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[ CAS No. 534-85-0 ] {[proInfo.proName]}

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Chemical Structure| 534-85-0
Chemical Structure| 534-85-0
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Product Details of [ 534-85-0 ]

CAS No. :534-85-0 MDL No. :MFCD00007685
Formula : C12H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :NFCPRRWCTNLGSN-UHFFFAOYSA-N
M.W :184.24 Pubchem ID :68297
Synonyms :

Calculated chemistry of [ 534-85-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 2.0
Molar Refractivity : 60.39
TPSA : 38.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.78
Log Po/w (WLOGP) : 3.02
Log Po/w (MLOGP) : 2.68
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 2.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.24
Solubility : 0.107 mg/ml ; 0.000581 mol/l
Class : Soluble
Log S (Ali) : -3.24
Solubility : 0.107 mg/ml ; 0.000582 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.61
Solubility : 0.00455 mg/ml ; 0.0000247 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 534-85-0 ]

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 [ 534-85-0 ]

* 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 [ 534-85-0 ]
  • Downstream synthetic route of [ 534-85-0 ]

[ 534-85-0 ] Synthesis Path-Upstream   1~8

  • 1
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  • [ 883-39-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 8, p. 2374 - 2378
[2] Chemische Berichte, 1890, vol. 23, p. 1843
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YieldReaction ConditionsOperation in experiment
94%
Stage #1: With triethylamine In dichloromethane at 0 - 20℃;
Stage #2: With trichlorophosphate In 1,4-dioxane at 115℃; for 1 h;
Compound 1 (Ge, Z.; Hayakawa, T.; Ando, S.; Ueda, M.; Akiike, T.; Miyamoto, H.; Kajita, T.; Kakimoto, M. Chem. Mater. 2008, 20(7), 2532-2537) was prepared as follows: to a chilled (ca. 0° C.), stirring solution of N-phenyl-o-phenylene-1,2-diamine (21.41 g, 116.2 mmol) in anhydrous dichloromethane (CH2Cl2) (575 mL) was added 4-bromobenzoyl chloride (25.00 g, 113.9 mmol) portion-wise, followed by dropwise addition of triethylamine (Et3N) (31.8 mL). The reaction was allowed to warm to room temperature and stirring continued until TLC (SiO2, 4:1 hexanes-ethyl acetate) indicated consumption of the starting material. Upon completion, the reaction was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting crude was then dissolved in anhydrous 1,4-dioxane (500 mL) and heated to about 80° C. Upon completely dissolving, phosphorus oxychloride (31.2 mL, 335 mmol) was added to the solution slowly via syringe and the reaction then maintained at about 115° C. Upon completion (ca. 1 h), the solution was cooled to room temperature (RT) and poured over CH2Cl2 (ca. 3 L) and washed with brine. The organics were then dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product by recrystallization from CH2Cl2 and hexanes provided Compound 1 (37.5 g, 94percent) as an off-white solid: confirmed by LCMS (APCI): calculated for C19H13BrN2 (M+): 349; Found: 349.
Reference: [1] Patent: US9112159, 2015, B2, . Location in patent: Page/Page column 43
[2] Patent: US2011/62386, 2011, A1,
[3] Patent: US2012/16449, 2012, A1,
[4] Inorganic Chemistry, 2017, vol. 56, # 16, p. 9979 - 9987
[5] Journal of Materials Chemistry C, 2017, vol. 5, # 47, p. 12553 - 12560
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YieldReaction ConditionsOperation in experiment
92% With sodium hydrogensulfite In N,N-dimethyl-formamide for 1 h; A solution of Ν-(4-phenyl)benzene-1,2-diamine (3.68 g, 20 mmol), 4-bromobenzaldehyde (3.70 g, 20 mmol) and sodium bisulfite (2.04 g, 10mmol) was dissolved in DMF (80 mL) and stirred in air for 1 h. After the completion of the reaction, the reaction solution was poured into water to precipitate the product. After standing for some time, the product was filtered and washed with a small amount of methanol. Finally, the crude product was purified by silica gel column chromatography using a mixture of n-hexane and ethyl acetate (1: 5) as eluent to give a white powdery solid product. Yield: 6.40 g, 92percent.
89% With sodium hydrogensulfite In N,N-dimethyl-formamide for 1 h; Reflux willN- (4-phenyl) benzene-1,2-diamine(3.68 g, 20 mmol),4-bromobenzaldehyde (3.70 g, 20 mmol) and sodium bisulfite (2.04 g, 10 mmol)Of the mixture was dissolved in DMF (80 mL)Mix in air for 1 h.Point plate test After the end of the reaction cooled to room temperature,The reaction solution was poured into water,Precipitation products.After standing for some time,Filter out the product,Wash with a small amount of methanol.At last,The crude product was mixed with n-hexane and ethyl acetate (1: 3)As a eluent by silica gel column chromatography to obtain a white powder solid product.Yield: 6.18 g, 89percent.
60% at 180℃; for 6 h; 4-bromo-benzaldehyde (8.3g, 45mmol) was dispersed in the benzene in 10ml of N-phenyl-1,2-phenylenediamine (N-phenyl-1,2-phenylenediamine, 8.3g, 45mmol ), which was heated at 180 °C for 6 hours. After cooling to room temperature, and then removed by distillation under reduced pressure to nitrobenzene, the resulting solid was filtered and dried in vacuo, washed with ethyl ether to obtain a compound A.
57.71% With toluene-4-sulfonic acid In toluene for 16 h; Heating / reflux Synthesis of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazoleN-Phenyl-o-phenylenediamine 13.27 g (72 mmole), 4-bromobenzaldehyde 16 g (87 mmole), and 2.8 g of PTSA (14 mmole) was stirred in 150 ml of Toluene, the reaction mixture was then heated to reflux for 16 hours, after cooling, the reaction mixture was extracted with water, and then the organic layer was evaporated to dry, the residue was then recrystallized with acetone to get 14.51 g of product (yield=57.71percent).
49% for 12 h; Reflux Acetic acid (20 mL) was added to a flask containing N-phenyl-o-phenylenediamine (1.50 g, 8.14 mmol) and 4-bromobenzaldehyde (1.66 g, 8.96 mmol).
After the mixture was refluxed for 12 h, distilled water was added and the organic layer was extracted with dichloromethane.
The organic layer was washed with sodium bicarbonate and brine and dried using anhydrous sodium sulfate.
The filtrate was concentrated in vacuo to give a crude mixture, which was then subjected to column chromatography on silica gel using ethyl acetate and hexane (v/v 1:20) as the eluent.
Analytically pure 2-(4-bromophenyl)-1-phenyl-1H-benz[d]imidazole was isolated as a white solid (1.39 g, 49percent).
1H NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.4 Hz, 1H), 7.53-7.42 (m, 7 H), 7.35-7.21 (m, 5H).
13C NMR (CDCl3, 100 MHz) δ 151.21, 142.90, 137.25, 136.75, 131.55, 130.84, 130.01, 128.90, 128.77, 127.37, 124.04, 123.58, 123.15, 119.90, 110.48. MALDI-TOF MS: calcd for C19H13BrN2 348.03, found 349.20.
35% With Oxone In N,N-dimethyl-formamide at 20 - 40℃; Inert atmosphere c) 2-(4-Bromophenyl)-1-phenyl-1H-benzimidazole N-Phenyl-o-phenylenediamine (50 g, 0.27 mol) is dissolved in anhydrous DMF (400 ml) under N2, and 4-bromobenzaldehyde (45.5 g, 0.25 mol) is added dropwise. The reaction mixture is warmed to 40° C., and Oxone (potassium hydrogen monopersulfate, 98.1 g, 0.16 mol) is added in portions. After the mixture has been stirred at room temperature for 120 min., 1 l of water is added. The precipitated product is filtered off, washed with water and dried in vacuo. Recrystallisation from acetonitrile gives a cream-coloured solid (31 g, 35percent).
23.6% at 140℃; Inert atmosphere 2.1Weigh 7.36 g of 4-bromobenzaldehyde and 7.3 g of o-aminodiphenylamine in 200 mL of acetic acid.After charging and discharging nitrogen for 3 times, the temperature was set to 140 ° C to start the reaction;2.2After the reaction, the temperature was lowered to room temperature, and a large amount of gray solid was precipitated after pouring into water, and filtered.After the filter cake was added with 5 g of silica gel, the column was passed to obtain 3.2 g of a white solid powder, the yield was 23.6percent, HPLC 99.7percent;

