[ CAS No. 2622-67-5 ] {[proInfo.proName]}

Name: 2622-67-5|1,2-Diphenyl-1H-benzo[d]imidazole|95%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 2622-67-5 ]

CAS No. :	2622-67-5	MDL No. :	MFCD00416995
Formula :	C₁₉H₁₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZLGVZKQXZYQJSM-UHFFFAOYSA-N
M.W :	270.33	Pubchem ID :	137661
Synonyms :

Safety of [ 2622-67-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2622-67-5 ]

* 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 [ 2622-67-5 ]
Downstream synthetic route of [ 2622-67-5 ]

[ 2622-67-5 ] Synthesis Path-Upstream 1~1

1
[ 2622-67-5 ]
[ 94928-86-6 ]

Yield	Reaction Conditions	Operation in experiment
0.29 g	With sodium carbonate In glycerol at 240℃; for 12 h; Inert atmosphere	Bis[1,2-diphenyl-1H-benzo[d]-imidazole](2-phenylpyridine)iridium(III) [Ir(ppy)₂pbi]: Hppy (0.31 g, 2.0 mmol) was dissolved into a mixed solution of 2-ethoxyethanol (12 mL) and water (4 mL) in a 25 mL round bottomed flask, and then IrCl₃·3H₂O (0.28 g, 0.8 mmol) was added. The mixture was stirred under nitrogen at 120 °C for 12 h. The mixture was cooled to room temperature and the precipitate was collected and washed with water, ethanol, and acetone, then dried in vacuum to give a cyclometalated Ir-μ-chloro-bridged dimer. The dimer complex, Hpbi (0.27 g, 1.0 mmol), Na₂CO₃ (0.34 g, 3.2 mmol) and 5mL glycerol were charged into a round bottomed flask, the mixture was then heated to 240 °C under an argon atmosphere for another 12 h. After cooling to room temperature, the mixture was poured into 100 mL water, yellow precipitate was filtered off and washed with water, ethanol and ether. The crude product was purified by silica column chromatography with dichloromethane/petroleum ether (1:2, v/v) as the eluent to give 0.29 g Ir(ppy)₂pbi as a yellow powder. Yield: 47.5percent, 0.14 g. Ir(ppy)₃ can also be obtained as a byproduct, yield: 27.5percent. ¹HNMR (CDCl₃, 600MHz): 7.90 (t, J=6.4Hz, 2H), 7.85 (d, J=4.8Hz, 1H), 7.77 (d, J=5.4Hz, 1H), 7.69–7.59 (m, 7H), 7.50–7.47 (m, 2H), 7.06 (t, J=7.8Hz, 1H), 6.97 (d, J=7.8Hz, 1H), 6.92–6.78 (m, 10H), 6.72 (t, J=7.8Hz, 1H), 6.63 (d, J=7.8Hz, 1H), 6.53 (t, J=7.8Hz, 1H), 6.05 (d, J=8.4Hz, 1H); ¹³CNMR (CDCl₃, 150MHz): 167.65, 166.68, 163.39, 162.61, 161.33, 148.06, 144.33, 143.92, 140.86, 137.90, 137.85, 136.91, 136.87, 136.32, 135.90, 135.80, 134.10, 130.38, 130.13, 129.89, 129.78, 129.74, 128.53, 128.17, 125.25, 123.94, 123.72, 123.23, 122.38, 122.00, 121.29, 119.66, 119.52, 119.09, 118.66, 118.54, 115.23, 110.53; HRMS (APCI): m/z calcd for C₄₁H₂₉IrN₄: 770.2021; found: 771.2094 (M+H)⁺.

Reference： [1] Dyes and Pigments, 2015, vol. 113, p. 649 - 654

[ 2622-67-5 ] Synthesis Path-Downstream 1~50

1
[ 39823-24-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With acetic acid at 118℃; for 0.333333h;
	With hydrogenchloride
	With acetic acid at 120℃;

100 %Chromat.	With water In 1-methyl-pyrrolidin-2-one at 400℃; for 0.00586111h; Flow reactor; Green chemistry;
	With acetic acid Reflux;	2.2.1.1 Synthesis of PBI General procedure: To a solution of N-phenyl-o-phenylenediamine (9.21g, 50.00mmol) in N,N-dimethylacetamide (20mL), benzoyl chloride (7.00g, 50.00mmol) was added slowly under nitrogen atmosphere and the mixture was stirred for 1h at room temperature. After addition of water, the precipitated solid was filtered off and washed with water and methanol. The solid was recrystallized from a N,N-dimethylacetamide/water mixture and then added into acetic acid (25mL) under reflux. The solvent was evaporated and purified by column chromatography on silica gel. Synthesis of MePBI and tBuPBI were similar to PBI. 1H NMR (500MHz, CDCl3, δ [ppm]): 7.90 (d, J=8.5Hz, 1H), 7.57 (d, J=7.0Hz, 2H), 7.52-7.45 (m, 3H), 7.37-7.25 (m, 8H).
99 %Chromat.	In 1-methyl-pyrrolidin-2-one; water at 445℃; for 0.00277778h; Supercritical conditions;	1-1 1.44 g of N- [2- (phenylamino) phenyl] benzamide was dissolved in N-methylpyrrolidone (NMP, manufactured by Wako Pure Chemical Industries, for peptide synthesis) to prepare a raw material solution having a concentration of 0.05 M . Water (purified by an ultra pure water apparatus manufactured by Organo Corporation) was brought into a supercritical state at a temperature of 495 ° C. and a pressure of 45 MPa.A raw material solution mixed in a reaction tube and supercritical water were introduced into a reactor having a volume of 0.88 mL, and the chemical reaction represented by the chemical reaction formula (4) was conducted at a temperature of 445 ° C. and a pressure of 45 MPa to obtain benzazoles 1,2-diphenyl-1H-benzo [d] imidazole was synthesized.The time (reaction time) during which the mixture of raw material solution and supercritical water passed through the reactor, that is, the residence time in the reactor was 10 seconds.Further, the total concentration of the raw materials in the reactor (mass of raw material / sum of mass of water and NMP × 100) was 1.44 mass%

Reference： [1]Berezin, Andrey A.; Koutentis, Panayiotis A. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 10, p. 1641 - 1648]
[2]Wolff [Justus Liebigs Annalen der Chemie, 1912, vol. 394, p. 85][Justus Liebigs Annalen der Chemie, 1913, vol. 399, p. 288,291]
[3]Jiao, Yan; Li, Ming; Wang, Ning; Lu, Tao; Zhou, Liang; Huang, Yan; Lu, Zhiyun; Luo, Daibing; Pu, Xuemei [Journal of Materials Chemistry C, 2016, vol. 4, # 19, p. 4269 - 4277]
[4]Nagao; Ishizaka; Kawanami [Green Chemistry, 2016, vol. 18, # 12, p. 3494 - 3498]
[5]Wen, Li-Li; Yu, Jing; Sun, Hai-Zhu; Shan, Guo-Gang; Zhao, Kai-Yue; Xie, Wen-Fa; Su, Zhong-Min [Organic electronics, 2016, vol. 35, p. 142 - 150]
[6]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2017/132722, 2017, A Location in patent: Paragraph 0021; 0022; 0024; 0025

2
[ 100-52-7 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonium acetate; cobalt(II) hydroxide In ethanol at 80℃; for 1h;
90%	In water monomer at 100℃; for 2h;
90%	In water monomer; N,N-dimethyl-formamide at 80℃;	Synthesis of benzimidazoles via metal-free aerobic oxidation in wet DMF (Table 5) General procedure: An ortho-phenylenediamine derivative 3 (1.0 mmol; 1.0 equiv) and an aldehyde 4 (1.0 mmol; 1.0 equiv) were dissolved in wet DMF (DMF 9.0 mL, H2O 1.0 mL). The resulting reaction mixture was stirred at 80°C in an open flask, and the reaction progress was monitored by TLC. On the complete consumption of 3, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude product obtained was purified by column chromatography on silica gel to afford the corresponding benzimidazole 5.

