Product Name

  • Name

    CINCHOPHEN

  • EINECS
  • CAS No. 132-60-5
  • Article Data87
  • CAS DataBase
  • Density 1.28g/cm3
  • Solubility Insoluble in water
  • Melting Point 214-215 °C(lit.)
  • Formula C16H11 N O2
  • Boiling Point 456.9°Cat760mmHg
  • Molecular Weight 249.269
  • Flash Point 230.1°C
  • Transport Information
  • Appearance
  • Safety A human poison by ingestion. An experimental poison by intraperitoneal and subcutaneous routes. Moderately toxic by an unspecified route. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 132-60-5 (CINCHOPHEN)
  • Hazard Symbols
  • Synonyms Cinchoninicacid, 2-phenyl- (8CI); 2-Phenyl-4-quinolinecarboxylic acid; 2-Phenylcinchonicacid; 2-Phenylcinchoninic acid; 4-Carboxy-2-phenylquinoline; Aciphenochinoline;Aciphenochinolinium; Agotan; Alutyl; Alutyo; Aminophan; Artam; Artexin; Atigoa;Atocin; Atofan; Atophan; Cinchophen; Cinchophene; Cinchophenic acid; Cinconal;Cincophen; Cincosal; Ikterosan; Mylofanol; NSC 2617; NSC 70178; Phenophan;Phenoquin; Polyphlogin; Quinofen; Quinophan; Quinophen; Rhematan; Rheumatan;Rheumin; Rheumine; Tervalon; Tophol; Tophosan; Traubofan; Vantyl; Viophan
  • PSA 50.19000
  • LogP 3.60000

Synthetic route

2-chloroquinoline-4-carboxylic acid
5467-57-2

2-chloroquinoline-4-carboxylic acid

phenylboronic acid
98-80-6

phenylboronic acid

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 50℃; for 4h; Suzuki-Miyaura coupling reaction; Inert atmosphere;96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 140℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation;
indole-2,3-dione
91-56-5

indole-2,3-dione

acetophenone
98-86-2

acetophenone

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 0.208333h; microwave irradiation;95%
Stage #1: indole-2,3-dione With cetyltrimethylammonium hydroxide In water at 20℃; for 0.166667h; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry;
Stage #2: acetophenone In water at 35℃; for 2.5h; Solvent; Reagent/catalyst; Temperature; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry;
95%
With potassium hydroxide In ethanol at 50 - 60℃; for 14h;90%
2-chloroquinoline-4-carboxylic acid
5467-57-2

2-chloroquinoline-4-carboxylic acid

tributylphenylstannane
960-16-7

tributylphenylstannane

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With cesium fluoride In ethanol; water at 50℃; for 5h; Stille coupling; Inert atmosphere;92%
3-Hydroxy-3-(2-oxo-2-phenyl-ethyl)-1,3-dihydro-indol-2-one
88730-73-8

3-Hydroxy-3-(2-oxo-2-phenyl-ethyl)-1,3-dihydro-indol-2-one

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With sulfuric acid In acetic acid for 5h; Heating;90%
With potassium hydroxide; ethanol
benzaldehyde
100-52-7

benzaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

aniline
62-53-3

aniline

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 0.05h; Reagent/catalyst; Solvent; Microwave irradiation; Green chemistry;80%
With ytterbium perfluorooctanoate In water for 3h; Doebner reaction; Reflux;72%
In ethanol for 3h; Reflux;51%
benzaldehyde
100-52-7

benzaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
Stage #1: benzaldehyde; 2-oxo-propionic acid With acetic acid for 1h; Reflux;
Stage #2: With aniline for 8h; Reflux;
62.2%
2-phenyl-4-quinolinecarboxaldehyde
117839-38-0

2-phenyl-4-quinolinecarboxaldehyde

A

4-hydroxymethyl-2-phenylquinoline
29268-33-5

4-hydroxymethyl-2-phenylquinoline

B

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With potassium hydroxide; ethanol; water
With potassium hydroxide; ethanol; water
3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one
31541-36-3, 34880-79-0, 56680-29-6

3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With hydrogenchloride; ethanol; water
With ethanol; water; potassium carbonate
1,5-diphenyltetrahydro-2,3-pyrroledione
960-53-2

