5 h / Reflux 5: trichlorophosphate / 1 h / Reflux View Scheme |
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: diphenylether / 0.25 h / Reflux 2: sodium hydroxide / 1 h / Reflux 3: diphenylether / 0.5 h / Reflux 4: trichlorophosphate / 1 h / Reflux View Scheme |
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diphenylether / Reflux 2: trichlorophosphate / 2 h / Reflux View Scheme |
ethyl 7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylate
4,7-dichloroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; ethanol / Reflux 2: diphenylether / Reflux 3: trichlorophosphate / 2 h / Reflux View Scheme |
4,7-dichloroquinoline
heptane-1,7-diamine
N-(7-chloro-[4]quinolyl)-heptanediyldiamine
Conditions | Yield |
---|---|
Inert atmosphere; | 100% |
In pentan-1-ol at 120℃; for 16h; | 80% |
With N-ethyl-N,N-diisopropylamine In pentan-1-ol for 18h; Heating; | 80% |
4,7-dichloroquinoline
ethylenediamine
N-(7-chloroquinolin-4-yl)ethylenediamine
Conditions | Yield |
---|---|
at 80 - 140℃; for 13h; | 100% |
at 80 - 135℃; for 4h; neat (no solvent); | 100% |
In neat (no solvent) at 110℃; | 100% |
Conditions | Yield |
---|---|
In ethanol for 24h; Reflux; | 100% |
for 0.166667h; microwave irradiation; | 95% |
With ethanol |
Conditions | Yield |
---|---|
In isopropyl alcohol at 100℃; for 20h; | 100% |
With triethylamine at 130℃; for 4h; Inert atmosphere; | 98% |
With potassium carbonate In isopropyl alcohol for 36h; Reflux; | 95% |
4,7-dichloroquinoline
1,8-diaminooctan
N-(7-chloroquinolin-4-yl)octane-1,8-diamine
Conditions | Yield |
---|---|
Inert atmosphere; | 100% |
at 80 - 140℃; for 2.75h; Microwave irradiation; | 69% |
at 80 - 135℃; for 4h; | 51% |
4,7-dichloroquinoline
diaminodecane
N-(7-chloroquinolin-4-yl)decane-1,10-diamine
Conditions | Yield |
---|---|
Inert atmosphere; | 100% |
at 80 - 135℃; for 4h; | 60% |
1.) 80 deg C, 1 h, 2.) 135-145 deg C, 3 h; |
4,7-dichloroquinoline
1,12-Diaminododecane
N1-(7-Chloro-quinolin-4-yl)-dodecane-1,12-diamine
Conditions | Yield |
---|---|
Inert atmosphere; | 100% |
1.) 80 deg C, 1 h, 2.) 135-145 deg C, 3 h; |
4,7-dichloroquinoline
Trimethylenediamine
N-(7-chloroquinolin-4-yl)propane-1,3-diamine
Conditions | Yield |
---|---|
In neat (no solvent) at 110℃; | 100% |
Inert atmosphere; | 100% |
In isopropyl alcohol at 100℃; for 20h; | 98% |
4,7-dichloroquinoline
1,4-diaminobutane
N1-(7-chloroquinolin-4-yl)butane-1,4-diamine
Conditions | Yield |
---|---|
Inert atmosphere; | 100% |
at 95℃; for 1h; Microwave irradiation; | 100% |
In isopropyl alcohol at 100℃; for 20h; | 99% |
4,7-dichloroquinoline
silver thiocyanate
7-chloro-4-isothiocyanatoquinoline
Conditions | Yield |
---|---|
In toluene at 110℃; for 12h; | 100% |
In toluene at 115℃; for 18h; | 89% |
In toluene at 90 - 120℃; for 18h; | 68% |
In toluene for 12h; Heating; | |
In toluene at 120℃; for 18h; |
4,7-dichloroquinoline
propan-1-ol-3-amine
3-[(7-chloroquinolin-4-yl)amino]propan-1-ol
Conditions | Yield |
---|---|
Inert atmosphere; | 100% |
With triethylamine In ethanol at 90℃; | 99% |
With triethylamine In N,N-dimethyl-formamide at 60 - 120℃; for 24h; | 96% |
5-amino-4'-trifluoromethyl-biphenyl-3-ol
4,7-dichloroquinoline
5-(7-chloro-quinolin-4-ylamino)-4'-trifluoromethyl-biphenyl-3-ol
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 100% |
Conditions | Yield |
---|---|
In ethanol for 24h; Reflux; | 100% |
In neat (no solvent) at 120℃; under 1500.15 Torr; for 0.166667h; Microwave irradiation; | 96% |
for 0.116667h; microwave irradiation; | 95% |
4,7-dichloroquinoline
7-amino-3-ethylquinazolin-4(3H)-one
C19H15ClN4O
Conditions | Yield |
---|---|
In ethanol for 48h; Reflux; | 100% |
4,7-dichloroquinoline
7-amino-3-propylquinazolin-4(3H)-one
C20H17ClN4O
Conditions | Yield |
---|---|
In ethanol for 48h; Reflux; | 100% |
4,7-dichloroquinoline
7-amino-3-benzylquinazolin-4(3H)-one
C24H17ClN4O
Conditions | Yield |
---|---|
In ethanol for 48h; Reflux; | 100% |
4,7-dichloroquinoline
4-methoxy-aniline
7-chloro-N-(4-methoxyphenyl)quinolin-4-amine