80%	With oxygen; 1-hexadecylpyridinium bromide In water monomer at 20℃; for 0.0833333h;
73%	With dodecatungstosilicic acid In ethyl acetate at 20℃; for 0.5h;
72%	In 2-ethoxy-ethanol
62%	With disodium metabisulfite In N,N-dimethyl-formamide at 100℃; for 0.1h; Microwave irradiation;
55%	at 110℃; for 1h; Neat (no solvent);	3 Synthesis of Dpb The synthesis of 1,2-diphenyl-1H-benzoimidazole (Dpb) is outlined in Scheme 3. To a round round-bottom flask (50 mL) was added N-phenyl-1,2-phenylene diamine (10 mmol) and benzaldehyde (20 mmol) which was allowed to react in a Kugelrohr oven at 110° C. for one hour. After the unreacted benzaldehyde was removed under vacuum, the crude product of high purity was obtained by raising the temperature to 180° C. Recrystallization of the crude product from Hexane/CH2Cl2 gave a white crystal of the title compound in 55% yield.
53%	In 2-methoxy-ethanol for 30h; Inert atmosphere; Reflux;
46%	With acetic acid In 2-ethoxy-ethanol for 24h; Inert atmosphere; Reflux;
	With nitrobenzene
	With ammonium acetate; cobalt(II) hydroxide In ethanol at 80℃; for 1h;	2.5.General procedure for the catalytic synthesis of benzimidazolederivatives (1-6) General procedure: A mixture of corresponding aldehyde (1 mmol1 (1 mmol), ammonium acetate (2.5 mmol) and cobalt hydroxide (II) (10 or 15mol %) was refluxed at 80 °C in ethanol for 1 hour. The reaction was monitored by TLC and purified by column chromatography using petroleum ether as the eluent.
2 g	In 2-methoxy-ethanol for 48h; Reflux;	Synthesis of 1,2-diphenyl-1H-benzo [d] imidazole N1-phenylbenzene-1,2-diamine (4.15 g, 22 mmol) and benzaldehyde (2.1 g, 20 mmol) were mixed with methoxyethanol (60 ml) in a three-necked flask. this The mixture was heated to reflux for 48 hours. After cooling to room temperature, the solvent was evaporated. The residue was purified by column chromatography using dichloromethane as eluent and 5% ethyl acetate in dichloromethane Purification. 2 g of the desired product was obtained.
	Multi-step reaction with 2 steps 1: ethanol / 1 h / Reflux 2: iodine; potassium carbonate / dichloromethane / 3 h / 20 °C
99.9 %Chromat.	With erbium trifluoromethanesulfonate In neat (no solvent) at 60℃; for 0.0833333h; Microwave irradiation; Green chemistry;	3.2. General Procedure for the Synthesis of 1-phenyl-2-Aryl(alkyl) Benzimidazoles 1a-11a General procedure: To the N-phenil-o-phenilendiammine (1 mmol) and Er(OTf)3 (1% mol) in a 3 mL glass,aryl o alkyl aldehyde (1 mmol) was added. The mixture reacted for 5 min in a Synthos3000 microwave instrument, fixed on a temperature value of 60 °C (IR limit). The reactionwas monitored by TLC and GC/MS analyses. After the completion of the conversionof N-phenil-o-phenilendiammine, the Er(OTf)3 was separated from the reaction mixtureby adding water (to separate the catalyst from the reaction mixture) and extracting theorganic product with ethyl acetate (4 3 mL). The products were isolated after its organicphases and was dried over Na2SO4, followed by evaporation under reduced pressure(1a-10a in 91-99% yields). Spectral data were in accordance with the literature [71]. SeeSupplementary Materials.

Reference： [1]Jayabharathi; Thanikachalam; Jayamoorthy [Photochemical and Photobiological Sciences, 2013, vol. 12, # 10, p. 1761 - 1773]
[2]Kommi, Damodara N.; Jadhavar, Pradeep S.; Kumar, Dinesh; Chakraborti, Asit K. [Green Chemistry, 2013, vol. 15, # 3, p. 798 - 810]
[3]Lee, Ye-Sol; Cho, Yeon-Ho; Lee, Seungjae; Bin, Jong-Kwan; Yang, Joonghwan; Chae, Geesung; Cheon, Cheol-Hong [Tetrahedron, 2015, vol. 71, # 4, p. 532 - 538]
[4]Location in patent: experimental part Chakrabarty, Manas; Karmakar, Sulakshana; Mukherjee, Ratna; Arima, Shiho; Harigaya, Yoshihiro [Monatshefte fur Chemie, 2009, vol. 140, # 4, p. 375 - 380]
[5]Chakrabarty, Manas; Mukherji, Ajanta; Mukherjee, Ratna; Arima, Shiho; Harigaya, Yoshihiro [Tetrahedron Letters, 2007, vol. 48, # 30, p. 5239 - 5242]
[6]Han, Liangliang; Zhang, Dongyu; Wang, Jun; Lan, Zhenggang; Yang, Renqiang [Dyes and Pigments, 2015, vol. 113, p. 649 - 654]
[7]Secci, Daniela; Bolasco, Adriana; D'Ascenzio, Melissa; Della Sala, Flavio; Yanez, Matilde; Carradori, Simone [Journal of Heterocyclic Chemistry, 2012, vol. 49, # 5, p. 1187 - 1195]
[8]Current Patent Assignee: INNOLUX CORP. - US2005/116626, 2005, A1 Location in patent: Page/Page column 11-12
[9]Zhao, Jin-Hui; Hu, Yong-Xu; Dong, Yan; Xia, Xin; Chi, Hai-Jun; Xiao, Guo-Yong; Li, Xiao; Zhang, Dong-Yu [New Journal of Chemistry, 2017, vol. 41, # 5, p. 1973 - 1979]
[10]Shan, Guo-Gang; Li, Hai-Bin; Sun, Hai-Zhu; Cao, Hong-Tao; Zhu, Dong-Xia; Su, Zhong-Min [Dalton Transactions, 2013, vol. 42, # 31, p. 11056 - 11065]
[11]Jerchel et al. [Justus Liebigs Annalen der Chemie, 1952, vol. 575, p. 162,167]
[12]Jayabharathi; Thanikachalam; Jayamoorthy [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 115, p. 74 - 78]
[13]Current Patent Assignee: UNIVERSAL DISPLAY CORP - JP5854839, 2016, B2 Location in patent: Paragraph 0094; 0095
[14]Hu, Zhiyuan; Zhao, Ting; Wang, Manman; Wu, Jie; Yu, Wenquan; Chang, Junbiao [Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 3152 - 3158]
[15]Bonacci, Sonia; Cano, Natividad Herrera; Nardi, Monica; Oliverio, Manuela; Procopio, Antonio [Molecules, 2022, vol. 27, # 5]

3
[ 98-88-4 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In dichloromethane at 0℃; for 6h;	1.1 40 ml of N-phenyl-1,2-phenylenediamine (7.36 g, 40 mmol) was charged in a 250 ml round bottle, 10 ml of triethylamine was then added, and the mixture was cooled to 0° C. Benzoyl chloride (5.6 g, 40 mmol) was dissolved in 40 ml of dichloromethane and then slowly added to the 250 ml round bottle. The reaction was conducted under a nitrogen atmosphere for 6 hours. After the reaction was complete, ether was added to form precipitation. The solid product was collected by filtration, washed with ether several times, and heated under reduced pressure to form 1,2-diphenyl-1H-benzoimidazole (yield=7.56 g, 70%).
	With triethylamine In dichloromethane	1 Organometallic compound (1): Iridium(III) bis[1,2-diphenyl-1H-benzoimidazole] (tetrakis(1-pyrazolyl) borate) EXAMPLE 1 Organometallic compound (1): Iridium(III) bis[1,2-diphenyl-1H-benzoimidazole] (tetrakis(1-pyrazolyl) borate) The synthesis pathway is as follows. 40 ml of N-phenyl-1,2-phenylenediamine (7.36 g, 40 mmol) was charged in a 250 ml round bottle, 10 ml of triethylamine was then added, and the mixture was cooled to 0° C. Benzoyl chloride (5.6 g, 40 mmol) was dissolved in 40 ml of dichloromethane and then slowly added to the 250 ml round bottle. The reaction was conducted under a nitrogen atmosphere for 6 hours. After the reaction was complete, ether was added to form precipitate. The solid product was collected by filtration, washed with ether several times, and heated under reduced pressure to form 1,2-diphenyl-1H-benzoimidazole (yield=7.56 g, 70%).
	Multi-step reaction with 2 steps 1: N,N-dimethyl acetamide / 1 h / 20 °C / Inert atmosphere 2: acetic acid / Reflux

Reference： [1]Current Patent Assignee: TESCOM CO.,LTD. - US6936716, 2005, B1 Location in patent: Page/Page column 5-6
[2]Biehringer; Busch [Chemische Berichte, 1902, vol. 35, p. 1970]
[3]Biehringer; Busch [Chemische Berichte, 1902, vol. 35, p. 1970] Wolff [Justus Liebigs Annalen der Chemie, 1912, vol. 394, p. 85][Justus Liebigs Annalen der Chemie, 1913, vol. 399, p. 288,291]
[4]Current Patent Assignee: TESCOM CO.,LTD. - US2006/78758, 2006, A1
[5]Wen, Li-Li; Yu, Jing; Sun, Hai-Zhu; Shan, Guo-Gang; Zhao, Kai-Yue; Xie, Wen-Fa; Su, Zhong-Min [Organic electronics, 2016, vol. 35, p. 142 - 150]

4
[ 65-85-0 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In 1,2-dichloro-ethane at 25℃; for 1h;
94%	With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In dichloromethane; 1,2-dichloro-ethane for 1h; Ambient temperature;
93%	With PS-PPh₃; trichloroacetonitrile In acetonitrile at 150℃; for 0.25h; microwave irradiation;

49%

With triphenyl phosphite In pyridine at 220℃; for 0.166667h; microwave irradiation;

Reference： [1]Hendrickson, James B.; Hussoin, Md. Sajjat [Journal of Organic Chemistry, 1989, vol. 54, # 5, p. 1144 - 1149]
[2]Hendrickson, James B.; Hussoin, Md. Sajjat [Journal of Organic Chemistry, 1987, vol. 52, # 18, p. 4137 - 4139]
[3]Wang, Ying; Sarris, Kathy; Sauer, Daryl R.; Djuric, Stevan W. [Tetrahedron Letters, 2006, vol. 47, # 28, p. 4823 - 4826]
[4]Lin, Shou-Yuan; Isome, Yuko; Stewart, Ethan; Liu, Ji-Feng; Yohannes, Daniel; Yu, Libing [Tetrahedron Letters, 2006, vol. 47, # 17, p. 2883 - 2886]

