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[ CAS No. 1792-41-2 ]

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Chemical Structure| 1792-41-2
Chemical Structure| 1792-41-2
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Product Details of [ 1792-41-2 ]

CAS No. :1792-41-2 MDL No. :MFCD00125906
Formula : C9H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :MVHOAOSHABGEFL-UHFFFAOYSA-N
M.W :146.19 Pubchem ID :74525
Synonyms :

Calculated chemistry of [ 1792-41-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.03
TPSA : 28.68 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 2.25
Log Po/w (WLOGP) : 2.18
Log Po/w (MLOGP) : 1.63
Log Po/w (SILICOS-IT) : 2.95
Consensus Log Po/w : 2.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.249 mg/ml ; 0.0017 mol/l
Class : Soluble
Log S (Ali) : -2.49
Solubility : 0.475 mg/ml ; 0.00325 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.66
Solubility : 0.0318 mg/ml ; 0.000217 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.32

Safety of [ 1792-41-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1792-41-2 ]

* 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 [ 1792-41-2 ]

[ 1792-41-2 ] Synthesis Path-Downstream   1~68

  • 1
  • [ 60-35-5 ]
  • [ 636-24-8 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
at 180℃; im Rohr;
  • 2
  • [ 155221-39-9 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
beim Erhitzen;
  • 3
  • [ 24780-84-5 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
beim Erhitzen;
  • 4
  • [ 2818-63-5 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
beim Erhitzen zum Sieden;
  • 5
  • [ 1034250-03-7 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
beim Erhitzen zum Sieden;
  • 6
  • [ 612-45-3 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; tin
With iron; acetic acid
With palladium on activated charcoal; ethanol at 30℃; Hydrogenation;
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation 2: Erhitzen auf Temperaturen oberhalb des Schmelzpunktes
Multi-step reaction with 2 steps 1: iron; acetic acid 2: 200 - 210 °C
Multi-step reaction with 2 steps 1: ammonium sulfide 2: 150 °C
Multi-step reaction with 2 steps 1: water; alcohol; acetic acid / gibt Eisenspaene in der Loesung 2: beim Destillieren

