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[ CAS No. 1450-94-8 ] {[proInfo.proName]}

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Chemical Structure| 1450-94-8
Chemical Structure| 1450-94-8
Structure of 1450-94-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1450-94-8 ]

CAS No. :1450-94-8 MDL No. :MFCD10697505
Formula : C4H8ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :JWMWVKLQTDSFTD-UHFFFAOYSA-N
M.W : 133.58 Pubchem ID :10154076
Synonyms :

Calculated chemistry of [ 1450-94-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.86
TPSA : 43.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.47
Log Po/w (WLOGP) : 0.81
Log Po/w (MLOGP) : -0.27
Log Po/w (SILICOS-IT) : -0.26
Consensus Log Po/w : 0.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.43
Solubility : 5.0 mg/ml ; 0.0374 mol/l
Class : Very soluble
Log S (Ali) : -0.96
Solubility : 14.7 mg/ml ; 0.11 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.35
Solubility : 59.1 mg/ml ; 0.443 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 1450-94-8 ]

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 [ 1450-94-8 ]

* 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 [ 1450-94-8 ]

[ 1450-94-8 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 1450-94-8 ]
  • [ 108-24-7 ]
  • <i>N</i>-(1-methyl-1<i>H</i>-imidazol-2-yl)-acetamide; hydrochloride [ No CAS ]
  • 3
  • [ 1943-83-5 ]
  • [ 1450-94-8 ]
  • 1-(1-methyl-imidazolyl)-2-imidazolidinone hydrochloride [ No CAS ]
  • 4
  • [ 60965-26-6 ]
  • [ 1450-94-8 ]
  • [ 138555-54-1 ]
  • 5
  • [ 1450-94-8 ]
  • [ 94944-72-6 ]
  • [ 94944-73-7 ]
  • 6
  • [ 1450-94-8 ]
  • [ 94-02-0 ]
  • [ 106263-65-4 ]
  • 7
  • 2-amino-5-bromo-1-methylimidazole hydrochloride [ No CAS ]
  • [ 1450-94-8 ]
  • 8
  • 2-amino-4-bromo-1-methylimidazole hydrochloride [ No CAS ]
  • [ 1450-94-8 ]
  • 12
  • hydrochloric acid-ethyl acetate [ No CAS ]
  • [ 1450-94-8 ]
  • [ 541-41-3 ]
  • 2-ethoxycarbonylamino-1-methylimidazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In pyridine; dichloromethane; water; Example 3 Preparation of 2-ethoxycarbonylamino-1-methylimidazole hydrochloride Ethyl chlorocarbonate (0.6 g) was added to a solution of <strong>[1450-94-8]2-amino-1-methylimidazole hydrochloride</strong> (0.3 g) in pyridine (5 ml), and the mixture was stirred under heating at 100 C. for 2 hours. The solvent was evaporated under reduced pressure, the residue was dissolved in water, and sodium carbonate was added until the solution became alkaline. The solvent was evaporated under reduced pressure, and then the residue was purified by column chromatography on silica gel (eluent: chloroform) to give 2-ethoxycarbonylamino-1-methylimidazole. This compound was dissolved in dichloromethane, and 4N hydrochloric acid-ethyl acetate (2 ml) was added to form its hydrochloric acid salt. The resulting crude crystals were washed with ether to give 2-ethoxycarbonylamino-1-methylimidazole hydrochloride (0.29 g, Yield: 56%) as colorless prisms. mp: 129-131 C. Elemental Analysis: Calcd. for C7 H12 ClN3 O2 *0.2H2 O: C,40.18%; H,5.97%; N,20.08% Found: C,40.00%; H,6.40%; N,20.05% IR (KBr)cm-1: 3170-2990, 1745, 1640, 1250. 1 H-NMR (DMSO-d6) delta: 1.30(3H,t,J=7.1 Hz), 3.66(3H,s), 4.28(2H,q,J=7.1 Hz), 7.32(1H,dJ=1.4 Hz), 7.43(1H,d,J=1.4 Hz).
