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Quality Control of [ 67370-32-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 67370-32-5 ]

Product Details of [ 67370-32-5 ]

CAS No. :	67370-32-5	MDL No. :	MFCD01237666
Formula :	C₁₃H₈Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	263.12	Pubchem ID :	-
Synonyms :

Safety of [ 67370-32-5 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 67370-32-5 ]

* 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.

Downstream synthetic route of [ 67370-32-5 ]

[ 67370-32-5 ] Synthesis Path-Downstream 1~26

1
[ 95-54-5 ]
[ 6287-38-3 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
98.1%	With air In ethanol at 20℃; for 6h; Green chemistry;
91%	With sodium meta-bisulphite In N,N-dimethyl-formamide for 2h; Reflux;
85%	With 2-oxo-propionic acid In lithium hydroxide monohydrate at 50℃; for 0.166667h; Sonication; Green chemistry;	4.2. General Procedure for the Synthesis of 3a-l Under Ultrasound Irradiation Condition General procedure: A mixture of o-phenylenediamine 1 (0.5 gm, 4.63 mmol), aromatic aldehyde 2 (4.63 mmol) & pyruvic acid (10 mol %) in water (10 ml) was sonicated at 50 oC for indicated time. After completion of the reaction (TLC check), the reaction mixture was cooled to R.T. and the solid crude product was isolated by simple filtration and washed with water. The crude product was purified by silica gel column chromatography technique using (10-50%) ethyl acetate: n-hexane as the eluent. All the products were characterized by the usual spectroscopic technique and the spectral data of all compounds are given below.

74%	With ammonium acetate at 70℃; for 1h;
62%	With disodium metabisulfite Microwave irradiation;
	With polyphosphoric acid at 250℃;
	With dihydrogen peroxide In methanol at 50℃;	General procedure: A mixture of benzene-1,2-diamine (9a) (540 mg, 5 mmol), 2-naphthaldehyde (781 mg, 5 mmol) in MeOH (25 ml) was stirred, and after the addition of 30% w/w H2O2 (1.2 g, 10 mmol) was heated at 50 °C for 3 h. After completion of the reaction, the reaction mixture was cooled and quenched with NaHSO3 (10 mmol). Methanol in the reaction mixture was removed up to 1/10 of the initial volume in vacuo. The concentrated mixture was filtered off and washed with ethyl acetate. The combined organic layer was concentrated in vacuo to produce crude product (10a) as a crude brown solid (48%). Without additional purification, 2-naphthalen-2-yl-1H-benzoimidazole (10a) was identified by LCMS and used in the next step.
	With disodium metabisulfite In N,N-dimethyl-formamide for 2h; Reflux;
	Stage #1: 3,4-dichloro-benzaldehyde With disodium metabisulfite In ethanol; lithium hydroxide monohydrate at 20℃; for 4.5h; Cooling with ice; Stage #2: 1,2-diamino-benzene In N,N-dimethyl-formamide at 130℃; for 5h;

