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Wikipedia

Benzamidine

January 01, 1970

Benzamidine is an organic compound with the formula C6H5C(NH)NH2. It is the simplest aryl amidine. The compound is a white solid that is slightly soluble in water. It is usually handled as the hydrochloride salt, a white, water-soluble solid.[2]

Benzamidine
Names
Preferred IUPAC name
Benzenecarboximidamide
Identifiers
  • 618-39-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:41033 Y
ChEMBL
  • ChEMBL20936 Y
ChemSpider
  • 2242 Y
ECHA InfoCard 100.009.589
  • 7566
KEGG
  • C01784 Y
  • 2332
UNII
  • KUE3ZY3J1F Y
  • DTXSID8045012
  • InChI=1S/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9) Y
    Key: PXXJHWLDUBFPOL-UHFFFAOYSA-N Y
  • InChI=1/C7H8N2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9)
    Key: PXXJHWLDUBFPOL-UHFFFAOYAU
  • [NH]=C(N)c1ccccc1
Properties
C7H8N2
Molar mass 120.155 g·mol−1
Appearance White solid
Density 1.22 g/cm3
Melting point 64–66 °C (147–151 °F; 337–339 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Structure edit

Benzamidine has one short C=NH bond and one longer C-NH2 bond, which are respectively 129 and 135 pm in length, respectively.[3]

The triangular diamine group gives it a distinctive shape which shows up in difference density maps.

Applications edit

Benzamidine is a reversible competitive inhibitor of trypsin, trypsin-like enzymes, and serine proteases.[4]

It is often used as a ligand in protein crystallography to prevent proteases from degrading a protein of interest. The benzamidine moiety is also found in some pharmaceuticals, such as dabigatran.

Condensation with various haloketones provides a synthetic route to 2,4-disubstituted imidazoles.[2]

 

References edit

  1. ^ Armarego, W. L. F.; Chai, Christina Li Lin (2003). Purification of Laboratory Chemicals. Amsterdam ; Boston: Butterworth-Heinemann. p. 119. ISBN 978-0-7506-7571-0. OCLC 52733960.
  2. ^ a b Li, Bryan; Chiu, Charles K-F; Hank, Richard F.; Murry, Jerry; Roth, Joshua; Tobiassen, Harry (2005). "Preparation of 2,4-Disubstituted Imidazoles: 4-(4-Methoxyphenyl)-2-Phenyl-1H-Imidazole". Organic Syntheses. 81: 105. doi:10.15227/orgsyn.081.0105.
  3. ^ Barker, J.; Phillips, P. R.; Wallbridge, M. G. H.; Powell, H. R. (1996). "Benzamidine". Acta Crystallographica Section C Crystal Structure Communications. 52 (10): 2617–2619. doi:10.1107/S0108270196006282.
  4. ^ Tanizawa, Kazutaka; Ishii, Shin-ichi; Hamaguchi, Kazo; Kanaoka, Yuichi (1971-05-01). "Proteolytic Enzymes. VI. Aromatic Amidines as Competitive Inhibitors of Trypsin". The Journal of Biochemistry. 69 (5): 893–899. doi:10.1093/oxfordjournals.jbchem.a129540. ISSN 0021-924X. PMID 5577153.

January 01, 1970
benzamidine, organic, compound, with, formula, c6h5c, simplest, aryl, amidine, compound, white, solid, that, slightly, soluble, water, usually, handled, hydrochloride, salt, white, water, soluble, solid, names, preferred, iupac, name, benzenecarboximidamide, i. Benzamidine is an organic compound with the formula C6H5C NH NH2 It is the simplest aryl amidine The compound is a white solid that is slightly soluble in water It is usually handled as the hydrochloride salt a white water soluble solid 2 Benzamidine Names Preferred IUPAC name Benzenecarboximidamide Identifiers CAS Number 618 39 3 Y 3D model JSmol Interactive image ChEBI CHEBI 41033 Y ChEMBL ChEMBL20936 Y ChemSpider 2242 Y ECHA InfoCard 100 009 589 IUPHAR BPS 7566 KEGG C01784 Y PubChem CID 2332 UNII KUE3ZY3J1F Y CompTox Dashboard EPA DTXSID8045012 InChI InChI 1S C7H8N2 c8 7 9 6 4 2 1 3 5 6 h1 5H H3 8 9 YKey PXXJHWLDUBFPOL UHFFFAOYSA N YInChI 1 C7H8N2 c8 7 9 6 4 2 1 3 5 6 h1 5H H3 8 9 Key PXXJHWLDUBFPOL UHFFFAOYAU SMILES NH C N c1ccccc1 Properties Chemical formula C 7H 8N 2 Molar mass 120 155 g mol 1 Appearance White solid Density 1 22 g cm3 Melting point 64 66 C 147 151 F 337 339 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesStructure editBenzamidine has one short C NH bond and one longer C NH2 bond which are respectively 129 and 135 pm in length respectively 3 The triangular diamine group gives it a distinctive shape which shows up in difference density maps Applications editBenzamidine is a reversible competitive inhibitor of trypsin trypsin like enzymes and serine proteases 4 It is often used as a ligand in protein crystallography to prevent proteases from degrading a protein of interest The benzamidine moiety is also found in some pharmaceuticals such as dabigatran Condensation with various haloketones provides a synthetic route to 2 4 disubstituted imidazoles 2 nbsp References edit Armarego W L F Chai Christina Li Lin 2003 Purification of Laboratory Chemicals Amsterdam Boston Butterworth Heinemann p 119 ISBN 978 0 7506 7571 0 OCLC 52733960 a b Li Bryan Chiu Charles K F Hank Richard F Murry Jerry Roth Joshua Tobiassen Harry 2005 Preparation of 2 4 Disubstituted Imidazoles 4 4 Methoxyphenyl 2 Phenyl 1H Imidazole Organic Syntheses 81 105 doi 10 15227 orgsyn 081 0105 Barker J Phillips P R Wallbridge M G H Powell H R 1996 Benzamidine Acta Crystallographica Section C Crystal Structure Communications 52 10 2617 2619 doi 10 1107 S0108270196006282 Tanizawa Kazutaka Ishii Shin ichi Hamaguchi Kazo Kanaoka Yuichi 1971 05 01 Proteolytic Enzymes VI Aromatic Amidines as Competitive Inhibitors of Trypsin The Journal of Biochemistry 69 5 893 899 doi 10 1093 oxfordjournals jbchem a129540 ISSN 0021 924X PMID 5577153 Retrieved from https en wikipedia org w index php title Benzamidine amp oldid 1212544086, wikipedia, wiki, book, books, library,

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