  • 13
  • [ 13574-13-5 ]
  • [ 1450-94-8 ]
  • [ 164583-64-6 ]
YieldReaction ConditionsOperation in experiment
With pyridine; anhydrous phosphorus trichloride; Example 10 Preparation of benzyl (4S)-4-t-butoxycarbonylamino-4-[(1-methylimidazol-2-yl)carbamoyl]butyrate: According to the same procedure as in Example 7, the title compound (857 mg) was obtained from <strong>[1450-94-8]2-amino-1-methylimidazole hydrochloride</strong> (668 mg), N-t-butoxycarbonyl-L-glutamic acid (gamma-benzyl ester)(1.69 g), dry pyridine (25 ml) and phosphorus trichloride (687 mg). IR (neat) cm-1: 3400, 3280, 2970, 1730, 1700, 1585, 1550, 1480, 1450, 1380, 1360, 1330, 1280, 1240, 1160, 1050, 1020. 1 H-NMR (CDCl3) delta: 1.45(9H,s), 2.00-2.60(4H,m), 3.49(3H,s), 4.23-4.46(1H,m), 5.08(2H,s), 5.62(1H,d,J=7.OHz), 6.51(1H,d,J=2.4 Hz), 6.65(1H,d,J=2.4 Hz), 7.33(5H,s).
  • 14
  • hydrochloric acid-ethyl acetate [ No CAS ]
  • hexane-diethyl ether [ No CAS ]
  • [ 1450-94-8 ]
  • [ 501-53-1 ]
  • 2-benzyloxycarbonylamino-1-methylimidazole hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In sodium hydroxide; chloroform; Example 4 Preparation of 2-benzyloxycarbonylamino-1-methylimidazole hydrochloride 2-Amino-1-methylimidazole hydrochloride (0.3 g) was dissolved in 1N sodium hydroxide solution (5 ml). Benzyloxycarbonyl chloride (0.43 g) and ether (2 ml) were added, and the mixture was stirred for 1 hour. The product was extracted with ethyl acetate, the extract was washed with water and aqueous saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Diethyl ether-hexane was added to the resulting residue for crystallization, and the crystals were separated by filtration. The crystals of 2-benzyloxycarbonylamino-1-methylimidazole thus obtained was dissolved in chloroform, and 4N hydrochloric acid-ethyl acetate (0.5 ml) was added to form its hydrochloric acid salt. The crude crystals thus obtained were washed with ether to give 2-benzyloxycarbonylamino-1-methylimidazole hydrochloride (0.2 g, Yield: 30%) as white powder. mp: 141-142 C. Elemental Analysis: Calcd. for C12 H14 ClN3 O2 *0.2H2 O: C,53.12%; H,5.35%; N,15.94% Found: C,53.17%; H,5.24%; N,15.45% IR (KBr)cm-1: 3070, 1740, 1625, 1250 1215. 1 H-NMR (DMSO-d6) delta: 3.64(3H,s), 5.29(2H,s), 7.30 (1H, d, J=2.2 Hz), 7.40-7.47(6H,m).
  • 15
  • hydrochloric acid-ethyl acetate [ No CAS ]
  • [ 1450-94-8 ]
  • [ 123-11-5 ]
  • N-(1-methylimidazol-2-yl)-4-methoxybenzylideneamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
26.9% With sodium methylate; In diethyl ether; ethanol; hexane; chloroform; Reference Example 9 Preparation of N-(1-methylimidazol-2-yl)-4-methoxybenzylideneamine hydrochloride: 2-Amino-1-methylimidazole hydrochloride (0.3 g) was dissolved in ethanol (4 ml), and sodium methoxide (28% methanol solution: 0.5 ml) and p-anisaldehyde (0.34 g) were added. The mixture was heated at reflux overnight. The solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: methanol-chloroform=5:95), and the solvent in the desired fraction was evaporated. The precipitated pale yellow prisms were separated by filtration using hexane. The resulting crystals were dissolved in chloroform, and 4N hydrochloric acid--ethyl acetate (0.22 ml) was added. The solvent was evaporated, and the precipitated pale yellow was separated by filtration using diethyl ether to give the title compound (0.17 g, 26.9%). mp: 191.0-192.0 C. Elemental Analysis: Calcd. for C12 H14 N3 0C1*0.3H2 0: C,56.06%; H,5.72%; N,16.34% Found: C,56.07%; H,5.62%; N,16.46% IR (KBr) cm-1: 2840-2670, 1585, 1255, 1160. 1 H-NMR (DMSO-d6) delta: 3.80 (3H, s), 3.90 (3H, s), 7.18 (2H,d,J=8.8.8 Hz), 7.57(1H,d,J=2.OHz), 7.62 (1H,d,J=2.OHz), 8.02 (2H,d,J=8.BHz), 9.12(1H,s).
