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Chemical Structure| 122-85-0 Chemical Structure| 122-85-0

Structure of N-(4-Formylphenyl)acetamide
CAS No.: 122-85-0

Chemical Structure| 122-85-0

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Product Details of [ 122-85-0 ]

CAS No. :122-85-0
Formula : C9H9NO2
M.W : 163.17
SMILES Code : CC(NC1=CC=C(C=O)C=C1)=O
MDL No. :MFCD00003380
InChI Key :SKLUWKYNZNXSLX-UHFFFAOYSA-N
Pubchem ID :73942

Safety of [ 122-85-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 122-85-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.11
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 46.14
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

46.17 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.23
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.25
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.27
Log Po/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.

0.88
Log Po/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

1.54
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.23

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.81
Solubility 2.52 mg/ml ; 0.0154 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.82
Solubility 2.48 mg/ml ; 0.0152 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-2.72
Solubility 0.308 mg/ml ; 0.00189 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

Yes
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

Yes
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.

-6.41 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

1.0 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)

1.0

Application In Synthesis of [ 122-85-0 ]

* 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 [ 122-85-0 ]

[ 122-85-0 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 7504-94-1 ]
  • [ 122-85-0 ]
  • acetic acid-[4-(pyrimidin-2-ylhydrazono-methyl)-anilide] [ No CAS ]
  • 2
  • [ 2406-90-8 ]
  • [ 122-85-0 ]
  • acetic acid-{4-[(2-chloro-benzothiazol-6-ylimino)-methyl]-anilide} [ No CAS ]
  • 3
  • [ 69583-00-2 ]
  • [ 122-85-0 ]
  • [ 101281-51-0 ]
  • 4
  • [ 16375-88-5 ]
  • [ 122-85-0 ]
YieldReaction ConditionsOperation in experiment
91% With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; In ethanol; at 50℃; for 24h; General procedure: Under an air atmosphere, a Schlenk tube was charged with MCM-41-bpy-CuI (40 mg, 0.025 mmol), alcohol (0.5 mmol), TEMPO (4 mg, 0.025 mmol), aqueous ammonia (0.5 mmol, 25e28%, w/w) and EtOH (1.0 mL). The mixture was stirred at 50 C for 18-48 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The MCM-41-bpy-CuI complex was washed with EtOH (2*5 mL), and Et2O (5 mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=15:1 to 10:1) to provide the desired product.
86%Spectr. With bismuth vanadate; oxygen; In acetonitrile; at 40℃; under 760.051 Torr; for 3h;Schlenk technique; Irradiation; General procedure: Bismuth vanadate (32.3 mg, 100 mmol) was added to a Schlenkflask containing benzyl alcohol stock solution (1 mL, 0.1 mmol inacetonitrile) and acetonitrile (9 mL). The mixture was left to stirfor 30 min to disperse the catalyst under a dioxygen atmospherevia a balloon. The mixture was then irradiated with a 30W blueLED array at a distance of 2 cmwith an irradiance of 245mWcm2.The mixture reached ca. 40 C by the end of the reaction and afterirradiation, the catalyst was removed using centrifugation at4000 rpm for 30 min. For GC analysis, 1 mL of supernatant wastaken and 1 lL injected. For NMR analysis, the supernatant wasreduced in volume using a rotary evaporator at 65 mbar at 20 C,and the residue dissolved in d6-DMSO containing maleic acid asan internal standard.
References: [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2262 - 2267.
[2]Tetrahedron,2015,vol. 71,p. 8725 - 8731.
[3]Synthetic Communications,2012,vol. 42,p. 2318 - 2326.
[4]RSC Advances,2015,vol. 5,p. 81415 - 81428.
[5]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2262 - 2267.
[6]Journal of Organic Chemistry,1988,vol. 53,p. 2154 - 2159.
[7]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 1767 - 1772.
[8]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 968 - 974.
[9]International Journal of Chemical Kinetics,1997,vol. 29,p. 9 - 16.
[10]Journal of Chemical Research, Miniprint,1998,p. 2251 - 2272.
[11]Journal of Chemical Research, Miniprint,1999,p. 2118 - 2135.
[12]Journal of Chemical Research, Miniprint,2001,p. 562 - 585.
[13]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2000,vol. 39,p. 1258 - 1263.