Reference: [1] Patent: CN107011268, 2017, A, . Location in patent: Paragraph 0083; 0085; 0087; 0088
[2] Monatshefte fur Chemie, 2009, vol. 140, # 4, p. 375 - 380
[3] Patent: CN106905242, 2017, A, . Location in patent: Paragraph 0038; 0046; 0047; 0048
[4] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 5, p. 1187 - 1195
[5] Patent: KR101597865, 2016, B1, . Location in patent: Paragraph 0115-0118
[6] Patent: US2008/265746, 2008, A1, . Location in patent: Page/Page column 6
[7] Organic Electronics: physics, materials, applications, 2013, vol. 14, # 10, p. 2497 - 2504
[8] Patent: US2012/292571, 2012, A1, . Location in patent: Page/Page column 37
[9] Patent: CN106800555, 2018, B, . Location in patent: Paragraph 0075; 0102; 0103
[10] Patent: WO2009/51390, 2009, A2, . Location in patent: Page/Page column 65-67
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Reference: [1] Patent: WO2011/34967, 2011, A1,
[2] Advanced Functional Materials, 2010, vol. 20, # 3, p. 399 - 408
[3] Patent: US2011/251401, 2011, A1,
[4] Patent: WO2012/88294, 2012, A1,
[5] Patent: WO2011/8560, 2011, A1,
[6] Patent: US2012/15998, 2012, A1,
[7] Journal of Materials Chemistry, 2012, vol. 22, # 43, p. 23005 - 23011
[8] Journal of Materials Chemistry C, 2013, vol. 1, # 11, p. 2217 - 2223
[9] Patent: WO2013/180376, 2013, A1,
[10] Patent: WO2014/93353, 2014, A1,
[11] Patent: US2015/87685, 2015, A1,
[12] Patent: CN104073249, 2016, B,
[13] Patent: CN104030988, 2016, B,
[14] Patent: US9425408, 2016, B2,
[15] Patent: US2016/351828, 2016, A1,
[16] Patent: WO2016/209895, 2016, A1,
[17] Chemistry - An Asian Journal, 2018, vol. 13, # 10, p. 1335 - 1341
  • 5
  • [ 586-76-5 ]
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Reference: [1] Journal of Materials Chemistry, 2010, vol. 20, # 45, p. 10113 - 10119
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  • [ 299-11-6 ]
Reference: [1] Chemische Berichte, 1913, vol. 46, p. 346
  • 7
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  • [ 952514-79-3 ]
Reference: [1] Patent: CN104073249, 2016, B,
[2] Patent: CN104030988, 2016, B,
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Reference: [1] Journal of Materials Chemistry C, 2017, vol. 5, # 47, p. 12553 - 12560
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