  • 16
  • diethylphosphoryl cyanide (DEPC) [ No CAS ]
  • [ 13734-34-4 ]
  • [ 1450-94-8 ]
  • [ 164583-68-0 ]
YieldReaction ConditionsOperation in experiment
45.1% With triethylamine; In methanol; water; N,N-dimethyl-formamide; Example 14 Preparation of 2-(N-Boc-phenylalanyl)amino-1-methylimidazole: 2-Amino-1-methylimidazole hydrochloride (0.3 g) was dissolved in water, and the solution was neutralized with sodium carbonate and concentrated to dryness. The residue was dissolved in DMF (5 ml). N-Boc-phenylalanine (1.0 g) and triethylamine (0.7 ml) were added, and then diethylphosphoryl cyanide (DEPC) (0.86 ml) was added dropwise under ice-cooling. The mixture was stirred at room temperature for 2 hours. Methanol (1 ml) and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: methanol-chloroform=5:95), and evaporation of the solvent in the desired fraction gave a pale brown oil (0.39 g, 45.1%). IR (KBr) cm-1: 3280, 3030-2940, 1700, 1600-1550, 1490, 1390-1365. 1 H-NMR (CDCl3) delta: 1.42(9H,s), 3.16-3.23(2H,m), 3.46(3H,s), 4.52-4.57 (1H,m), 5.44(1H,d,J=8.6 Hz), 6.54(1H,d,J=2.4Hz), 6.67(1H,d,J=2.4Hz), 7.21 (5H, s).
  • 17
  • D-N-(t-butyloxycarbonyl)glutamic acid γ-methyl ester [ No CAS ]
  • [ 1450-94-8 ]
  • [ 7719-12-2 ]
  • methyl (2S)-2-t-butoxycarbonylamino-4-[(1-methylimidazol-2-yl)carbamoyl]butyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine; chloroform; Example 7 Preparation of methyl (2S)-2-t-butoxycarbonylamino-4-[(1-methylimidazol-2-yl)carbamoyl]butyrate: 2-Amino-1-methylimidazole hydrochloride (668 mg) and N-t-butoxycarbonyl-L-glutamic acid alpha-methyl ester (1.31 g) were dissolved in dry pyridine (25 ml). Phosphorous trichloride (687 mg) was added under ice-cooling, and then the mixture was stirred at room temperature for 3 hours. The precipitated materials were filtered off, and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in chloroform, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flush column chromatography on silica gel eluent: methanol-chloroform=3:97-1:19) to give the title compound (300 mg). IR (KBr)cm-1: 3370, 3130, 2970, 2950, 1735, 1680, 1555, 1520, 1480, 1460, 1440, 1360, 1320, 1300, 1260, 1180, 1160, 1080, 1060. 1 H-NMR (DMSO-d6) delta: 1.39 (9H, s), 1.60-2.10 (2H,m), 2.40(2H,t,J=7.OHz), 3.39(3H,s), 3.63(3H,s), 3.95-4.08(1H,m), 6.73(1H,d,J=1.2 Hz), 7.03(1H,d,J=1.2 Hz), 7.29(1H,d,J=8.OHz), 9.99(1H,s).
  • 18
  • [ 1450-94-8 ]
  • [ 98045-03-5 ]
  • methyl (2S)-2-t-butoxycarbonylamino-3-[(1-methylimidazol-2-yl)carbamoyl]propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; anhydrous phosphorus trichloride; Example 12 Preparation of methyl (2S)-2-t-butoxycarbonylamino-3-[(1-methylimidazol-2-yl)carbamoyl]propionate: According to the same procedure as in Example 7, the title compound (300 mg) was obtained from <strong>[1450-94-8]2-amino-1-methylimidazole hydrochloride</strong> (1.34 g), N-t-butoxycarbonyl-L-aspartic acid (alpha-methyl ester) (1.24 g), dry pyridine (35 ml) and phosphorus trichloride (687 mg). IR (KBr) cm-1: 3420, 2970, 1740, 1710, 1585, 1550, 1490, 1390, 1360, 1340, 1280, 1240, 1210, 1160, 1050, 1020. 1 H-NMR (CDCl3) delta: 1.45(9H,s), 2.82(1H,dd,J=4.4 Hz,16.8 Hz), 3.11(1H,dd,J=4.4 Hz,16.8Hz), 3.50(3H,s), 3.73(3H,s),4.53-4.62(1H,m), 5.40-5.80(H,brs), 6.03(1H,d,J=8.2 Hz), 6.55(1H,d,J=2.4 Hz), 6.67(1H,d,J=2.4 Hz).
  • 19
  • acetone diethyl ether [ No CAS ]
  • MeOH-ether [ No CAS ]
  • [ 1450-94-8 ]
  • [ 103-72-0 ]
  • N-(1-methylimidazol-2-yl)-N'-phenylthiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In dichloromethane; EXAMPLE X N-(1-methylimidazol-2-yl)-N'-phenylthiourea A 4.8 g (0.036 mole) sample of <strong>[1450-94-8]2-amino-1-methylimidazole hydrochloride</strong> is suspended in 20 ml of methylene chloride and stirred with 10 ml of 50% NaOH. The organic layer is separated and the aqueous layer is extracted twice with 20 ml portions of fresh methylene chloride. The combined organic extracts are dried over K2 CO3 and filtered. The filtrate is treated with 4.86 g (0.036 mole) of phenyl isothiocyanate. The solution is heated under reflux for 4 hr. Evaporation of the solvent in vacuo followed by recrystallization of the residue from acetone-ether (1:1) and MeOH-ether (1:1) gives the product, N-(1-methylimidazol-2-yl)-N'-phenylthiourea; m.p. 170-172 C.
  • 20
  • N-benzyl-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-benzyl-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 21
  • 4'-fluoro-5-(hydroxymethyl)-2'-methyl-N-(3-methylbenzyl)-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • 4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-N-(3-methylbenzyl)-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 22
  • N-(3-chlorobenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3-chlorobenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 23
  • N-(3-methoxybenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3-methoxybenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazole-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 24
  • 4'-fluoro-5-(hydroxymethyl)-2'-methyl-N-(3-(trifluoromethoxy)benzyl)-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • 4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-N-(3-(trifluoromethoxy)benzyl)-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 25
  • N-(3,4-dichlorobenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3,4-dichlorobenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 26
  • N-(4-chloro-3-methylbenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(4-chloro-3-methylbenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 27
  • N-(4-fluoro-3-methylbenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3-methyl,4-fluorobenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazole-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 28
  • N-(4-fluoro-3-methoxylbenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3-methoxy,4-fluorobenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 29
  • N-(3,5-dimethylbenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3,5-dimethylbenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 30
  • N-(3,5-dichlorobenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3,5-dichlorobenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 31
  • N-(3,5-dimethoxybenzyl)-4'-fluoro-5-(hydroxymethyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • [ 1450-94-8 ]
  • N-(3,5-dimethoxybenzyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide [ No CAS ]
  • 32
  • 7-(bromomethyl)-2-(4-chloro-3-methylbenzyl)-5-(4-fluoro-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
  • [ 1450-94-8 ]
  • 2-(4-chloro-3-methylbenzyl)-5-(4-fluoro-2-methylphenyl)-7-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
  • 33
  • 7-(bromomethyl)-5-(4-fluoro-2-methylphenyl)-2-(4-fluoro-3-methylbenzyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
  • [ 1450-94-8 ]
  • 5-(4-fluoro-2-methylphenyl)-2-(4-fluoro-3-methylbenzyl)-7-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
  • 34
  • 7-(bromomethyl)-2-(3,5-dimethoxybenzyl)-5-(4-fluoro-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
  • [ 1450-94-8 ]
  • 2-(3,5-dimethoxybenzyl)-5-(4-fluoro-2-methylphenyl)-7-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
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