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[ CAS No. 376592-93-7 ] {[proInfo.proName]}

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Chemical Structure| 376592-93-7
Chemical Structure| 376592-93-7
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Product Details of [ 376592-93-7 ]

CAS No. :376592-93-7 MDL No. :MFCD10001467
Formula : C13H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZXLYSSHNDUXXIN-UHFFFAOYSA-N
M.W : 229.23 Pubchem ID :11492332
Synonyms :

Calculated chemistry of [ 376592-93-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 65.26
TPSA : 83.55 ?2

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 : No
Log Kp (skin permeation) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.18
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.265 mg/ml ; 0.00116 mol/l
Class : Soluble
Log S (Ali) : -3.42
Solubility : 0.0866 mg/ml ; 0.000378 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.36
Solubility : 0.0996 mg/ml ; 0.000435 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 376592-93-7 ]

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 [ 376592-93-7 ]

* 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.

  • Downstream synthetic route of [ 376592-93-7 ]

[ 376592-93-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 376591-95-6 ]
  • [ 376592-93-7 ]
YieldReaction ConditionsOperation in experiment
95% With palladium 10% on activated carbon; hydrogen; In ethanol; water; at 50℃; under 3750.38 - 7500.75 Torr; The above product was added to a hydrogenation vessel, and 2 g of 10% palladium carbon (about 63% aqueous), and 150 ml of ethanol were added.The reaction was carried out by introducing hydrogen gas at 0.5-1.0 MPa/50 C.After the reaction was completed, it was filtered, concentrated, dissolved in 100 ml of water, and adjusted to pH 5.5 with 1 M hydrochloric acid.The solid is precipitated, suction filtered and dried to give a pale yellow solid(9 g, yield: 95%, HPLC purity: 99%).
72.8% With palladium on activated charcoal; hydrazine hydrate; In water; at 25 - 85℃; for 2h; 2) 300g of Intermediate I, 6g of Pd / C, and 1.5L of water were added into a 5L three-necked flask, and 1.5L of hydrazine hydrate (98%) was added to the system dropwise. During this period, exothermic gas was released and the temperature was controlled at 25 C. After the dropwise addition was completed, the temperature was raised to 85 C. After two hours of reaction, the temperature was reduced to room temperature with suction filtration. The filtrate was cooled to 5 C, the pH was adjusted to 7-8 with concentrated hydrochloric acid, and the filtration cake was washed with 500 ml of water and blow dried at 55 C. 193.14 g of light brown solid intermediate II was obtained with a yield of 72.8% and a purity of 97.3%.
50.5% With hydrogen;5% Pd(II)/C(eggshell); In methanol; at 20℃; for 8h; A solution of 2'-hydroxy-3'-nitrobiphenyl-3-carboxylic acid (800 g, 3.2 mol) in methanol (5 L) was hydrogenated over 5% Pd/C (160 g) at room temperature for 8 hours. The reaction mixture was filtered, concentrated and slurried in THF (2.5 L) to give 3'-amino-2'-hydroxybiphenyl-3-carboxylic acid (690 g, 50.5%) as a brown solid. PXRD analysis provided the diffractogram as shown in FIG. 32.
With hydrogen; potassium acetate;palladium over charcoal; Scheme I [0137] The process of Scheme I is a mult-step synthetic sequence that commences with the palladium catalyzed cross-coupling of a phenylboronic acid such as structure 2 and an aryl bromide such as structure 1 to form the biaryl structure 3 Deprotection of the methyl ether is followed by nitration and hydrogenation to give the biphenyl ammo acid such as structure 4 The ammo group is then diazotized under standard conditons and is treated with the approp?ate coupling partner to give the final product of structure 6; Example 187: 3 '- ITV-^-Aza- 1 -(3 ,4-dimethylph.enyl)-2-oxo- 1.2-dihvdroindol-3 - ylidenelhvdrazino|-2'-nydroxybiphenyl-3-carbox:ylic acid ("Compound 287) [0371] This compound was prepared as described in Scheme I. 1H NMR (500 MHz, DMSO-4) 13.10 (s, IH), 13.04 (s, IH), 9.36 (s, IH), 8.16 (dd, J= 5.1, 1.6 Hz, IH), 8.12 (t, J= 1.6 Hz, IH), 8.04 (dd, J= 7.4, 1.6 Hz, IH), 7.94 (ddd, J= 7.7, 1.6, 1.2 Hz, IH), 7.80 (ddd, J= 7.7, 1.6, 1.2 Hz, IH), 7.74 (dd, J= 7.8, 1.6 Hz, IH), 7.60 (t, J = 7.7 Hz, IH), 7.34 (d, J= 1.8 Hz, IH), 7.30 (d, J = 8.1 Hz, IH), 7.28 (dd, J = 8.1, 1.8 Hz, I H), 7.21 (dd, J = 7.4, 5.1 Hz, IH), 7.13 (t, J = 7.8 Hz, IH), 7.03 (dd, J= 7.8, 1.6 Hz, IH), 2.30 (s, 3H), 2.29 (s, 3H).