  • 9
  • [ 85-44-9 ]
  • [ 1792-41-2 ]
  • [ 63786-63-0 ]
YieldReaction ConditionsOperation in experiment
at 200℃;
  • 10
  • [ 1792-41-2 ]
  • [ 100-52-7 ]
  • [ 189056-67-5 ]
YieldReaction ConditionsOperation in experiment
at 200℃;
at 200℃;
  • 11
  • [ 1792-41-2 ]
  • [ 100-44-7 ]
  • [ 53811-91-9 ]
YieldReaction ConditionsOperation in experiment
With ethanol; sodium ethanolate
  • 12
  • [ 1792-41-2 ]
  • [ 75-03-6 ]
  • [ 1034250-03-7 ]
  • 1,3-diethyl-2,5-dimethyl-benzimidazolium; periodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 150℃; im Rohr;
  • 13
  • [ 1792-41-2 ]
  • [ 75-03-6 ]
  • 1,3-diethyl-2,5-dimethyl-benzimidazolium; periodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 200 - 230℃; im Rohr;
  • 14
  • [ 1792-41-2 ]
  • [ 75-87-6 ]
  • 2,2,2-trichloro-1-(2,5-dimethyl-benzimidazol-1-yl)-ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 100℃; im Rohr;
  • 15
  • [ 1792-41-2 ]
  • [ 105-39-5 ]
  • (2,5-dimethyl-benzimidazol-1-yl)-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate
  • 16
  • [ 1792-41-2 ]
  • [ 67-64-1 ]
  • 2-(2,5-dimethyl-benzimidazol-1-yl)-propane-2-sulfonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfur dioxide
  • 17
  • [ 1792-41-2 ]
  • [ 77-78-1 ]
  • [ 155221-39-9 ]
  • 18
  • [ 1792-41-2 ]
  • [ 74-88-4 ]
  • [ 155221-39-9 ]
  • [ 24780-84-5 ]
YieldReaction ConditionsOperation in experiment
With methanol at 20℃;
  • 19
  • [ 1792-41-2 ]
  • [ 74-88-4 ]
  • [ 21337-19-9 ]
YieldReaction ConditionsOperation in experiment
With methanol at 20℃;
With methanol at 120 - 130℃; im Rohr;
  • 20
  • [ 1792-41-2 ]
  • 4,5,7-trichloro-2,6-dimethyl-1(3)<i>H</i>-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; calcium chloride
  • 22
  • [ 1792-41-2 ]
  • [ 96048-73-6 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; calcium chloride at 0 - 5℃;
  • 24
  • [ 1792-41-2 ]
  • 4-bromo-2,5-dimethyl-1(3)<i>H</i>-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bromine; acetic acid
With carbon disulfide; bromine
With chloroform; bromine
  • 26
  • [ 5433-07-8 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
bei der Destillation;
  • 27
  • [ 39623-57-9 ]
  • [ 1792-41-2 ]
  • [ 141-78-6 ]
YieldReaction ConditionsOperation in experiment
at 107 - 116℃;
  • 28
  • [ 108-24-7 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate
  • 29
  • [ 75-07-0 ]
  • [ 496-72-0 ]
  • [ 1034250-03-7 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
With acetic acid
  • 31
  • [ 496-72-0 ]
  • [ 75-36-5 ]
  • [ 1792-41-2 ]
  • 32
  • [ 534-26-9 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
81% In various solvent(s) Heating;
  • 33
  • [ 1792-41-2 ]
  • [ 120209-26-9 ]
  • [ 147021-92-9 ]
  • [ 90349-14-7 ]
YieldReaction ConditionsOperation in experiment
1: 8% 2: 17% 3: 31% With sulfuric acid; nitric acid at 0 - 20℃;
1: 31% 2: 17% With sulfuric acid; nitric acid at 0 - 20℃;
  • 34
  • [ 1076-59-1 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
  • [ 64376-02-9 ]
YieldReaction ConditionsOperation in experiment
80% In acetic acid at 90℃;
  • 35
  • [ 39214-83-0 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
  • [ 142335-32-8 ]
YieldReaction ConditionsOperation in experiment
85% In acetic acid at 90℃;
  • 36
  • [ 496-72-0 ]
  • [ 25755-82-2 ]
  • [ 1792-41-2 ]
  • [ 142335-30-6 ]
YieldReaction ConditionsOperation in experiment
70% In acetic acid at 90℃;
  • 37
  • [ 496-72-0 ]
  • [ 25755-85-5 ]
  • [ 1792-41-2 ]
  • [ 142335-31-7 ]
YieldReaction ConditionsOperation in experiment
74% In acetic acid at 90℃;
  • 38
  • [ 496-72-0 ]
  • [ 123-54-6 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
84% With water; toluene-4-sulfonic acid In acetonitrile at 80℃; for 16h; Sealed tube;
84% With sodium iodide dichloride In tetrahydrofuran; water Reflux; 2.2 General procedure for the synthesis of2-substituted 1,3-Benzazoles 3, 5 and 7 General procedure: To a mixture of o-substituted (-NH2 or -SH or -OH) anilines(1.0 mmol) and appropriate 1,3-diketones (1.1 mmol) in THF(5 mL) was added 30%w/w aqueous NaICl2 (0.2 mmol, 20mol%). The reaction was allowed to remain stirred at refluxtemperature for 2-3 h. After the reaction was complete, asindicated by TLC, the mixture was cooled to room temperature.The volatiles were removed under reduced pressureand treated successively with aqueous sodium thiosulphatesolution and saturated solution of NaHCO3, and extractedby ethylacetate (2×10 mL). The combined organic phaseswere washed with brine and dried over Na2SO4 and evaporatedunder vacuum. The crude reaction mixture was purifiedby column chromatography on silica gel using petroleumether/ethyl acetate as eluents.
58% With hydrogenchloride In ethanol Heating;
  • 39
  • [ 496-72-0 ]
  • [ 31709-47-4 ]
  • [ 1792-41-2 ]
  • [ 65958-38-5 ]
YieldReaction ConditionsOperation in experiment
72% In acetic acid at 90℃;
  • 40
  • [ 141-97-9 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
With Montmorillonite KSF In solid at 133℃; for 0.0666667h; Irradiation;
  • 41
  • [ 141-97-9 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
75% With bentonite K10 clay In benzene for 16h; Heating;
  • 42
