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Product Details of [ 6946-29-8 ]

CAS No. :6946-29-8 MDL No. :MFCD01684522
Formula : C7H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FYZGXAKJVDHGDR-UHFFFAOYSA-N
M.W : 167.17 Pubchem ID :72490
Synonyms :

Calculated chemistry of [ 6946-29-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 4.0
Molar Refractivity : 43.77
TPSA : 101.37 Ų

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) : -7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.82
Log Po/w (XLOGP3) : 0.32
Log Po/w (WLOGP) : -0.41
Log Po/w (MLOGP) : -0.02
Log Po/w (SILICOS-IT) : -0.98
Consensus Log Po/w : -0.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.32
Solubility : 8.07 mg/ml ; 0.0483 mol/l
Class : Very soluble
Log S (Ali) : -2.01
Solubility : 1.63 mg/ml ; 0.00973 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.1
Solubility : 13.3 mg/ml ; 0.0798 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 6946-29-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6946-29-8 ]

* 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.

  • Downstream synthetic route of [ 6946-29-8 ]

[ 6946-29-8 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 13302-21-1 ]
  • [ 6946-29-8 ]
  • 4-amino-2-hydroxy-benzoic acid-[2-bromo-3ξ-(5-nitro-[2]furyl)-allylidenehydrazide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol
  • 2
  • [ 1122-54-9 ]
  • [ 6946-29-8 ]
  • 4-amino-2-hydroxy-benzoic acid-[(1-[4]pyridyl-ethylidene)-hydrazide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol
  • 3
  • [ 698-63-5 ]
  • [ 6946-29-8 ]
  • [ 100137-26-6 ]
YieldReaction ConditionsOperation in experiment
With ethanol
  • 4
  • [ 79-36-7 ]
  • [ 6946-29-8 ]
  • 4-(2,2-dichloro-acetylamino)-2-hydroxy-benzoic acid-(<i>N</i>'-dichloroacetyl-hydrazide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,4-dioxane; sodium acetate
  • 6
  • [ 590-28-3 ]
  • [ 6946-29-8 ]
  • 1-(4-amino-2-hydroxy-benzoyl)-semicarbazide [ No CAS ]
  • 7
  • [ 6946-29-8 ]
  • [ 333-20-0 ]
  • [ 4923-11-9 ]
  • 8
  • [ 6946-29-8 ]
  • [ 1874-22-2 ]
  • [ 100621-40-7 ]
YieldReaction ConditionsOperation in experiment
With methanol
  • 9
  • [ 6946-29-8 ]
  • [ 120-92-3 ]
  • 4-amino-2-hydroxy-benzoic acid cyclopentylidenehydrazide [ No CAS ]
  • 10
  • [ 4136-97-4 ]
  • [ 6946-29-8 ]
YieldReaction ConditionsOperation in experiment
78.4% With hydrazine hydrate for 1.5h; Reflux; Methyl 4-aminosalicylate (4.0 g, 23 mmol) was added to 80% hydrazine monohydrate (12 mL), and the mixture was refluxed for 90 min. After evaporation, the residue was added to distilled H2O to obtain a crude crystal. The crude crystal was recrystallized from EtOH to obtain 4-aminosalicyl hydrazide (yield 78.4%). Subsequently, 4-aminosalicyl hydrazide (0.5 g, 3.0 mmol) in EtOH (100 mL) was made to react with o-vanillin (0.45 g, 3.0 mmol) for 2 h in a water bath at 100 °C. After cooling to room temperature, the precipitate was collected by filtration and was recrystallized from MeOH to obtain the final product, HMB-ASH (yield 82.5%).
78.4% With hydrazine hydrate for 90h; Reflux; HMB-ASH was synthesized according to our previouspaper (Yamada et al. 2012). Briefly, methyl4-aminosalicylate (4.0 g, 23 mmol) was added to80 % hydrazine monohydrate (12 mL), and the mixturewas refluxed for 90 min. After evaporation, theresidue was added to distilled H2O (20 mL) to obtain acrude crystal. The crude crystal was recrystallized inEtOH to obtain 4-aminosalicylic hydrazide (yield78.4 %).
46% With hydrazine hydrate In ethanol for 18h; Reflux; 5.1.1. General procedure for the preparation of benzohydrazides(4-13) General procedure: Various benzohydrazides 5-7 and 9-13 were obtained accordingto known procedures [40,65] except for benzohydrazides 4and 8 which were commercially available. A solution of the methylbenzoate (1 equiv) in ethanol was added dropwise to 65% hydrazinemonohydrate (5 equiv). The reaction mixture was then heatedunder reflux and stirred overnight. The reaction progress was followedup by TLC. Crude product was collected by filtration aftercooling of the reaction medium and finally washed with coldethanol unless specified otherwise. The desired benzohydrazides were used without any further purification.The analysis of spectral data (1H and 13C NMR), the yields, HRMS,Mp and Rf of these precursors are presented in SupplementaryInformation.
With hydrazine hydrate
With hydrazine hydrate
With hydrazine hydrate In methanol

