[ CAS No. 74575-17-0 ] {[proInfo.proName]}

Name: 74575-17-0|3-Bromo-4-chloroquinoline|97%
Brand: Ambeed
SKU: A432083
Price: 15.0 USD
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Quality Control of [ 74575-17-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 74575-17-0 ]

SDS Specification

Alternatived Products of [ 74575-17-0 ]

Product Details of [ 74575-17-0 ]

CAS No. :	74575-17-0	MDL No. :	MFCD05738886
Formula :	C₉H₅BrClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WRRLTIGYGHAAOP-UHFFFAOYSA-N
M.W :	242.50	Pubchem ID :	618306
Synonyms :

Calculated chemistry of [ 74575-17-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.45
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.3
Log Po/w (XLOGP3) :	3.51
Log Po/w (WLOGP) :	3.65
Log Po/w (MLOGP) :	3.12
Log Po/w (SILICOS-IT) :	3.76
Consensus Log Po/w :	3.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.17
Solubility :	0.0163 mg/ml ; 0.0000674 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.46
Solubility :	0.0833 mg/ml ; 0.000343 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.17
Solubility :	0.00162 mg/ml ; 0.00000668 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.45

Safety of [ 74575-17-0 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P280-P301+P310-P305+P351+P338	UN#:	2923
Hazard Statements:	H301-H318	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 74575-17-0 ]

* 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 [ 74575-17-0 ]
Downstream synthetic route of [ 74575-17-0 ]

[ 74575-17-0 ] Synthesis Path-Upstream 1~8

1
[ 68158-36-1 ]
[ 74575-17-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With trichlorophosphate In acetonitrile at 20℃; for 7 h; Reflux	To a stirred suspension of 3-bromo-1H-quinolin-4-one (10) (22.44 g, 0.10 mol) in acetonitrile (100 mL) phosphorus oxychloride (18.43 g, 0.12 mol) was added dropwise at room temperature. The reaction mixture was refluxed for 7 h. After cooling to room temperature it was poured on crushed ice (400 mL) and the pH was adjusted to 9 with potassium carbonate solution (10percent, 220 mL). The resulting precipitate was filtered off, washed with water, and dried in vacuo. The title compound was obtained as a brown solid (22.58 g, 93percent), mp 182-188 °C (lit., ³¹ mp 69-69,5 °C); ¹H NMR (DMSO-d₆, 400 MHz) δ 9.08 (s, 1H), 8.25 (dd, 1H, J=0.8, 8.4 Hz), 8.12 (d, 1H, J=8.0 Hz), 7.95-7.89 (m, 1H), 7.86-7.80 (m, 1H); ¹³C NMR (DMSO-d₆, 400 MHz) δ 151.6, 146.5, 140.2, 130.9, 129.5, 129.2, 126.4, 124.0, 117.7; C₉H₅BrClN (242.50); LCMS (ESI⁺) m/z 242, 244 [M+H]⁺. Anal. Calcd for C₉H₅BrClN (242.50) C, 44.58; H, 2.08; N, 5.78. Found: C, 44.43; H, 2.09; N, 5.79.

Reference： [1] Tetrahedron, 2013, vol. 69, # 45, p. 9512 - 9519
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 1831 - 1843

2
[ 64965-47-5 ]
[ 74575-17-0 ]

Reference： [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1229,1231
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 2570,2573

3
[ 611-36-9 ]
[ 74575-17-0 ]

Reference： [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1229,1231

4
[ 861357-59-7 ]
[ 74575-17-0 ]

Reference： [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2570,2573

5
[ 495409-73-9 ]
[ 74575-17-0 ]

Reference： [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2570,2573

6
[ 529-37-3 ]
[ 74575-17-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 1831 - 1843
[2] Tetrahedron, 2013, vol. 69, # 45, p. 9512 - 9519

7
[ 62-53-3 ]
[ 74575-17-0 ]

Reference： [1] Tetrahedron, 2013, vol. 69, # 45, p. 9512 - 9519

8
[ 15568-92-0 ]
[ 74575-17-0 ]

Reference： [1] Tetrahedron, 2013, vol. 69, # 45, p. 9512 - 9519

[ 74575-17-0 ] Synthesis Path-Downstream 1~25

1
[ 64965-47-5 ]
[ 74575-17-0 ]

Reference： [1]Journal of the Chemical Society,1950,p. 384,389

2
[ 74575-17-0 ]
[ 62-53-3 ]
3-bromo-4-(phenylamino)quinoline [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 2570,2573

3
[ 74575-17-0 ]
[ 140-80-7 ]
[ 32571-36-1 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 2570,2573

4
[ 74575-17-0 ]
[ 95-53-4 ]
[ 142782-12-5 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3413 - 3422

5
[ 74575-17-0 ]
[ 74575-18-1 ]
[ 74575-19-2 ]

Reference： [1]Polish Journal of Chemistry,1980,vol. 54,p. 33 - 40

7
[ 74575-17-0 ]
[ 50634-26-9 ]

Reference： [1]Polish Journal of Chemistry,1980,vol. 54,p. 33 - 40

8
[ 861357-59-7 ]
[ 74575-17-0 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 2570,2573

9
[ 495409-73-9 ]
[ 74575-17-0 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 2570,2573

10
[ 611-36-9 ]
[ 74575-17-0 ]

Reference： [1]Journal of the Chemical Society,1950,p. 384,389

11
[ 74575-17-0 ]
[ 7518-70-9 ]
[ 19968-85-5 ]
3-bromo-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate;	EXAMPLE 19 3-Bromo-N-(1-hydroxycyclohexylmethyl)-4-quinolinamine A mixture of <strong>[74575-17-0]3-bromo-4-chloroquinoline</strong> (12.1 g), 1-aminomethyl-1-cyclohexanol.HCl (8.3 g), triethylamine (7.2 g) and 30 ml of ethoxyethanol was stirred at 120 C. for 5 hours and poured into 250 ml of ice water. The solid was filtered and recrystallized from acetone. The yield was 6.5 g, mp 130-132 C. Analysis: Calculated for C16 H19 BrN2 O: 57.33%C; 5.67%H; 8.36%N. Found: 56.97%C; 5.67%H; 8.17%N.

