603-87-2|2-Amino-6-nitrophenol| Ambeed

Structure of 603-87-2

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Quality Control of [ 603-87-2 ] Purity: 95% SDS Specification

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Product Details of [ 603-87-2 ]

CAS No. :	603-87-2
Formula :	C₆H₆N₂O₃
M.W :	154.12
SMILES Code :	NC1=C(O)C(=CC=C1)[N+]([O-])=O
MDL No. :	MFCD02751769
InChI Key :	AACMNEWXGKOJJK-UHFFFAOYSA-N
Pubchem ID :	5127291

Safety of [ 603-87-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 603-87-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	41.69
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	92.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.6
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.89
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.3
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.49
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.14
Solubility	1.11 mg/ml ; 0.00722 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.14
Solubility	0.11 mg/ml ; 0.000716 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.83
Solubility	22.8 mg/ml ; 0.148 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.1 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	4.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.99

Application In Synthesis of [ 603-87-2 ]

* 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 [ 603-87-2 ]
Downstream synthetic route of [ 603-87-2 ]

[ 603-87-2 ] Synthesis Path-Upstream 1~7

1
[ 573-56-8 ]
[ 603-87-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen In ethyl acetate for 5 h;	To a nitrogen flushed solution of 2, 6-dinitrophenol (10 g, 54.3 mmol) in ethyl acetate (100 ml) was added 10percent palladium on carbon (0.5 g) and the resulting mixture stirred under a balloon of hydrogen for 5 hours. The catalyst was removed by filtration and the filtrate evaporated to give the title compound (8.0 g, 95percent). 1H NMR (400 MHz, CDC13) 8 3.95 (2H, br s), 6.78 (1H, t, J 8. 4 and 8.0), 6.95 (1H, dd, J7. 6 and 1.2), 7.46 (1H, DD, J 8. 6 AND 1.2).
92%	With palladium 10% on activated carbon; hydrogen In methanol for 1 h;	To a of solution of 2,6-dinitrophenol (5.43 mmol, 1.00 g) in methanol (100 mL), 10percent palladium on activated carbon (10 wtpercent of 2,6-dinitrophenol, 0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for one hour. The reaction was monitored closely by thin layer chromatography to avoid over reduction.1 Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a brown solid. Silica gel column chromatography (10:1 hexanes/ethyl acetate) provided a crystalline red solid in a 92percent yield.
60%	Stage #1: With sodium sulfide; ammonia; ammonium chloride In water at 70℃; for 2 h; Stage #2: With hydrogenchloride In water	2-Amino-6-nitrophenol: A suspension of 2,6-dinitrophenol 5.0 g (27 mmol), ammonium hydroxide (3 ml) and ammonium chloridel4. 3 g (270 mmol) in 30 ml of water was heated to 70°C. A solution of sodium sulfide nonahydrate (24.19 g, 100 mmol) in water was added and the resulting mixture stirred at 70°C for 2h. The reaction was cooled to room temperature, acidified (pH 3.2) with 2N HC1, and the brown precipitate separated by filtration. The filtrate was extracted with chloroform (6 x 75 ml), the organic extracts combined with the precipitate, and evaporated in-vacuo to yield 2.5 g (60 percent) of product as a dark brown solid. 1H NMR (CDC13) 5 4.09 (s, 2H), 6.78 (t, 1H, J = 8. 2 Hz), 6.95 (d, 1H, J = 7.8 Hz), 7.47 (d, 1H, J = 8.6 Hz), 10.73 (s, 3H).

48%	With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 144 h;	Step 1 2-Amino-6-nitrophenol 8.6 g of 2,6-dinitrophenol (46.71 mmol) were dissolved in 95 ml of ethyl acetate. The solution was degassed and then 0.86 g (10percent by weight) of palladium on carbon at 10percent was added. The reaction medium was stirred under a hydrogen atmosphere for 6 days at ambient temperature. The reaction medium was filtered through celite and concentrated to dryness. The residue obtained was chromatographed on a cartridge of silica gel eluted with 100percent dichloromethane to 80/20 dichloromethane/ethyl acetate. 3.43 g of product were obtained in the form of a dark copper solid. Yield=48percent.
2.41 g	With palladium 10% on activated carbon; hydrogen In ethyl acetate for 5 h;	(1) A solution of 2,6-dinitrophenol (6.31 g, 27.4 mmol) in ethyl acetate (50 mL) was cooled to 0°C, 10percent palladium activated carbon (250 mg) was added thereto, and the mixture was stirred under a hydrogen atmosphere for 5 hr. The reaction mixture was filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure. The resulting residue was diluted with chloroform, anhydrous sodium sulfate was added thereto, and the mixture was stirred for 15 min. Anhydrous sodium sulfate was filtered off, followed by concentration under reduced pressure. The resulting residue was powdered with hexane and collected by filtration to afford 2-amino-6-nitrophenol as a brown amorphous substance (2.41 g).