1,5-diphenyltetrahydro-2,3-pyrroledione

benzaldehyde
100-52-7

benzaldehyde

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With ethanol; acetic acid; aniline
2-(4-nitrophenyl)quinoline-4-carboxylic acid
70097-13-1

2-(4-nitrophenyl)quinoline-4-carboxylic acid

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
beim Nitrieren;
N-[2-oxo-1-(2-oxo-indolin-3-yl)-2-phenyl-ethyl]-benzamide
859068-53-4

N-[2-oxo-1-(2-oxo-indolin-3-yl)-2-phenyl-ethyl]-benzamide

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With hydrogenchloride; ethanol
benzylidene phenylamine
538-51-2

benzylidene phenylamine

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With ethanol
ethanol
64-17-5

ethanol

benzaldehyde
100-52-7

benzaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

aniline
62-53-3

aniline

A

cinchophen
132-60-5

cinchophen

B

1,5-diphenyl-3-phenylimino-pyrrolidin-2-one
102704-29-0

1,5-diphenyl-3-phenylimino-pyrrolidin-2-one

isatic acid
484-38-8

isatic acid

acetophenone
98-86-2

acetophenone

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With potassium hydroxide
2-(2-acetamidophenyl)-N,N-diethyl-2-oxoacetamide
99686-93-8

2-(2-acetamidophenyl)-N,N-diethyl-2-oxoacetamide

acetophenone
98-86-2

acetophenone

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With sodium hydroxide 1.) reflux, 1 h, 2.) reflux, 18 h; Yield given. Multistep reaction;
N-[2-((3S,3aS,6aR)-5-Hydroxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

N-[2-((3S,3aS,6aR)-5-Hydroxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3R,3aS,6aR)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

N-[2-((3R,3aS,6aR)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3S,3aS,6aR)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

N-[2-((3S,3aS,6aR)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3R,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

N-[2-((3R,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3S,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

N-[2-((3S,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-acetamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3S,3aR,6aS)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

N-[2-((3S,3aR,6aS)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3R,3aR,6aS)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

N-[2-((3R,3aR,6aS)-5-Methoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3R,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

N-[2-((3R,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
N-[2-((3S,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

N-[2-((3S,3aS,6aR)-5-Ethoxy-4,4-dimethyl-2-oxo-6a-phenyl-hexahydro-furo[2,3-b]furan-3-yl)-phenyl]-benzamide

A

cinchophen
132-60-5

cinchophen

B

isobutyraldehyde
78-84-2

isobutyraldehyde

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating; decomposition;
β-<2-phenyl-quinolyl-(4)>-trimethylene glycol

β-<2-phenyl-quinolyl-(4)>-trimethylene glycol

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With chromium(III) oxide; sulfuric acid
2-phenyl-quinoline-carboxylic acid-(4)-amide

2-phenyl-quinoline-carboxylic acid-(4)-amide

cinchophen
132-60-5

cinchophen

Conditions
ConditionsYield
With sulfuric acid at 130℃;
hydrogenchloride
7647-01-0

hydrogenchloride

N-[2-oxo-1-(2-oxo-indolin-3-yl)-2-phenyl-ethyl]-benzamide
859068-53-4

N-[2-oxo-1-(2-oxo-indolin-3-yl)-2-phenyl-ethyl]-benzamide

cinchophen
132-60-5

cinchophen

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one
31541-36-3, 34880-79-0, 56680-29-6

3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one

water
7732-18-5

water

cinchophen
132-60-5

cinchophen

ethanol
64-17-5

ethanol

3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one
31541-36-3, 34880-79-0, 56680-29-6

3-(2-oxo-2-phenyl-ethylidene)-1,3-dihydro-indol-2-one

water
7732-18-5

water

potassium carbonate

potassium carbonate

cinchophen
132-60-5

cinchophen

methanol
67-56-1

methanol

cinchophen
132-60-5

cinchophen

methyl 2-phenylquinoline-4-carboxylate
4546-48-9

methyl 2-phenylquinoline-4-carboxylate

Conditions
ConditionsYield
With sulfuric acid Reflux;100%
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 0 - 20℃; for 13h;99%
With thionyl chloride at 0℃; Reflux;84.9%
cinchophen
132-60-5

cinchophen

3-amino-2-methyl-6-bromoquinazolin-4(3H)-one
71822-97-4

3-amino-2-methyl-6-bromoquinazolin-4(3H)-one

2-Phenyl-quinoline-4-carboxylic acid (6-bromo-2-methyl-4-oxo-4H-quinazolin-3-yl)-amide
98832-98-5