Reference： [1]Chen, Guo-Feng; Shen, Hai-Dong; Jia, Hui-Ming; Zhang, Li-Yan; Kang, Hong-Yan; Qi, Qing-Qing; Chen, Bao-Hua; Cao, Jia-Li; Li, Ji-Tai [Australian Journal of Chemistry, 2013, vol. 66, # 2, p. 262 - 266]
[2]Location in patent: body text Khan, Khalid Mohammed; Khan, Momin; Ambreen, Nida; Rahim, Fazal; Naureen, Shagufta; Perveen, Shahnaz; Choudhary, M. Iqbal; Voelterc, Wolfgang [Medicinal Chemistry, 2012, vol. 8, # 3, p. 421 - 427]
[3]Deshmukh, Santosh Rangnath; Nalkar, Archana Subhash; Thopate, Shankar Ramchandra [Letters in Organic Chemistry, 2022, vol. 19, # 7, p. 511 - 519]
[4]Location in patent: experimental part Zhang, Qiu-Gen; Xie, Yu; Hu, Jin-Gang; Liu, Jin-Mei; Wang, Juan; Zhong, Rong; Gao, Yun-Hua [Asian Journal of Chemistry, 2012, vol. 24, # 10, p. 4611 - 4613]
[5]Location in patent: experimental part Patil, Vaishali M.; Gurukumar; Chudayeu, Maksim; Gupta, Satya Prakash; Samanta, Subeer; Masand, Neeraj; Kaushik-Basu, Neerja [Medicinal Chemistry, 2012, vol. 8, # 4, p. 629 - 635]
[6]Hein et al. [Journal of the American Chemical Society, 1957, vol. 79, p. 426]
[7]Kim, Mi-Hyun; Lee, Junghun; Jung, Kyungjin; Kim, Minjung; Park, Yun-Jin; Ahn, Heechul; Kwon, Young Hye; Hah, Jung-Mi [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2271 - 2285]
[8]Khan, Khalid Mohammed; Khan, Momin; Saleem, Muhammad; Taha, Muhammad; Perveen, Shahnaz; Choudhary, Mohammad Iqbal [Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 3, p. 901 - 904]
[9]Ahmad, Muhammad Umair; Rafiq, Muhammad; Zahra, Bakhtawar; Islam, Muhamamd; Ashraf, Muhammad; al-Rashida, Mariya; Khan, Ajmal; Hussain, Javid; Shafiq, Zahid; Al-Harrasi, Ahmed [Drug Development Research, 2021, vol. 82, # 7, p. 1033 - 1043]

2
[ 95-54-5 ]
[ 6287-38-3 ]
[ 67370-32-5 ]
[ 102184-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid

Reference： [1]Rao; Ratnam [Proceedings - Indian Academy of Sciences, Section A, 1956, # 43, p. 173,178]

Yield	Reaction Conditions	Operation in experiment
		Following the above procedure and using, in place of 2-phenylbenzimidazole, an equivalent amount of a. 2-(p-chlorophenyl)benzimidazole, b. 2-(p-tolyl)benzimidazole, c. 2-(p-anisyl)benzimidazole, d. 2-(p-trifluoromethylphenyl)benzimidazole, e. 2-(3,4-dichlorophenyl)benzimidazole, f. 2-(3,4-methylenedioxyphenyl)benzimidazole, g. 2-(m-tolyl)benzimidazole, or h. 2-(o-fluorophenyl)benzimidazole,
	/BRN= 606074/, /BRN= 636379/, <NaHSO3> <H2O>;

4
[ 51-44-5 ]
[ 95-54-5 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 3,4-dichlorbenzoic acid In dichloromethane at 0℃; for 0.25h; Stage #2: 1,2-diamino-benzene With pyridine In dichloromethane at 20℃; for 6h; Further stages.;
	With polyphosphoric acid at 140℃; for 4h;	2-(4-chlororophenyl)-1H-benzimidazole (1c) General procedure: 2.0 g (18.5 mmol) of 1,2-phenylenediamine and 3.2 g (20.4 mmol) of 4-chlorobenzoic acid were added to 20 g polyphosphoric acid (PPA) and mixed homogeneously. The reaction mixture was heated at 140 oC for 4 h. Then the reaction mixture was cooled to room temperature and neutralized with 5N NaOH. The resulting solid was filtered, washed with water and dried in vacuo. The title compound was obtained by recrystallization using ethanol. (4.0g, 95%)

Reference： [1]Kaul, Savita; Kumar, Ajay; Sain, Bir; Bhatnagar [Synthetic Communications, 2007, vol. 37, # 15, p. 2457 - 2460]
[2]Lim, Chae Jo; Kim, Nakjeong; Lee, Eun Kyoung; Lee, Byung Ho; Oh, Kwang-Seok; Yoo, Sung-Eun; Yi, Kyu Yang [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2309 - 2312]