5
[ 1227476-15-4 ]
[ 100-51-6 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
21%	With carbon monoxide; sodium acetate; triphenylphosphine In various solvent(s) at 180℃; for 8h;

Reference： [1]Spencer, Alwyn [Journal of Organometallic Chemistry, 1985, vol. 295, p. 79 - 90]

6
[ 100-51-6 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetramethyl ammoniumhydroxide; potassium carbonate In ethylene glycol at 125℃; for 24h;
76%	With hydrogenchloride; manganese(IV) oxide; 4 A molecular sieve In diethyl ether; toluene at 105℃; for 18h;
40 %Chromat.	With Pt-TiO₂ at 32℃; for 4h; UV-irradiation; Inert atmosphere;	The photocatalytic and catalytic synthesis was carried out using the following procedure. Appropriate amounts of catalyst and 2-nitrodiphenylamine or 2-aminodiphenylamine in 25 mL of alcohol were taken in a reaction tube. The reaction tube was sealed with a rubber septum and purged with nitrogen for 30 min. The reaction mixture was irradiated with UV (365 nm) medium-pressure mercury lamp (Sankyo Denki, Japan; intensity I = 1.381 × 10-6 einstein L-1 s-1)/ solar light at constant stirring. The temperature of the reaction medium during UV irradiation was 32 °C and it was nearly constant. With solar light, the temperature of the solution changed gradually from 32 to 48 °C for all the experiments. The progress of the reaction was monitored using thin layer chromatography (TLC). Product analysis was performed by GC analysis, Perkin-Elmer GC-9000 with a capillary column of DB-5 and flame ionization detector was used. GC-MS analysis was carried out using Varian 2000 Thermo with the following features: capillary column VF5MS (5% phenyl-95% methylpolysiloxane), 30 m length, 0.25 mm internal diameter, 0.25 μm film thickness, temperature of column range from 50-280 °C (10 °C/min) and injector temperature 250 °C, attached with mass spectrometer model SSQ 7000. The isolation was performed by column chromatography on a silica gel column by eluting with a co-solvent of dichloromethane and methanol (volume ratio: 8:2). For solar experiments, all reactions have been carried out under similar conditions on sunny days of different months of 2008-2009 between 10 A.M. and 2 P.M. The intensity of solar light was measured using a LT Lutron LX-10/A digital Lux meter and it was found to be 1250 × 100 (+/-100) lux. The intensity was nearly constant during the experiments.

Reference： [1]Adimurthy, Subbarayappa; Badhani, Gaurav; Joshi, Abhisek [European Journal of Organic Chemistry, 2021, vol. 2021, # 48, p. 6705 - 6716]
[2]Wilfred, Cecilia D.; Taylor, Richard J. K. [Synlett, 2004, # 9, p. 1628 - 1630]
[3]Location in patent: experimental part Selvam; Swaminathan [Tetrahedron Letters, 2011, vol. 52, # 26, p. 3386 - 3392]

7
[ 93-98-1 ]
[ 609-73-4 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
83%		8 Example 8 Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and benzanilide (118 mg, 0.6 mmol) yielded the title compound as pale yellow solid (112mg, 83%). mp 105-107°C.1H NMR (DMSO) δ 7.24 (d, J = 7.9 Hz, 1 H), 7.35-7.62 (m, 12 H), 7.84 (d, J = 7.6 Hz, 1 H);13C NMR δ 111.0, 118.1, 123.7, 124.1, 127.5, 127.9, 128.4, 129.2, 129.3, 130.0, 130.2, 135.5, 136.2, 139.3, 151.3. HRMS (FAB): calculated for C19H15N2 [M+H+]: 271.1235; found: 271.1230.
70%	Stage #1: N-phenyl benzoyl amide; o-nitroiodobenzene With potassium phosphate; N-methyl-ethane-1,2-diamine In toluene at 100℃; for 18h; Stage #2: With water In toluene Stage #3: With iron; sodium hydrogencarbonate; acetic acid more than 3 stages;	7.a The title compound was prepared with the analogous procedure described in example 1 using 1-lodo-2-nitrobenzene (125 mg, 0.5 mmol) and benzanilide (118 mg, 0.6 mmol) as starting materials to yield the title compound as pale yellow solid (95 mg, 70%). mp 105-1070C. 1H NMR (DMSO) δ 7.24 (d, J = 7.9 Hz, 1 H), 7.35-7.62 (m, 12 H), 7.84 (d, J = 7.6 Hz, 1 H); 13C NMR δ 111.0, 118.1 , 123.7, 124.1 , 127.5, 127.9, 128.4, 129.2, 129.3, 130.0, 130.2, 135.5, 136.2, 139.3, 151.3. HRMS (FAB): cal. for C19H15N2 [M+H+]: 271.1235; found: 271.1230.
67%	Stage #1: N-phenyl benzoyl amide; o-nitroiodobenzene With potassium phosphate; N-methyl-ethane-1,2-diamine In toluene at 100℃; for 18h; Stage #2: With iron; acetic acid In toluene for 1h; Heating / reflux; Stage #3: With sodium hydrogencarbonate In water; ethyl acetate	7.b A reaction tube containing 1-iodo-2-nitrobenzene (124 mg, 0.5 mmol), λ/-phenyl- benzamide (118 mg, 0.6 mmol), CuI (4.8 mg, 0.025 mmol), λ/-methylethylenediamine (4.4 μl_, 0.05 mmol), potassium phosphate (212 mg, 1 mmol) in dry toluene (1.5 ml_) was purged with dry argon for 3 min. After heating at 100 0C for 18 h, the iron powder (10 mol.-eq.) and glacial acetic acid (5 ml_) are directly added. Then the reaction mixture is heated at reflux for 30 min. An additional 10 mol.-eq. of iron powder are added and the reaction mixture is heated at reflux for further 30 min. The solvents were removed under reduced pressure and the crude was extracted with ethyl acetate against saturated sodium bicarbonate solution. The organic phase was dried and the solvent was removed on a rotary evaporator. Then the residue was purified by preparative HPLC, affording the title compound as a solid (90 mg, 67 % yield).

Multi-step reaction with 2 steps 1: palladium(II) trifluoroacetate; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / toluene / 18 h / 80 °C / Inert atmosphere 2: iron; acetic acid / 0.5 h / Reflux

Reference： [1]Current Patent Assignee: SANOFI - EP1878724, 2008, A1 Location in patent: Page/Page column 16
[2]Current Patent Assignee: SANOFI - WO2009/413, 2008, A1 Location in patent: Page/Page column 29
[3]Current Patent Assignee: SANOFI - WO2009/413, 2008, A1 Location in patent: Page/Page column 29-30
[4]Alonso, Jorge; Halland, Nis; Nazare, Marc; R'Kyek, Omar; Urmann, Matthias; Lindenschmidt, Andreas [European Journal of Organic Chemistry, 2011, # 2, p. 234 - 237]

8
iridium(III) chloride [ No CAS ]
[ 2622-67-5 ]
[Ir(1,2-diphenyl-1H-benzoimidazole)₂(μ-Cl)]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In 2-ethoxy-ethanol; water at 80℃; for 12h;	16 Synthesis of Ir(Dpb)2(acac) (II-3) To a flask with side neck (25ml) was added 1 mmol of iridium trichloride hydrate, 2.5 mmol of Dpb obtained in Example 3, and 10 mL of 2-ethoxyethanol/water (3/1). The reaction mixture was allowed to react at 80° C. for 6 h. After filtering the yellow precipitate, the residual liquid was added back to the flask and allowed to react for another 6 h. The yellow precipitate was filtered again and washed with a small amount of ethanol and n-hexane. The precipitate was scraped, dried, and weighed to give a yellow iridium dimer in 90% yield. To a flask with side neck (25 mL) was added Immol of the yellow iridium dimer product, acetylacetone (2 mmol), Na2CO3 (10 mmol), and 2-ethoxyethanol (4 mL). The reaction mixture was allowed to react at 50° C. for 3 h and then distilled under reduced pressure to remove the 2-ethoxyethanol. The residue was purified by column chromatography using n-hexane/EA (4/1) as eluent. The title iridium complex II-3 was obtained in 86% yield. The UV absorption spectrum and the phosphorescence emission spectrum of the complex II-3 in dichloromethane are shown in FIG. 5. The complex II-3 emits a green light having a peak wavelength of 518 nm. 1H NMR (CDCl3, δ): 1.86 (s, 6 H), 5.27 (s, 1 H), 6.58-6.44 (m, 8 H), 7.32-7.26 (m, 4 H), 7.66-7.57 (m, 12 H), 7.77-7.72 (m, 2 H). 13C NMR (CDCl3, δ): 28.45, 101.29, 110.30, 116.65, 119.81, 122.82, 123.89, 124.91, 128.29, 128.41, 128.87, 129.85, 130.21, 134.90, 135.13, 135.77, 136.52, 140.53, 149.76, 164.20, 184.80. HRMS (FAB): calculated for C43H33IrN4O2 (M+) 830.2233, measured 830.2247.
	In 2-ethoxy-ethanol; water for 12h; Heating / reflux;	1.2 1,2-diphenyl-1H-benzoimidazole (6.75 g, 25 mmol) and iridium(III) chloride trihydrate (4.2 g, 12 mmol) were mixed and then a mixed solution containing 60 ml of ethyoxyethanol and 20 ml of water was added. The mixture was heated to reflux under a nitrogen atmosphere for 12 hours and then cooled to form yellow precipitate. The precipitate was washed with D.I. water and hexane several times to give iridium dichloro-bridged dimer (7.35 g, 4.8 mmol).