[14]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2002,vol. 41,p. 493 - 499.
[15]Journal of Physical Organic Chemistry,2002,vol. 15,p. 721 - 727.
[16]Journal of the Indian Chemical Society,2004,vol. 81,p. 467 - 473.
[17]Journal of Chemical Research,2004,p. 581 - 584.
[18]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2008,vol. 47,p. 669 - 676.
[19]Journal of the Indian Chemical Society,2008,vol. 85,p. 496 - 501.
[20]Chemistry of Materials,2011,vol. 23,p. 4844 - 4856.
[21]Journal of Catalysis,2017,vol. 354,p. 152 - 159.
  • 5
  • [ 122-85-0 ]
  • [ 16375-88-5 ]
YieldReaction ConditionsOperation in experiment
85% With sodium tetrahydroborate; In methanol; at 20℃; To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mL) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes: EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mL) and ethyl acetate (4*50 mL) and the organic layer was washed with brine (25 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85%); 1H NMR (DMSO-d6): delta 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H).
85% With methanol; sodium tetrahydroborate; at 20℃; Preparation of 4-acetamidobenzyl alcohol. To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mE) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes:EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mE) and ethyl acetate (4x50 mE) and the organic layer was washed with brine (25 mE). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85%); ?H NMR (DMSO-d5): oe 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H) ppm.
61% With ReOBr2(2-(2-hydroxy-5-methylphenyl)benzotriazole-(H))(PPh3); phenylsilane; In tetrahydrofuran; for 1.33333h;Reflux; General procedure: In a typical experiment, to a mixture of carbonyl compound (1.0mmol) and [ReOBr2(hmpbta)(PPh3)] (5mol%) in THF (3mL) at reflux temperature was added PhSiH3 (2.0mmol). The reaction mixture was stirred under air atmosphere (the reaction times are indicated in the Table 4) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction was quenched with 1equiv of tetrabutylammonium fluoride (TBAF) (1.0M THF) during 1h. Then, the reaction mixture was evaporated and purified by silica gel column chromatography with the appropriate mixture of n-hexane and ethyl acetate to afford the alcohols, which are all known compounds.
  • 7
  • [ 104-87-0 ]
  • [ 122-85-0 ]
  • [ 147804-55-5 ]
  • [ 57412-12-1 ]
  • [ 14527-51-6 ]
  • [ 106295-93-6 ]
  • 8
  • [ 122-85-0 ]
  • [ 62-53-3 ]
  • [ 16375-88-5 ]
  • N-(4-((phenylamino)methyl)phenyl)acetamide [ No CAS ]
  • 9
  • [ 122-85-0 ]
  • [ 13361-34-7 ]
  • 2-ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In isopropyl alcohol; a) Preparation of 2-ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate A mixture of 35 g (0.18 mol) of 2-ethylhexyl cyanoacetate and 30 g (0.18 mol) of 4-acetamidobenzaldehyde in 300 ml of isopropanol is refluxed for 3 hours. The reaction mixture is then allowed to cool and is crystallized. The crystals formed are separated out by filtration and are recrystallized from a minimum amount of isopropanol. After filtration and drying, 33.3 g (54% yield) of 2-ethylhexyl 3-(4-acetylaminophenyl)-2-cyanoacrylate are obtained in the form of a pale yellow powder. Melting point: 119 C. UW absorption (as a solution in ethanol): λmax=351 nm, εmax=30 960, EI %=904 Elemental analysis for C20H26N2O3 calculated: C 70.15; H 7.65; N 8.18; O 14.02 found: C 70.08; H 7.65; N 8.16; O 14.03
  • 10
  • [ 18699-02-0 ]
  • [ 16375-88-5 ]
  • [ 122-85-0 ]
  • 11
  • [ 18699-02-0 ]
  • [ 16375-88-5 ]
  • [ 122-85-0 ]
  • [ 103-84-4 ]
  • 12
  • [ 1138324-46-5 ]
  • [ 122-85-0 ]
  • [ 1272598-59-0 ]
  • 13
  • [ 136725-50-3 ]
  • [ 122-85-0 ]
  • C14H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h; A mixture of 4-acetamidobenzaldehyde (200mg), piperidine (0.121 mL), NaBH(OAc)3 (636mg) and DIPEA (0.617ml) in DCM (4ml) was stirred at RT for 4h. DCM and sat. NaHCO3 were added. The phases were separated, the org. layer was dried (Na2SO4), filtered off and evaporated to dryness to afford 267 mg of white solid. LC-MS (B): tR = 0.45 min; [M+H]+: 233.24.
  • 14
  • [ 122-85-0 ]
  • [ 1986-47-6 ]
  • N-(4-((((1S*,2R*)-2-phenylcyclopropyl)amino)methyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.
  • 15
  • [ 67-56-1 ]
  • [ 122-85-0 ]
  • [ 17012-22-5 ]
  • [ 16375-88-5 ]
 

Historical Records

Technical Information

• Acyl Group Substitution • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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