  • 2
  • [ 376592-93-7 ]
  • [ 925633-57-4 ]
  • [ 141-43-5 ]
  • eltrombopag olamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.15% Methanolic HCl acid (22 ml, 1.25 M), 50 ml methanol and 2.5 g BPCA (2',3'-dihydroxybiphenyl-3-carboxylic acid) were stirred and cooled down to 0-5 C. at which point 0.770 g NaNO2 (dissolved in 3 ml water) was added dropwise. The resulting solution was stirred at 0-5 C. for 30 min., and then 2 ml of conc. HCl acid were added dropwise. The resulting solution was stirred at 0-5 C. for 30 min. followed by addition of 40 mg sulfamic acid (dissolved in 3 ml water). The resulting reaction mixture was stirred for 45 min at 5-25 C. followed by addition 2.2 g of 1-(3,4-dimethylphenyl)-3-methyl-1,2-dihydropyrazol-5-one. The resulting solution was stirred for 10-15 min at room temperature and 4 ml of ethanolamine was added. The resulting suspension was stirred for 45 min, followed by filtration. 4.56 g of purple powder was obtained. Yield 74.15%
  • 3
  • [ 376592-93-7 ]
  • [ 925633-57-4 ]
  • Eltrombopag [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.4% 3'-Amino-2'-hydroxybiphenyl-3-carboxylic acid (?BPCA?) Form I (90 g, 392.6 mmol), was added slowly with stirring at room temperature to a solvent mixture of tech. methanol (1.8 L) and 4 M hydrochloric acid (0.245 L, 981.5 mmol) in 3 L reactor. The resulting red solution was stirred for thirty minutes. The solution was then cooled to 0-5 C. and a cold solution of sodium nitrite (27 g, 391.3 mmol) in 90 mL of water was added over twenty minutes such that the reaction mixture temperature did not rise above 10 C. The reaction mixture was stirred for one hour at 5-10 C. Sulfamic acid (4 g, 41.2 mmol) in 90 mL of water was added at 5 C. and the resulting mixture was stirred for additionally one hour at the same temperature. The reaction mixture was warmed to room temperature and triethylamine (ca 104 mL) was added to adjust pH 7-8. 1-(3,4-dimethylphenyl)-3-methyl-1H-pyrazol-5-ol (?pyrazole?) form I (72 g, 357.8 mmol), was added in one portion to the reaction mixture and the resulting mixture was stirred for additionally two hours at room temperature. Hydrochloric acid (4M, ca 140 mL) was slowly added with stirring over twenty minutes to adjust pH to 1.8. A solid precipitated and was collected by filtration, washed with of mixture MeOH:water (1:1, 100 mL) and dried at 40 C./0 bar in vacuum oven for about 18 hours giving 151 g of crude orange to brown crystals of Eltrombopag crude (XRPD: form III with small percentage (less than 10%) of form I. (HPLC: 98.5%, Yield=95.4%)
  • 4
  • [ 376592-93-7 ]
  • C15H14N2O [ No CAS ]