References: [1] Patent: WO2005/28445, 2005, A2, . Location in patent: Page/Page column 38.
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525.
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1319 - 1321.
[4] Patent: WO2005/44793, 2005, A2, . Location in patent: Page/Page column 135.
[5] Patent: US2014/309208, 2014, A1, . Location in patent: Paragraph 0237; 0238.
[6] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2512 - 2515.
[7] Justus Liebigs Annalen der Chemie, 1880, vol. 205, p. 72.
[8] Chemische Berichte, 1959, vol. 92, p. 407,410.
[9] Patent: US5496853, 1996, A, .
[10] Patent: US2006/264631, 2006, A1, . Location in patent: Page/Page column 27; 39.
[11] Patent: EP2687507, 2014, A1, . Location in patent: Paragraph 0347.

2
[ 95-55-6 ]
[ 603-87-2 ]
[ 99-57-0 ]

References: [1] Russian Journal of Organic Chemistry, 1997, vol. 33, # 3, p. 348 - 352.

3
[ 74255-39-3 ]
[ 603-87-2 ]

References: [1] Journal of the Chemical Society, 1927, p. 1057.

4
[ 614-80-2 ]
[ 603-87-2 ]

References: [1] Journal of the Chemical Society, 1927, p. 1057.

5
[ 7664-93-9 ]
[ 860728-40-1 ]
[ 603-87-2 ]

References: [1] Chemische Berichte, 1914, vol. 47, p. 1007.

6
[ 7664-93-9 ]
[ 861528-05-4 ]
[ 603-87-2 ]

References: [1] Chemische Berichte, 1914, vol. 47, p. 1007.

7
[ 7647-01-0 ]
[ 860728-44-5 ]
[ 603-87-2 ]

References: [1] Journal of the Chemical Society, 1928, p. 3070.

[ 603-87-2 ] Synthesis Path-Downstream 1~35

1
[ 573-56-8 ]
[ 603-87-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; for 5h;	To a nitrogen flushed solution of 2, 6-dinitrophenol (10 g, 54.3 mmol) in ethyl acetate (100 ml) was added 10% palladium on carbon (0.5 g) and the resulting mixture stirred under a balloon of hydrogen for 5 hours. The catalyst was removed by filtration and the filtrate evaporated to give the title compound (8.0 g, 95%). 1H NMR (400 MHz, CDC13) 8 3.95 (2H, br s), 6.78 (1H, t, J 8. 4 and 8.0), 6.95 (1H, dd, J7. 6 and 1.2), 7.46 (1H, DD, J 8. 6 AND 1.2).
92%	With palladium 10% on activated carbon; hydrogen; In methanol; for 1h;	To a of solution of 2,6-dinitrophenol (5.43 mmol, 1.00 g) in methanol (100 mL), 10% palladium on activated carbon (10 wt% of 2,6-dinitrophenol, 0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for one hour. The reaction was monitored closely by thin layer chromatography to avoid over reduction.1 Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a brown solid. Silica gel column chromatography (10:1 hexanes/ethyl acetate) provided a crystalline red solid in a 92% yield.
60%		2-Amino-6-nitrophenol: A suspension of 2,6-dinitrophenol 5.0 g (27 mmol), ammonium hydroxide (3 ml) and ammonium chloridel4. 3 g (270 mmol) in 30 ml of water was heated to 70C. A solution of sodium sulfide nonahydrate (24.19 g, 100 mmol) in water was added and the resulting mixture stirred at 70C for 2h. The reaction was cooled to room temperature, acidified (pH 3.2) with 2N HC1, and the brown precipitate separated by filtration. The filtrate was extracted with chloroform (6 x 75 ml), the organic extracts combined with the precipitate, and evaporated in-vacuo to yield 2.5 g (60 %) of product as a dark brown solid. 1H NMR (CDC13) 5 4.09 (s, 2H), 6.78 (t, 1H, J = 8. 2 Hz), 6.95 (d, 1H, J = 7.8 Hz), 7.47 (d, 1H, J = 8.6 Hz), 10.73 (s, 3H).

48%	With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; for 144h;	Step 1 2-Amino-6-nitrophenol 8.6 g of 2,6-dinitrophenol (46.71 mmol) were dissolved in 95 ml of ethyl acetate. The solution was degassed and then 0.86 g (10% by weight) of palladium on carbon at 10% was added. The reaction medium was stirred under a hydrogen atmosphere for 6 days at ambient temperature. The reaction medium was filtered through celite and concentrated to dryness. The residue obtained was chromatographed on a cartridge of silica gel eluted with 100% dichloromethane to 80/20 dichloromethane/ethyl acetate. 3.43 g of product were obtained in the form of a dark copper solid. Yield=48%.
	palladium-carbon; In methanol;	REFERENCE EXAMPLE 1 Synthesis of 2-amino-6-nitrophenol 100 ml of methanol was added to 5.0 g of 2,6-dinitrophenol in a vessel. The inside of the vessel was purged with argon. About 1.5 g of 10% palladium-carbon was added thereto, the inside of the vessel was purged with argon and then with hydrogen, and the reaction mixture was stirred at room temperature overnight. After the completion of the reaction, the palladium-carbon was removed by filtration with Celite, and the filtrate was concentrated to provide 4.1 g of the title compound, that is, 2-amino-6-nitrophenol. 1 H NMR (CDCl3) delta (ppm): 10.70 (s, 1H, OH), 7.46(dd, J=2.0Hz, 8.2Hz, 1H, ArH), 6.94(dd, J=2.0Hz, 7.7Hz, 1H, ArH), 6.76(dd, J=8.2Hz, 7.7Hz, 1H, ArH), 3.70-4.50(br, 2H, NH2)
		Example 14 2-Amino-6-nitro phenol: Ref.: WO 96/11917. A slurry of 2,6-dinitro phenol (20% in H2O, 5 g, 0.0271 mol), NH4Cl (14.30 g, 0.267 mol), and ammonium hydroxide solution (3 mL) was heated in a 70 C. bath. A warm solution of Na2S-9H2O (24.19 g, 0.1 mol) in H2O (23 mL) was added to the slurry and the resulting orange suspension was heated with stirring for 3 h, then allowed to cool to room temperature. The mixture was cooled in an ice bath and slowly acidified with 6 N HCl to pH 2. The mixture was filtered and the filtrate was extracted with CHCl3 (3*75 mL). The combined organic extracts were concentrated in vacuo and the crude material was adsorbed onto silica gel. Purification by silica gel chromatography, eluding with 25% hexane/CH2Cl2 then CH2Cl2, afforded the title compound (1.47 g) as a brick red powder. MS (ESI-POS): [M+H]+=155.
2.41 g	With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 5h;	(1) A solution of 2,6-dinitrophenol (6.31 g, 27.4 mmol) in ethyl acetate (50 mL) was cooled to 0C, 10% palladium activated carbon (250 mg) was added thereto, and the mixture was stirred under a hydrogen atmosphere for 5 hr. The reaction mixture was filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure. The resulting residue was diluted with chloroform, anhydrous sodium sulfate was added thereto, and the mixture was stirred for 15 min. Anhydrous sodium sulfate was filtered off, followed by concentration under reduced pressure. The resulting residue was powdered with hexane and collected by filtration to afford 2-amino-6-nitrophenol as a brown amorphous substance (2.41 g).
	With palladium on activated charcoal; hydrogen; In 1,2-dichloro-ethane; at 35 - 40℃; under 1500.15 - 4500.45 Torr;Large scale;	Mixing 2,6-dinitrophenol (II)-1,2-dichloroethane solution obtained in step 1), 15 kg of palladium carbon, venting with nitrogen, stirring, and introducing at 35-40 C 0.2 to 0.6 MPa of hydrogen, stirred to the end of the reaction; the catalyst was recovered by filtration, and allowed to stand for separation to obtain a 2-amino-6-nitrophenol (III)-dichloroethane solution.

References: [1]Patent: WO2005/28445,2005,A2 .Location in patent: Page/Page column 38.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3521 - 3525.
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 1319 - 1321.
[4]Patent: WO2005/44793,2005,A2 .Location in patent: Page/Page column 135.
[5]Patent: US2014/309208,2014,A1 .Location in patent: Paragraph 0237; 0238.
[6]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2512 - 2515.
[7]Justus Liebigs Annalen der Chemie,1880,vol. 205,p. 72.
[8]Chemische Berichte,1959,vol. 92,p. 407,410.
[9]Patent: US5496853,1996,A .
[10]Patent: US2006/264631,2006,A1 .Location in patent: Page/Page column 27; 39.
[11]Patent: EP2687507,2014,A1 .Location in patent: Paragraph 0347.
[12]Patent: CN110156712,2019,A .Location in patent: Paragraph 0043; 0046-0047.

2
[ 603-87-2 ]
[ 74255-39-3 ]

References: [1]Journal of the Chemical Society,1928,p. 3048.

3
[ 603-87-2 ]
[ 33842-02-3 ]
[ 43183-94-4 ]

References: [1]Angewandte Chemie,1973,vol. 85,p. 446 - 447.

4
[ 603-87-2 ]
[ 102-01-2 ]
[ 93021-17-1 ]

References: [1]Bulletin of the Chemical Society of Japan,1963,vol. 36,p. 492 - 500.

5
[ 614-80-2 ]
[ 603-87-2 ]

References: [1]Journal of the Chemical Society,1927,p. 1057.

6
[ 603-87-2 ]
[ 101084-62-2 ]