Reference： [1]Patent: US4743601,1988,A

12
[ 74575-17-0 ]
3-bromo-N-(2-hydroxypropyl)-4-quinolinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water;	EXAMPLE 14 3-Bromo-N-(2-hydroxypropyl)-4-quinolinamine A mixture of 3 g of <strong>[74575-17-0]3-bromo-4-chloro-quinoline</strong> and 10 g of aminopropanol-2 was heated to 150 C. for 20 minutes. The mixture was cooled and poured into 120 ml of water and the product was extracted with 100 ml of ether. The ether layer was dried over sodium sulfate, the solvent removed by evaporation and the residue recrystallized from ether/hexane. The yield was 2.6 g, mp 82-83 C. Analysis: Calculated for C12 H13 BrN2 O: 51.25%C; 4.63%H; 9.96%N. Found: 50.85%C; 4.51%H; 9.80%N.

Reference： [1]Patent: US4743601,1988,A

13
[ 74575-17-0 ]
[ 7568-93-6 ]
3-bromo-N-(2-hydroxy-2-phenylethyl)-4-quinolinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1-ethoxyethanol; water;	EXAMPLE 18 3-Bromo-N-(2-hydroxy-2-phenylethyl)-4-quinolinamine A solution of 4 g of <strong>[74575-17-0]3-bromo-4-chloro-quinoline</strong> and 6 g of 2-hydroxy-2-phenyl-ethylamine was heated at 150 C. for 3 hours in 10 ml of ethoxyethanol. The mixture was cooled and poured into 150 ml of water. The product was extracted with two 50 ml portions of ether. The ether layer was dried over sodium sulfate, the solvent was evaporated and the residue was recrystallized from isopropanol. The yield was 3.0 g, mp 131-132 C. Analysis: Calculated for C17 H15 BrN2 O: 59.48%C; 4.37%H; 8.16%N. Found: 59.04%C; 4.34%H; 8.01%N.

Reference： [1]Patent: US4743601,1988,A

14
[ 74575-17-0 ]
[ 141-43-5 ]
3-bromo-N-(2-hydroxyethyl)-4-quinolinamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water;	EXAMPLE 9 3-Bromo-N-(2-hydroxyethyl)-4-quinolinamine A mixture of 9.1 g of <strong>[74575-17-0]3-bromo-4-chloro-quinoline</strong> and 2.0 g of ethanolamine was heated at 150 C. for 30 minutes. The reaction mixture was cooled, 60 ml of water was added and the precipitate was collected by filtration and recrystallized from isopropanol. The yield was 9.5 g, mp 163-165 C. Analysis: Calculated for C11 H11 BrN2 O: 49.44%C; 4.12%H; 10.49%N. Found: 49.31%C; 4.19%H; 10.32%N.

Reference： [1]Patent: US4743601,1988,A

15
[ 74575-17-0 ]
[ 1361005-33-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1831 - 1843

16
[ 74575-17-0 ]
[ 1361005-32-4 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1831 - 1843

17
[ 74575-17-0 ]
[ 71597-85-8 ]
[ 1361005-29-9 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1831 - 1843

18
[ 68158-36-1 ]
[ 74575-17-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With trichlorophosphate; In acetonitrile; at 20℃; for 7h;Reflux;	To a stirred suspension of 3-bromo-1H-quinolin-4-one (10) (22.44 g, 0.10 mol) in acetonitrile (100 mL) phosphorus oxychloride (18.43 g, 0.12 mol) was added dropwise at room temperature. The reaction mixture was refluxed for 7 h. After cooling to room temperature it was poured on crushed ice (400 mL) and the pH was adjusted to 9 with potassium carbonate solution (10%, 220 mL). The resulting precipitate was filtered off, washed with water, and dried in vacuo. The title compound was obtained as a brown solid (22.58 g, 93%), mp 182-188 C (lit., 31 mp 69-69,5 C); 1H NMR (DMSO-d6, 400 MHz) delta 9.08 (s, 1H), 8.25 (dd, 1H, J=0.8, 8.4 Hz), 8.12 (d, 1H, J=8.0 Hz), 7.95-7.89 (m, 1H), 7.86-7.80 (m, 1H); 13C NMR (DMSO-d6, 400 MHz) delta 151.6, 146.5, 140.2, 130.9, 129.5, 129.2, 126.4, 124.0, 117.7; C9H5BrClN (242.50); LCMS (ESI+) m/z 242, 244 [M+H]+. Anal. Calcd for C9H5BrClN (242.50) C, 44.58; H, 2.08; N, 5.78. Found: C, 44.43; H, 2.09; N, 5.79.

Reference： [1]Tetrahedron,2013,vol. 69,p. 9512 - 9519
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 1831 - 1843

19
[ 529-37-3 ]
[ 74575-17-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1831 - 1843
[2]Tetrahedron,2013,vol. 69,p. 9512 - 9519

20
[ 62-53-3 ]
[ 74575-17-0 ]