  • [ 70254-61-4 ]
  • [ 496-72-0 ]
  • [ 5400-75-9 ]
  • [ 1792-41-2 ]
  • 4-acetonylidene-7-methyl-1,5-benzodiazepin-2-one [ No CAS ]
  • 4-acetonylidene-8-methyl-1,5-benzodiazepin-2-one [ No CAS ]
  • 43
  • [ 1792-41-2 ]
  • 6(5)-chloro-2,5(6)-dimethylbenzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With N-chloro-succinimide In chloroform for 2h; Heating;
  • 44
  • [ 1792-41-2 ]
  • 5,6-dibromo-2,5(6)-dimethylbenzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With bromine In acetic acid 1) reflux, 30 min; 2) rt, 2 h; further reagent;
  • 45
  • [ 1792-41-2 ]
  • [ 74-88-4 ]
  • [ 24780-84-5 ]
YieldReaction ConditionsOperation in experiment
With methanol at 120 - 130℃; im Rohr;
  • 46
  • [ 1792-41-2 ]
  • [ 74-88-4 ]
  • [ 24780-84-5 ]
YieldReaction ConditionsOperation in experiment
With methanol at 20℃;
YieldReaction ConditionsOperation in experiment
at 100℃;
YieldReaction ConditionsOperation in experiment
at 107 - 120℃;
YieldReaction ConditionsOperation in experiment
With zinc at 270℃;
YieldReaction ConditionsOperation in experiment
With ethanol; sodium
  • 51
  • 2,6-dimethyl-3<i>H</i>-benzimidazole-1-oxide [ No CAS ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
at 270℃;
  • 52
  • <i>N</i>-(5-methyl-2-nitro-phenyl)-acetimidic acid methyl ester [ No CAS ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
86% With ammonium sulfate; magnesium In methanol at 60℃; for 0.5h;
  • 53
  • [ 77900-13-1 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
89.2% With silica gel for 0.0833333h; microwave irradiation;
  • 54
  • [ 78-39-7 ]
  • [ 496-72-0 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
99% With nano-Ni(II)/Y zeolite catalyst In neat (no solvent) at 60℃; for 0.766667h; Green chemistry;
97% With mesoporous anchored Cu(II) Schiff-base complex from salicylaldehyde and (3-aminopropyl)trimethoxysilane In neat (no solvent) at 80℃; Green chemistry; General procedure for the preparation of benzimidazole derivatives General procedure: A mxiture of phenylenediamine (1 mmol) with triethylorthoformate (1 mmol) in the presence of Cu/SBA15 as catalyst (0.0012 mmol) was stirred at 80 °C for 5 h under solvent free conditions. After completion of the reaction, the mixture was cooled to room temperature, and the mixture was washed with ethanol (20 mL) and the product was purified by crystallization or column chromatography to afford the final products.
96% With [PVP-SO3H] HSO4 at 60℃; for 0.0666667h; General procedure for the preparation of benzimidazole, benzoxazole, andbenzothiazole derivatives General procedure: o-Phenylenediamine, o-aminophenol or o-aminothiophenol (1 mmol), ortho esters(1.5 mmol) and [PVP-SO3H] HSO4 (7 mg, 4 mol %) were mixed and the resulting mixturewas stirred at 60 C for the appropriate time (Table 2). After completion of thereaction, as indicated by TLC (EtOAc:n-hexane; 1:3), ethyl acetate (10 mL) was addedand the catalyst was separated by filtration. The organic phase was washed with water,and then the organic phase was dried by Na2SO4. After filtration of the drying agent,ethyl acetate was removed under reduced pressure to get the desired product. The spectraldata of representative compounds follow.
95% With ammonium chloride In water Inert atmosphere; Reflux; Green chemistry;
93% With zirconium(IV) oxychloride octahydrate for 0.0833333h; Microwave irradiation;
93% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 85℃; for 0.1h;
93% With gallium(III) triflate at 20℃; for 0.183333h;
92% With silica supported fluoroboric acid at 80℃; for 0.833333h; Neat (no solvent);
90% at 90℃; for 1h;
90% With tris(trifluoroacetato)bismuth(III) at 85℃; for 0.0833333h;
89% With o-benzenedisulfonimide In neat (no solvent) at 20 - 25℃; for 4h; Green chemistry;
89% With TiO2 modified with bis-3-(trimethoxysilylpropyl)-ammonium hydrogen sulfate In neat (no solvent) at 90℃; for 0.25h;
79% With mesoporous nanocomposite of Fe3O4 and -NHSO3H functionalized silica (MCM-41) In neat (no solvent) at 90℃; for 0.5h; General procedure for the synthesis of benzimidazole, benzoxazole, andbenzothiazole derivatives 2(a-o) General procedure: To a mixture of 1,2-phenylenediamine, 2-aminophenol, or 2-aminothiophenol, asappropriate (1 mmol), and the desired ortho ester (trimethyl orthoformate, triethylorthoformate, or triethyl orthoacetate) (1.5 mmol), in neat conditions, Fe3O4MCM-41NH-SO3H (0.03 g) was added and the resulting mixture was stirred in an oil bath at90 C for the proper time as determined by TLC [EtOAc: n-hexane (1:2)]. After endingthe reaction, ethyl acetate (20 mL) was added and the catalyst was separated by an externalmagnet. The organic phase was washed with brine and dried over Na2SO4. After filtration,the solvent was removed from the product under reduced pressure to obtainthe pure product. In some cases, the product was purified by recrystallization from nhexane.The known compounds were identified by matching their IR and NMR datawith literature values from the references cited, as well as melting points for those compoundswhich were solids. For the sake of completeness, the spectral data of some representativecompounds follow.