5
[ 1081112-34-6 ]
[ 67370-32-5 ]
[ 1081111-16-1 ]

Yield	Reaction Conditions	Operation in experiment
67 mg	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;	2-(4-chlorophenyl)-1-{3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl}-1H-benzimidazole (4c) General procedure: 70 mg (0.31 mmol) of 2-(4-chlororophenyl)-1H-benzimidazole (1c) was dissolved in 5 ml of N,N-dimethylformamide, and 127 mg (0.36 mmol) of 3-[4-(3-acetylaminophenyl) piperidin-1-yl] propylmethanesulfonate (9) and 150 mg (1.08 mmol) of K2CO3 were added to the resulting solution, followed by mixing the solution at 80 for 5 hours. The reaction mixture was combined with 50 ml of water and extracted with ethylacetate (50 ml X 2) being washed with water and a sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (5% MeOH/CH2Cl2) to obtain 77 mg (yield 51%) of the title compound.

Reference： [1]Lim, Chae Jo; Kim, Nakjeong; Lee, Eun Kyoung; Lee, Byung Ho; Oh, Kwang-Seok; Yoo, Sung-Eun; Yi, Kyu Yang [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2309 - 2312]

6
[ 67370-32-5 ]
3-{4-[2-(3,4-dichloro-phenyl)-benzoimidazol-1-yl]-pyrimidin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BINAP; sodium t-butanolate / toluene / 3 h / 130 °C / Inert atmosphere 1.2: 8 h / 20 °C 2.1: tetrahydrofuran / 10 h / 60 °C

Reference： [1]Kim, Mi-Hyun; Lee, Junghun; Jung, Kyungjin; Kim, Minjung; Park, Yun-Jin; Ahn, Heechul; Kwon, Young Hye; Hah, Jung-Mi [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2271 - 2285]

7
[ 67370-32-5 ]
C₂₂H₂₀Cl₂N₆*(x)ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BINAP; sodium t-butanolate / toluene / 3 h / 130 °C / Inert atmosphere 1.2: 8 h / 20 °C 2.1: tetrahydrofuran / 10 h / 60 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 °C

8
[ 67370-32-5 ]
[ 1428959-05-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BINAP; sodium t-butanolate / toluene / 3 h / 130 °C / Inert atmosphere 1.2: 8 h / 20 °C 2.1: tetrahydrofuran / 5 h / 60 °C

9
[ 67370-32-5 ]
cyclopropyl-(3-{4-[2-(3,4-dichloro-phenyl)-benzoimidazol-1-yl]-pyrimidin-2-ylamino}-piperidin-1-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BINAP; sodium t-butanolate / toluene / 3 h / 130 °C / Inert atmosphere 1.2: 8 h / 20 °C 2.1: tetrahydrofuran / 10 h / 60 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 4.2: 2 h / 0 - 20 °C

10
[ 67370-32-5 ]
[ 1428958-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BINAP; sodium t-butanolate In toluene at 130℃; for 3h; Inert atmosphere;	General procedure: The mixture of compound 10a (317 mg, 1.3 mmol), 4-iodo-2-(methylthio)pyrimidine (320 mg, 1.3 mmol), Pd2(dba)3 (140 mg, 0.13 mmol), BINAP (81 mg, 0.13 mmol) and NaOtBu (242 mg, 2.5 mmol) was purged with N2, and then toluene (13 mL) was added to the mixture. After sonication under N2 for 5 min, the mixture was heated up to 130 °C under N2 and was stirred without N2 at 130 °C for 3 h. After cooling down to ambient temperature, the reaction mixture was filtered through a celite pad, removed in vacuo, and purified by flash column chromatography on silica gel using EA/Hex (1:1) as the eluent. This produced a mixture of 1-(2-methylsulfanyl-pyrimidin-4-yl)-2-naphthalen-2-yl-1H-benzoimidazole (11a) and 10a (ratio 2:1 in 1H NMR) as a pale yellow solid (66%).

