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[ CAS No. 10040-96-7 ] {[proInfo.proName]}

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Chemical Structure| 10040-96-7
Chemical Structure| 10040-96-7
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Product Details of [ 10040-96-7 ]

CAS No. :10040-96-7 MDL No. :MFCD00060489
Formula : C9H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :SERULNRLZWOYPK-UHFFFAOYSA-N
M.W :223.07 Pubchem ID :2735604
Synonyms :

Calculated chemistry of [ 10040-96-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.26
TPSA : 17.82 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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 2.63
Log Po/w (MLOGP) : 2.04
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 2.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.106 mg/ml ; 0.000476 mol/l
Class : Soluble
Log S (Ali) : -2.37
Solubility : 0.942 mg/ml ; 0.00422 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.0365 mg/ml ; 0.000164 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 10040-96-7 ]

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 [ 10040-96-7 ]

* 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 [ 10040-96-7 ]
  • Downstream synthetic route of [ 10040-96-7 ]

[ 10040-96-7 ] Synthesis Path-Upstream   1~11

  • 1
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  • [ 5467-74-3 ]
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YieldReaction ConditionsOperation in experiment
90% With copper(I) sulfide; N,N,N,N,-tetramethylethylenediamine In methanol at 20℃; for 24 h; General procedure: A 10mL round bottom flask was charged with a magnetic stirring bar, benzimidazole 1 (59mg, 0.5mmol), boronic acid 2 (1.0mmol), Cu2S (4mg, 0.025mmol), and MeOH (2mL), followed with the addition of TMEDA (0.075mL, 0.5mmol). The flask was sealed with a septum, through which was inserted 18-gauche needle. This setup allowed air to go into the reaction and avoid contamination of a mixture. The reaction mixture was stirred from 400 to 600rpm for appropriate time and extracted with EtOAc (2×15mL). Combined organic layers were washed with saturated aqueous solution of ethylenediaminetetraacetic acid disodium salt (15mL), and then dried over anhydrous Na2SO4. Volatiles were removed under reduced pressure and the residue was purified by column chromatography (silica gel, hexanes – EtOAc) to yield the title product, which was characterized by 1H NMR, 13C NMR, HRMS, and melting point (if solid).
81% With triethylamine In methanol at 20℃; for 5 h; General procedure: In a typical reaction, arylboronic acid (1 mmol), amino-compound (1 mmol), catalyst (5 wtpercent), Et3N (2 mmol) were mixed in methanol ( 5mL) in a 25mL round bottomed flask. The reaction mixture was subjected under continuous stirring at room temperature for 5 h. Reaction was monitored from time to time using TLC. After completion of the reaction, catalyst was separated with the aid of an external magnet and reaction mixture was taken in ethyl acetate. The organiclayer was washed using brine solution, dried over sodium sulfate. After evaporating the solvent, the crude product was puried by column chromatography using 230–400 silica mesh. The recovered catalyst was washed with methanol and ethyl acetate, dried in oven and kept in desiccator for further use.
74% With [2,2]bipyridinyl; oxygen; copper diacetate In water at 20℃; for 24 h; General procedure: Under an O2 atmosphere, a mixture of 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol), imidazole (2a, 13.6 mg, 0.20 mmol), Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand I (3.7 mg, 0.020 mmol), and Brij 30 (21.8 mg, 0.060 mmol) in H2O (4 mL) was stirred at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL.x.3). The organic layer was washed with H2O (10 mL.x.3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (23.7 mg, 68percent).
Reference: [1] Synthesis, 2008, # 5, p. 795 - 799
[2] Tetrahedron, 2018, vol. 74, # 5, p. 606 - 617
[3] Green Chemistry, 2018, vol. 20, # 21, p. 4891 - 4900
[4] Catalysis Communications, 2018, vol. 109, p. 38 - 42
[5] Tetrahedron, 2012, vol. 68, # 38, p. 7794 - 7798
  • 2
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YieldReaction ConditionsOperation in experiment
90% With copper(l) iodide; caesium carbonate; dimethylbiguanide In N,N-dimethyl-formamide at 20 - 110℃; for 15.1667 h; General procedure: A 25 mL flask with a magnetic stirring bar was charged with CuI(9.6 mg, 0.05 mmol), metformin (0.1 mmol), Cs2CO3 (652 mg,2.0 mmol), imidazole (1.0 mmol), an aryl halide (1.1 mmol), andDMF (5 mL). The mixture was stirred for 10 min at room temperature,and then heated to 110C for the appropriate amount of time(see Table 2). The progress of the reaction was monitored by TLC.After completion of the reaction, the mixture was extracted with EtOAc (5 1 mL) and the organic phase separated and evaporated. Further purification by column chromatography gave the desired coupled product.
85% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 12 h; General procedure: A mixture of aryl halide (2.4 mmol) and Cs2CO3(4.0 mmol,0.650 g), nitrogen-containing heterocycle (2.0 mmol), dry DMF(3 mL) solvent and catalyst was stirred at 100C in an oil bath under air. After cooling to room temperature, catalyst was first separated out by centrifugation and the liquid part was extracted with water and diethylether (2 × 15 mL). The organic layers thus collected were combined and washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified bycolumn chromatography on silica gel (mesh 60–120) using an n-hexane/ethylacetate mixture as the eluent to collect the desiredproduct. The product was analyzed by 1H and13C NMR and mass spectroscopy.
81% With C40H34CuIN6O6; sodium hydroxide In dimethyl sulfoxide at 100℃; for 4 h; Sealed tube General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.
Reference: [1] Synlett, 2012, vol. 23, # 8, p. 1240 - 1244
[2] Tetrahedron Letters, 2013, vol. 54, # 52, p. 7095 - 7099
[3] Journal of Organic Chemistry, 2007, vol. 72, # 8, p. 2737 - 2743
[4] Applied Catalysis A: General, 2016, vol. 513, p. 53 - 66
[5] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2018, vol. 57A, # 2, p. 181 - 185
[6] Applied Organometallic Chemistry, 2017, vol. 31, # 11,
[7] Tetrahedron, 2017, vol. 73, # 16, p. 2191 - 2195
[8] Synlett, 2008, # 19, p. 3068 - 3072
  • 3
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YieldReaction ConditionsOperation in experiment
94% With C40H34CuIN6O6; sodium hydroxide In dimethyl sulfoxide at 100℃; for 4 h; Sealed tube General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.
92% With copper(l) chloride; sodium hydroxide; 3-(diphenylphosphino)propionic acid In dimethyl sulfoxide at 120℃; for 14 h; Inert atmosphere; Sealed tube General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 molpercent) and ligand 1 (20.0 molpercent) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 °C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT‑IR and NMR) and melting points were consistent with those reported in the literature.
82% With Cu/Al2O3; potassium hydroxide In N,N-dimethyl-formamide at 80℃; Green chemistry General procedure: To equimolar amounts (0.1mmol) of the halide and the nitrogenated nucleophile in DMF were added KOH and the 3D heterogeneous Cu/Al2O3 catalytic system. The reaction mixture was heated at 80°C under orbital stirring in a Kimble vial (7mL) for 2–4h. Once the reaction had finished (TLC control), the solvent was separated from the catalyst and this was successively washed with methanol and dichloromethane (5mL). The organic solvents were removed under vacuum and the residue was purified by column chromatography to afford the desired compound (2–4).
82% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 1 h; General procedure: The reaction flask, containing 0.02 g Cu(II) nanocatalyst(contains 0.4 molpercent of Cu(II)), imidazole (2.0 mmol),K2CO3 (1.0 mmol), and corresponding aryl halide(1.0 mmol) in 2.5 cm3 DMF, was immersed in a preheated oil bath and the reaction mixture was stirred under air atmosphere at 120 C until no further conversion of the starting aryl halide was observed by thin-layer chromatography(TLC). After completion of the reaction, the resulting mixture was allowed to cool to room temperature,and then the catalyst was separated out by an external permanent magnet, washed with ethyl acetate (EtOAc) anddried. The residue mixture was diluted by H2O and extracted with EtOAc (3 9 10 cm3). The extracted organic phases were dried over anhydrous Na2SO4, filtrated, concentrated and, finally, purified by silica gel chromatography using petroleum ether/ethyl acetate to afford the corresponding pure N-arylimidazole.
70% With potassium carbonate In toluene at 110℃; for 14 h; To a solution of N–H heterocycle (1 mmol) and aryl halide (2 mmol) in toluene were added catalyst (0.07 g, 0.016 mmol) and K2CO3 (276 g, 2 mmol) and the mixture stirred at 110 °C for the specified time. The progress of the reaction was monitored by TLC. The reaction mixture allowed cooling to room temperature and ethyl acetate (25 mL) was added and the mixture stirred for 15 min to ensure product removal from catalyst. Then the catalyst was filtered, washed with ethyl acetate (2 9 25 mL). The organic layer was evaporated under vacuum on a rotary evaporator and the crude product was obtained. Further purification was achieved by column chromatography using ethyl acetate/n-hexane gradient. Structural assignments of the products are based on their 1H NMR and melting point.

Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 20, p. 7951 - 7954
[2] Tetrahedron Letters, 2007, vol. 48, # 24, p. 4207 - 4210
[3] Journal of the Chinese Chemical Society, 2013, vol. 60, # 8, p. 1007 - 1013
[4] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2018, vol. 57A, # 2, p. 181 - 185
[5] Journal of Chemical Research, 2014, vol. 38, # 2, p. 128 - 129
[6] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 40, p. 4803 - 4807
[7] Synthesis, 2010, # 9, p. 1505 - 1511
[8] Organic Letters, 2009, vol. 11, # 15, p. 3294 - 3297
[9] Chemistry - A European Journal, 2004, vol. 10, # 22, p. 5607 - 5622
[10] Chemistry - A European Journal, 2006, vol. 12, # 13, p. 3636 - 3646
[11] European Journal of Organic Chemistry, 2011, # 18, p. 3353 - 3360
[12] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 2200 - 2202
[13] Chemistry - A European Journal, 2009, vol. 15, # 36, p. 8971 - 8974
[14] ChemSusChem, 2017, vol. 10, # 24, p. 4855 - 4863
[15] Advanced Synthesis and Catalysis, 2006, vol. 348, # 15, p. 2197 - 2202
[16] Synlett, 2009, # 16, p. 2663 - 2668
[17] Journal of Catalysis, 2016, vol. 334, p. 110 - 115
[18] Monatshefte fur Chemie, 2018, vol. 149, # 6, p. 1101 - 1109
[19] Letters in Organic Chemistry, 2011, vol. 8, # 5, p. 325 - 331
[20] Organic Letters, 2006, vol. 8, # 13, p. 2779 - 2782
[21] Synlett, 2008, # 19, p. 3068 - 3072
[22] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9680 - 9696
[23] Catalysis Letters, 2016, vol. 146, # 1, p. 193 - 203
[24] Asian Journal of Chemistry, 2013, vol. 25, # 11, p. 6240 - 6242
  • 4
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Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 16, p. 6190 - 6199
  • 5
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Reference: [1] European Journal of Inorganic Chemistry, 2006, # 6, p. 1268 - 1274
[2] Dalton Transactions, 2012, vol. 41, # 17, p. 5377 - 5390
[3] Organometallics, 2014, vol. 33, # 4, p. 898 - 908
[4] Organic Letters, 2018, vol. 20, # 19, p. 6215 - 6219
  • 6
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 32, p. 8012 - 8016
  • 7
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Reference: [1] Journal of Chemical Research - Part S, 2000, # 8, p. 367 - 369
  • 8
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Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 13, p. 3636 - 3646
  • 9
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 3, p. 863 - 867
[2] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1325 - 1327
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Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1151 - 1154
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 3, p. 863 - 867
[2] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1325 - 1327
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