[ CAS No. 90767-01-4 ]

Name: 90767-01-4|4-Bromo-2-nitronaphthalen-1-amine|95%
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Quality Control of [ 90767-01-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 90767-01-4 ]

SDS Specification

Alternatived Products of [ 90767-01-4 ]

Product Details of [ 90767-01-4 ]

CAS No. :	90767-01-4	MDL No. :	MFCD23703106
Formula :	C₁₀H₇BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HDIRDIWTOYQFJI-UHFFFAOYSA-N
M.W :	267.08 g/mol	Pubchem ID :	19027050
Synonyms :

Calculated chemistry of [ 90767-01-4 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	64.87
TPSA :	71.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.8
Log Po/w (XLOGP3) :	3.56
Log Po/w (WLOGP) :	3.1
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	0.69
Consensus Log Po/w :	2.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.17
Solubility :	0.0182 mg/ml ; 0.0000682 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.75
Solubility :	0.00471 mg/ml ; 0.0000176 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.95
Solubility :	0.0301 mg/ml ; 0.000113 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.44

Safety of [ 90767-01-4 ]

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 [ 90767-01-4 ]

* 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 [ 90767-01-4 ]
Downstream synthetic route of [ 90767-01-4 ]

[ 90767-01-4 ] Synthesis Path-Upstream 1~12

1
[ 90767-01-4 ]
[ 74924-94-0 ]

Reference： [1] Journal of the Chemical Society, 1935, p. 1850,1852
[2] Journal of Organic Chemistry, 1961, vol. 26, p. 3214 - 3216
[3] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3347 - 3355
[4] Molecular Pharmacology, 2013, vol. 84, # 5, p. 726 - 735

2
[ 7499-73-2 ]
[ 90767-01-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sulfuric acid In ethanol at 20℃; for 4 h;	A solution of 1-(acethylamino)-4-bromo-2-nitronaphthalene (535 mg, 1.73 mmol) in 50 percent H2SO4 (10 ml) and EtOH (10 ml) was stirredat ambient temperature for 4hrs. The suspension was washed with diethyl ether. The product(93 percent, orange solid) was filtered and dried in vacuo. 1H – NMR (400 MHz, CDCl3) δ 8.47 (s,1H), 8.23 (d, J = 8.4 Hz, 1H), 7.99 (d, J = 8.4 Hz, 1H), 7.78 (dd, J = 8.2, 7.2 Hz, 1H), 7.65(dd, J = 8.1, 7.3 Hz, 1H), 7.37 (bs, 2H)

Reference： [1] Molecular Pharmacology, 2013, vol. 84, # 5, p. 726 - 735
[2] Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 250
[3] Journal of the Chemical Society, 1943, p. 321
[4] Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 250
[5] Journal of the Chemical Society, 1892, vol. 61, p. 769
[6] Chem. News J. Ind. Sci., 1892, vol. 65, p. 59[7] Chemische Berichte, 25 Ref. <1892>,750,
[8] Journal of the Chemical Society, 1885, vol. 47, p. 523[9] Journal of the Chemical Society, 1895, vol. 67, p. 912
[10] Journal of Organic Chemistry, 1961, vol. 26, p. 3214 - 3216

3
[ 91394-66-0 ]
[ 90767-01-4 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 250
[2] Journal of Organic Chemistry, 1961, vol. 26, p. 3214 - 3216
[3] Molecular Pharmacology, 2013, vol. 84, # 5, p. 726 - 735

4
[ 2298-07-9 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1910, vol. 97, p. 1716
[2] Molecular Pharmacology, 2013, vol. 84, # 5, p. 726 - 735

5
[ 871901-44-9 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1910, vol. 97, p. 1716

6
[ 607-23-8 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1935, p. 1850,1852
[2] Journal of the Chemical Society, 1935, p. 1596
[3] Journal of the Chemical Society, 1935, p. 1850,1852
[4] Journal of the Chemical Society, 1935, p. 1596
[5] Journal of the Chemical Society, 1935, p. 1850,1852
[6] Journal of the Chemical Society, 1935, p. 1596

7
[ 2437-30-1 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1892, vol. 61, p. 769

8
[ 15309-82-7 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1910, vol. 97, p. 1716

9
[ 500699-70-7 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1910, vol. 97, p. 1716

10
[ 64-17-5 ]
[ 7499-73-2 ]
[ 7664-41-7 ]
[ 90767-01-4 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1876, vol. 183, p. 250

11
[ 67-66-3 ]
[ 607-23-8 ]
[ 7726-95-6 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1935, p. 1596

12
[ 607-23-8 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 90767-01-4 ]