Reference: [1]Mobinikhaledi; Zendehdel; Goudarzi; Bardajee, G. Rezanejade [Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2016, vol. 46, # 10, p. 1526 - 1531]
[2]Ghaedi, Aseyeh; Goudarzi, Farideh; Hekmat, Shohreh; Rezanejade Bardajee, Ghasem [Inorganic and Nano-Metal Chemistry, 2022]
[3]Roudsari, Fatemeh Pakpour; Seddighi, Mohadeseh; Shirini, Farhad; Tajik, Hassan [Organic Preparations and Procedures International, 2020, p. 1 - 14]
[4]Fortenberry, Chelsea; Nammalwar, Baskar; Bunce, Richard A. [Organic Preparations and Procedures International, 2013, vol. 45, # 1, p. 57 - 65]
[5]Location in patent: experimental part Sanjeeva Reddy; Nagaraj [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 7, p. 1154 - 1159]
[6]Location in patent: experimental part Hojati, Seyedeh Fatemeh; Maleki, Behrooz; Beykzadeh, Zahra [Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 87 - 91]
[7]Location in patent: experimental part Liu, Juyan; Liu, Qian; Xu, Wei; Wang, Weilu [Chinese Journal of Chemistry, 2011, vol. 29, # 8, p. 1739 - 1744]
[8]Location in patent: experimental part Patil, Abasaheb V.; Bandgar, Babasaheb P.; Lee, Soo-Hyoung [Bulletin of the Korean Chemical Society, 2010, vol. 31, # 6, p. 1719 - 1722]
[9]Wang, Limin; Sheng, Jia; Tian, He; Qian, Changtao [Synthetic Communications, 2004, vol. 34, # 23, p. 4265 - 4272]
[10]Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad R.; Hojati, Seyedeh F. [Monatshefte fur Chemie, 2007, vol. 138, # 7, p. 663 - 667]
[11]Barbero, Margherita; Cadamuro, Silvano; Dughera, Stefano [ARKIVOC, 2012, vol. 2012, # 9, p. 262 - 279]
[12]Mazloumi; Shirini; Goli-Jolodar; Seddighi [New Journal of Chemistry, 2018, vol. 42, # 8, p. 5742 - 5752]
[13]Pourhasan-Kisomi, Reyhaneh; Shirini, Farhad; Golshekan, Mostafa [Organic Preparations and Procedures International, 2021, vol. 53, # 2, p. 166 - 175]
  • 56
  • [ 6974-32-9 ]
  • [ 1792-41-2 ]
  • C35H30N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tin(IV) chloride In 1,2-dichloro-ethane for 5h; Heating;
  • 57
  • [ 507453-85-2 ]
  • [ 75-07-0 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
33% In ethanol for 24h; Heating;
  • 58
  • [ 1792-41-2 ]
  • 2,5-dimethyl-1-(β-D-erythropentofuranosyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SnCl4 / 1,2-dichloro-ethane / 5 h / Heating 2: 0.57 g / NH3 / methanol
  • 59
  • [ 1792-41-2 ]
  • 6(5)-bromo-2,5(6)-dimethyl-4(7)-nitrobenzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / Br2 / acetic acid / 1) reflux, 30 min; 2) rt, 2 h; further reagent 2: aq. HNO3 (42 percent), aq. H2SO4 (92 percent) / 1 h / 0 - 5 °C
  • 60
  • [ 1792-41-2 ]
  • 6(5)-bromo-2,5(6)-dimethyl-7(4)-nitrobenzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / Br2 / acetic acid / 1) reflux, 30 min; 2) rt, 2 h; further reagent 2: aq. HNO3 (42 percent), aq. H2SO4 (92 percent) / 1 h / 0 - 5 °C
  • 61
  • [ 7418-36-2 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium / Hydrogenation 2: cymene
  • 62
  • [ 58010-91-6 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bei der Reduktion 2: sodium acetate
  • 63
  • [ 89-62-3 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: palladium; ethanol / Hydrogenation 3: Erhitzen auf Temperaturen oberhalb des Schmelzpunktes
  • 64
  • [ 1792-41-2 ]
  • 2'-methyl-1<i>H</i>,1'(3')<i>H</i>-[2,5']bibenzimidazolyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CrO3; aqueous H2SO4 2: aqueous HCl / 200 °C
  • 65
  • [ 1792-41-2 ]
  • 5,2'-dimethyl-1(3)<i>H</i>,1'(3')<i>H</i>-[2,5']bibenzimidazolyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CrO3; aqueous H2SO4 2: aqueous HCl / 200 °C
  • 66
  • [ 95-63-6 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: bei der Destillation
  • 67
  • [ 742054-04-2 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: beim Erhitzen zum Sieden
  • 68
  • [ 115835-41-1 ]
  • [ 1792-41-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: beim Erhitzen zum Sieden
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