[ CAS No. 14548-51-7 ]

Name: 14548-51-7|7-Bromo-3,4-dihydroquinolin-2(1H)-one|97%
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Quality Control of [ 14548-51-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 14548-51-7 ]

CAS No. :	14548-51-7	MDL No. :	MFCD09878790
Formula :	C₉H₈BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JEZXCJXCRWALSO-UHFFFAOYSA-N
M.W :	226.07 g/mol	Pubchem ID :	27281844
Synonyms :

Calculated chemistry of [ 14548-51-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.24
TPSA :	29.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	2.03
Log Po/w (WLOGP) :	1.76
Log Po/w (MLOGP) :	2.17
Log Po/w (SILICOS-IT) :	2.76
Consensus Log Po/w :	2.14

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.89
Solubility :	0.291 mg/ml ; 0.00129 mol/l
Class :	Soluble
Log S (Ali) :	-2.27
Solubility :	1.22 mg/ml ; 0.00538 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.03
Solubility :	0.0212 mg/ml ; 0.000094 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 14548-51-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14548-51-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 14548-51-7 ]
Downstream synthetic route of [ 14548-51-7 ]

[ 14548-51-7 ] Synthesis Path-Upstream 1~4

1
[ 14548-39-1 ]
[ 14548-51-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium azide; methanesulfonic acid In chloroform for 3 h; Reflux	The compound 6-bromo-2,3-dihydro-1H-inden-1-one (2.0 g, 9.5 mmol) was dissolved in chloroform (30 mL)Methanesulfonic acid (6 mL) was then added dropwise to the reaction system,Finally, sodium azide (1.90 g, 9.5 mmol) was added portionwise to the reaction system,Reflux for three hours.After completion of the reaction, the mixture was cooled to room temperature, and then the reaction solution was poured into ice water. The mixture was separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried over anhydrous sodium sulfate, filtered and dried. The crude product was purified by column chromatography (Petroleum ether / ethyl acetate: 2/1) to give 7-bromo-3,4-dihydroquinolin-2 (1H) -one(0.90 g) in 42percent yield.

Reference： [1] Patent: CN106349241, 2017, A, . Location in patent: Paragraph 0538; 0539; 0540; 0541; 0542
[2] Patent: WO2010/38901, 2010, A1, . Location in patent: Page/Page column 44
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 662 - 667

2
[ 1643-30-7 ]
[ 14548-51-7 ]

Reference： [1] Chemische Berichte, 1880, vol. 13, p. 1680

3
[ 501-52-0 ]
[ 14548-51-7 ]

Reference： [1] Chemische Berichte, 1880, vol. 13, p. 1680

4
[ 14548-51-7 ]
[ 114744-51-3 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 662 - 667

[ 14548-51-7 ] Synthesis Path-Downstream 1~34

1
3-(4-bromo-2-nitro-phenyl)-propionic acid [ No CAS ]
[ 14548-51-7 ]

Reference： [1]Chemische Berichte,1880,vol. 13,p. 1680

3
[ 1643-30-7 ]
[ 14548-51-7 ]

Reference： [1]Chemische Berichte,1880,vol. 13,p. 1680

4
[ 501-52-0 ]
[ 14548-51-7 ]

Reference： [1]Chemische Berichte,1880,vol. 13,p. 1680

5
[ 557-21-1 ]
[ 14548-51-7 ]
[ 903557-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N,N,-tetramethylethylenediamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 180℃; for 0.08333330000000001h;Microwave irradiation;	Step 1-3: To a DMF solution (14.5 mL) of the compound (3.00 g) obtained in Step 1-2, zinc cyanide (1.04 g) , Pd2(dba)3 (122 mg) , Xantphos (154 mg) and TMEDA (590 muL) were added and the mixture was stirred under microwave irradiation (1800C) for 5 minutes. To the reaction mixture, CHCl3 was added and the mixture was filtrated by Celite and washed with DMF. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane = 50/50 to 100/0; v/v) . To the solid substance obtained, EtOAc was added at room temperature and the mixture was stirred for 30 minutes. A solid substance was obtained by filtration and washed with EtOAc to obtain 2-oxo-l, 2, 3,4- tetrahydroquinoline-7-carbonitrile (15.5 g, a light yellow solid) .1H NMR (600 MHz, CDCl3, delta) : 2.64-2.68 (m, 2H), 3.00-3.04 (m, 2H), 7.04 (s, IH), 7.23-7.29 (m, 2H), 8.46 (brs, IH); ESl/APCI MS m/z 173 [M+H]+.

Reference： [1]Patent: WO2010/38901,2010,A1 .Location in patent: Page/Page column 44-45

6
[ 14548-39-1 ]
[ 14548-51-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium azide; methanesulfonic acid; In chloroform; for 3.0h;Reflux;	The compound 6-bromo-2,3-dihydro-1H-inden-1-one (2.0 g, 9.5 mmol) was dissolved in chloroform (30 mL)Methanesulfonic acid (6 mL) was then added dropwise to the reaction system,Finally, sodium azide (1.90 g, 9.5 mmol) was added portionwise to the reaction system,Reflux for three hours.After completion of the reaction, the mixture was cooled to room temperature, and then the reaction solution was poured into ice water. The mixture was separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried over anhydrous sodium sulfate, filtered and dried. The crude product was purified by column chromatography (Petroleum ether / ethyl acetate: 2/1) to give 7-bromo-3,4-dihydroquinolin-2 (1H) -one(0.90 g) in 42% yield.
		Step 1-2: To the CHCl3 solution (560 mL) of the compound (39.5 g) obtained in Step 1-1 and methanesulfonic acid (122 mL) , sodium azide (36.5 g) was added separately in parts under ice cooling, and then the mixture was heated to reflux for 2.5 hours. To H2O (400 mL) , the reaction mixture was added under ice cooling, adjusted to pH 9 with 28% ammonia water and extracted with CHCl3 three times. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. Thereafter, the residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane = 50/50 to 75/25; v/v) . The solid substance obtained was suspended in a solution of EtOAc/hexane (1/1; v/v) and the mixture was stirred at room temperature for one hour. A solid substance was obtained by filtration to give 7-bromo-3,4- dihydroquinolin-2 (IH) -one (15.5 g, a light yellow solid) . 1H NMR (200 MHz, CDCl3, delta) : 2.59-2.68 (m, 2H),2.88-2.97 (m, 2H), 6.91-7.16 (m, 3H), 8.27 (brs, IH); ESI/APCI MS m/z 226 [M+H]+.

Reference： [1]Patent: CN106349241,2017,A .Location in patent: Paragraph 0538; 0539; 0540; 0541; 0542
[2]Patent: WO2010/38901,2010,A1 .Location in patent: Page/Page column 44
[3]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 662 - 667

7
[ 14548-51-7 ]
[ 98-16-8 ]
[ 1579950-30-3 ]