[ CAS No. 59649-56-8 ] {[proInfo.proName]}

Name: 59649-56-8|2,3-Diaminophenol|97%
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Quality Control of [ 59649-56-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 59649-56-8 ]

CAS No. :	59649-56-8	MDL No. :	MFCD00075199
Formula :	C₆H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PCAXITAPTVOLGL-UHFFFAOYSA-N
M.W :	124.14	Pubchem ID :	579937
Synonyms :

Calculated chemistry of [ 59649-56-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	3.0
Molar Refractivity :	37.27
TPSA :	72.27 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.47
Log Po/w (XLOGP3) :	0.2
Log Po/w (WLOGP) :	0.57
Log Po/w (MLOGP) :	0.18
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	0.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.23
Solubility :	7.33 mg/ml ; 0.059 mol/l
Class :	Very soluble
Log S (Ali) :	-1.28
Solubility :	6.57 mg/ml ; 0.0529 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.06
Solubility :	10.8 mg/ml ; 0.0871 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 59649-56-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 59649-56-8 ]

* 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 [ 59649-56-8 ]
Downstream synthetic route of [ 59649-56-8 ]

[ 59649-56-8 ] Synthesis Path-Upstream 1~9

1
[ 59649-56-8 ]
[ 122-51-0 ]
[ 67021-83-4 ]

Reference： [1] Heterocycles, 1994, vol. 38, # 11, p. 2415 - 2422

2
[ 59649-56-8 ]
[ 64-18-6 ]
[ 67021-83-4 ]

Reference： [1] Helvetica Chimica Acta, 1952, vol. 35, p. 1736,1740

3
[ 59649-56-8 ]
[ 517-21-5 ]
[ 17056-99-4 ]

Reference： [1] Chemical Communications, 2015, vol. 51, # 84, p. 15458 - 15461
[2] Helvetica Chimica Acta, 1951, vol. 34, p. 427,429
[3] Journal of Organic Chemistry, 1951, vol. 16, p. 438,441

4
[ 59649-56-8 ]
[ 17056-99-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3256 - 3263

5
[ 603-85-0 ]
[ 59649-56-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen In ethanol at 20℃; for 12 h;	Example 1 : 1 l-(3-chlorophenyl)-6-hydroxy-3,3-dimethyl-2,3,4,5,10,l 1-hexahydro- dibenzo\|", e]\\ ,41diazepin- 1 -one (6).; Step l; A mixture of 2-amino-3-nitrophenol (10.0 g, 64.9 mmol), 10percent Pd/C in ethanol (150 mL), was hydrogenated at room temperature for 12 h. Then, the reaction mixture was degassed with nitrogen. The catalyst was removed by filtration and washed extensively with ethanol. The filtrate was evaporated to give 8.0 g (99percent) of the desired product as a black solid.
99%	With hydrogen In ethanol at 20℃; for 12 h;	Step 3. synthesis of 2,3-diaminophenol (4). ; <n="39"/>A mixture of 2-amino-3-nitrophenol (10.0 g, 64.9 mmol), 10percent Pd/C in ethanol (150 mL), was hydrogenated at room temperature for 12h. Then, the reaction mixture was degassed with nitrogen. The catalyst was removed by filtration and washed extensively with ethanol. The filtrate was evaporated to give 8.0 g (99percent) of the desired product as a black solid.
98%	at 20℃; for 6 h;	General procedure: To a solution of 4-amino-3-nitrophenol (28, 5.0 g, 32.44 mmol) was added cautiously Raney-Ni (1.0 g, wet weight) under N₂ atmosphere. Then the suspended solution was degassed with H₂ three times. The mixture was stirred for 6 h at room temperature under H₂ balloon. The resulting reaction mixture was filtered through a celite pad. The filtrate was evaporated directly under reduced pressure to provide the intermediate 29 (3.83 g, 95percent yield) as a black solid which was used directly in the next step.

Reference： [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3309 - 3324
[2] Patent: WO2008/99019, 2008, A1, . Location in patent: Page/Page column 49
[3] Patent: WO2008/99022, 2008, A1, . Location in patent: Page/Page column 37-38
[4] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 380 - 396
[5] Helvetica Chimica Acta, 1951, vol. 34, p. 427,429
[6] Chemische Berichte, 1938, vol. 71, p. 34,41
[7] Bulletin de la Societe Chimique de France, 1927, vol. <4>41, p. 449
[8] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3256 - 3263
[9] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7105 - 7126
[10] Archives of Pharmacal Research, 2017, vol. 40, # 4, p. 469 - 479

6
[ 66-56-8 ]
[ 59649-56-8 ]

Reference： [1] Journal of Organic Chemistry, 1951, vol. 16, p. 438,441
[2] Journal of Organic Chemistry, 1951, vol. 16, p. 438,441
[3] Zeitschrift fuer Naturforschung, 1956, vol. 11 b, p. 68,72
[4] Bulletin de la Societe Chimique de France, 1910, vol. <4>7, p. 955
[5] Journal of Chemical Research, Miniprint, 1982, # 3, p. 834 - 851
[6] Patent: US5106862, 1992, A,

7
[ 872-50-4 ]
[ 80-05-7 ]
[ 2526-64-9 ]
[ 59649-56-8 ]

Reference： [1] Patent: US2009/30173, 2009, A1,

8
[ 767-66-8 ]
[ 59649-56-8 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1992, vol. 28, # 8, p. 956 - 961[2] Khimiya Geterotsiklicheskikh Soedinenii, 1992, # 8, p. 1135 - 1140
[3] Pharmaceutical Chemistry Journal, 1991, vol. 25, # 12, p. 900 - 906[4] Khimiko-Farmatsevticheskii Zhurnal, 1991, vol. 25, # 12, p. 49 - 53