  • 11
  • [ 6946-29-8 ]
  • [ 105767-05-3 ]
  • Bis-<4-amino-salicyloylhydrazon> d. 17α-Methyl-2-hydroxymethylen-dihydrotestosterons [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol
  • 12
  • [ 6946-29-8 ]
  • [ 95462-32-1 ]
  • Bis-<4-amino-salicyloylhydrazon> d. Hydroxymethylen-dihydrotestosterons [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol
  • 13
  • [ 6946-29-8 ]
  • (S)-N-trifluoroacetyl-aspartic Anhydride [ No CAS ]
  • [ 70449-53-5 ]
  • 14
  • [ 6946-29-8 ]
  • 3-Oxo-13α-hydroxy-13,17-seco-androstansaeure-(17) [ No CAS ]
  • 4-Amino-salicyloylhydrazon d. 3-Oxo-13α-hydroxy-13,17-seco-androstansaeure-(17) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 15
  • [ 483-55-6 ]
  • [ 6946-29-8 ]
  • [ 62830-48-2 ]
  • 16
  • [ 619-19-2 ]
  • [ 6946-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: nickel-aluminium-alloy; aq. NaOH solution 2: sulfuric acid 3: hydrazine hydrate
Multi-step reaction with 3 steps 1: nickel-aluminium-alloy; aq. NaOH solution 2: diethyl ether 3: hydrazine hydrate
Multi-step reaction with 3 steps 1: hydrogen chloride 2: platinum; ethanol / Hydrogenation 3: hydrazine hydrate
  • 17
  • [ 13684-28-1 ]
  • [ 6946-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: platinum; ethanol / Hydrogenation 2: hydrazine hydrate
  • 18
  • [ 65-49-6 ]
  • [ 6946-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrazine hydrate
Multi-step reaction with 2 steps 1: diethyl ether 2: hydrazine hydrate
Multi-step reaction with 2 steps 1: sulfuric acid / 4 h / Reflux 2: hydrazine hydrate / 1.5 h / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / Reflux; Inert atmosphere 2: hydrazine hydrate / Reflux; Inert atmosphere

