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[ CAS No. 934-22-5 ] {[proInfo.proName]}

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Chemical Structure| 934-22-5
Chemical Structure| 934-22-5
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Product Details of [ 934-22-5 ]

CAS No. :934-22-5 MDL No. :MFCD00831692
Formula : C7H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :WFRXSXUDWCVSPI-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :13623
Synonyms :

Calculated chemistry of [ 934-22-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.5
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) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.63
Log Po/w (XLOGP3) : 1.13
Log Po/w (WLOGP) : 1.15
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 0.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.2 mg/ml ; 0.00905 mol/l
Class : Soluble
Log S (Ali) : -1.87
Solubility : 1.79 mg/ml ; 0.0134 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.404 mg/ml ; 0.00303 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 934-22-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P322-P330-P332+P313-P337+P313-P340-P362-P363-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 934-22-5 ]

* 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.

  • Upstream synthesis route of [ 934-22-5 ]
  • Downstream synthetic route of [ 934-22-5 ]

[ 934-22-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 94-52-0 ]
  • [ 934-22-5 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In methanol for 20 h; Example 10; 1H-Benzimidazol-5-amine A solution of 5-nitrobenzin-ddazole (10. 0 g, 61.3 mmol) in methanol (250 mL) was hydrogenated in the presence of 10percent Pd/C (0. 40 g) at atmospheric pressure for 20h. The mixture was filtered through CeliteNo. and the solvent removed under reduced pressure to afford the pure product () percent).
92% With hydrogen In tetrahydrofuran; ethanol at 20℃; for 4 h; A mixture of 5-nitrobenzoimidazol (2.00 g, 12.3 mmol) and 10percent palladium carbon (200 mg) in ethanol (100 ML) and THF (100 ML) was stirred under hydrogen atmosphere at room temperature for 4 hours..
The insolubles were filtered off, the filtrate was evaporated under reduced pressure, to obtain the titled compound as a solid. 1.50 g (92.0percent) 1H-NMR (CDCl3) δ; 6.67 (1H, dd, J = 2.2, 9.2 Hz), 6.86 (1H, d, J = 2.2 Hz), 7.43 (1H, d, J = 9.2 Hz), 7.84 (1H, s)
85% at 20℃; for 16 h; Intermediate Example 14.Ethyl 1 -(1 H-benzo[d}imidazol-5-yl)- 1 H-i ,2,3-triazole-4-carboxylate‘a) 1H-benzo[djimidazol-5-amineTo a solution of 5-nitro-1H-benzo[d]imidazole (5 g, 44.2 mmol) in methanol (‘100 ml) was added Pd/C and the reaction mixture was stirred at RT for 16 h and filtered. The filtrate was diluted with water and extracted with ethyl acetate (3 x 100ml). The ‘combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the crude residue which was purified by washing with diethyl ether to afford the title product in 85 percent yield (2.5 g). LC-MS (ESI):Calculated rnassi33.06 Observed mass: 134.2 [M+F1J + (rt: 0.175 mm).
0.163 g With palladium on activated charcoal; hydrazine hydrate In ethanol for 4 h; Reflux Next, 5-nitrobenzoimidazole (0.25 g) was dissolved in ethanol (20 mL).
The solution was stirred and heated to reflux, and the palladium-on-charcoal catalyst (0.15 g) and hydrazine hydrate (1.6 mL) were added.
Then the mixture was stirred for 4 h, and filtered in hot.
The filtrate was evaporated, and the residue was recrystallised from ethanol to give rise to the precursor compound 5-aminobenzoimidazole (0.163 g).
99 %Chromat. With hydrogen In methanol at 100℃; for 8 h; Autoclave General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

Reference: [1] Patent: WO2005/66156, 2005, A1, . Location in patent: Page/Page column 33
[2] Patent: EP1437344, 2004, A1, . Location in patent: Page 37
[3] Patent: WO2014/162039, 2014, A1, . Location in patent: Page/Page column 40
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2362 - 2370
[5] Recueil des Travaux Chimiques des Pays-Bas, 1948, vol. 67, p. 45,48,51
[6] Helvetica Chimica Acta, 1949, vol. 32, p. 135,143,144
[7] Journal of Biological Chemistry, 1944, vol. 152, p. 225,227
[8] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1953, vol. 11, p. 42
[9] Helvetica Chimica Acta, 1949, vol. 32, p. 135,143,144
[10] Journal of the Chemical Society, 1950, p. 1515,1516
[11] Collection of Czechoslovak Chemical Communications, 1992, vol. 57, # 3, p. 531 - 539
[12] Patent: US6329380, 2001, B1,
[13] Chemical Communications, 2011, vol. 47, # 39, p. 10972 - 10974
[14] Patent: WO2012/115480, 2012, A2, . Location in patent: Page/Page column 57
[15] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 84 - 94
[16] Combinatorial Chemistry and High Throughput Screening, 2014, vol. 17, # 1, p. 89 - 95
[17] Journal of Molecular Catalysis A: Chemical, 2016, vol. 420, p. 56 - 65
[18] Catalysis Letters, 2017, vol. 147, # 2, p. 491 - 501
[19] Journal of Materials Chemistry A, 2018, vol. 6, # 34, p. 16680 - 16689
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  • [ 64-18-6 ]
  • [ 615-71-4 ]
  • [ 934-22-5 ]
Reference: [1] Journal of the Korean Chemical Society, 2010, vol. 54, # 5, p. 589 - 593
[2] Journal of the Chilean Chemical Society, 2012, vol. 57, # 2, p. 1122 - 1125,4
[3] Patent: DE181783, , ,
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 553
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 553
  • 3
  • [ 99-56-9 ]
  • [ 934-22-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 84 - 94
  • 4
  • [ 51-17-2 ]
  • [ 934-22-5 ]
Reference: [1] Combinatorial Chemistry and High Throughput Screening, 2014, vol. 17, # 1, p. 89 - 95
  • 5
  • [ 95-54-5 ]
  • [ 934-22-5 ]
Reference: [1] Combinatorial Chemistry and High Throughput Screening, 2014, vol. 17, # 1, p. 89 - 95
  • 6
  • [ 934-22-5 ]
  • [ 177843-26-4 ]
Reference: [1] Patent: US2001/345, 2001, A1,
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