  • 3'-{N'-[7-aza-1-(3,4-dimethylphenyl)-2-oxo-1,2-dihydroindol-3-ylidene]hydrazino}-2'-hydroxybiphenyl-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Scheme I [0137] The process of Scheme I is a mult-step synthetic sequence that commences with the palladium catalyzed cross-coupling of a phenylboronic acid such as structure 2 and an aryl bromide such as structure 1 to form the biaryl structure 3 Deprotection of the methyl ether is followed by nitration and hydrogenation to give the biphenyl ammo acid such as structure 4 The ammo group is then diazotized under standard conditons and is treated with the approp?ate coupling partner to give the final product of structure 6; Example 187: 3 '- ITV-^-Aza- 1 -(3 ,4-dimethylph.enyl)-2-oxo- 1.2-dihvdroindol-3 - ylidenelhvdrazino|-2'-nydroxybiphenyl-3-carbox:ylic acid ("Compound 287) [0371] This compound was prepared as described in Scheme I. 1H NMR (500 MHz, DMSO-4) 13.10 (s, IH), 13.04 (s, IH), 9.36 (s, IH), 8.16 (dd, J= 5.1, 1.6 Hz, IH), 8.12 (t, J= 1.6 Hz, IH), 8.04 (dd, J= 7.4, 1.6 Hz, IH), 7.94 (ddd, J= 7.7, 1.6, 1.2 Hz, IH), 7.80 (ddd, J= 7.7, 1.6, 1.2 Hz, IH), 7.74 (dd, J= 7.8, 1.6 Hz, IH), 7.60 (t, J = 7.7 Hz, IH), 7.34 (d, J= 1.8 Hz, IH), 7.30 (d, J = 8.1 Hz, IH), 7.28 (dd, J = 8.1, 1.8 Hz, I H), 7.21 (dd, J = 7.4, 5.1 Hz, IH), 7.13 (t, J = 7.8 Hz, IH), 7.03 (dd, J= 7.8, 1.6 Hz, IH), 2.30 (s, 3H), 2.29 (s, 3H).
  • 5
  • [ 913382-64-6 ]
  • [ 376592-93-7 ]
  • 3'-{N'-[1-(3,4-dimethyl-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidene]-hydrazino}-2'-hydroxy-biphenyl-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Scheme II [0138] The process of Scheme II is a multi-step synthetic sequence that commences with the copper catalyzed cross-coupling of an oxindole such as structure 7 and an aryl or alkyl bromide to provide an N-substituted oxindole of structure 8. This is then followed by coupling the N-substituted oxindole with the diazonium salt of the biphenyl amino acid such as structure 4 to give the final product of structure 9.; Example 1: 3'-{N'-[l-(3,4-Dimethyl-phenyl)-2-oxo-l,2-dihvdro-indol-3-ylidene1-hydrazino|- 2'-hydroxy-biphenyl-3-carboxylic acid (Compound 101 ) [0185] This compound was prepared as described in Scheme II. 1H NMR (500 MHz, DMSO-O delta 13.07 (s, I H), 13.03 (s, IH), 9.26 (s, IH), 8.12 (t, J=1.6 Hz, IH), 7.94 (ddd, /=7.7, 1.6, 1.3 Hz, IH), 7.79 (ddd, J=7.7, 1.6, 1.3 Hz, IH), 7.73 (dd, /==7.9, 1.6 Hz, IH), 7.72 (m, IH), 7.60 (t, /=7.7 Hz, IH), 7.35 (d, /=8.1 Hz, IH), 7.30 (d, /=2.1 Hz, IH), 7.28 (td, /=7.7, 1.3 Hz, IH), 7.23 (dd, /=8.1, 2.1 Hz, IH), 7.18 (td, /=7.7, 0.9 Hz, IH), 7.11 (t, /=7.9 Hz, IH), 7.00 (dd, /=7.9, 1.6 Hz, IH), 6.85 (m, IH), 2.31 (s, 3H), 2.30 (s, 3H).
  • 6
  • [ 376592-93-7 ]
  • [ 303056-85-1 ]
