18672-03-2

Basic information

• Product Name: 5,6-DICHLORO-1H-BENZIMIDAZOL-2-AMINE
• Synonyms: 5,6-DICHLORO-1H-BENZO[D]IMIDAZOL-2-AMINE;5,6-DICHLORO-1H-BENZIMIDAZOL-2-AMINE;2-Amino-5,6-dichlorobenzimidazole;1H-Benzimidazol-2-amine, 5,6-dichloro-;2-Amino-5,6-dichloro-1H-benzimidazole
• CAS NO: 18672-03-2
• Molecular Formula: C₇H₅Cl₂N₃
• Molecular Weight: 202.04
• Product Categories: blocks;Imidazoles;pharmacetical
• Mol File: 18672-03-2.mol

Chemical Properties

• Melting Point: 244-246℃
• Boiling Point: 435.4 °C at 760 mmHg
• Flash Point: 217.1 °C
• Appearance: /
• Density: 1.665 g/cm³
• Vapor Pressure: 8.78E-08mmHg at 25°C
• Refractive Index: 1.775
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.47±0.10(Predicted)
• CAS DataBase Reference: 5,6-DICHLORO-1H-BENZIMIDAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DICHLORO-1H-BENZIMIDAZOL-2-AMINE(18672-03-2)
• EPA Substance Registry System: 5,6-DICHLORO-1H-BENZIMIDAZOL-2-AMINE(18672-03-2)

Safety Data

• Hazardous Substances Data: 18672-03-2(Hazardous Substances Data)

Usage

Uses

2-Amino-5,6-dichlorobenzimidazole is used as pharmaceutical intermediate.

InChI:InChI=1/C7H5Cl2N3/c8-3-1-5-6(2-4(3)9)12-7(10)11-5/h1-2H,(H3,10,11,12)

Upstream product

• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 506-68-3 bromocyane 
• 7440-44-0 pyrographite 
• 934-32-7 1H-benzimidazol-2-amine 
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Downstream Products

• 142356-40-9 2-bromo-5,6-dichloro-1H-1,3-benzodiazole 
• 16865-11-5 2,5,6-trichloro-1H-benzo[d]imidazole 
• 62908-78-5 2,5,6-trichloro-1-β-D-ribofuranosyl-1H-benzimidazole 
• 142356-43-2 2-bromo-5,6-dichloro-1-β-D-ribofuranosylbenzimidazole 

Relevant articles and documents

Cu-Catalyzed Synthesis of 3-Formyl Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources

A highly efficient synthesis of 3-formyl imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine, under Cu-catalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of C-C bond and C-N bond of ethyl group with molecular oxygen as terminal oxidant in this one-pot protocol is reported for the first time. This reaction features broad substrate scope, good functional group tolerance, as well as diversified and valuable products.

MRGX Receptor Antagonists

The invention relates to a method for preventing or treating a disease or disorder that is associated with the MrgX2 receptor. The invention also relates to MrgX2 antagonists and physiologically acceptable salts thereof. The invention also relates to pharmaceutical compositions and dosage forms comprising an MrgX2 antagonist.

Catalyst-controlled chemoselective arylation of 2-aminobenzimidazoles

What N would you like? The chemoselective and complementary Pd- and Cu-catalyzed N-arylation of 2-aminobenzimidazoles is described. Selective N-arylation of the amino group was achieved with a Pd-catalyzed method, while selective N-arylation of azole nitrogen was achieved with a Cu-catalyzed procedure (see scheme). Copyright

Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA

The novel benzimidazole derivatives (3, 5, 8, 9, 12-14, 18-41) were prepared in this paper and the antimicrobial activities of these compounds against Staphylococcus aureus, methicillin-resistant S. aureus (MRSA, standard and clinical isolates), Bacillus subtilis, Escherichia coli and Candida albicans were evaluated. Compounds 24-26 which have no substitution of N-1 position displayed better antibacterial activities than those of standards (ciprofloxacin, ampicillin and sultamicillin) against both the drug-resistant bacteria (MRSA, standard and clinical isolates). These derivatives (24-26), 2,5,6-trihalogenobenzimidazole analogues (8, 12), 5,6-dichloro-2-amino derivative (13), and 5-chloro-2-(4-benzyloxyphenyl)benzimidazole (35) exhibited the most potent antibacterial activity with MIC 3.12 μg/ml against S. aureus.