  • 20
  • [ 6946-29-8 ]
  • [ 148-53-8 ]
  • [ 1369535-48-7 ]
YieldReaction ConditionsOperation in experiment
82.5% In ethanol at 100℃; for 2h; 2.3. Synthesis of HMB-ASH Methyl 4-aminosalicylate (4.0 g, 23 mmol) was added to 80% hydrazine monohydrate (12 mL), and the mixture was refluxed for 90 min. After evaporation, the residue was added to distilled H2O to obtain a crude crystal. The crude crystal was recrystallized from EtOH to obtain 4-aminosalicyl hydrazide (yield 78.4%). Subsequently, 4-aminosalicyl hydrazide (0.5 g, 3.0 mmol) in EtOH (100 mL) was made to react with o-vanillin (0.45 g, 3.0 mmol) for 2 h in a water bath at 100 °C. After cooling to room temperature, the precipitate was collected by filtration and was recrystallized from MeOH to obtain the final product, HMB-ASH (yield 82.5%).FAB-MS: m/z 302 (M+H)+; Anal. Calcd. for C15H15O4N3: C, 59.80; H, 5.02; N, 13.95. Found: C, 60.02; H, 4.89; N, 13.77. 1H NMR (DMSO-d6) δ (ppm): 12.27 (s,1H), 11.67 (s,1H), 11.00 (s,1H), 8.55 (s,1H), 7.59 (d,1H), 7.06 (d,1H), 6.96 (d,1H), 6.80 (t,1H), 6.09 (d,1H), 5.99 (s,2H), 4.32 (s, 3H). 13C NMR (DMSO-d6) δ (ppm): 166.31, 162.33, 163.33, 155.25, 148.42, 148.02, 147.63, 129.44, 121.42, 119.46, 114.31, 106.41, 101.88, 99.86, 56.34. FT-IR (solid phase) (cm-1): 3352 (vOH), 1595 (vCN), 1249, 1200 (vArO). Melting point: 252-254 °C.
82.5% With hydrazine hydrate In ethanol at 100℃; for 2h; Reflux; Synthesis of HMB-ASH HMB-ASH was synthesized according to our previouspaper (Yamada et al. 2012). Briefly, methyl4-aminosalicylate (4.0 g, 23 mmol) was added to80 % hydrazine monohydrate (12 mL), and the mixturewas refluxed for 90 min. After evaporation, theresidue was added to distilled H2O (20 mL) to obtain acrude crystal. The crude crystal was recrystallized inEtOH to obtain 4-aminosalicylic hydrazide (yield78.4 %). Subsequently, 4-aminosalicylic hydrazide(0.5 g, 3.0 mmol) in EtOH (100 mL) was reacted witho-vanillin (0.45 g, 3.0 mmol) for 2 h in a water bath at100 C. After cooling to room temperature, theprecipitate was collected by filtration and was recrystallizedfrom MeOH to obtain the final product,HMB-ASH (yield 82.5 %).FAB-MS: m/z 302 (M ? H)?; Anal. Calcd. forC15H15O4N3: C, 59.80; H, 5.02; N, 13.95. Found: C,60.02; H, 4.89; N, 13.77. 1H NMR (DMSO-d6) (ppm):12.27 (s, 1H), 11.67 (s, 1H), 11.02 (s, 1H), 8.55 (s, 1H),7.59 (d, 1H), 7.06 (d, 1H), 6.96 (d, 1H), 6.80 (t, 1H),6.14 (m, 2H), 6.03 (d, 1H), 5.88 (s, 1H), 3.81 (s, 3H).13C NMR (DMSO-d6) (ppm): 166.31, 162.33, 163.33,155.25, 148.42, 148.02, 147.63, 129.44, 121.42, 119.46,114.31, 106.41, 101.88, 99.86, 56.34. FT-IR (solidphase) (cm-1): 3358 (vNH), 3236, 1352 (vOH), 1599(vC=N), 1250 (vO-CH3). Melting point: 252-254 C.
  • 21
  • [ 6946-29-8 ]
  • [ 90-02-8 ]
  • (E)-2-hydroxy-N'-(2-hydroxybenzylidene)-4-((E)-(2-hydroxybenzylidene)amino)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol for 6h; Reflux;
  • 22
  • [ 6946-29-8 ]
  • [ 6590-94-9 ]
  • 1-(2-hydroxy-4-aminobenzoyl)-4-(3,4-dichlorophenyl)-3-thiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% In methanol at 20℃; for 1.5h; 5.1.2. General procedure for the preparation of thiosemicarbazides(3, 14-48 and 51-52) General procedure: A series of thiosemicarbazides 3, 14-48 and 51-52 were preparedaccording to a procedure adapted from the literature [40,41]by adding an isothiocyanate (1 equiv) dropwise to a solution ofbenzohydrazide (1 equiv) in methanol. The reaction mixture wasstirred at room temperature and its progress was followed by TLC.The precipitate was then collected by filtration, washed with coldethanol and then recrystallized from ethanol as many times asnecessary to obtain a pure product.