  • 3'-{N'-[3-(3,4-dimethyl-phenyl)-4-oxo-2-thioxo-thiazolidin-5-ylidene]-hydrazino}-2'-hydroxy-biphenyl-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Scheme IV [0140] The process of Scheme IV is a multi-step synthetic sequence that commences with the conversion of an amine of structure 13 into an N-aryl rhodanine of structure 14 with bis(carboxymethyl) trithiocarbonate. The rhodanine is then coupled to the diazonium salt of the biphenyl amino acid such as structure 4 to give the final product of structure 15. Example 19: 3 '- |N'-[3 -(3 ,4-Dimethyl-phenyl)-4-oxo-2-thioxo-thiazolidin-5-ylicLene1 -hydrazinol - 2'-hydroxy-biphenyl-3-carboxylic acid (Compound 119) [02031 This compound was prepared as described in Scheme IV. 1H INMR (500 MHz, DMSO-dbeta) delta 12.83 (s, IH), 10.76 (s, IH), 9.35 (s, IH), 8.15 (t, 7=1.5 Hz, IH), 7.91 (m, IH), 7.79 (dt, 7=7.7, 1.5 Hz, IH), 7.56 (t, 7=7.7 Hz, IH), 7.34 (m, IH), 7.29 (d, 7=7.9 Hz, i H), 7.14-6.96 (m, 4H), 2.28 (s, 3H), 2.26 (s, 3H).
  • 7
  • [ 376592-93-7 ]
  • [ 17630-75-0 ]
  • 3'-[N'-(1-benzyl-5-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-hydrazino]-2'-hydroxy-biphenyl-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Scheme III [0139] The process of Scheme III is a multi-step synthetic sequence that commences with the reductive animation of an aniline such as structure 10 with a benzaldehyde and conversion into the chloroacetanilide of structure 11 with chloroacetyl chloride. Palladium catalyzed ring closure gives the N-benzyl oxindole such as structure 12, which is then coupled to the diazonium salt of the biphenyl amino acid of structure 4 to give the final product of structure 9. ; Example 11: 3 '-[N'-( 1 -Benzyl-5 -chloro-2-oxo - 1 ,2-dihvdro-indol-3 -ylidene)-hvdrazino] -T- hydroxy-biphenyl-3-carboxylic acid (Compound 111) [0195] This compound was prepared as described in Scheme III. 1H NMR (500 MHz, DMSCW5) delta 13.10 (s, IH), 13.03 (s, IH), 9.36 (s, IH), 8.13 (t, j =1.7 Hz, IH), 7.95 (ddd, J =7.7, 1.7, 1.3 Hz, IH), 7.80 (ddd, J=7.7, 1.7, 1.3 Hz, IH), 7.76 (dd, J=7.7, 1.6 Hz, IH), 7.68 (d, /=2.1 Hz, EPO <DP n="66"/>IH), 7.60 (t, J=I .1 Hz, IH), 7.37-7.32 (m, 4H), 7.30 (dd, 7=8.5, 2.1 Hz, IH), 7.27 (m, IH), 7.11 (t, J=7.7 Hz, IH), 7.09 (d, J=8.5 Hz, IH), 7.03 (dd, 7=7.7, 1.6 Hz, IH), 5.05 (s, 2H).
  • 8
  • [ 695-96-5 ]
  • [ 376592-93-7 ]
  • 10
  • [ 376592-57-3 ]
  • [ 376592-93-7 ]
  • 11
  • [ 376592-58-4 ]
  • [ 376592-93-7 ]
YieldReaction ConditionsOperation in experiment
86.7% With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; at 20℃; under 7500.75 Torr; for 21h;Autoclave; [0058] 5'-Chloro-2'-hydroxy-3'-nitrobiphenyl-3-carboxylic acid (Compound 2b) (5.0 g) was dissolved in a mixture of MeOH (300 mL) and Et3N (4.75 mL). Pd/C (0.5 g) was added to the solution and the mixture was hydrogenated for 21 h at room temperature and 10 bars pressure. The catalyst was then removed by filtration, the filtrate was concentrated to dryness, and the residue was dissolved in water (40 mL). The pH was adjusted to 5.5 by dropwise addition of 0.5 M HC1 and the resulting suspension was stirred at RT for 30 min. The suspension was filtered, and the collected solid was washed with water (2 x 10 mL) and dried at 50 C/50 mbar to provide BPCA (3.4 g; 86.7%; HPLC purity 97.9%).
