3,4-Dihydroquinolin-2(1H)-one

Names

[ CAS No. ]:
553-03-7

[ Name ]:
3,4-Dihydroquinolin-2(1H)-one

[Synonym ]:
Dihydro-α-quinolone
3,4-Dihydroquinolin-2(1H)-one
3,4-dihydro-1H-quinolin-2-one
2(1H)-Quinolinone, 3,4-dihydro-
MFCD00016722
3,4-Dihydro-2(1H)-quinolinone
T66 BMVT&J

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
328.1±31.0 °C at 760 mmHg

[ Melting Point ]:
165-167ºC

[ Molecular Formula ]:
C₉H₉NO

[ Molecular Weight ]:
147.174

[ Flash Point ]:
189.4±9.8 °C

[ Exact Mass ]:
147.068420

[ PSA ]:
29.10000

[ LogP ]:
1.34

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.564

MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H317-H319-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22;R36/37/38;R43

[ Safety Phrases ]:
S26-S36/37

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
2

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

Propanamide,3-chloro-N-phenyl-
tert-butyl [2-oxo-3,4-dihydroquinolin-1(2H)-yl]carbonate
2-Propenoic acid,3-(2-nitrophenyl)-, ethyl ester
2-nitrocinnamic Acid
3-(2-aminophenyl)propan-1-ol
(E)-2,3-dihydro-1H-inden-1-one oxime
1,2,3,4-Tetrahydroquinoline
carbon monoxide
Benzenamine, 2-ethenyl-
N-Boc-3,4-Dihydro-2(1H)-Quinolinone

DownStream

1-benzyl-3,4-dihydroquinolin-2-one
6-Bromo-3,4-dihydro-1H-quinolin-2-one
1,2,4,4a,5,6-hexahydrobenzo[f]quinolizin-3-one
6-BROMO-3,4-DIHYDROQUINOLINE-2(1H)-THIONE
1,2,3,4-Tetrahydroquinoline
leucoline
quinolone
6,8-Dinitro-3,4-dihydro-1H-quinolin-2-one
2-(Difluoromethoxy)quinoline
6-Iodo-3,4-dihydro-2(1H)-quinolinone

Articles

Synthesis and biological evaluation of a novel sigma-1 receptor antagonist based on 3,4-dihydro-2(1H)-quinolinone scaffold as a potential analgesic.

Eur. J. Med. Chem. 79 , 216-30, (2014)

The synthesis and sigma-1 receptor (1R) antagonist activity of a new series of 3,4-dihydro-2(1H)-quinolinone derivatives are reported. The new compounds were evaluated in vitro in sigma-1 and sigma-2 ...

Novel approach to 3,4-dihydro-2(1H)-quinolinone derivatives via cyclopropane ring expansion.

Org. Lett. 11(5) , 1043-5, (2009)

N-(1'-Alkoxy)cyclopropyl-2-haloanilines are transformed to 3,4-dihydro-2((1)H)-quinolinones via palladium-catalyzed cyclopropane ring expansion. The reaction tolerates a variety of functional groups s...

Synthesis of 4-amino-3, 4-dihydro-2 (1H)-quinolinones via β-lactam intermediates on the solid-phase. Pei Y, et al.

Tetrahedron Lett. 38(19) , 3349-52, (1997)

3-cyano-3,4-dihydroquinolin-2(1H)-one
5-Bromo-3,4-dihydroquinolin-2(1H)-one
6-Amino-3,4-dihydroquinolin-2(1H)-one
3-amino-3,4-dihydroquinolin-2(1H)-one
8-Amino-3,4-dihydroquinolin-2(1H)-one
6-Bromo-3,4-dihydroquinolin-2(1H)-one
4,6-Difluoro-2-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)benzo[d]thiazole
4,7-Dimethoxy-2-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)benzo[d]thiazole
7-Chloro-4-methyl-2-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)benzo[d]thiazole
Ethyl 2-formamido (3,4-dimethoxyphenyl) acrylate
2-Chloro-6-(1-methylpropyl)phenol
(Z)-N-(3-ethyl-4-methoxy-7-methylbenzo[d]thiazol-2(3H)-ylidene)thiophene-2-sulfonamide
2-(4-((5-Chlorothiophen-2-yl)sulfonyl)piperazin-1-yl)-6-methoxybenzo[d]thiazole
2-(4-((5-Chlorothiophen-2-yl)sulfonyl)piperazin-1-yl)-6-ethoxybenzo[d]thiazole
2-(4-((5-Chlorothiophen-2-yl)sulfonyl)piperazin-1-yl)-4-ethylbenzo[d]thiazole
2-(4-((5-Chlorothiophen-2-yl)sulfonyl)piperazin-1-yl)-5,7-dimethylbenzo[d]thiazole

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