  • 23
  • [ 492-88-6 ]
  • [ 6946-29-8 ]
  • (E)-4-amino-2-hydroxy-N'-(2-hydroxy-3-ethoxybenzylidene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In methanol for 3h; Reflux; 2.2.1. Preparation of ( E )-4-amino-2-hydroxy-N’-(2-hydroxy-3-ethoxybenzylidene) benzohydrazide (H 2 L) In a 250 mL round-bottomed flask, 4-amino-2- hydroxybenzohydrazide (10 mmol, 1.67 g) was added into a 100 mL methanolic solution of 3-ethoxysalicylaldehyde (10 mmol, 1.66 g) and then the mixture was refluxed for 3 h. The resulting yellow solid was filtered and washed with cold methanol. H 2 L: Yield 76%. Anal. Calc. for C 16 H 17 N 3 O 4 : C, 60.94; H, 5.43; N, 13.33, Found: C, 61.07; H, 5.45; N, 13.28%. FT-IR (KBr, cm -1 ); 3577 ( νN-H ); 1696 ( νC = O ); 1647 ( νC = N ); 1207 ( νC-O ); 1078 ( νN-N ). 1 H NMR (400 MHz, DMSO- d 6 , ppm): 1.35 [3 H, (H-C8), t, 3 J = 7.2 Hz], 4.06 [2 H, (H-C7), q, 3 J = 7.2 Hz], 5.99 [2 H, s, (-NH 2 )], 6.04 [1 H, (H-C13), d, 4 J = 1.6 Hz], 6.15 [1 H, (H-C15), dd, 3 J = 8.8 Hz, 4 J = 1.6 Hz], 6.85 [1 H, (H-C4), t, 3 J = 7.6 Hz], 7.01 [1 H, (H-C3), d, 3 J = 7.6 Hz], 7.11 [1 H, (H-C5), d, 3 J = 7.6 Hz], 7.63 [1 H, (H-C16), d, 3 J = 8.8 Hz], 8.60 [1 H, s, (-CH = N)], 11.07 [1 H, s, (-NH)], 11.76 [1 H, s, (-OH)], 12.35 [1 H, s, (-OH)]. 13 C NMR (100 MHz, DMSO- d 6 , ppm): 14.7 (C7), 64.1 (C8), 99.3 (C13), 101.2 (C11), 105.9 (C15), 115.6 (C1), 118.9 (C6), 119.0 (C4), 121.0 (C5), 128.9 (C16), 147.0 (C2), 147.4 (C1), 147.6 (C9), 154.8 (C14), 162.8 (C12), 165.8 (C10).
  • 24
  • [ 6946-29-8 ]
  • [ 148-53-8 ]
  • (E)-4-amino-2-hydroxy-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In methanol for 3h; Reflux; 2.2.1. Preparation of (E)-4-amino-2-hydroxy-N’-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (H2L) H2L was prepared by dissolving 4-amino-2-hydroxybenzohydrazide [31] (10mmol, 1.67g) and 3-methoxysalicylaldehyde (10mmol, 1.52g) separately in 50mL of hot MeOH. The reactants were then mixed-up drop by drop and the resultant mixture was refluxed for approximately three hours until the reactants were completely converted into products as monitored by thin layer chromatography. For this, aliquots from the mixture were taken periodically to look for the disappearance of spots of reactants and the emergence of new spot of product at a particular Rf value. After complete satisfaction with the accomplishment of the reaction, the contents were allowed to cool. Cooling of the reaction contents decreases the solubility and the product descends in the form of precipitates. The precipitates were then sorted out by the process of filtration under reduced pressure with the help of a rotary evaporator and cleansed in triplicate with cold methanol to purify them. H2L: Yield 67%. Anal. Calc. for C15H15N3O4: C, 59.80; H, 5.02; N, 13.95, Found: C, 59.91; H, 5.06; N, 14.07%. FT-IR (KBr, cm-1); 3470 (νN-H); 1645 (νC=O); 1605 (νC=N); 1159 (νC-O); 1078 (νN-N). 1H NMR (400MHz, DMSO-d6, ppm): 3.81 [3H, s, (H-C7)], 5.99 [2H, s, (-NH2)], 6.03 [1H, (H-C12), d, 4J=2.0Hz], 6.14 [1H, (H-C14), dd, 3J=8.8Hz, 4J=2.0Hz], 6.86 [1H, (H-C4), t, 3J=8.0Hz], 7.02 [1H, (H-C3), dd, 3J=8.0Hz, 4J=1.2Hz], 7.12 [1H, (H-C5), dd, 3J=8.0Hz, 4J=1.2Hz], 7.63 [1H, (H-C15), d, 3J=8.8Hz], 8.60 [1H, s, (-CH=N)], 11.07 [1H, s, (-NH)], 11.76 [1H, s, (-OH)], 12.35 [1H, s, (-OH)]. 13C NMR (100MHz, DMSO-d6, ppm): 55.8 (C7) 99.3 (C12), 101.3 (C10), 105.9 (C14), 113.6 (C3), 118.9 (C6), 119.0 (C4), 120.8 (C5), 128.9 (C15), 147.0 (C2), 147.4 (C1), 147.9 (C8), 154.8 (C13), 162.8 (C11), 165.8 (C9).
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