Reference： [1]Current Patent Assignee: INNOLUX CORP. - US2005/116626, 2005, A1 Location in patent: Page/Page column 15
[2]Current Patent Assignee: TESCOM CO.,LTD. - US6936716, 2005, B1 Location in patent: Page/Page column 6

9
[ 337913-25-4 ]
[ 98-88-4 ]
[ 124-63-0 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In diethyl ether; ethyl acetate	1 Synthesis of 1,2-diphenylbenzimidazole EXAMPLE 1 Synthesis of 1,2-diphenylbenzimidazole N-phenyl-o-phenylenediamine (10 mmol, 1.84 grams) was added to diethyl ether (100 ml) and stirred at room temperature as benzoyl chloride (10 mmol, 1.41 g) was added dropwise (a precipitate formed after about one half of the benzoyl chloride was added). After addition of the benzoyl chloride, the solution was stirred at room temperature for about 15 minutes. The reaction mixture was partitioned between aqueous sodium hydroxide and diethyl ether. The organic layer was removed and the aqueous layer was extracted with ethyl acetate (3100 ml). The organic fractions were combined and dried over magnesium sulfate. The magnesium sulfate was filtered out and the solvent removed in vacuo to yield a red/brown solid (2.88 g, 99.8%) which was suitable for use in the cyclization reaction. NMR, mp 136-137° C. A solution of the intermediate synthesised supra (2.5 g, 8.6 mmol) and phosphorous pentoxide/methanesulfonyl chloride (1:10) (30 ml) was heated at 100° C. for about one hour. The reaction mixture was then stirred with ice as 5N sodium hydroxide was added to raise the pH to 14. This moisture was then partitioned with ethyl acetate in a separation funnel. The ethyl acetate layer was removed and the aqueous layer was washed with ethyl acetate (3100 ml). The organic layers were combined and dried over potassium carbonate overnight. The solution was filtered and the solvent removed in vacuo to yield 2.2 grams (94.6%) of crude product. The product was purified by chromatography using a hexanes/ethyl acetate (4:1) solution as the eluent to yield 1.98 grams (85.2%) of the pure title product. NMR, MS 271(M+), mp 108-110° C. Analysis for C19 H14 N2: Theory: C, 84.42; H, 5.22; N, 10.36. Found: C, 84.72; H, 5.27; N, 10.35.
	With sodium hydroxide In diethyl ether; ethyl acetate	1 Synthesis of 1,2-diphenylbenzimidazole EXAMPLE 1 Synthesis of 1,2-diphenylbenzimidazole N-phenyl-o-phenylenediamine (10 mmol, 1.84 grams) was added to diethyl ether (100 ml) and stirred at room temperature as benzoyl chloride (10 mmol, 1.41 g) was added dropwise (a precipitate formed after about one half of the benzoyl chloride was added). After addition of the benzoyl chloride, the solution was stirred at room temperature for about 15 minutes. The reaction mixture was partitioned between aqueous sodium hydroxide and diethyl ether. The organic layer was removed and the aqueous layer was extracted with ethyl acetate (3100 ml). The organic fractions were combined and dried over magnesium sulfate. The magnesium sulfate was filtered out and the solvent removed in vacuo to yield a red/brown solid (2.88 g, 99.8%) which was suitable for use in the cyclization reaction. NMR, mp 136-137° C. A solution of the intermediate synthesised supra (2.5 g, 8.6 mmol) and phosphorous pentoxide/methanesulfonyl chloride (1:10) (30 ml) was heated at 100° C. for about one hour. The reaction mixture was then stirred with ice as 5N sodium hydroxide was added to raise the pH to 14. This mixture was then partitioned with ethyl acetate in a separation funnel. The ethyl acetate layer was removed and the aqueous layer was washed with ethyl acetate (3100 ml). The organic layers were combined and dried over potassium carbonate overnight. The solution was filtered and the solvent removed in vacuo to yield 2.2 grams (94.6%) of crude product. The product was purified by chromatography using a hexanes/ethyl acetate (4:1) solution as the eluent to yield 1.98 grams (85.2%) of the pure title product. NMR, MS 271(M+), mp 108-110° C. Analysis for C19 H14 N2: Theory: C, 84.42; H, 5.22; N, 10.36. Found: C, 84.72; H, 5.27; N, 10.35.
	With sodium hydroxide In diethyl ether; ethyl acetate	1 Synthesis of 1,2-diphenylbenzimidazole EXAMPLE 1 Synthesis of 1,2-diphenylbenzimidazole N-phenyl-o-phenylenediamine (10 mmol, 1.84 grams) was added to diethyl ether (100 ml) and stirred at room temperature as benzoyl chloride (10 mmol, 1.41 g) was added dropwise (a precipitate formed after about one half of the benzoyl chloride was added). After addition of the benzoyl chloride, the solution was stirred at room temperature for about 15 minutes. The reaction mixture was partitioned between aqueous sodium hydroxide and diethyl ether. The organic layer was removed and the aqueous layer was extracted with ethyl acetate (3100 ml). The organic fractions were combined and dried over magnesium sulfate. The magnesium sulfate was filtered out and the solvent removed in vacuo to yield a red/brown solid (2.88 g, 99.8%) which was suitable for use in the cyclization reaction. NMR, mp 136°-137° C. A solution of the intermediate synthesised supra (2.5 g, 8.6 mmol) and phosphorous pentoxide/methanesulfonyl chloride (1:10) (30 ml) was heated at 100° C. for about one hour. The reaction mixture was then stirred with ice as 5N sodium hydroxide was added to raise the pH to 14. This mixture was then partitioned with ethyl acetate in a separation funnel. The ethyl acetate layer was removed and the aqueous layer was washed with ethyl acetate (3100 ml). The organic layers were combined and dried over potassium carbonate overnight. The solution was filtered and the solvent removed in vacuo to yield 2.2 grams (94.6%) of crude product. The product was purified by chromatography using a hexanes/ethyl acetate (4:1) solution as the eluent to yield 1.98 grams (85.2%) of the pure title product. NMR, MS 271 (M+), mp 108°-110° C. Analysis for C19 H14 N2: Theory: C, 84.42; H, 5.22; N, 10.36. Found: C, 84.72; H, 5.27; N, 10.35.

With sodium hydroxide In diethyl ether; ethyl acetate

1 Synthesis of 1,2-diphenylbenzimidazole Example 1 Synthesis of 1,2-diphenylbenzimidazole N-phenyl-o-phenylenediamine (10 mmol, 1.84 grams) was added to diethyl ether (100 ml) and stirred at room temperature as benzoyl chloride (10 mmol, 1.41 g) was added dropwise (a precipitate formed after about one half of the benzoyl chloride was added). After addition of the benzoyl chloride, the solution was stirred at room temperature for about 15 minutes. The reaction mixture was partitioned between aqueous sodium hydroxide and diethyl ether. The organic layer was removed and the aqueous layer was extracted with ethyl acetate (3 x 100 ml). The organic fractions were combined and dried over magnesium sulfate. The magnesium sulfate was filtered out and the solvent removed in vacuo to yield a red/brown solid (2.88 g, 99.8%) which was suitable for use in the cyclization reaction. NMR, mp 136-137°C. A solution of the intermediate synthesised supra (2.5 g, 8.6 mmol) and phosphorous pentoxide/methanesulfonyl chloride (1:10) (30 ml) was heated at 100°C for about one hour. The reaction mixture was then stirred with ice as 5N sodium hydroxide was added to raise the pH to 14. This mixture was then partitioned with ethyl acetate in a separation funnel. The ethyl acetate layer was removed and the aqueous layer was washed with ethyl acetate (3 x 100 ml). The organic layers were combined and dried over potassium carbonate overnight. The solution was filtered and the solvent removed in vacuo to yield 2.2 grams (94.6%) of crude product. The product was purified by chromatography using a hexanes/ethyl acetate (4:1) solution as the eluent to yield 1.98 grams (85.2%) of the pure title product. NMR, MS 271 (M+), mp 108-110°C.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US6025379, 2000, A
[2]Current Patent Assignee: ELI LILLY & CO - US6030992, 2000, A
[3]Current Patent Assignee: ELI LILLY & CO - US5552426, 1996, A
[4]Current Patent Assignee: ELI LILLY & CO - EP694535, 1996, A1

10
[ 615-42-9 ]
[ 1527-91-9 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;
58%	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1-methyl-pyrrolidin-2-one at 170℃; Inert atmosphere;

Reference： [1]Yu, Dan; You, Qing; Zhang, Xinming; Tao, Guide; Zhang, Wu [Applied Organometallic Chemistry, 2016, vol. 30, # 8, p. 695 - 698]
[2]Deng, Xiaohu; McAllister, Heather; Mani, Neelakandha S. [Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5742 - 5745]

11
[ 1262283-70-4 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With copper(II) oxide; potassium hydroxide In dimethyl sulfoxide at 110℃; for 3h;
38%	With copper(I) oxide; potassium carbonate; N,N`-dimethylethylenediamine In water at 100℃; for 30h; Sealed tube;