Reference： [1] Journal of the Chemical Society, 1935, p. 1596

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Yield	Reaction Conditions	Operation in experiment
93%	With sulfuric acid; In ethanol; at 20℃; for 4h;	A solution of 1-(acethylamino)-4-bromo-2-nitronaphthalene (535 mg, 1.73 mmol) in 50 % H2SO4 (10 ml) and EtOH (10 ml) was stirredat ambient temperature for 4hrs. The suspension was washed with diethyl ether. The product(93 %, orange solid) was filtered and dried in vacuo. 1H - NMR (400 MHz, CDCl3) delta 8.47 (s,1H), 8.23 (d, J = 8.4 Hz, 1H), 7.99 (d, J = 8.4 Hz, 1H), 7.78 (dd, J = 8.2, 7.2 Hz, 1H), 7.65(dd, J = 8.1, 7.3 Hz, 1H), 7.37 (bs, 2H)
80%	With hydrogenchloride; In tetrahydrofuran; ethanol; water; for 8h;Reflux; Inert atmosphere;	In a two-necked flask, Compound 2-1 (38.0 g, 122.9 mmol), 2M HCl (246 ml), THF (500 ml) 250 ml of EtOH were heated under reflux conditions in an argon atmosphere for 8 hours.After completion of the reaction, the reaction mixture was cooled to room temperature and the organic solvent was concentrated under reduced pressure.The concentrate was neutralized with aqueous 2M NaOH, transferred to a separatory funnel and extracted with CH2Cl2. The extract was dried over MgSO4 and then purified by silica gel column chromatography to obtain 28.4 g (yield 80%, MS [M + H] + = 267) of Compound 4-2 as a solid.
80%	With hydrogenchloride; In tetrahydrofuran; ethanol; water; for 8h;Inert atmosphere; Reflux;	Compound 4-1 (38.0 g, 122.9 mmol), 2M HCl (246 ml, 491.7 mmol), THF (500 ml) and EtOH (250 ml) were heated under reflux in an argon atmosphere for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic solvent was concentrated under reduced pressure. The concentrate was neutralized with aqueous 2M NaOH, transferred to a separatory funnel and extracted with CH2Cl2. The extract was dried over MgSO4 and then purified by silica gel column chromatography to obtain 28.4 g (yield 80%, MS[M+H]+=267) of Compound 4-2 as a solid.

Yield	Reaction Conditions	Operation in experiment
0.9 g (74%)	With triethylamine; In tetrahydrofuran; ethanol;	a. 4-Bromo-1-ethoxalylamino-2-nitronaphthalene A solution of ethyl oxalylchloride (1.1 ml, 9.8 mmol) in 15 ml of dry tetrahydrofuran was added dropwise to a solution of <strong>[90767-01-4]1-amino-4-bromo-2-nitronaphthalene</strong> (0.9 g, 3.2 mmol) and dry triethylamine (1.37 ml, 9.8 mmol) in 20 ml of dry tetrahydrofuran with stirring at 0 C. The mixture was stirred for 1 h at room temperature, and filtered. The filtrate was evaporated to dryness, and the oily residue was boiled in 25 ml of 96% ethanol for 15 min. After cooling on ice, the solid product was isolated by filtration and washed with a small amount of cold ethanol to give 0.9 g (74%) of the title compound. M.p. 191-192 C.; 1 H-NMR (CDCl3) 1.4 (t, J =7 Hz, 3H, CH3), 4.40 (q, J =7 Hz, 2H, CH2), 7.43-8.33 (m, 5H, ArH), 10.0 (broad s, 1H, NH).
4.5 g (82%)	With triethylamine; In tetrahydrofuran;	a. 4-Bromo-1-ethoxalylamino-2-nitronaphthalene To a solution of 4.0 g (15.0 mmol) <strong>[90767-01-4]4-bromo-2-nitro-1-naphthylamine</strong> and 4.0 ml (29.1 mmol) dry triethylamine in 200 ml dry tetrahydrofuran was added a solution of 3.8 ml (34.2 mmol) ethyl oxalylchloride in 30 ml dry tetrahydrofuran. The reaction mixture was stirred at 25 C. for 24 h, and then filtered and evaporated in vacuo. The residue was recrystallized (ethanol-water) to give 4.5 g (82%) of 4-bromo-1-ethoxalylamino-2-nitronaphthalene. M.p. 190 C.
0.9 g (74%)	With triethylamine; In tetrahydrofuran; ethanol;	a. 4-Bromo-1-ethoxalylamino-2-nitronaphthalene A solution of ethyl oxalylchloride (1.1 ml, 9.8 mmol) in 15 ml of dry tetrahydrofuran was added dropwise to a solution of <strong>[90767-01-4]1-amino-4-bromo-2-nitronaphthalene</strong> (0.9 g, 3.2 mmol) and dry triethylamine (1.37 ml, 9.8 mmol) in 20 ml of dry tetrahydrofuran with stirring at 0 C. The mixture was stirred for 1 h at room temperature, and filtered. The filtrate was evaporated to dryness, and the oily residue was boiled in 25 ml of 96% ethanol for 15 min. After cooling on ice, the solid product was isolated by filtration and washed with a small amount of cold ethanol to give 0.9 g (74%) of the title compound. M.p. 191-192 C.; 1 H-NMR (CDCl3): 1.4 (t, J=7 Hz, 3H, CH3), 4.40 (q, J=7 Hz, 2H, CH2), 7.43-8.33 (m, 5H, ArH), 10.0 (broad s, 1H, NH).

