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[ CAS No. 29528-28-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 29528-28-7
Chemical Structure| 29528-28-7
Chemical Structure| 29528-28-7
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Product Details of [ 29528-28-7 ]

CAS No. :29528-28-7 MDL No. :MFCD00297065
Formula : C9H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :CENKJXADYBDCLM-UHFFFAOYSA-N
M.W : 159.19 Pubchem ID :910176
Synonyms :

Calculated chemistry of [ 29528-28-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.43
TPSA : 54.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.86
Log Po/w (XLOGP3) : 1.04
Log Po/w (WLOGP) : 1.67
Log Po/w (MLOGP) : 0.44
Log Po/w (SILICOS-IT) : 1.86
Consensus Log Po/w : 1.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.28 mg/ml ; 0.00804 mol/l
Class : Soluble
Log S (Ali) : -1.78
Solubility : 2.65 mg/ml ; 0.0166 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.38
Solubility : 0.0662 mg/ml ; 0.000416 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 29528-28-7 ]

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 [ 29528-28-7 ]

* 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 [ 29528-28-7 ]

[ 29528-28-7 ] Synthesis Path-Downstream   1~59

  • 1
  • [ 38980-93-7 ]
  • [ 29528-28-7 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 18.0h; [0003681 To a stirred solution of compound 1 (0.7 g, 1 eq) in methanol (10 mL), 10% Pd-C (0.1 g) was added under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 18 h under hydrogen balloon pressure. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 5% MeOH-DCM to afford the title compound2. LCMS (mlz): 160.00 (M + 1).
  • 2
  • [ 50-00-0 ]
  • [ 62830-97-1 ]
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  • 3
  • [ 64-18-6 ]
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  • 4
  • [ 23602-10-0 ]
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  • 5
  • [ 4428-98-2 ]
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  • [ 83184-32-1 ]
  • 6
  • [ 75-15-0 ]
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  • [ 118714-29-7 ]
  • 7
  • [ 67434-79-1 ]
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  • C12H11N5S [ No CAS ]
  • 9
  • [ 29528-28-7 ]
  • ethyl N-tert-butylformimidate tetrafluoroborate [ No CAS ]
  • [ 83184-14-9 ]
  • 10
  • [ 29528-28-7 ]
  • [ 72798-67-5 ]
  • 11
  • [ 29528-28-7 ]
  • [ 103-71-9 ]
  • 1-[4-(1H-Imidazol-4-yl)-phenyl]-3-phenyl-urea [ No CAS ]
  • 13
  • [ 29528-28-7 ]
  • [ 124-40-3 ]
  • 4-[4-(3,3-dimethyl-1-triazeno)phenyl]imidazole [ No CAS ]
  • 14
  • [ 943749-53-9 ]
  • [ 29528-28-7 ]
  • (4Z)-4-([4-(1H-Imidazol-4-yl)phenyl]amino}methylene)-1,4-dihydro-3(2H)-isoquinolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% In toluene; at 110℃; for 4.0h; Example 3; (4Z)-4-([4-(1H-Imidazol-4-yl)phenyl]amino}methylene)-1,4-dihydro-3(2H)-isoquinolinone; A toluene (3 mL) solution containing (4E)-4-[(dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone (300 mg, 1.48 mmol) and <strong>[29528-28-7]4-(1H-imidazol-4-yl)aniline</strong> (265 mg, 1.66 mmol) is heated at 110 C. for 4 h. Using the same workup as example 1, 0.13 g (28%) orange solid is obtained: mp 151-152 C. (dec.); HRMS (ESI) m/z calcd for C19H16N4O 317.13969, found 317.13894 (M+H)+1.