2-Phenyl-quinoline-4-carboxylic acid (6-bromo-2-methyl-4-oxo-4H-quinazolin-3-yl)-amide

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In toluene for 0.75h; Product distribution; Heating; other aromatic acids, also with 3-amino-2-methyl-4(3H)-quinazolone, influence of Et3N;99%
With triethylamine; trichlorophosphate In toluene for 0.75h; Heating;99%
cinchophen
132-60-5

cinchophen

2-phenylquinoline-4-carbonyl fluoride

2-phenylquinoline-4-carbonyl fluoride

Conditions
ConditionsYield
With tetramethylammonium trifluoromethanethiolate In dichloromethane at 25℃; for 2h;96%
With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;95%
With tetramethylammonium trifluoromethanethiolate In dichloromethane at 20℃; for 1h;89%
cinchophen
132-60-5

cinchophen

3-(tert-butyldimethylsilyloxy)-17α-(3'-hydroxyprop-1'-ynyl)estradiol
211183-97-0

3-(tert-butyldimethylsilyloxy)-17α-(3'-hydroxyprop-1'-ynyl)estradiol

3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate
959414-78-9

3-O-tert-butyldimethylsilyl-17α-hydroxypropargyl-β-estradiolyl 2-phenylquinoline-4-carboxylate

Conditions
ConditionsYield
With dmap; N,N'-1,2-ethylenediylbis-(L-cysteine) diethyl ester dihydrochloride In dichloromethane at 0 - 20℃; for 2h;95%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;95%
cinchophen
132-60-5

cinchophen

1-(dimethylamino)-2-propylamine
108-15-6

1-(dimethylamino)-2-propylamine

N‐[1‐(dimethylamino)propan‐2‐yl]‐2‐phenylquinoline‐4‐carboxamide

N‐[1‐(dimethylamino)propan‐2‐yl]‐2‐phenylquinoline‐4‐carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;94.3%
ethanol
64-17-5

ethanol

cinchophen
132-60-5

cinchophen

ethyl 2-phenylquinoline-4-carboxylate
4420-46-6

ethyl 2-phenylquinoline-4-carboxylate

Conditions
ConditionsYield
With sulfuric acid for 0.166667h; microwave irradiation;94%
With sulfuric acid Reflux;89%
With sulfuric acid Fischer-Speier Esterification; Reflux;75%
cinchophen
132-60-5

cinchophen

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

(+)-(S)-N-(α-methylbenzyl)-2-phenylquinoline-4-carboxamide

(+)-(S)-N-(α-methylbenzyl)-2-phenylquinoline-4-carboxamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;94%
cinchophen
132-60-5

cinchophen

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

(-)-(R)-N-(α-methylbenzyl)-2-phenylquinoline-4-carboxamide

(-)-(R)-N-(α-methylbenzyl)-2-phenylquinoline-4-carboxamide

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h;94%
cinchophen
132-60-5

cinchophen

2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
258857-73-7

2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside

2-Phenyl-quinoline-4-carboxylic acid 2-[(2S,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester
258857-75-9

2-Phenyl-quinoline-4-carboxylic acid 2-[(2S,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 4.5h; Esterification;93%
cinchophen
132-60-5

cinchophen

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

N-[2-(dimethylamino)ethyl]-2-phenylquinoline-4-carboxamide
124340-46-1

N-[2-(dimethylamino)ethyl]-2-phenylquinoline-4-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;93%
1-methyl-azetidin-3-amine
959957-92-7