  • 12
  • [ 89-64-5 ]
  • [ 376592-93-7 ]
  • 13
  • [ 15969-10-5 ]
  • [ 376592-93-7 ]
  • 14
  • 2’-benzyloxy-3’-nitrobiphenyl-3-carboxylic acid [ No CAS ]
  • [ 376592-93-7 ]
YieldReaction ConditionsOperation in experiment
89% With palladium 10% on activated carbon; hydrogen; In methanol; at 20 - 25℃; A mixture of 2'-(benzyloxy)-3'-nitro-1,1'-biphenyl-3-carboxylic acid (270 mg, 0.777 mmol) and Pd/C (paste 10%, 170 mg) in MeOH (10 mL) was stirred under hydrogen atmosphere overnight at room temperature. The reaction mixture was filtered through a pad of Celite and the pad was washed with MeOH. The filtrate was concentrated to give 3'-amino-2'-hydroxy-1,1'-biphenyl-3-carboxylic acid as a brown solid (235 mg, 89%).
89% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; A mixture of 2'-(benzyloxy)-3'-nitro-1 ,1 '-biphenyl-3-carboxylic acid (270 mg, 0.777 mmol) and Pd/C (paste 10%, 170 mg) in MeOH (10 mL) was stirred under hydrogen atmosphere overnight at room temperature. The reaction mixture was filtered through a pad of Celite and the pad was washed with MeOH. The filtrate was concentrated to give 3'-amino-2'-hydroxy-1 ,1 '- biphenyl-3-carboxylic acid as a brown solid (235 mg, 89%).
80% With 5%-palladium/activated carbon; hydrogen; In methanol; at 50℃; under 3000.3 Torr; for 8h; The solution obtained by dissolving in methanol (400 ml) the 2'-benzyloxy-3'-nitrobiphenyl-3-carboxylic acid (97 g, 0.278 mol) obtained as in Example 2 is placed in a 1 L hydrogenator. 5% Pd/C (23.68 g, 13.9 mmol Pd, moisture about 50%) is added to the solution.The suspension is purged under nitrogen atmosphere, placed at a hydrogen pressure of about 4 bars and maintained under stirring at about 50C for 8 hours. The suspension is then cooled to about 25C and filtered through a Celite bed. The panel is washed with hot methanol, and the organic phases are combined and concentrated at low pressure. The solid residue thus obtained is suspended in hexane (400 ml), and the resulting suspension is heated at 55C for 2 hours. The suspension is then cooled to about 25C and filtered, and the solid is stove-dried at 50C. 50 g of 3'-amino-2'-hydroxybiphenyl-3-carboxylic acid of formula (II) is obtained, with a yield of 80% and HPLC chemical purity exceeding 98%. 1H-NMR (DMSO-d6, 300 MHz), delta: 8.12 (s, 1H), 7.81 (d, 1H) 7.63 (d, 1H), 7.45 (t, 1H), 6.75-6.60 (m, 2H), 6.45 (d, 1H).
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 10h; 3 '- nitro - 2' hydroxy-biphenyl-3-formic acid (V) dissolved in ethyl acetate (350 ml) and catalyst 10% (1.05g) Palladium-carbon was added, the hydrogen gas undergoes a reduction reaction for 10 hours, cooled, filtered, and concentrated to dryness to give 6.6 g of a dark yellow solid which was recrystallized from methanol to give a yellow solid, namely 3'-amino-2'-hydroxybiphenyl-3-formic acid(VI).

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