JAK-2 MODULATORS AND METHODS OF USE

This invention relates to the field of protein tyrosine kinases and inhibitors thereof. In particular, the invention relates to inhibitors of JAK-2, pharmaceutical compositions of the compounds for inhibiting JAK-2, methods of inhibiting JAK-2 in a cell, comprising contacting a cell in which inhibition of JAK-2 is desired with a compound or pharmaceutical composition comprising a compound according to the invention. The also comprises methods of treating a disease or condition that involves JAK-2 comprising administering to a patient a pharmaceutical composition comprising a compound according to the invention

Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4

High-throughput screening of a small-molecule compound library resulted in the identification of a novel series of N-acyl 2-aminobenzimidazoles that are potent inhibitors of interleukin-1 receptor-associated kinase-4.

Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.

Compounds 1-18 have been synthesized and tested in vitro against the protozoa Giardia lamblia, Entamoeba histolytica and the helminth Trichinella spiralis. Inhibition of rat brain tubulin polymerization was also measured and compared for each compound. Results indicate that most of the compounds tested were more active as antiprotozoal agents than Metronidazole and Albendazole. None of the compounds was as active as Albendazole against T. spiralis. Although only compounds 3, 9 and 15 (2-methoxycarbonylamino derivatives) inhibited tubulin polymerization, these were not the most potent antiparasitic compounds.

Design, synthesis, and antiviral evaluations of 1-(substituted benzyl)- 2-substituted-5,6-dichlorobenzimidazoles as nonnucleoside analogues of 2,5,6- trichloro-1-(β-D-ribofuranosyl)benzimidazole

We have recently reported that certain ribosylated polyhalogenated benzimidazoles are potent and selective inhibitors of HCMV replication at noncytotoxic concentrations. To extend the structure-activity relationship beyond these first-generation compounds, we alkylated 5,6dichloro-2- substituted-benzimidazoles with either a series of substituted benzyl halides or (2bromoethyl)benzene to obtain five series of nonnucleoside analogues. Evaluation of these compounds for activity against herpes viruses revealed that the new compounds were less active than the benzimidazole ribonucleosides against human cytomegalovirus (HCMV) and inactive against herpes simplex virus type 1 (HSV-1). However, as part of our broader antiviral testing, we found that some of these compounds were active against HIV. Comparisons of the biological data revealed that a chloro or bromo group was required at the 2-position for the best separation of activity against HIV and cytotoxicity. Evaluation of the most active compounds against drug- resistant HIV suggested that they act by a mechanism other than inhibition of reverse transcriptase.

Polysubstituted benzimidazoles as antiviral agents

Polysubstituted benzimidazoles and pharmaceutical compositions containing them as the active ingredients. These compounds and compositions exhibit antiviral activity against viruse of the herpes family, particularly human cytomegalovirus and herpes simplex viruses (HSV).

Design, Synthesis, and Antiviral Activity of Certain 2,5,6-Trihalo-1-(β-D-ribofuranosyl)benzimidazoles

A new series of 2-substituted 5,6-dichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpes viruses and for cytotoxicity. 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB) was prepared by ribosylation of the heterocycle 2,5,6-trichlorobenzimidazole followed by a removal of the protecting groups.The 2-bromo derivative (BDCRB) was made in a similar fashion from 2-bromo-5,6-dichlorobenzimidazole.In contrast, the 2-iodo derivative presented a more difficult problem since the appropriate heterocycle was unavailable.This prompted us to prepare the 2-amino derivative followed by nonaqueous diazotization and removal of the blocking groups.Biological evaluation revealed marked differences in the activities of these compounds and the closely related known compound 5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (DRB).DRB was weakly active against both human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1), (IC50's = 42 and 30 μM, respectively) but was cytotoxic to uninfected human foreskin fibroblasts and KB cells in the same dose range.Similar results were obtained with the heterocycle 2,5,6-trichlorobenzimidazole.In marked contrast, the ribonucleoside of 2,5,6-trichlorobenzimidazole (TCRB) was active against HCMV (IC50 = 2.9 μM, plaque assay; IC90 = 1.4 μM, yield assay) but only weakly active against HSV-1 (IC50 = 102 μM, plaque assay).Little to no cytotoxicity was observed in HFF and KB cells at concentrations up to 100 μM.By changing the substituent at the 2-position from chlorine to bromine (BDCRB), a 4-fold increase in activity against HCMV was observed without any significant increase in cytotoxicity.In contrast, the 2-I and 2-NH2 derivatives were only weakly active against HCMV and HSV-1 with activity not well-separated from cytotoxicity.These data establish that for maximum activity against HCMV with separation from cytotoxicity, ribose is preferred at the 1-position and that Cl or Br is apparently preferred at the 2-position.The activity and selectivity of both TCRB and BDCRB were better than that observed with either ganciclovir or foscarnet.