11
[ 67370-32-5 ]
[ 1428958-95-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(3,4-dichlorophenyl)-1H-benzo[d]imidazole; 4-halo-2-(methylthio)pyrimidine With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; BINAP; sodium t-butanolate In toluene at 130℃; for 3h; Inert atmosphere; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 8h;	General procedure: The mixture of compound 10a (317 mg, 1.3 mmol), 4-iodo-2-(methylthio)pyrimidine (320 mg, 1.3 mmol), Pd2(dba)3 (140 mg, 0.13 mmol), BINAP (81 mg, 0.13 mmol) and NaOtBu (242 mg, 2.5 mmol) was purged with N2, and then toluene (13 mL) was added to the mixture. After sonication under N2 for 5 min, the mixture was heated up to 130 °C under N2 and was stirred without N2 at 130 °C for 3 h. After cooling down to ambient temperature, the reaction mixture was filtered through a celite pad, removed in vacuo, and purified by flash column chromatography on silica gel using EA/Hex (1:1) as the eluent. This produced a mixture of 1-(2-methylsulfanyl-pyrimidin-4-yl)-2-naphthalen-2-yl-1H-benzoimidazole (11a) and 10a (ratio 2:1 in 1H NMR) as a pale yellow solid (66%). The mixture of compound 11a (mixture 170 mg, 0.51 mmol) and 70% m-CPBA (360 mg, 1.5 mmol) in methylene chloride (5 ml) was stirred at ambient temperature for 8 h. After compound 11a disappeared in LCMS, the reaction mixture was extracted with ethyl acetate and washed with saturated NaHCO3 (aq). The extracted organic layer was dried usingMgSO4and filtered. The filtrate was concentrated in vacuo and then the crude product was purified by flash column chromatography with EA/Hex 1:1 to produce1-(2-methanesulfonyl-pyrimidin-4-yl)-2-naphthalen-2-yl-1H-benzoimidazole (12a)as a white solid (52%).

12
[ 3815-80-3 ]
[ 50-00-0 ]
[ 67370-32-5 ]
C₂₃H₁₆Cl₂N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With acetic acid In ethanol at 70℃; for 3h;

Reference： [1]Savaliya, Piyush P.; Akbari, Vikunjana K.; Modi, Jigisha A.; Patel, Keshav C. [Medicinal Chemistry Research, 2013, vol. 22, # 12, p. 5789 - 5797]

13
[ 95-54-5 ]
[ 18880-04-1 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydrogencarbonate; copper(I) bromide In dimethyl sulfoxide at 120℃; for 24h;
67%	In acetonitrile Irradiation; chemoselective reaction;	3.3. Synthesis of 2-substituted benzimidazoles and benzothiazoles (3&5) General procedure: A mixture of 1,2-Diaminobenzene 1 or 2-Mercaptoaniline 4(1 mmol), benzyl bromides (1 mmol) 2 and 4 % Cu:ZnS NPs (10 mol %)in 10 ml of CH3CN were irradiated in visible light (100W OSRAMTungsten Lamp, EFP 64627 HLX) with continuous stirring for the appropriatetime. Catalyst was separated by centrifugation after thecompletion of reaction. Evaporation of the above solution gave thecrude product which was purified using crystallization.

Reference： [1]Qiu, Dezhi; Wei, Haidong; Zhou, Lihong; Zeng, Qingle [Applied Organometallic Chemistry, 2014, vol. 28, # 2, p. 109 - 112]
[2]Dandia, Anshu; Bansal, Sarika; Sharma, Ruchi; Kumar Mahawar, Dinesh; Rathore, Kuldeep S.; Lal Meena, Mohan; Parewa, Vijay [Journal of Photochemistry and Photobiology A: Chemistry, 2020, vol. 389]

