| 词条 | Benzimidazole |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443415791 | ImageFile = Benzimidazole 2D numbered.svg | ImageSize = 160 | ImageAlt = Skeletal formula with numbering convention | ImageFileL1 = Benzimidazole-3D-balls.png | ImageSizeL1 = 140 | ImageAltL1 = Ball-and-stick model | ImageFileR1 = Benzimidazole-3D-spacefill.png | ImageAltR1 = Space-filling model | PIN = 1H-Benzimidazole | OtherNames = 1H-Benzo[d]imidazole |Section1={{Chembox Identifiers | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C02009 | InChIKey = HYZJCKYKOHLVJF-UHFFFAOYAX | SMILES = c1ccc2c(c1)[nH]cn2 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HYZJCKYKOHLVJF-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 51-17-2 | PubChem = 5798 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 306226 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID =5593 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = E24GX49LD8 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 41275 | InChI = 1/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)}} |Section2={{Chembox Properties | C=7 | H=6 | N=2 | Appearance = | Density = | MeltingPtC = 170 to 172 | MeltingPt_notes = | BoilingPt = | Solubility = | pKa = 12.8 (for benzimidazole) and 5.6 (for the conjugate acid) [1] }} |Section3={{Chembox Hazards | ExternalSDS = External MSDS | EUClass = Harmful (Xn) | RPhrases = {{R20}} {{R21}} {{R22}} {{R36}} {{R37}} {{R38}} | SPhrases = {{S26}} {{S36}} | FlashPt = | AutoignitionPt = }} Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole. It is a colorless solid. PreparationBenzimidazole is produced by condensation of o-phenylenediamine with formic acid,[2] or the equivalent trimethyl orthoformate: C6H4(NH2)2 + HC(OCH3)3 → C6H4N(NH)CH + 3 CH3OH 2-substituted derivatives are obtained when the condensation is conducted with aldehydes in place of formic acid, followed by oxidation. This method afford 2-substituted benzimidazoles.[3] ReactionsBenzimidazole is a base: C6H4N(NH)CH + H+ → [C6H4(NH)2CH]+ It can also be deprotonated with stronger bases: C6H4N(NH)CH + LiH → Li [C6H4N2CH] + H2 The imine can be alkylated and also serves as a ligand in coordination chemistry. The most prominent benzimidazole complex features N-ribosyl-dimethylbenzimidazole as found in vitamin B12.[4] N,N'-Dialkylbenzimidazolium salts are precursors to certain N-heterocyclic carbenes.[5][6]ApplicationsBenzimidazoles are often bioactive. Many anthelmintic drugs (albendazole, mebendazole, triclabendazole etc.) belong to the benzimidazole class of compounds. Benzimidazole fungicides are commercialized. They act by binding to the fungal microtubules and stopping hyphal growth. It also binds to the spindle microtubules and blocks nuclear division. Other pharmaceutical drugs which contain a benzimidazole group include etonitazene, galeterone, mavatrep, and dovitinib. In printed circuit board manufacturing, benzimidazole can be used as an organic solderability preservative. Several dyes are derived from benzimidazoles.[7] See also
References1. ^Walba, H. & Isensee, R. W. Acidity constants of some arylimidazoles and their cations. J. Org. Chem. 26, 2789-2791 (1961). 2. ^{{OrgSynth | title = Benzimidazole | prep = cv2p0065 | collvol = 2 | collvolpages = 65 | year = 1943 | author = E. C. Wagner and W. H. Millett}}. 3. ^Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a19_405}} 4. ^{{cite journal|author1=H. A. Barker |author2=R. D. Smyth |author3=H. Weissbach |author4=J. I. Toohey |author5=J. N. Ladd |author6=B. E. Volcani |last-author-amp=yes | title = Isolation and Properties of Crystalline Cobamide Coenzymes Containing Benzimidazole or 5,6-Dimethylbenzimidazole| journal = Journal of Biological Chemistry| date = February 1, 1960 | volume = 235| issue = 2| pages = 480–488| url = http://www.jbc.org/cgi/reprint/235/2/480| pmid = 13796809}} 5. ^{{cite journal |author1=R. Jackstell |author2=A. Frisch |author3=M. Beller |author4=D. Rottger |author5=M. Malaun |author6=B. Bildstein | title = Efficient telomerization of 1,3-butadiene with alcohols in the presence of in situ generated palladium(0)carbene complexes | year = 2002 | journal = Journal of Molecular Catalysis A: Chemical | volume = 185 | issue = 1–2 | pages = 105–112 | doi = 10.1016/S1381-1169(02)00068-7}} 6. ^{{cite journal |author1=H. V. Huynh |author2=J. H. H. Ho |author3=T. C. Neo |author4=L. L. Koh | title = Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity | year = 2005 | journal = Journal of Organometallic Chemistry | volume = 690 | issue = 16 | pages = 3854–3860 | doi = 10.1016/j.jorganchem.2005.04.053}} 7. ^Horst Berneth "Methine Dyes and Pigments" in Ullmann's Encyclopedia of Industrial Chemistry, 2008, Wiley-VCH, Weinheim. {{DOI| 10.1002/14356007.a16_487.pub2}} Further reading
3 : Benzimidazoles|Aromatic bases|Simple aromatic rings |
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