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[ CAS No. 17374-26-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 17374-26-4
Chemical Structure| 17374-26-4
Structure of 17374-26-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 17374-26-4 ]

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Product Details of [ 17374-26-4 ]

CAS No. :17374-26-4 MDL No. :MFCD06411399
Formula : C6HBr4N3 Boiling Point : -
Linear Structure Formula :- InChI Key :OMZYUVOATZSGJY-UHFFFAOYSA-N
M.W : 434.71 Pubchem ID :1694
Synonyms :

Calculated chemistry of [ 17374-26-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 64.69
TPSA : 41.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 3.86
Log Po/w (WLOGP) : 4.01
Log Po/w (MLOGP) : 3.92
Log Po/w (SILICOS-IT) : 4.28
Consensus Log Po/w : 3.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.48
Solubility : 0.00144 mg/ml ; 0.00000332 mol/l
Class : Moderately soluble
Log S (Ali) : -4.43
Solubility : 0.0162 mg/ml ; 0.0000372 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.84
Solubility : 0.000633 mg/ml ; 0.00000146 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.17

Safety of [ 17374-26-4 ]

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 [ 17374-26-4 ]

* 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 [ 17374-26-4 ]
  • Downstream synthetic route of [ 17374-26-4 ]

[ 17374-26-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 95-14-7 ]
  • [ 17374-26-4 ]
YieldReaction ConditionsOperation in experiment
68% at 60 - 80℃; for 49 h; General procedure: A slightly modification of the previously described procedure [39] was used. 1H-Benzimidazole (31, 3g) or 193 1H-benzotriazole (32, 3g) was dissolved in a mixture of 69percent 194 HNO3 (50mL) and 100percent HNO3 (3mL). Next, the solution was heated to a temperature of 80°C and 195 Br2 (6 equiv.) was added drop by drop within 1h. The reaction mixture was then vigorously stirred at 60°C for 48h, and after this time it was cooled to room temperature, the excess of unreacted Br2 was removed in the flow of 196 nitrogen and trapped in a 20percent aqueous solution of 197 Na2S2O5 (100mL). Next, the content of the flask was poured into mixture of ice-cold 15 H2O (200mL) and saturated aqueous solution of Na2S2O5 (10mL). The resulting orange precipitate was filtered off and washed with H2O (50mL) and EtOH (50mL). The resulting crude product was washed several times with hot MeOH (50mL) yielding 198 4,5,6,7-tetrabromo-1H-benzimidazole (TBBi, 33, 5.56g, 12.82mmol, 50percent) or 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt, 34, 7.45g, 17.14mmol, 68percent) as white solids, respectively. The identity of both polybrominated products (33 and 34) was confirmed by high-resolution mass spectrometry (HRMS). The 1H, 13C NMR and melting point values were consistent with the literature data. For 48 TBBi 33: white solid; mp 339–340°C (MeOH) [339°C (no data)] [88]; HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C7H3Br4N2+ m/z: 434.6983, Found 434.7024; [2M+H]+ Calcd for C14H5Br8N4+ m/z: 868.3893, Found 868.4806. For TBBt 34: white solid; mp 264–266°C (MeOH) [262–266°C (acetic acid)] [89]; HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C9H7Br5N3+ m/z: 435.6941, Found 435.6629.
59% at 60 - 80℃; for 49 h; Inert atmosphere; Irradiation 1H-Benzotriazole 4 (6 g, 50.4 mmol) was dissolved in a mixture of 69percent HNO3 (150 mL) and fuming 100percent HNO3 (10 mL). Next, the solution was heated to a temperature of 80 °C and Br2 (48.3 g, 302 mmol, 15 mL) was added dropwise within 1 h. The reaction mixture was stirred vigorously using mechanical stirrer at 60 °C for 48 h and irradiated by exposure to UV light. Subsequently, content of the flask was cooled to room temperature, the excess of unreacted bromine was removed in the gentle flow of nitrogen and trapped into a 20percent solution of sodium pyrosulfite (150 mL). The suspension was poured into mixture of ice-cold H2O (300mL) and saturated Na2S2O5 (20mL). The resulting yellowish precipitate was filtered off, and washed with H2O (100mL) and EtOH (100mL), respectively. The obtained crude product was refluxed several times in the mixture of MeOH (50mL) and i-PrOH (25mL), and hot saturated solution was filtered off yielding white crystals 5 (13g, 29.9mmol, 59percent). The purity of the compound 5 was confirmed by high-resolution mass spectrometry (HRMS). The 1H, 13C NMR and m.p. were consistent with the literature data [46]. White solid; mp 264–266°C; Rf [CHCl3/MeOH (99:1, v/v)] 0.16; HRMS (ESI+, m/z): [M+H]+calcd=435.6941, [M+H]+found=435.6629.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 307 - 333
[2] European Journal of Medicinal Chemistry, 2014, vol. 84, p. 364 - 374
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 4395,4399
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1573 - 1578
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