  • 15
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  • [ 56337-96-3 ]
  • 16
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  • [ 118714-34-4 ]
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  • [ 118714-30-0 ]
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  • [ 118714-35-5 ]
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  • [ 118714-32-2 ]
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  • [ 118714-31-1 ]
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  • [ 118714-33-3 ]
  • 22
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  • [ 83184-12-7 ]
  • 23
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  • [ 83184-40-1 ]
  • 24
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  • [ 83184-43-4 ]
  • 25
  • [ 29528-28-7 ]
  • [ 83184-52-5 ]
  • 26
  • [ 29528-28-7 ]
  • C11H10N6 [ No CAS ]
  • 27
  • [ 29528-28-7 ]
  • 2-cyano-1-[4-(1H-imidazol-4-yl)phenyl]-3-methylguanidine [ No CAS ]
  • 28
  • [ 29528-28-7 ]
  • [ 88304-51-2 ]
  • 29
  • [ 29528-28-7 ]
  • [ 88304-59-0 ]
  • 30
  • [ 29528-28-7 ]
  • [ 88304-60-3 ]
  • 31
  • [ 29528-28-7 ]
  • [ 83184-48-9 ]
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  • [ 83184-45-6 ]
  • 33
  • [ 29528-28-7 ]
  • [ 89250-14-6 ]
  • 34
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  • [ 89250-47-5 ]
  • 35
  • [ 29528-28-7 ]
  • [ 89258-89-9 ]
  • 36
  • Rh(C) [ No CAS ]
  • 1H-4(5)-imidazoyl-4-cyclohexylamine [ No CAS ]
  • [ 29528-28-7 ]
  • 1H-4(5)-imidazoyl-4-cyclohexylamine dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With H2; In water; EXAMPLE 1 STR17 Preparation of 1H-4(5)-imidazoyl-4-cyclohexylamine 1H-4(5)-imidazoyl-4-cyclohexylamine was prepared according to the method outlined by Schunack, Arch. Pharmaz. 306, 934-943, (1973) as follows: 4-(4-aminophenyl)-imidazole (3.65 g, 19.2 mM) was dissolved in 50 ml of water and 2.5 ml of HC1. Rh(C) (5%, 2.5 g) was added, and the reaction mixture hydrogenated under 80 atm of H2 for 24 hours in an autoclave. The reaction was filtered through a pad of celite, the pad was washed with water (50 ml) and ethanol (50 ml), and then the filtrate was evaporated in vacuo to give 3.40 grams of 1H-4(5)-imidazoyl-4-cyclohexylamine dihydrochloride. NMR (300 MHz, D2 O): d 8.4 (d, 1H), 7.11 (d, 1H), 3.20 (m, 1H), 2.85 (m, 1H), 1.90 (m, 1H), 1.75 (m, 4H), 1.40 (m, 3H). Mass Spectrum (DCl, NH3): M+1=166, MW=166.2392, C9 H15 N3
  • 37
  • (E)-1-acetyl-3-(ethoxy-phenyl-methylene)-indolin-2-one [ No CAS ]
  • [ 29528-28-7 ]
  • 3-{(Z)-1-[4-(1H-imidazol-4-yl)anilino]-1-phenylmethylidene}-2-indolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydroxide; In methanol; N,N-dimethyl-formamide; 2.4 3-{(Z)-1-[4-(1H-imidazol-4-yl)anilino]-1-phenylmethylidene}-2-indolinone Prepared from 1-acetyl-3-(1-ethoxy-1-phenylmethylidene}-2-indolinone and 1.5 equivalents of 4-(1H-imidazol-4-yl)-aniline in DMF followed by treatment with 1N sodium hydroxide solution in MeOH. Yield: 68% of theory; Melting point: 280-285 C.; C24 H18 N4 O; Calc.: C, 76.17; H, 4.79; N, 14.80; Found: 75.83; 4.83; 14.62; Calc.: molar peak M+ =378; Found: molar peak M+ =378.