14
[ 67370-32-5 ]
[ 102-92-1 ]
[ 1609007-48-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	21 (E)-1-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one (3u). General procedure: Substituted benzimidazole (1 eq.) was added slowly at reducedtemperature to a solution of sodium hydride (1.1 eq.) in anhydrousTHF and the contents were stirred for 15e20 min. To this, a solutionof freshly prepared cinnamoyl chloride (1 eq.) in THF was addeddropwise at 0e5 C for about 30 min. The reaction was carried outin an inert atmosphere. Then, the reaction mixture was allowed toattain ambient temperature and the stirring was continued for 60e90 min (monitored by TLC). After the completion of the reaction,the volume of the THF was reduced to half in vacuo and poured tocrushed ice and the pH was adjusted to neutral. The separated solidwas filtered, washed with water, dried and finally purification wasachieved on silica gel (60e120 mesh) column chromatographyusing ethyl acetate/hexane as the eluent.

Reference： [1]Kalalbandi, Veerendra Kumar A.; Seetharamappa; Katrahalli, Umesha; Bhat, Kishore G. [European Journal of Medicinal Chemistry, 2014, vol. 79, p. 194 - 202]

15
[ 102-49-8 ]
[ 95-54-5 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With oxygen; iron(II) bromide In chlorobenzene at 110℃; for 7.5h; Schlenk technique; Green chemistry;

Reference： [1]Gopalaiah, Kovuru; Chandrudu, Sankala Naga [RSC Advances, 2015, vol. 5, # 7, p. 5015 - 5023]

16
C₂₅H₁₈Cl₂O₂P⁽¹⁺⁾*Cl^(1-) [ No CAS ]
[ 95-54-5 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	In 1,4-dioxane for 0.666667h; Reflux;	Typical Procedure for the Preparation of2-Phenyl-1H-benzimidazole General procedure: To a cold solution of triphenylphosphine (0.262 g, 1 mmol) in 1,4-dioxane (6 mL), trichloroisocyanuric acid (0.076 g, 0.3 mmol) was added with continuous stirring. Benzoic acid (0.122 g, 1 mmol) was added, and stirring was continued for 30 min. The temperature was raised to room temperature. o-Phenylenediamine (0.108 g, 1mmol) was added, and stirring of the pale yellow suspension was continued for 1 h under refluxing conditions. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the crude product was filtered, washed with CHCl3 (10 mL), and re-crystallised from ethanol. 2-Phenyl-1H-benzimidazole was obtained in 90% yield (0.174 g).

Reference： [1]Rezazadeh, Soodabeh; Akhlaghinia, Batool; Razavi, Nasrin [Australian Journal of Chemistry, 2015, vol. 68, # 1, p. 145 - 155]

17
[ 51-44-5 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichloroisocyanuric acid / 1,4-dioxane / 0.5 h / Cooling 2: 1,4-dioxane / 0.67 h / Reflux

Reference： [1]Rezazadeh, Soodabeh; Akhlaghinia, Batool; Razavi, Nasrin [Australian Journal of Chemistry, 2015, vol. 68, # 1, p. 145 - 155]

18
[ 615-43-0 ]
[ 18880-04-1 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 50 °C 2: copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; N-ethyl-N,N-diisopropylamine; sodium azide / dimethyl sulfoxide / 24 h / 130 °C

Reference： [1]Chen, Zhengkai; Li, Hongli; Cao, Gangjian; Xu, Jianfeng; Miao, Maozhong; Ren, Hongjun [Synlett, 2017, vol. 28, # 4, p. 504 - 508]

19
N-(3,4-dichlorobenzyl)-2-iodoaniline [ No CAS ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	With copper(l) iodide; sodium azide; N,N,N,N,-tetramethylethylenediamine; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 130℃; for 24h;	Typical Procedure for the Product Benzimidazoles General procedure: CuI (12 mg, 20 mol %), TMEDA (14 mg, 40 mol %) and DIPEA (77 mg, 0.6 mmol) were added to amixture of substrate 1 (0.3 mmol), NaN3 (39 mg, 0.6 mmol) in DMSO (1 mL). The mixture was stirred at130 °C under air for 24 h. After the completion of the reaction (monitored by TLC), the reaction mixturewas cooled to ambient temperature, quenched by water and extracted with ethyl acetate (3 x 15 mL). Thecombined organic layer was washed with brine (25 mL), and dried over Na2SO4. After the evaporation, theresidue was purified by column chromatography on silica gel with petroleum ether/EtOAc as eluent toafford the product 2 or 3.