1-methyl-azetidin-3-amine

cinchophen
132-60-5

cinchophen

N‐(1‐methylazetidin‐3‐yl)‐2‐phenylquinoline‐4‐carboxamide

N‐(1‐methylazetidin‐3‐yl)‐2‐phenylquinoline‐4‐carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;92.3%
cinchophen
132-60-5

cinchophen

aniline
62-53-3

aniline

N,2-diphenylquinoline-4-carboxamide
110662-85-6

N,2-diphenylquinoline-4-carboxamide

Conditions
ConditionsYield
Stage #1: cinchophen; aniline With benzotriazol-1-ol In N,N-dimethyl-formamide for 0.25h;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 4h; Reagent/catalyst; Solvent; Temperature;
90.1%
With trichlorophosphate for 8h; Reflux;56%
With Tetraethyl pyrophosphate; toluene
With Tetraethyl pyrophosphate
cinchophen
132-60-5

cinchophen

2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-β-D-arabinohexopyranoside
258857-74-8

2-hydroxyethyl 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-β-D-arabinohexopyranoside

2-Phenyl-quinoline-4-carboxylic acid 2-[(2R,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester
258857-76-0

2-Phenyl-quinoline-4-carboxylic acid 2-[(2R,4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 4.5h; Esterification;90%
cinchophen
132-60-5

cinchophen

propargyl bromide
106-96-7

propargyl bromide

prop-2-ynyl-2-phenylquinoline-4-carboxylate

prop-2-ynyl-2-phenylquinoline-4-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;90%
N-[2-(aminoethyl)]imidazole
5739-10-6

N-[2-(aminoethyl)]imidazole

cinchophen
132-60-5

cinchophen

N‐[2‐(1H‐imidazol‐1‐yl)ethyl]‐2‐phenylquinoline‐4‐carboxamide

N‐[2‐(1H‐imidazol‐1‐yl)ethyl]‐2‐phenylquinoline‐4‐carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;89.2%
cinchophen
132-60-5

cinchophen

4-amino-N,N-dimethylaniline
99-98-9

4-amino-N,N-dimethylaniline

N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide
300852-09-9

N-(4-(dimethylamino)phenyl)-2-phenylquinoline-4-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;89%
8-amino quinoline
578-66-5

8-amino quinoline

cinchophen
132-60-5

cinchophen

2-phenyl-N-(quinolin-8-yl)quinoline-4-carboxamide

2-phenyl-N-(quinolin-8-yl)quinoline-4-carboxamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;88%
cinchophen
132-60-5

cinchophen

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

N-[3-(dimethylamino)propyl]-2-phenylquinoline-4-carboxamide

N-[3-(dimethylamino)propyl]-2-phenylquinoline-4-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;87%
cinchophen
132-60-5

cinchophen

2-(2-amino-3-methoxyphenyl)-benzoxazole-4-carboxylic acid methyl ester
1086562-05-1

2-(2-amino-3-methoxyphenyl)-benzoxazole-4-carboxylic acid methyl ester

2-[3-methoxy-2-[(2-phenylquinoline-4-carbonyl)-amino]-phenyl]-benzoxazole-4-carboxylic acid methyl ester
1086562-34-6

2-[3-methoxy-2-[(2-phenylquinoline-4-carbonyl)-amino]-phenyl]-benzoxazole-4-carboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: cinchophen With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃;
Stage #2: 2-(2-amino-3-methoxyphenyl)-benzoxazole-4-carboxylic acid methyl ester With pyridine In dichloromethane
86%
cinchophen
132-60-5

cinchophen

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-phenyl-4-(benzimidazol-2-yl)quinoline
42039-62-3

2-phenyl-4-(benzimidazol-2-yl)quinoline

Conditions
ConditionsYield
With PPA at 210 - 270℃; for 0.0416667h; microwave irradiation;85%
With PPA70%
cinchophen
132-60-5

cinchophen

2'-(tert-butyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-7'(6'H)-one
1198001-03-4

2'-(tert-butyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-7'(6'H)-one

2’-(tert-butyl)-1-(2-phenylquinoline-4-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one