4.5 g (82%)	With triethylamine; In tetrahydrofuran;	a. 4-Brono-1-ethoxalylamino-2-nitronaphthaIene To a solution of 4.0 g (15.0 mmol) <strong>[90767-01-4]4-bromo-2-nitro-1-naphthylamine</strong> and 4.0 ml (29.1 mmol) dry triethylamine in 200 ml dry tetrahydrofuran was added a solution of 3.8 ml (34.2 mmol) ethyl oxalylchloride in 30 ml dry tetrahydrofuran. The reaction mixture was stirred at 25 C. for 24 h, and then filtered and evaporated in vacuo. The residue was recrystallized (ethanol-water) to give 4.5 g (82%) of 4-bromo-1-ethoxalylamino-2-nitronaphthalene. M.p. 190-1 C.
0.9 g (74%)	With triethylamine; In tetrahydrofuran; ethanol;	a. 4-Bromo-1-ethoxalylamino-2-nitronaphthalene A solution of ethyl oxalylchloride 1.1 ml, 9.8 mmol) in 15 ml of dry tetrahydrofuran was added dropwise to a solution of <strong>[90767-01-4]1-amino-4-bromo-2-nitronaphthalene</strong> (0.9 g, 3.2 mmol) and dry triethylamine (1.37 ml, 9.8 mmol) in 20 ml of dry tetrahydrofuran with stirring at 0 C. The mixture was stirred for 1 h at room temperature, and filtered. The filtrate was evaporated to dryness, and the oily residue was boiled in 25 ml of 96% ethanol for 15 min. After cooling on ice, the solid product was isolated by filtration and washed with a small amount of cold ethanol to give 0.9 g (74%) of the title compound. M.p. 191-192 C.; 1 H-NMR (CDCl3): 1.4 (t, J=7 Hz, 3H, CH3), 4.40 (q, J=7 Hz, 2H, CH2), 7.43-8.33 (m, 5H, ArH), 10.0 (broad s, 1H, NH).

Yield	Reaction Conditions	Operation in experiment
72%		3-neck flask was put in the compound 4-2 (25.0g, 93.6mmol) and 1M HCl 187ml, 300ml of water was cooled to 0 was stirred for 1 hour.300 ml of NaNO2 (12.9 g, 187.2 mmol) aqueous solution was added dropwise to the reaction solution at the same temperature, followed by stirring for 1 hour.Thereafter, 400 ml of an aqueous solution of potassium iodide (70.3 g, 280.8 mmol) was slowly added dropwise and the mixture was stirred for 5 hours.After completion of the reaction, Na2S2O3 aqueous solution was added to the separatory funnel, which was then extracted with ethyl acetate.The extract was dried over MgSO4 and purified by silica gel column chromatography to give 25.5 g (yield 72%,) of compound 4-3 as a solid.
72%		To the three-necked flask, Compound 4-2 (25.0 g, 93.6 mmol), 1M HCl (187 ml) and water (300 ml) were added and the mixture was cooled to 0 C and stirred for 1 hour. 300 ml of NaNO2 (12.9 g, 187.2 mmol) aqueous solution was added dropwise to the reaction solution at the same temperature, followed by stirring for 1 hour. Then, 400 ml of an aqueous solution of potassium iodide (70.3 g, 280.8 mmol) was slowly added dropwise and the mixture was stirred for 5 hours.After completion of the reaction, Na2S2O3 aqueous solution was added to the separatory funnel, which was then extracted with ethyl acetate. The extract was dried over MgSO4 and purified by silica gel column chromatography to give 25.5 g (yield 72%, MS[M+H]+=378) of compound 4-3 as a solid.
72%		In a three-necked flask Compound 4-2 (25.0g, 93.6mmol), 187ml of 1M HCl, and 300ml of water were added, cooled to 0 C, and stirred for 1 hour. At the same temperature, 300 ml of a NaNO 2 (12.9 g, 187.2 mmol) aqueous solution was added dropwise to the reaction solution, followed by stirring for 1 hour. Then, 400 ml of potassium iodide (70.3 g, 280.8 mmol) aqueous solution was slowly added dropwise and stirred for 5 hours. After the reaction was completed, Na2S2O3 aqueous solution was added and transferred to a separatory funnel, followed by extraction with ethyl acetate. The extract was dried over MgSO 4 and purified by silica gel column chromatography to obtain 25.5 g of a solid compound 4-3 (yield 72%

[ CAS No. 90767-01-4 ]

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