Reference： [1]Saha, Prasenjit; Ramana, Tamminana; Purkait, Nibadita; Ali, Md. Ashif; Paul, Rajesh; Punniyamurthy, Tharmalingam [Journal of Organic Chemistry, 2009, vol. 74, # 22, p. 8719 - 8725]
[2]Peng, Jinsong; Ye, Min; Zong, Cuijuan; Hu, Fangyun; Feng, Lingtong; Wang, Xiaoyan; Wang, Yufeng; Chen, Chunxia [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 716 - 719]

12
[ 1262283-70-4 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 1,10-Phenanthroline; bis-acetylacetonatocobalt(II) dihydrate; potassium carbonate In toluene at 110℃; for 12h;

Reference： [1]Location in patent: experimental part Saha, Prasenjit; Ali, Md Ashif; Ghosh, Pokhraj; Punniyamurthy, Tharmalingam [Organic and Biomolecular Chemistry, 2010, vol. 8, # 24, p. 5692 - 5699]

13
[ 62-53-3 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / dimethyl sulfoxide / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / toluene / 24 h / 140 °C / Molecular sieve; Inert atmosphere
	Multi-step reaction with 2 steps 1.1: sodium hydride / dimethyl sulfoxide / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / toluene / 24 h / 140 °C / Molecular sieve; Inert atmosphere
	Multi-step reaction with 3 steps 1: water / 12 h / 100 °C 2: indium; hydrogenchloride / water / 1 h / 100 °C 3: water / 2 h / 100 °C

	Multi-step reaction with 3 steps 1: water / 2.5 h / 100 °C 2: indium; hydrogenchloride / water / 1 h / 100 °C 3: water / 2 h / 100 °C
	Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere 2: iodine; oxygen / 1,1,2,2-tetrachloroethane / 24 h / 140 °C
	Multi-step reaction with 2 steps 1: sodium hydride / mineral oil; dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere 2: iodine; oxygen / 1,1,2,2-tetrachloroethane / 24 h / 140 °C

Reference： [1]Zhao, Dongbing; Hu, Junyi; Wu, Ningjie; Huang, Xiaolei; Qin, Xurong; Lan, Jingbo; You, Jingsong [Organic Letters, 2011, vol. 13, # 24, p. 6516 - 6519]
[2]Zhao, Dongbing; Hu, Junyi; Wu, Ningjie; Huang, Xiaolei; Qin, Xurong; Lan, Jingbo; You, Jingsong [Organic Letters, 2011, vol. 13, # 24, p. 6516 - 6519]
[3]Kommi, Damodara N.; Jadhavar, Pradeep S.; Kumar, Dinesh; Chakraborti, Asit K. [Green Chemistry, 2013, vol. 15, # 3, p. 798 - 810]
[4]Kommi, Damodara N.; Jadhavar, Pradeep S.; Kumar, Dinesh; Chakraborti, Asit K. [Green Chemistry, 2013, vol. 15, # 3, p. 798 - 810]
[5]Lu, Guoqiang; Luo, Nan; Hu, Fangpeng; Ban, Zihui; Zhan, Zhenzhen; Huang, Guo-Sheng [Advanced Synthesis and Catalysis, 2020, vol. 362, # 3, p. 487 - 492]
[6]Lu, Guoqiang; Luo, Nan; Hu, Fangpeng; Ban, Zihui; Zhan, Zhenzhen; Huang, Guo-Sheng [Advanced Synthesis and Catalysis, 2020, vol. 362, # 3, p. 487 - 492]

14
[ 95-50-1 ]
[ 1527-91-9 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;
30%	With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;

Reference： [1]Zhao, Dongbing; Hu, Junyi; Wu, Ningjie; Huang, Xiaolei; Qin, Xurong; Lan, Jingbo; You, Jingsong [Organic Letters, 2011, vol. 13, # 24, p. 6516 - 6519]
[2]Yu, Dan; You, Qing; Zhang, Xinming; Tao, Guide; Zhang, Wu [Applied Organometallic Chemistry, 2016, vol. 30, # 8, p. 695 - 698]

15
[ 1527-91-9 ]
[ 583-53-9 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;
51%	With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;

16
[ 615-43-0 ]
[ 4903-36-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yu, Hui; Zhang, Mei Shu; Cui, Li Ren [Chinese Chemical Letters, 2012, vol. 23, # 5, p. 573 - 575]

17
[ 4903-36-0 ]
[ 95-51-2 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
45%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yu, Hui; Zhang, Mei Shu; Cui, Li Ren [Chinese Chemical Letters, 2012, vol. 23, # 5, p. 573 - 575]

18
[ 4903-36-0 ]
[ 615-36-1 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 12h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Yu, Hui; Zhang, Mei Shu; Cui, Li Ren [Chinese Chemical Letters, 2012, vol. 23, # 5, p. 573 - 575]

19
[ 51-17-2 ]
[ 591-50-4 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 140℃; for 22h; Inert atmosphere;

Reference： [1]Jeyachandran, Rajkumar; Potukuchi, Harish Kumar; Ackermann, Lutz [Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1771 - 1777,7]

20
[ 100-52-7 ]
[ 62-53-3 ]
[ 1493-27-2 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: aniline; ortho-nitrofluorobenzene In dimethyl sulfoxide at 130℃; for 2h; Inert atmosphere; Stage #2: benzaldehyde With sodium dithionite at 130℃; for 1h; Inert atmosphere;	General procedure for the preparation of 1,2-disubstituted Benzimidazoles. General procedure: A mixture of 1-fluoro-2-nitrobenzene 1 (1.0mmol) and amine 2 (1.0 mmol) in DMSO (2 mL) was stirred for 2 h at 130 °C temperature. Sodium dithionite (1.5mmol) and aldehyde 5 (1.2 mmol) was then added and heating was continued for 1 h. Water (10 mL) was added to the mixture and extracted with EtOAc (3 × 15 mL). The combined organic layer waswashed with brine (5 mL) and dried over anhydrous Na2SO4.Evaporation of solvent and purification by column chromatography (silica gel, ethyl acetate/petroleumether 1:2) gave the pure products .

Reference： [1]Roy, Priyabrata; Pramanik, Animesh [Tetrahedron Letters, 2013, vol. 54, # 38, p. 5243 - 5245]

21
copper(II) tetrafluroborate hexahydrate [ No CAS ]
[ 2622-67-5 ]
[ 501-65-5 ]
5,6,12-triphenyl-12H-benzo[4,5]imidazo[2,1-a]isoquinolin-7-ium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen In tert-Amyl alcohol at 100℃; for 24h; Schlenk technique; Sealed tube;

Reference： [1]Luo, Ching-Zong; Gandeepan, Parthasarathy; Jayakumar, Jayachandran; Parthasarathy, Kanniyappan; Chang, Yu-Wei; Cheng, Chien-Hong [Chemistry - A European Journal, 2013, vol. 19, # 42, p. 14181 - 14186]

22
[ 54346-53-1 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With acetic acid; zinc at 118℃; for 0.333333h;

Reference： [1]Berezin, Andrey A.; Koutentis, Panayiotis A. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 10, p. 1641 - 1648]

23
[ 1569089-15-1 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With acetic acid; zinc at 118℃; for 15h;

Reference： [1]Berezin, Andrey A.; Koutentis, Panayiotis A. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 10, p. 1641 - 1648]

24
[ 1519051-12-7 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide In dimethyl sulfoxide at 120℃; for 16h; Inert atmosphere; Sealed tube;

Reference： [1]Baars, Hannah; Beyer, Astrid; Kohlhepp, Stefanie V.; Bolm, Carsten [Organic Letters, 2014, vol. 16, # 2, p. 536 - 539]

25
iridium(III) chloride trihydrate [ No CAS ]
[ 2622-67-5 ]
[Ir(1,2-diphenyl-1H-benzoimidazole)₂(μ-Cl)]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 2-ethoxy-ethanol; water for 20h; Inert atmosphere; Reflux;	Preparation of μ-chloro-bridge iridium dimer General procedure: To a 25ml round-bottomed flask containing IrCl3·3H2O (80mg, 0.25mmol) and mpbi (316mg, 0.96mmol) a mixture of 2-ethoxyethanol and water (3:1 v/v, 10ml) was added. The mixture was refluxed for 20h under argon atmosphere and cooled to room temperature. Distilled water (3ml) was added and the precipitate formed was collected by filtration, washed several times with water, ethanol, acetone, and dried in vacuo at 60°C during 12h.
	In 2-ethoxy-ethanol; water for 24h; Inert atmosphere;
	In 2-ethoxy-ethanol; water for 24h; Reflux; Inert atmosphere; Schlenk technique;	Synthesis of (pbi)2Ir(pypz) (1) A mixture of IrCl33H2O (0.70 g, 2.20 mmol) and Hpbi (1.18 g, 4.40 mmol) in a mixture of 2-ethoxyethanol and water (40 mL, 3:1,v/v) was refluxed under nitrogen for 24 h. The reaction mixture wasthen cooled down to room temperature and water (30 mL) was added. The mixture was filtered and the residue was washed with water (60 mL) and ethanol (60 mL). The crude dichloro-bridged diiridium complex (1.10 g), [Ir(pbi)2Cl]2, was collected without further purification after it was dried out. A solution of ligand Hpypz (0.06 g, 0.40 mmol) and the dichloro-bridged diiridium complex [Ir(pbi)2Cl]2 (0.24 g, 0.16 mmol) in dichloromethane (30 mL) and ethanol (10 mL)was refluxed under nitrogen for 12 h inthe dark. After cooling to room temperature, the mixture was precipitated into n-hexanes (150 mL) with stirring. Then, the precipitate was filtered and washed with n-hexanes. The crude product was purified by silica gel column chromatography using an ethyl acetate-dichloromethane mixture (10:1, v/v) and then a dichloromethane-methanol mixture (25:1, v/v) as eluent to afford complex 1 in 65% yield (0.21 mmol, 0.18 g). 1H NMR (500 MHz,d6-DMSO, δ [ppm]): 8.36 (d, J 7.5 Hz, 1H), 8.20-8.23 (m, 1H), 8.00(d, J 4.5 Hz, 1H), 7.73-7.82 (m, 9H), 7.62-7.67 (m, 4H), 7.21-7.25(m, 2H), 7.03-7.09 (m, 3H), 6.99 (t, J 8.5 Hz, 1H), 6.79-6.82 (m,1H), 6.71 (t, J 7.5 Hz, 2H), 6.63 (t, J 7.0 Hz, 1H), 6.56 (d, J 8.0 Hz,1H), 6.49-6.52 (m, 2H), 6.44 (d, J 7.5 Hz, 1H), 5.82 (d, J 8.5 Hz,1H), 5.70 (d, J 8.5 Hz, 1H). IR (cm-1): v 3416 (m), 3032 (w), 1611(w), 1500 (m), 1457 (s), 1423 (m), 1304 (w), 1154 (w), 1043 (w), 800(w), 775 (s), 738 (s), 698 (m), 645 (w), 578 (w). HRMS (m/z), found:[M + H] 876.2325; molecular formula C46H32IrN7, requires [M + H] 876.2348.

	In 2-ethoxy-ethanol; water at 135℃; for 24h; Inert atmosphere;
	In 2-ethoxy-ethanol; water for 24h; Reflux; Inert atmosphere;	2.2.2.1. Synthesis of complex 1. General procedure: PBI (0.59g, 2.20mmol) and IrCl3·3H2O (0.35g, 1.00mmol) were mixed in 2-ethoxyethanol/water (3:1, 20mL). The reaction mixture was stirred and heated to reflux for 24h under nitrogen atmosphere. After cooling to room temperature, the product was filtered, washed with water, ethanol and diethyl ether. The product was isolated as a yellow powder. To a suspension of dimer [Ir(pbi)2(μ-Cl)]2 (0.37g, 0.24mmol) in dichloromethane/ethanol (3:1, 60mL) was added Htfmptz (0.13g, 0.60mmol). The reaction mixture was stirred and heated to reflux for 18h under nitrogen atmosphere, and the product was extracted by dichloromethane. The organic phase was washed with water, dried over by anhydrous Na2SO4 and the solvent was evaporated. The product was then purified by column chromatography on silica gel. The pure product was isolated as a powder.

Reference： [1]Bezzubov, Stanislav I.; Doljenko, Vladimir D.; Troyanov, Sergey I.; Kiselev, Yuri M. [Inorganica Chimica Acta, 2014, vol. 415, p. 22 - 30]
[2]Bezzubov; Dolzhenko; Kiselev [Russian Journal of Inorganic Chemistry, 2014, vol. 59, # 6, p. 571 - 577][Zh. Neorg. Khim., 2014, vol. 59, # 6, p. 749 - 755,7]
[3]Cao, Hong-Tao; Shan, Guo-Gang; Yin, Yong-Ming; Sun, Hai-Zhu; Wu, Yong; Xie, Wen-Fa; Su, Zhong-Min [Dyes and Pigments, 2015, vol. 112, p. 8 - 16]
[4]Bezzubov, Stanislav I.; Kiselev, Yuri M.; Churakov, Andrey V.; Kozyukhin, Sergey A.; Sadovnikov, Alexey A.; Grinberg, Vitaly A.; Emets, Viktor V.; Doljenko, Vladimir D. [European Journal of Inorganic Chemistry, 2016, vol. 2016, # 3, p. 347 - 354]
[5]Wen, Li-Li; Yu, Jing; Sun, Hai-Zhu; Shan, Guo-Gang; Zhao, Kai-Yue; Xie, Wen-Fa; Su, Zhong-Min [Organic electronics, 2016, vol. 35, p. 142 - 150]

26
[ 4657-12-9 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol for 3h; Reflux;	Synthesis of pbi N-Phenyl-o-phenylenediamine (1.56g, 8.5mmol) was dissolved in ethanol (25ml). To this solution benzaldehyde sodium bisulfite adduct (2.23g, 13.9mmol) and ethanol (5ml) were added. The mixture was refluxed for 3h and cooled. Distilled water (20ml) was added and the resulting precipitate was filtered and washed sufficiently with water. After two recrystallizations from aqueous ethanol the solid was dried in vacuo at 50°C during 10h. Yield: 1.62g, 70%, colorless needles. 1H NMR (DMSO-d6, ppm): δ 7.79 (d, 1H, J=7.4Hz), 7.49-7.58 (m, 5H), 7.23-7.42 (m, 7H), 7.17 (d, 1H, J=7.5Hz). 13C NMR (DMSO-d6, ppm): 152.3, 143.0, 137.5, 136.9, 130.5, 130.3, 130.0, 129.6, 129.3, 128.8, 128.0, 123.8, 123.2, 119.9, 110.9. MS (MALDI-TOF): m/z=271.2 (Calc. 271.3 for [M+H]+).

Reference： [1]Bezzubov, Stanislav I.; Doljenko, Vladimir D.; Troyanov, Sergey I.; Kiselev, Yuri M. [Inorganica Chimica Acta, 2014, vol. 415, p. 22 - 30]

27
[ 141417-98-3 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
52%	With [bis(acetoxy)iodo]benzene In acetonitrile at 120℃; for 1h; Sealed tube;

Reference： [1]Lin, Jian-Ping; Zhang, Feng-Hua; Long, Ya-Qiu [Organic Letters, 2014, vol. 16, # 11, p. 2822 - 2825]

28
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
[ 2622-67-5 ]
[ 94928-86-6 ]
C₄₁H₂₉IrN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.29 g	With sodium carbonate; In glycerol; at 240℃; for 12h;Inert atmosphere;	Bis[1,2-diphenyl-1H-benzo[d]-imidazole](2-phenylpyridine)iridium(III) [Ir(ppy)2pbi]: Hppy (0.31 g, 2.0 mmol) was dissolved into a mixed solution of 2-ethoxyethanol (12 mL) and water (4 mL) in a 25 mL round bottomed flask, and then IrCl3·3H2O (0.28 g, 0.8 mmol) was added. The mixture was stirred under nitrogen at 120 °C for 12 h. The mixture was cooled to room temperature and the precipitate was collected and washed with water, ethanol, and acetone, then dried in vacuum to give a cyclometalated Ir-mu-chloro-bridged dimer. The dimer complex, Hpbi (0.27 g, 1.0 mmol), Na2CO3 (0.34 g, 3.2 mmol) and 5mL glycerol were charged into a round bottomed flask, the mixture was then heated to 240 °C under an argon atmosphere for another 12 h. After cooling to room temperature, the mixture was poured into 100 mL water, yellow precipitate was filtered off and washed with water, ethanol and ether. The crude product was purified by silica column chromatography with dichloromethane/petroleum ether (1:2, v/v) as the eluent to give 0.29 g Ir(ppy)2pbi as a yellow powder. Yield: 47.5percent, 0.14 g. Ir(ppy)3 can also be obtained as a byproduct, yield: 27.5percent. 1HNMR (CDCl3, 600MHz): 7.90 (t, J=6.4Hz, 2H), 7.85 (d, J=4.8Hz, 1H), 7.77 (d, J=5.4Hz, 1H), 7.69?7.59 (m, 7H), 7.50?7.47 (m, 2H), 7.06 (t, J=7.8Hz, 1H), 6.97 (d, J=7.8Hz, 1H), 6.92?6.78 (m, 10H), 6.72 (t, J=7.8Hz, 1H), 6.63 (d, J=7.8Hz, 1H), 6.53 (t, J=7.8Hz, 1H), 6.05 (d, J=8.4Hz, 1H); 13CNMR (CDCl3, 150MHz): 167.65, 166.68, 163.39, 162.61, 161.33, 148.06, 144.33, 143.92, 140.86, 137.90, 137.85, 136.91, 136.87, 136.32, 135.90, 135.80, 134.10, 130.38, 130.13, 129.89, 129.78, 129.74, 128.53, 128.17, 125.25, 123.94, 123.72, 123.23, 122.38, 122.00, 121.29, 119.66, 119.52, 119.09, 118.66, 118.54, 115.23, 110.53; HRMS (APCI): m/z calcd for C41H29IrN4: 770.2021; found: 771.2094 (M+H)+.

Reference： [1]Dyes and Pigments,2015,vol. 113,p. 649 - 654

29
[ 100-46-9 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 4-tert-butyl-5-methoxy-1,2-benzoquinone; oxygen; toluene-4-sulfonic acid In acetonitrile at 60℃; for 24h; Schlenk technique;
92%	With C₁₁H₁₇I₂N₃OZn In toluene at 100℃; for 24h;
82%	With 1-(3-amino-2,4-dihydroxyphenyl)-1-ethanone; copper (II) bromide In methanol at 45℃; for 24h;

With Mo_0.03Co_2.97O₄ In butan-1-ol at 100℃; for 5h; Green chemistry;

Reference： [1]Zhang, Ruipu; Qin, Yan; Zhang, Long; Luo, Sanzhong [Organic Letters, 2017, vol. 19, # 20, p. 5629 - 5632]
[2]Bano, Kulsum; Kisan, Devadkar Ajitrao; Panda, Tarun K. [European Journal of Inorganic Chemistry, 2022, vol. 2022, # 10]
[3]Nguyen, Khac Minh Huy; Largeron, Martine [Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12606 - 12610]
[4]Weerakkody, Chandima; Rathnayake, Dinithi; He, Junkai; Dutta, Biswanath; Kerns, Peter; Achola, Laura; Suib, Steven L. [ChemCatChem, 2019, vol. 11, # 1, p. 528 - 537]

30
[ 780-25-6 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1-(3-amino-2,4-dihydroxyphenyl)-1-ethanone; copper(ll) bromide In methanol at 45℃; for 24h;

Reference： [1]Nguyen, Khac Minh Huy; Largeron, Martine [Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12606 - 12610]

31
[ 2622-60-8 ]
[ 6969-90-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With nickel(II) triflate; potassium phosphate; 1,2-bis-(dicyclohexylphosphino)ethane In tert-Amyl alcohol at 110℃;

Reference： [1]Muto, Kei; Hatakeyama, Taito; Yamaguchi, Junichiro; Itami, Kenichiro [Chemical Science, 2015, vol. 6, # 12, p. 6792 - 6798]

32
[ 2622-60-8 ]
[ 108-90-7 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With nickel(II) triflate; potassium phosphate; 1,2-bis-(dicyclohexylphosphino)ethane In tert-Amyl alcohol at 110℃; for 36h;
57%	With potassium <i>tert</i>-butylate In water; toluene for 7h; Irradiation;

Reference： [1]Muto, Kei; Hatakeyama, Taito; Yamaguchi, Junichiro; Itami, Kenichiro [Chemical Science, 2015, vol. 6, # 12, p. 6792 - 6798]
[2]Chopra, Radhika; Kumar, Manoj; Bhalla, Vandana [Chemical Communications, 2016, vol. 52, # 66, p. 10179 - 10182]

33
[ 13556-72-4 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium peroxodisulfate In acetonitrile at 90℃; Sealed tube;
70%	With iodine; dimethyl sulfoxide at 130℃; for 6h;
70%	With iodine In dimethyl sulfoxide at 130℃; for 6h;	15 Example 15: Synthesis method of 1,2-diphenyl-1H-benzo[d]imidazole Add N1-benzyl-N2-phenylbenzene-1,2-diamine (0.36mmol, 100mg), elemental iodine (0.04mmol, 11mg), and dimethyl sulfoxide (2ml) into the test tube in sequence, and react at 130 After 6h, the reaction solution was extracted 3 times with ethyl acetate, the combined organic phases were concentrated to dryness, and separated by column chromatography (petroleum ether: ethyl acetate=4:1) to obtain 1,2-diphenyl-1H- Benzo[d]imidazole, yield: (69mg, 70%).

66%

With oxygen In diethylene glycol dimethyl ether at 120℃; for 2h; Schlenk technique;

Reference： [1]Laha, Joydev K.; Tummalapalli, K. S. Satyanarayana; Nair, Akshay; Patel, Nidhi [Journal of Organic Chemistry, 2015, vol. 80, # 22, p. 11351 - 11359]
[2]Wen, Simiaomiao; Du, Yifan; Liu, Yiwen; Cui, Xiaofeng; Liu, Qixing; Zhou, Haifeng [European Journal of Organic Chemistry, 2022, vol. 2022, # 4]
[3]Current Patent Assignee: CHINA THREE GORGES UNIVERSITY - CN113563272, 2021, A Location in patent: Paragraph 0063-0065
[4]Fu, Hao; Liu, Mengna; Liu, Qixing; Wen, Simiaomiao; Zhao, Rongrong; Zhou, Haifeng [Green Chemistry, 2022, vol. 24, # 4, p. 1644 - 1649]

34
N<SUP>1</SUP>-methyl-N<SUP>2</SUP>-phenylbenzene-1,2-diamine [ No CAS ]
[ 100-46-9 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With C₈H₇NO₃; copper(ll) bromide In methanol at 45℃; for 24h; Green chemistry;

Reference： [1]Nguyen, Khac Minh Huy; Largeron, Martine [European Journal of Organic Chemistry, 2016, vol. 2016, # 5, p. 1025 - 1032]

35
[ 93-97-0 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	In 1-methyl-pyrrolidin-2-one; water at 445℃; for 0.00277778h; Supercritical conditions;	2-1 Except for using N-phenyl-1,2-benzenediamine (manufactured by Wako Pure Chemical Industries, Ltd.) and Benzoic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) as raw materials, the following chemical reaction The chemical reaction represented by the formula (5) was carried out in supercritical water.
> 99 %Chromat.	With water In 1-methyl-pyrrolidin-2-one at 445℃; for 0.001075h; Flow reactor; Green chemistry;
	Multi-step reaction with 2 steps 1: 1-methyl-pyrrolidin-2-one; water / 0 h / 445 °C / 300030 Torr / Supercritical conditions 2: 1-methyl-pyrrolidin-2-one; water / 0 h / 445 °C / 337534 Torr / Supercritical conditions

Reference： [1]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2017/132722, 2017, A Location in patent: Paragraph 0027-0028
[2]Nagao; Ishizaka; Kawanami [Green Chemistry, 2016, vol. 18, # 12, p. 3494 - 3498]
[3]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2017/132722, 2017, A

36
[ 583-55-1 ]
[ 1527-91-9 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;

Reference： [1]Yu, Dan; You, Qing; Zhang, Xinming; Tao, Guide; Zhang, Wu [Applied Organometallic Chemistry, 2016, vol. 30, # 8, p. 695 - 698]

37
[ 201024-81-9 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide In 1,2-dichloro-ethane at 120℃; for 12h; Schlenk technique; Inert atmosphere;	1 The reaction was carried out in a 10 ml Schlenk reaction tube and the reaction tube was evacuated and replaced with argon three times. (0.15 mg, 11.9 mg) of Cp * Co (C0) I2, lOmol% AgSbF6 (0.55 mmol, 17.2 mg) and 2 ml of dissolved 1,2-dichloroethane, stirring lOmin; Then 0.5 mmol (98.6 mg) of nitrione la was added to the reaction at 120 ° C for 12 hours. After completion of the reaction, the solvent was extracted with a rotary evaporator and the solid was dissolved in dichloromethane. The column was subjected to silica gel column chromatography Oil ether: ethyl acetate = 10: 1 (by volume) eluent to give 57.4 mg of a white solid benzimidazole derivative The yield was 81%

Reference： [1]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN106866541, 2017, A Location in patent: Paragraph 0016-0018

38
[ 108-86-1 ]
[ 100-52-7 ]
[ 95-54-5 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,10-Phenanthroline; copper(II) sulfate; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 24h;	22 Example 22: 1mmol of o-phenylenediamine, 1.2mmol of benzaldehyde,1 mmol of bromobenzene israw material,Into a 50 mL pressure tube, using 10 mol% CuSO4 as the catalyst, 2 mmol KOH as the base,1,10-phenanthroline is used in an amount of 20 mol%N, N-dimethylformamide was used in an amount of 5 mL and the temperature was 120 ° C. The reaction was stirred for 24 h.The reaction solution was suction filtered and distilled under reduced pressure to obtain a pale yellow solid after passing through the column.90% yield of 1,2-diarylbenzimidazole as a pale yellow solid

Reference： [1]Current Patent Assignee: JIANGSU XIANKE PHARMACEUTICAL - CN104557725, 2017, B Location in patent: Paragraph 0170; 0171; 0172; 0173; 0174; 0175; 0176

39
[ 100-52-7 ]
[ 108-90-7 ]
[ 95-54-5 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With 1,10-Phenanthroline; copper(II) sulfate; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 24h;	26 Example 26: 1mmol of o-phenylenediamine, 1.2mmol of benzaldehyde, 1mmol of chlorobenzene as raw materials, into the 50mL pressure tube, using 10mol% CuSO4 as a catalyst, 2mmol KOH as a base,1,10-phenanthroline is used in an amount of 20 mol%N, N-dimethylformamide was used in an amount of 5 mL and the temperature was 120 ° C. The reaction was stirred for 24 h.The reaction solution was suction filtered and distilled under reduced pressure to give a white solid.65% yield of 1,2-diphenyl-1H-benzimidazole as a white solid

Reference： [1]Current Patent Assignee: JIANGSU XIANKE PHARMACEUTICAL - CN104557725, 2017, B Location in patent: Paragraph 0197; 0198; 0199; 0200; 0201; 0202; 0203

40
[ 591-50-4 ]
[ 100-52-7 ]
[ 95-54-5 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,10-Phenanthroline; copper(II) sulfate; potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 24h;	11 Example 11: 1 mmol of o-phenylenediamine, 1.2 mmol of benzaldehyde and 1 mmol of iodobenzene was charged into a 50 mL pressure tube using 10 mol% CuSO4 as a catalyst, 2 mmol KOH as base, 1,10-phenanthroline in an amount of 20 mol% ,N, N-dimethylformamide was used in an amount of 5 mL and the temperature was 120 ° C. The reaction was stirred for 24 h.The reaction solution was suction filtered and distilled under reduced pressure to give a white solid.92% yield of 1,2-diphenyl-1H-benzimidazole as a white solid