9
[ 554-84-7 ]
[ 59649-56-8 ]

Reference： [1] Zeitschrift fuer Naturforschung, 1956, vol. 11 b, p. 68,72

[ 59649-56-8 ] Synthesis Path-Downstream 1~88

1
[ 59649-56-8 ]
[ 79591-73-4 ]
[ 79556-66-4 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1110 - 1116

2
[ 767-66-8 ]
[ 59649-56-8 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 956 - 961
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1135 - 1140
[2]Pharmaceutical Chemistry Journal,1991,vol. 25,p. 900 - 906
Khimiko-Farmatsevticheskii Zhurnal,1991,vol. 25,p. 49 - 53

3
[ 59649-56-8 ]
[ 99-61-6 ]
[ 109-77-3 ]
2,7,8-triamino-4-(3-nitro-phenyl)-4H-chromene-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751

4
[ 59649-56-8 ]
[ 3132-99-8 ]
[ 109-77-3 ]
2,7,8-triamino-4-(3-bromo-phenyl)-4H-chromene-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751

5
[ 59649-56-8 ]
[ 7311-34-4 ]
[ 109-77-3 ]
2,7,8-triamino-4-(3,5-dimethoxy-phenyl)-4H-chromene-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751

6
[ 59649-56-8 ]
[ 2973-76-4 ]
[ 109-77-3 ]
2,7,8-triamino-4-(3-bromo-4-hydroxy-5-methoxy-phenyl)-4H-chromene-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751

7
[ 59649-56-8 ]
[ 24964-64-5 ]
[ 109-77-3 ]
2,7,8-triamino-4-(3-cyano-phenyl)-4H-chromene-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751

8
[ 59649-56-8 ]
[ 18268-68-3 ]
[ 109-77-3 ]
2,7,8-triamino-4-(3-chloro-4,5-dimethoxy-phenyl)-4H-chromene-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751

9
[ 59649-56-8 ]
[ 6948-30-7 ]
[ 109-77-3 ]
[ 475576-83-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With piperidine; In ethanol; at 80℃; for 16h;Inert atmosphere;	General procedure: To a mixture of 9 (100mg, 0.74mmol) (the general procedure for the synthesis of intermediate 9 was presented in supporting information), 3-chlorobenzaldehyde (104mg, 0.74mmol) and ethyl 2-cyanoacetate (83muL, 0.78mmol) in anhydrous EtOH (5mL) was added piperdine (136muL, 1.48mmol). The reaction mixture was stirred for 16hat 80°C under N2 atmosphere. The resulting reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography eluting with CH2Cl2/MeOH (200:1-100:1, v/v) to afford the title compound (9a) as a slight yellow solid (210mg, 77percent yield).

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 380 - 396
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751

10
[ 59649-56-8 ]
[ 100-07-2 ]
2,3-bis[(4-methoxybenzoyl)amino]phenoxy 4-methoxybenzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 859 - 872

11
[ 59649-56-8 ]
[ 109-77-3 ]
[ 475576-83-1 ]

Yield	Reaction Conditions	Operation in experiment
82%		A suspension of 3-bromo-4,5-dimethoxybenzaldehyde (1500 g, 6.12 moles, 1.1 eq) and malononitrile (404 g, 6.12 moles, 1.1 eq) in ethanol 99percent (12 L, 7 volumes) was stirred at room temperature under N2(g). Dimethylisopropylamine (339 mL, 2.78 moles, 0.5 eq) was added slowly (which caused an exotherm from about 14°C to about 26 0C) and the reaction mixture was stirred at room temperature for about 2 h under N2(g). The yellow thick suspension was analyzed by etaPLC to monitor the appearance of the Knoevenagel intermediate and the disappearance of the aldehyde. <strong>[59649-56-8]2,3-Diaminophenol</strong> (690.66 g, 5.56 moles, 1 eq) was added and the reaction mixture was stirred at room temperature overnight. The resulting beige-brown suspension was filtered and the cake was washed with cold CH2Cb (3000 mL). The solids were dried under vacuum to give 2,7,8-triamino-4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromene (1.9 kg, 82percent yield). eta NMR (300 MHz) (DMSO-c/6, ppm): 3.71(s, 3H), 3.82 (s, 3H), 4.43 (s, 2H), 4.56 (s, IH), 4.70 (s, 2H), 6.09 (d, J= 8 Hz, IH), 6.26 (d, J= 8 Hz, IH), 6.76 (s, 2H), 6.78 (d, J= 2 Hz, IH), 6.90 (d, J= 2 Hz, IH).

Reference： [1]Patent: WO2008/5572,2008,A2 .Location in patent: Page/Page column 35

12
[ 59649-56-8 ]
[ 797047-27-9 ]
C₁₀H₁₂N₄O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 5535 - 5538

13
[ 59649-56-8 ]
[ 177477-41-7 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2853 - 2863

14
[ 59649-56-8 ]
3-(6-acetylamino-pyridin-3-yl)-N-([3-(1-benzyl-2-methoxy-1H-benzoimidazol-4-yloxymethyl)-2,4-dichloro-phenyl]-methyl-carbamoyl}-methyl)-acrylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2853 - 2863

15
[ 59649-56-8 ]
4-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-(pyridin-2-ylmethyl)-1H-benzimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2853 - 2863

16
[ 59649-56-8 ]
{4-[3-({2-[(E)-3-(6-Acetylamino-pyridin-3-yl)-acryloylamino]-acetyl}-methyl-amino)-2,6-dichloro-benzyloxy]-2-methoxy-benzoimidazol-1-yl}-acetic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2853 - 2863

17
[ 59649-56-8 ]
2,3-bis[(4-methoxybenzoyl)amino]phenol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 859 - 872

18
[ 59649-56-8 ]
[ 179622-77-6 ]