Reference： [1]Chen, Zhengkai; Li, Hongli; Cao, Gangjian; Xu, Jianfeng; Miao, Maozhong; Ren, Hongjun [Synlett, 2017, vol. 28, # 4, p. 504 - 508]

20
[ 95-54-5 ]
[ 2642-63-9 ]
[ 67370-32-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With iodine; nitrobenzene In 1,4-dioxane at 140℃; for 20h; Sealed tube; chemoselective reaction;	General Procedure for synthesis of 3 General procedure: Acetophenone 1 (1mmol), 2-amino aniline 2 (1mmol), I2 (13mg, 5mol%), PhNO2 (123mg, 1mmol) and 1,4-dioxane (3 mL) were added to a reaction tube. The reaction mixture was stirred in a sealed tube at 140 °C for 20 h. The reaction was monitored by TLC. Once the reaction was completed, the reaction mixture was treated with H2O (15.0 mL) and EtOAc (8.0 mL). The organic phase was then separated, and the aqueous phase was extracted with EtOAc (3 x 8 mL). The combined organic phase was dried over Na2SO4, then the solvent was removed under a reduced pressure and the remaining residue was purified by column chromatography.

Reference： [1]Ding, Yuxin; Ma, Renchao; Ma, Yongmin [Tetrahedron Letters, 2021, vol. 70]

21
[ 67370-32-5 ]
(E)-2-(2-[3,4-dichlorophenyl]-1H-benzo[d]imidazol-1-yl)-N'-(2-oxoindolin-3-ylidene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide 2: hydrazine hydrate / ethanol / 0.25 h / Reflux 3: ethanol / Reflux

Reference： [1]Ahmad, Muhammad Umair; Rafiq, Muhammad; Zahra, Bakhtawar; Islam, Muhamamd; Ashraf, Muhammad; al-Rashida, Mariya; Khan, Ajmal; Hussain, Javid; Shafiq, Zahid; Al-Harrasi, Ahmed [Drug Development Research, 2021, vol. 82, # 7, p. 1033 - 1043]

22
[ 67370-32-5 ]
(E)-2-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-1-yl)-N'-(5-fluoro-2-oxoindolin-3-ylidene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide 2: hydrazine hydrate / ethanol / 0.25 h / Reflux 3: ethanol / Reflux

23
[ 67370-32-5 ]
(E)-2-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-1-yl)-N'-(5-nitro-2-oxoindolin-3-ylidene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide 2: hydrazine hydrate / ethanol / 0.25 h / Reflux 3: ethanol / Reflux

24
[ 67370-32-5 ]
C₁₅H₁₂Cl₂N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide / dimethyl sulfoxide 2: hydrazine hydrate / ethanol / 0.25 h / Reflux

25
[ 67370-32-5 ]
(E)-2-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-1-yl)-N'-([4-oxo-4H-chromen-3-yl]methylene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide 2: hydrazine hydrate / ethanol / 0.25 h / Reflux 3: ethanol / Reflux

26
[ 67370-32-5 ]
[ 105-39-5 ]
C₁₇H₁₄Cl₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In dimethyl sulfoxide

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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. 67370-32-5 ] {[proInfo.proName]}

Quality Control of [ 67370-32-5 ]

Related Doc. of [ 67370-32-5 ]

Product Details of [ 67370-32-5 ]

Safety of [ 67370-32-5 ]

Application In Synthesis of [ 67370-32-5 ]

[ 67370-32-5 ] Synthesis Path-Downstream 1~26

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry