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[ CAS No. 4887-88-1 ] {[proInfo.proName]}

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Chemical Structure| 4887-88-1
Chemical Structure| 4887-88-1
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Product Details of [ 4887-88-1 ]

CAS No. :4887-88-1 MDL No. :MFCD00160001
Formula : C7H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :GEDVWGDBMPJNEV-UHFFFAOYSA-N
M.W :197.03 Pubchem ID :785299
Synonyms :

Calculated chemistry of [ 4887-88-1 ]

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 : 1.0
Molar Refractivity : 43.79
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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 2.5
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.3
Solubility : 0.0982 mg/ml ; 0.000498 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.352 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0337 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 4887-88-1 ]

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 [ 4887-88-1 ]

* 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 [ 4887-88-1 ]
  • Downstream synthetic route of [ 4887-88-1 ]

[ 4887-88-1 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 1575-37-7 ]
  • [ 149-73-5 ]
  • [ 4887-88-1 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1 h;
Stage #2: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide
Step 87a: 73/4rt-butyl 5-bromo-lH-benzo[d]imidazole-l-carboxylate (Compound 0601-187)To a solution of 4-bromobenzene-l,2-diamine (3 g, 16 mmol) in DMF (22 mL) were added trimethyl orthoformate (44 mL) and cone. HC1 (1.5 mL) and the mixture was stirred at room temperature for 1 h. The mixture was diluted with water (200 mL) and adjusted to pH7 with saturated aqueous NaHC03, extract with ethyl acetate (200 mL). The organic layer was dried over Na2S04, concentrated to give 5-bromo-lH-benzo[d]imidazole (3.25 g, 100percent) as an off-white solid. LCMS: 197 [M+l]+. 1H NMR (400 MHz, DMSO-<3/4) δ 7.33 (t, J= 8.8 Hz, 1H), 7.55 (dd, J; = 7.6 Hz, J= 40 Hz, 1H), 7.79 (d, J= 47.2 Hz, 1H), 8.26 (s, 1H), 12.61 (d, J= 25.6 Hz, 1H).
100% With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1 h; Step 87a: Tert-butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate (Compound 0601-187)[0581]To a solution of 4-bromobenzene-1,2-diamine (3 g, 16 mmol) in DMF (22 mL) were added trimethyl orthoformate (44 mL) and conc. HCl (1.5 mL) and the mixture was stirred at room temperature for 1 h. The mixture was diluted with water (200 mL) and adjusted to pH7 with saturated aqueous NaHCO3, extract with ethyl acetate (200 mL). The organic layer was dried over Na2SO4, concentrated to give 5-bromo-1H-benzo[d]imidazole (3.25 g, 100percent) as an off-white solid. LCMS: 197 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 7.33 (t, J=8.8 Hz, 1H), 7.55 (dd, J1=7.6 Hz, J=40 Hz, 1H), 7.79 (d, J=47.2 Hz, 1H), 8.26 (s, 1H), 12.61 (d, J=25.6 Hz, 1H).
100% With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1 h; 4-bromobenzene -l, 2-diamine (3 g, 16 mmol) in solution in DMF (22 mL) of trimethyl orthoformate (44 mL) and concentrated HCl (1.5 mL) was added, 1 hour and the mixture is stirred at room temperature did. The mixture was diluted with water (200 mL), adjusted to pH7 with saturated aqueous NaHCO3, issued extracted with ethyl acetate (200 mL). The organic layer was dried over Na2SO4, and concentrated to give 5-bromo -1H- benzo [d] imidazole as an off-white solid (3.25g, 100percent).
Reference: [1] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 228
[2] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0580; 0581
[3] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0493
[4] Patent: US2009/326029, 2009, A1, . Location in patent: Page/Page column 33
  • 2
  • [ 122-51-0 ]
  • [ 1575-37-7 ]
  • [ 4887-88-1 ]
YieldReaction ConditionsOperation in experiment
95% With zirconium(IV) chloride In methanol at 20℃; for 3 h; General procedure: A mixture of o-phenylenediamine (1.0 mmol), triethyl orthoformate (1.2 mmol) and ZrCl4 (0.1 mmol) in 10 mL MeOH was stirred at room temperature for 3 h. After completion of the reaction, as indicated by TLC, the solvent was concentrated and the resulting product was directly purified by silica gel column chromatography (4:1 / 1:1, v/v, petroleum ether/EtOAc) to afford compound 11a-h.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 90, p. 241 - 250
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 5, p. 827 - 832
[3] Patent: US2008/300247, 2008, A1, . Location in patent: Page/Page column 38
  • 3
  • [ 64-18-6 ]
  • [ 1575-37-7 ]
  • [ 4887-88-1 ]
YieldReaction ConditionsOperation in experiment
100% at 100℃; Example 8 (5)- N2 -(l-(lH-benzo[d]imidazol-5-yl)ethyl)- N4 -(5-cyclopropyl-lH-pyrazol-3-yl)- N2 - methylpyrimidine-2,4-diamine (1-9) and (R)- N2 -(l-(lH-benzo[d]imidazol-5-yl)ethyl)- N4 -(5- cyclopropyl- 1 H-pyrazol-3 -yl)-N2-methylpyrimidine-2,4-diamine (1-55) step 1 : A mixture of 4-bromobenzene-l,2-diamine (4.0 g, 21.5 mmol) and formic acid (95 percent>, 100 mL) was stirred at 100 °C overnight. The reaction mixture was cooled to RT and concentrated in vacuo to afford a dark oil. The crude oil was partitioned between EtOAc (500 mL) and NH3/H20 (50 mL). The EtOAc layer was separated and concentrated in vacuo to afford 4.5 g (100percent) of 5-bromo-lH- benzo[d] imidazole (78) as brown solid: MS (ESI) m/z = 197.0 (M+l).
85% for 2 h; Reflux [0990] A solution of XXXV-1 (10 g, 53.4 mmol) in HCOOH (50 mL) was heated at reflux for 2 hours, after cooled to rt, aq.NaOH (10percent) was added slowly until the mixture was basic.Then extracted with EtOAc (100 mLx3), the combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give XXXV-2 (9 g, 85percent yield).
Reference: [1] Patent: WO2013/26914, 2013, A1, . Location in patent: Page/Page column 131
[2] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223
[3] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0990
[4] Journal of the Chemical Society, 1931, p. 1143,1153
[5] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 42
  • 4
  • [ 875-51-4 ]
  • [ 1758-73-2 ]
  • [ 4887-88-1 ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydroxide In ethanol; water at 70℃; for 1.5 h; Green chemistry General procedure: TUD (20 mmol) was added in batches to a solution of substituted 2‑nitroanilines (5 mmol) and NaOH (20 mmol) in H2O (15 mL) and EtOH (5 mL) at 70 °C. The reaction mixture was stirred for a certain period of time as required to complete the reaction (monitored byTLC). After cooling, 10percent NaOH solutions were added until pH = 9–10, the precipitated solid was filtered off and washed with water to obtain crude product. The crude product was recrystallised from water to give a white solid. The physical and spectra data of the compounds 2a–h were as follows.
Reference: [1] Journal of Chemical Research, 2014, vol. 38, # 2, p. 118 - 120
  • 5
  • [ 51-17-2 ]
  • [ 4887-88-1 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 49, p. 8693 - 8697
  • 6
  • [ 64-18-6 ]
  • [ 610-38-8 ]
  • [ 4887-88-1 ]
Reference: [1] ChemSusChem, 2015, vol. 8, # 18, p. 3029 - 3035
  • 7
  • [ 124-38-9 ]
  • [ 1575-37-7 ]
  • [ 4887-88-1 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 1, p. 95 - 99
  • 8
  • [ 144-62-7 ]
  • [ 1575-37-7 ]
  • [ 4887-88-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1337 - 1342
  • 9
  • [ 64-18-6 ]
  • [ 1575-37-7 ]
  • [ 149-73-5 ]
  • [ 4887-88-1 ]
Reference: [1] Patent: WO2007/143456, 2007, A2, . Location in patent: Page/Page column 88-89
  • 10
  • [ 875-51-4 ]
  • [ 4887-88-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 5, p. 827 - 832
  • 11
  • [ 68-12-2 ]
  • [ 1575-37-7 ]
  • [ 4887-88-1 ]
Reference: [1] New Journal of Chemistry, 2016, vol. 40, # 10, p. 8282 - 8287
  • 12
  • [ 124-38-9 ]
  • [ 4887-88-1 ]
  • [ 15788-16-6 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5 h;
Stage #3: at -20℃; for 0.5 h;
To a solution of 5-Bromo-1H-benzimidazole (0.87 g, 4.4 mmol,1.0 equiv.) in dry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF (2.2 mL,1 equiv.) during 5 min. The clear solution was stirred at that temperature for an additional 5 min,and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was added dropwise during5 min, while maintaining the temperature below 20 C. The resulting mixture was stirred at thattemperature for 0.5 h, dry CO2 (0.20 g, 4.4mmol, 1.0 equiv.) was added to 20 C. The resultingmixture was warmed to 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixturebelow 20 C for 10 min, the phases were separated and the water phase was extracted one additionaltime with ethyl acetate. The resulting suspension was allowed to reach room temperature and ®teredthrough a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate. The ®ltrate was concentratedand the residue was puri®ed by ash chromatography on silica gel (eluent:petroleum ether/ethylacetate = 3:1) to afford product 3g as brown solid, 0.5 g (yield: 71percent). 1H-NMR (600 MHz, DMSO) 8.43 (s, 1H), 8.26 (s, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.67 (d, J = 8.4 Hz, 1H). 13C-NMR (151 MHz, DMSO) 168.47, 144.83, 125.10, 123.74, 118.13, 115.12.
Reference: [1] Molecules, 2017, vol. 22, # 11,
  • 13
  • [ 4887-88-1 ]
  • [ 74-88-4 ]
  • [ 53484-15-4 ]
  • [ 53484-16-5 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6334 - 6353
  • 14
  • [ 4887-88-1 ]
  • [ 74-88-4 ]
  • [ 53484-15-4 ]
  • [ 53484-16-5 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6334 - 6353
  • 15
  • [ 4887-88-1 ]
  • [ 1021918-86-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6793 - 6799
[2] Patent: WO2011/66211, 2011, A1,
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