Reference： [1]Current Patent Assignee: JIANGSU XIANKE PHARMACEUTICAL - CN104557725, 2017, B Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026; 0027; 0028-0098

41
[ 93-97-0 ]
[ 534-85-0 ]
[ 2622-67-5 ]
[ 39823-24-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 7% 2: 92%	In 1-methyl-pyrrolidin-2-one; water at 445℃; for 0.00277778h; Supercritical conditions;	2-2 Except for using N-phenyl-1,2-benzenediamine (manufactured by Wako Pure Chemical Industries, Ltd.) and Benzoic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) as raw materials, the following chemical reaction The chemical reaction represented by the formula (5) was carried out in supercritical water. The results are shown in

Reference： [1]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2017/132722, 2017, A Location in patent: Paragraph 0027-0028

42
[ 119-75-5 ]
[ 100-51-6 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2 mol-% Pd/C; potassium <i>tert</i>-butylate In chlorobenzene at 80℃; for 4h; Inert atmosphere;

Reference： [1]Guan, Qianqian; Sun, Qi; Wen, Lixian; Zha, Zhenggen; Yang, Yu; Wang, Zhiyong [Organic and Biomolecular Chemistry, 2018, vol. 16, # 12, p. 2088 - 2096]

43
[ 573-57-9 ]
[ 2622-67-5 ]
exo-1-phenyl-2-[2-(1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)phenyl]-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With rhenium(I) pentacarbonyl bromide; sodium acetate In 1,4-dioxane at 130℃; for 12h; Sealed tube; High pressure; stereoselective reaction;

Reference： [1]Prakash, Sekar; Chang, Yu-Che; Cheng, Chien-Hong [Chemistry - An Asian Journal, 2018, vol. 13, # 13, p. 1664 - 1668]

44
[ 2622-60-8 ]
[ 100-66-3 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; C₂₃H₃₀N₄; para-methylphenylmagnesium bromide In m-xylene at 90℃; for 16h;

Reference： [1]Wang, Ting-Hsuan; Ambre, Ram; Wang, Qing; Lee, Wei-Chih; Wang, Pen-Cheng; Liu, Yuhua; Zhao, Lili; Ong, Tiow-Gan [ACS Catalysis, 2018, vol. 8, # 12, p. 11368 - 11376]

45
[ 2622-67-5 ]
[ 6710-92-5 ]
C₆₃H₃₉N₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 48h;	5 (5) Compound L7 In the is provided with a 1, 2 - diphenyl - 1H - benzo [d] imidazole of CH2Cl2(200 Ml) mixed solution of three bottle by adding AlCl3Solution of ice-water bath to control the temperature 0°C40 minutes. Then, the 3 A is slowly added to the mixed solution, the three port added to the bottom of the bottle 25 °C the left and right, and fully stirred 48 hours later, the reaction solution is added to the NaOH/H2O solution and then fully stirred 10 hours. The final reaction solution through the chloroform solution to perform a plurality of extraction, extraction of the organic phase after the use of the saturated brine for flushing, for magnesium sulfate desiccant drying treatment is carried out after the vacuum filtering, filtering the obtained product is further by chromatographic column processing (pre-organic phase is toluene/hexane=1:1, the latter part of the organic phase is toluene/hexane solution=2:1) to obtain 98% purity of more than product L7. In order to further improve L7 of purity, by using vacuum sublimator once or a plurality of sublimation, can get the purity is greater than 99.0% of the L7 product.

Reference： [1]Current Patent Assignee: AAC ACOUSTIC TECHNOLOGIES HOLDINGS INC. - CN108929327, 2018, A Location in patent: Paragraph 0106; 0107; 0108

46
[ 2622-67-5 ]
[ 6710-92-5 ]
C₆₃H₃₉N₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 48h;	2 (2) Compound L2 In the is provided with a 1, 2 - diphenyl - 1H - benzo [d] imidazole of CH2Cl2(200 Ml) mixed solution of three bottle by adding AlCl3Solution of ice-water bath to control the temperature 0°C40 minutes. Then, the 3 A is slowly added to the mixed solution, the three port added to the bottom of the bottle 25 °C the left and right, and fully stirred 48 hours later, the reaction solution is added to the NaOH/H2O solution and then fully stirred 10 hours. The final reaction solution through the chloroform solution to perform a plurality of extraction, extraction of the organic phase after the use of the saturated brine for flushing, for magnesium sulfate desiccant drying treatment is carried out after the vacuum filtering, filtering the obtained product is further by chromatographic column processing (pre-organic phase is toluene/hexane=1:1, the latter part of the organic phase is toluene/hexane solution=2:1) to obtain 98% purity of more than product L2. In order to further improve L2 of purity, by using vacuum sublimator once or a plurality of sublimation, can get the purity is greater than 99.0% of L2 product.

Reference： [1]Current Patent Assignee: AAC ACOUSTIC TECHNOLOGIES HOLDINGS INC. - CN108929327, 2018, A Location in patent: Paragraph 0088-0090

47
[ 88-99-3 ]
[ 534-85-0 ]
[ 2622-67-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	In water at 375℃; for 3h; Autoclave; Inert atmosphere;	12 (Example 12)As shown in the following chemical reaction formula, N-phenyl-1,2-benzenediamine and phthalic acid were reacted in supercritical water to synthesize 1,2-diphenyl-1H-benzimidazole. First, N-phenyl-1,2-benzenediamine (3 mmol, 655 mg) and phthalic acid (3 mmol, 498 mg) were placed in an autoclave container made of SUS 316 and having a volume of about 10 mL. After making the inside of the autoclave container into a nitrogen gas atmosphere, deaerated pure water was introduced. The autoclave vessel was placed in a heating furnace, and the temperature in the furnace was raised to 375 ° C. At this time, the pressure was maintained at 25 MPa. After 3 hours, the inside of the heating furnace was rapidly cooled. In addition, the pressure inside the autoclave vessel was reduced to atmospheric pressure. The solid reaction product was then recovered from within the autoclave vessel and dried under vacuum for 24 hours. As a result of analysis by NMR spectroscopy, the yield of 1,2-diphenyl-1H-benzimidazole was 88%.

Reference： [1]Current Patent Assignee: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2019/26576, 2019, A Location in patent: Paragraph 0110; 0111

48
[ 2622-67-5 ]
C₂₆H₂₈O [ No CAS ]
C₄₅H₄₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With boron trifluoride diethyl etherate In dichloromethane for 24h; Inert atmosphere;	Take (2.2mmol, 0.78g), (2.0mmol, 0.54g) and 100mL of dichloromethane into a 250mL two-necked flask, Under the protection of Ar2, add BF3·Et2O (2.2mmol, 0.3mL) solution dropwise, and stir for 24h;Add a little water to the above reaction solution to quench, then pour it into 100 mL of water,Extract three times with dichloromethane, combine the organic phases, dry, filter, and vacuum dry;Column chromatography was separated and purified to obtain 60.79 g of white powder with a yield of 65%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN110129034, 2020, B Location in patent: Paragraph 0077-0082

49
[ 2622-67-5 ]
C₃₈H₅₄IrN₂O₂Si₂*CF₃O₃S^(1-) [ No CAS ]
C₅₅H₆₁IrN₄Si₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	In 2-ethoxy-ethanol for 24h; Reflux;	4 Synthesis of Compound 1 General procedure: Compound 1B (2.0 g, 2.3 mmol) and 1-methyl-2-phenyl-1H-benzo[d]imidazole (0.6 g, 2.8 mmol) were mixed with 100 mL of 2-ethoxyethanol, and then the mixture was stirred while refluxing for 24 hours and cooled to room temperature. A compound obtained therefrom was concentrated to obtain a solid which was then subject to column chromatography (eluent: methylene chloride (MC) and hexane) to obtain 0.9 g (yield of 46%) of Compound 1.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD. - US2021/163517, 2021, A1 Location in patent: Paragraph 0223; 0226; 0233-0236

50
[ 2622-67-5 ]
[ 13520-76-8 ]
C₃₈H₂₆Cl₂N₄O₄W₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With anhydrous sodium carbonate In lithium hydroxide monohydrate at 120℃; for 12h;	10 Synthesis of intermediate (284-b): Put 1,2-diphenyl-1H-benzimidazole (1.2eq) into a single-necked bottle, add tungsten dichloride (1eq) and sodium carbonate (5eq), add a mixture of 300mL of ethylene glycol ether and 100mL of water The solution was heated to 120° C., reacted for 12 hours, cooled to room temperature, poured into an aqueous sodium chloride solution, filtered and dried to obtain intermediate (284-b) with a yield of 39%.

Reference： [1]Current Patent Assignee: GUANGZHOU CORE PHOTOELECTRIC MAT - CN114369121, 2022, A Location in patent: Paragraph 0230-0231; 0234-0235

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2622-67-5 ] {[proInfo.proName]}

Quality Control of [ 2622-67-5 ]

Related Doc. of [ 2622-67-5 ]

Product Details of [ 2622-67-5 ]

Safety of [ 2622-67-5 ]

Application In Synthesis of [ 2622-67-5 ]

[ 2622-67-5 ] Synthesis Path-Upstream 1~1

[ 2622-67-5 ] Synthesis Path-Downstream 1~50

Related Functional Groups of [ 2622-67-5 ]

Aryls

Related Parent Nucleus of [ 2622-67-5 ]

Benzimidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2622-67-5 ]

Related Parent Nucleus of
[ 2622-67-5 ]