  • 38
  • 1-Acetyl-3-{1-hydroxy-1-[4-(imidazol-1-yl-methyl)-phenyl]-methylidene}-5-nitro-2-indolinone [ No CAS ]
  • [ 29528-28-7 ]
  • 3-{(Z)-1[4-(1H-Imidazol-4-yl)anilino]-1-[4-(imidazol-1-yl-methyl)phenyl]methylidene}-5-nitro-2-indolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With phosphorus pentachloride; triethylamine; In tetrahydrofuran; toluene; 11.5 3-{(Z)-1[4-(1H-Imidazol-4-yl)anilino]-1-[4-(imidazol-1-yl-methyl)phenyl]methylidene}-5-nitro-2-indolinone Prepared analogously to Example 11.4(b) by reacting 1-acetyl-3-{1-hydroxy-1-[4-(imidazol-1-yl-methyl)-phenyl]methylidene}-5-nitro-2-indolinone with PCl5 in toluene and subsequently with <strong>[29528-28-7]4-(1H-imidazol-4-yl)aniline</strong> and triethylamine in THF. Yield: 25% of theory; melting point: 230-235 C.; C28 N21 N7 O3 (503.53); Calc.: molar peak (M+H)+ =504 Found: molar peak (M+H)+ =504; C27 N24 N4 O5 *H2 O (521.54); Calc.: C, 64.45; N, 4.40; N, 18.57; Found: 64.30; 4.40; 18.57.
  • 39
  • [ 13707-46-5 ]
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  • 40
  • [ 555-16-8 ]
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  • 41
  • [ 79463-77-7 ]
  • [ 29528-28-7 ]
  • C17H13N5O [ No CAS ]
  • 42
  • [ 29528-28-7 ]
  • [ 1354280-05-9 ]
  • 43
  • [ 29528-28-7 ]
  • [ 1354280-07-1 ]
  • 44
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  • [ 1354280-10-6 ]
  • 45
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  • [ 1354280-13-9 ]
  • 46
  • [ 670-95-1 ]
  • [ 29528-28-7 ]
  • 47
  • C17H18ClN5O [ No CAS ]
  • [ 29528-28-7 ]
  • N-(4-(1H-imidazol-4-yl)phenyl)-6-(1,3-dimethyl-1H-indazol-6-yl)-2-morpholinopyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 18.0h;Inert atmosphere; [0003691 To a stirred solution of compound 3 (0.2 g, 1 eq) and compound 2 (0.093 g, 1 eq) in 1 ,4-dioxane (10 mL), cesium carbonate (0.285g ,1.5 eq) was added and purged with argon for 10 mm, followed by the addition of xantphos (0.033 g,0. 15 eq) and purged with argon for additional 5 mi Pd2(dba)3 (0.053 g,0.1 eq) was added and stirred at 100 C for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated to dryness. The residue was dissolved in ethyl acetate (50 mL), washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by preparative HPLC to afford thedesiredproduct. ?H NMR (400 MHz, MeOD) oe: 8.97 (d, J= 1.4 Hz, 1H), 8.10 (s, 1H), 7.85 (q, J= 8.5 Hz, 4H), 7.78 -7.71 (m, 2H), 7.67 (dd, J= 8.5, 1.4 Hz, 1H), 6.66 (s, 1H), 4.08 (s, 3H),3.96 - 3.84 (m, 8H),2.58 (s, 3H); HPLC purity: 98.24%; LCMS Calculated for C26H26N80:466.22; Observed: 467.25 (M + 1).
  • 48
  • (2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-(4'-{ [1-(tert-butoxypolyethylenecarbonyl)piperidin-4-yl]amineformyl}-2'-methylbiphenyl-4-yl)propionic acid [ No CAS ]
  • [ 29528-28-7 ]
  • tert-butyl 4-[({4'-[(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-[4-(1H-imidazol-4-yl)phenyl]amino}-3-oxopropyl]-2-methylbiphenyl-4-yl}carbonyl)amino]piperidin-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16.0h; A solution of 75 mg (0.10 mmol) of (2S) -2- [(iraws-4- [(ieri-butoxycarbonyl) - amino] methyl}cyclohexyl) carbonyl] amino} -3- (4 '- [1 - (ieri-butoxycarbonyl) -piperidin-4-yl] - carbamoyl} -2'-methyl-biphenyl-4-yl) propanoic acid and 44 mg (0:28 mmol) of 4- (l / i-imidazol-4-yl) aniline in 1 ml ofdimethylformamide with 72.5 mu (0:42 mmol) Nu, Nu-diisopropylethylamine and 63.3 mg (0:17 mmol)N-[(Dimethylamino)(3/i-[l,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminiumhexafluorophosphatand stirred at RT for 16 h. The contents were diluted with water and suctionfiltered precipitate, washed with water and dried under high vacuum. There were 143 mg (quant.)Of the title compound obtained.
  • 49
  • [ 29528-28-7 ]
  • N-(4-(1H-imidazol-4-yl)phenyl)-2-((4-(4-bromophenyl)-1H-imidazol-2-yl)thio)acetamide [ No CAS ]
  • 50
  • [ 29528-28-7 ]
  • 1-(4-(1H-imidazol-4-yl)phenyl)-3-((5-(4-bromophenyl)-1H-imidazol-2-yl)methyl)urea [ No CAS ]
  • 51
  • [ 29528-28-7 ]
  • N-(4-(1H-imidazol-4-yl)phenyl)-2-((4-phenyl-1H-imidazol-2-yl)-thio)acetamide [ No CAS ]
  • 52
  • [ 29528-28-7 ]
  • [ 79-04-9 ]
  • N-(4-(1H-imidazol-4-yl)phenyl)-2-chloroacetamide [ No CAS ]
  • 53
  • [ 29528-28-7 ]
  • [ 530-62-1 ]
  • N-(4-(1H-imidazol-4-yl)phenyl)-1H-imidazole-1-carboxamide [ No CAS ]
  • 54
  • [ 29528-28-7 ]
  • N-(tert-butyloxycarbonyl)nipecotic acid [ No CAS ]
  • C20H26N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 5h;
  • 55
  • [ 29528-28-7 ]
  • N-(tert-butyloxycarbonyl)nipecotic acid [ No CAS ]
  • N-(4-(1H-imidazol-4-yl)phenyl)-1-(3,4-difluorobenzyl)piperidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 20 °C 2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 2.2: 12 h / 20 °C
  • 56
  • [ 586-78-7 ]
  • [ 29528-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / 5 h / 90 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C
  • 57
  • [ 29528-28-7 ]
  • [ 173300-83-9 ]
  • di-tert-butyl 2-((4-(1H-imidazol-4-yl)phenyl)imino)imidazolidine-1,3-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; mercury (II) chloride In dichloromethane at 0 - 20℃; for 49h; 59.A Step A Mercury(ll) chloride (1 .1 equiv.) was added to a solution of 4-(1 H-imidazol-4-yl)aniline (250 mg, 1.57 mmol, 1 equiv.), di-tert-butyl 2-thioxoimidazolidine-1 ,3-dicarboxylate (1 equiv.) and triethylamine (3.1 equiv.) in 10 mL DCM at 0°C. The resulting mixture was stirred at 0°C for 1 h and then at r.t. for 2 days. The reaction mixture was diluted with water and DCM. The mixture was filtered and the filtrate was washed with sat. aq. NaHCO3, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting beige solid was used in the next step without any further purification (470 mg, 1 .1 mmol, 70% yield).
70% With triethylamine; mercury (II) chloride In dichloromethane at 0 - 20℃; for 49h; 59.A Step A Mercury(ll) chloride (1 .1 equiv.) was added to a solution of 4-(1 H-imidazol-4-yl)aniline (250 mg, 1.57 mmol, 1 equiv.), di-tert-butyl 2-thioxoimidazolidine-1 ,3-dicarboxylate (1 equiv.) and triethylamine (3.1 equiv.) in 10 mL DCM at 0°C. The resulting mixture was stirred at 0°C for 1 h and then at r.t. for 2 days. The reaction mixture was diluted with water and DCM. The mixture was filtered and the filtrate was washed with sat. aq. NaHCO3, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting beige solid was used in the next step without any further purification (470 mg, 1 .1 mmol, 70% yield).
  • 58
  • [ 29528-28-7 ]
  • di-tert-butyl 2-((4-(1-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-1H-imidazol-4-yl)phenyl)imino)imidazolidine-1,3-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine; mercury (II) chloride / dichloromethane / 49 h / 0 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h 2.2: 16 h / 20 °C
  • 59
  • [ 29528-28-7 ]
  • N-(4-(1-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-1H-imidazol-4-yl)phenyl)-4,5-dihydro-1H-imidazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine; mercury (II) chloride / dichloromethane / 49 h / 0 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h 2.2: 16 h / 20 °C 3.1: trifluoroacetic acid / 1,2-dichloro-ethane / 20 °C
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