Conditions | Yield |
---|---|
With trifluoroacetic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane for 8.53333h; Inert atmosphere; Reflux; | 99% |
With phenol at 120℃; for 0.5h; | 98% |
for 0.25h; microwave irradiation; | 78% |
With silica gel-loaded acidic ionic liquid IL/TFA at SiO2 In 1-methyl-pyrrolidin-2-one at 70℃; | 36.8% |
With hydrogenchloride |
4,7-dichloroquinoline
ethanolamine
3-(7-chloroquinolin-4-ylamino)propyl alcohol
Conditions | Yield |
---|---|
With triethylamine In ethanol at 90℃; | 99% |
at 130 - 140℃; for 24h; | 97% |
In neat (no solvent) at 130℃; | 95% |
Conditions | Yield |
---|---|
With ammonium carbonate; phenol at 110 - 165℃; | 99% |
With ammonia In phenol at 170℃; for 2h; | 92% |
With ammonia; phenol at 150℃; for 2h; | 89% |
Conditions | Yield |
---|---|
In ethanol Reflux; | 99% |
With hydrogenchloride; potassium iodide In ethanol for 12h; Heating; |
4,7-dichloroquinoline
dimethyl amine
7-chloro-4-N,N-dimethylamino-quinoline
Conditions | Yield |
---|---|
In water; acetonitrile at 50℃; for 48h; | 99% |
In water; acetonitrile at 50℃; for 48h; | 90% |
With acetic acid at 130 - 135℃; for 3h; | 40% |
4,7-dichloroquinoline
m-Hydroxyaniline
4-(3'-hydroxyphenyl)amino-7-chloroquinoline
Conditions | Yield |
---|---|
In ethanol Reflux; | 99% |
for 0.25h; microwave irradiation; | 75% |
With hydrogenchloride; potassium iodide In ethanol Heating; |
1H-imidazole
4,7-dichloroquinoline
7-chloro-4-(1H-imidazol-1-yl)quinoline
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; Green chemistry; | 99% |
for 0.0333333h; microwave irradiation; | 85% |
4,7-dichloroquinoline
1 ,5-pentanediol
O-(7-chloro-4-quinolyl)-1,5-pentanediol
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 18h; Inert atmosphere; | 99% |
4,7-dichloroquinoline
trimethyleneglycol
O-(7-chloro-4-quinolyl)-1,3-propanediol
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 18h; Inert atmosphere; | 99% |
With potassium tert-butylate In tert-butyl alcohol at 80℃; for 18h; |
4,7-dichloroquinoline
5-amino-4'-chloro<1,1'-biphenyl>-2-ol
4’-chloro-5-[(7-chloro-4-quinolinyl)amino]-[1,1’-biphenyl]-2-ol
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water for 10h; Reflux; | 99% |
With hydrogenchloride In ethanol; water for 4h; Inert atmosphere; Reflux; | 87% |
4,7-dichloroquinoline
methyl trifluoromethanesulfonate
4,7-dichloro-1-methylquinolinium triflate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 18h; | 99% |
In toluene at 20℃; for 24h; | 65% |
Conditions | Yield |
---|---|
In ethanol Reflux; | 99% |
Conditions | Yield |
---|---|
In ethanol Reflux; | 99% |
Conditions | Yield |
---|---|
In ethanol Reflux; | 99% |
IUPAC Name: 4,7-Dichloroquinoline
Synonyms of 4,7-Dichloroquinoline (CAS NO.86-98-6): 5-20-07-00316 (Beilstein Handbook Reference) ; AI3-50374 ; BRN 0125359 ; EINECS 201-714-7 ; NSC 593 ; TL 1473 ; Quinoline, 4,7-dichloro-
CAS NO: 86-98-6
Classification Code: Mutation data
Molecular Formula of 4,7-Dichloroquinoline (CAS NO.86-98-6): C9H5Cl2N
Molecular Weight: 198.0487
Molecular Structure:
Melting Point: 81-83 °C
Polar Surface Area: 12.89 Å2
Index of Refraction: 1.66
Molar Refractivity: 51.97 cm3
Molar Volume: 140.6 cm3
Surface Tension: 51.5 dyne/cm
Density of 4,7-Dichloroquinoline (CAS NO.86-98-6): 1.407 g/cm3
Flash Point: 158.7 °C
Enthalpy of Vaporization: 51.11 kJ/mol
Boiling Point: 292.9 °C at 760 mmHg
Vapour Pressure: 0.00313 mmHg at 25°C
4,7-DICHLOROQUINOLINE(86-98-6) is used as a drug chloroquine phosphate intermediate.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LDLo | subcutaneous | 80mg/kg (80mg/kg) | National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. 30101, Pg. 8, 1945. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S22: Do not breathe dust.
WGK Germany: 3
RTECS: VB4200000
Hazard Note: Irritant
HS Code: 29334910
Poison by subcutaneous route. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx and Cl−.
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