2’-(tert-butyl)-1-(2-phenylquinoline-4-carbonyl)-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12.5h;85%
With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 12h;85%
homoalylic alcohol
627-27-0

homoalylic alcohol

cinchophen
132-60-5

cinchophen

C20H17NO2

C20H17NO2

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 48h;84%
cinchophen
132-60-5

cinchophen

4-nitro-aniline
100-01-6

4-nitro-aniline

2-phenyl-N-(4-nitrophenyl)-quinoline-4-carboxamide

2-phenyl-N-(4-nitrophenyl)-quinoline-4-carboxamide

Conditions
ConditionsYield
With trichlorophosphate for 8h; Reflux;84%
3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one
17832-99-4

3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one

cinchophen
132-60-5

cinchophen

(2-oxobenzo[d]oxazol-3(2H)-yl)methyl-2-phenylquinoline-4-carboxylate

(2-oxobenzo[d]oxazol-3(2H)-yl)methyl-2-phenylquinoline-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 5℃; for 2h;84%
1,3,5-tripropyl-1,3,5-triazinane
13036-81-2

1,3,5-tripropyl-1,3,5-triazinane

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

cinchophen
132-60-5

cinchophen

C25H29N3O2

C25H29N3O2

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 45℃; Ugi Condensation;83%
cinchophen
132-60-5

cinchophen

4-bromo-aniline
106-40-1

4-bromo-aniline

2-phenyl-N-(4-bromophenyl)-quinoline-4-carboxamide

2-phenyl-N-(4-bromophenyl)-quinoline-4-carboxamide

Conditions
ConditionsYield
With trichlorophosphate for 8h; Reflux;82%

Cinchophen Chemical Properties

Empirical Formula: C16H11NO2
Molecular Weight: 249.264 g/mol
EINECS: 205-067-1
Melting point: 214-215 °C(lit.)
Sensitive: Light sensitive
Index of Refraction: 1.682
Density: 1.28 g/cm3
Flash Point: 230.1 °C
Enthalpy of Vaporization: 75.55 kJ/mol
Boiling Point: 456.9 °C at 760 mmHg
Vapour Pressure: 3.84E-09 mmHg at 25 °C 
Structure of Cinchophen (CAS NO.132-60-5):
                    
IUPAC Name: 2-Phenylquinoline-4-carboxylic acid
Product Categories: API intermediates;Quinolinecarboxylic Acids

Cinchophen Uses

 Cinchophen (CAS NO.132-60-5) has been used as antipyretic analgesic for acute and chronic arthritis, rheumatic pain, neuralgia, lumbago, gout, headache and so on.

Cinchophen Production

First, having the preparation of isatin to be its sodium salt, and generated by the open-loop, and then with the cyclization of acetophenone to get Sim sodium , or with acetic acid or hydrochloric acid can be derived Xin-fen .

Cinchophen Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 1250mg/kg (1250mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
human LDLo oral 214mg/kg (214mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 177, 1969.
man LDLo unreported 74mg/kg (74mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 subcutaneous 350mg/kg (350mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 116, Pg. 154, 1958.
mouse LDLo oral 1500mg/kg (1500mg/kg)   "Narkoseversuche mit Hoheren Alkoholen und Stickstoffderivaten, Dissertation," Leube, F., Pharmakologischen Institut der Universitat Tubingen, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LDLo unreported 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacology and Experimental Therapeutics. Vol. 74, Pg. 365, 1942.
rat LD50 intravenous 600mg/kg (600mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
rat LDLo oral 500mg/kg (500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947.

 Cinchophen (CAS NO.132-60-5) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

Cinchophen Safety Profile

A human poison by ingestion. An experimental poison by intraperitoneal and subcutaneous routes. Moderately toxic by an unspecified route. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes of Cinchophen (CAS NO.132-60-5): HarmfulXn
Risk Statements: 22 
R22:Harmful if swallowed.
Safety Statements: 36/37/39-26 
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.

Cinchophen Specification

 Cinchophen ,its cas register number is 132-60-5. It also can be called Cinchoninic acid, 2-phenyl- ; and 4-Quinolinecarboxylic acid, 2-phenyl- . 1g of the product can be dissolved in about 400ml chloroform, 100ml ether, 120ml of ethanol, almost insoluble in water. It is hazardous,so the first aid measures and others should be known. Such as: When on the skin: first,should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly,Get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically.
In addition, Cinchophen (CAS NO.132-60-5) may discolor on exposure to light. It is not compatible with strong oxidizing agents, strong bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide.

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