Benzamidine

Structural formula
General
Surname	Benzamidine
other names	Benzene carboximidamide
Molecular formula	C 7 H 8 N 2
Brief description	white to beige solid
External identifiers / databases
EC number	210-546-3
ECHA InfoCard	100.009.589
PubChem	2332
ChemSpider	2242
Wikidata	Q4890748
properties
Molar mass	120.155 g mol −1
Physical state	firmly
Melting point	64-66 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-319
	P: 305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benzamidine is an organic compound with the semi-structural formula C ₆ H ₅ C (NH) NH ₂ . It is the simplest arylamidine .

properties

The compound is a colorless solid that is only slightly soluble in water. It is often handled as the hydrochloride , a colorless but water-soluble solid.

In terms of its molecular structure , benzamidine has a short C = NH bond (129 pm ) and a longer C-NH ₂ bond (135 pm).

application

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

It is often called ligand in protein crystallography used proteins against proteases to protect. A partial benzamidine structure can be found in some drugs , including dabigatran .

Derivatized imidazoles are formed by condensation with α-haloketones .

Individual evidence

↑ ^a ^b ^c Datasheet Benzamidine from Sigma-Aldrich , accessed on June 28, 2020 ( PDF ).
↑ WLF Armarego, Christina Li Lin Chai: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2003, ISBN 978-0-7506-7571-0 , pp. 596 ( limited preview in Google Book search).
↑ External identifiers of or database links for benzamidine hydrochloride hydrate : CAS number: 206752-36-5, EC number: 606-598-5, ECHA InfoCard: 100.132.412 , PubChem : 16219042 , ChemSpider : 11348235 , Wikidata : Q72445010 .
^ ^A ^b Bryan Li, Charles KF Chiu, Richard F. Hank, Jerry Murry, Joshua Roth, Harry Tobiassen: Preparation of 2,4-Disubstituted Imidazoles: 4- (4-Methoxyphenyl) -2-Phenyl-1H-Imidazoles . In: Organic Syntheses . 81, 2005, p. 105. doi : 10.15227 / orgsyn.081.0105 .
↑ J. Barker, PR Phillips, MGH Wallbridge, HR Powell: Benzamidine . In: Acta Crystallographica Section C Crystal Structure Communications . 52, No. 10, 1996, pp. 2617-2619. doi : 10.1107 / S0108270196006282 .
↑ Kazutaka Tanizawa, Shin-ichi Ishii, Kazo Hamaguchi, Yuichi Kanaoka: Proteolytic EnzymesVI. Aromatic Amidines as Competitive Inhibitors of Trypsin . In: The Journal of Biochemistry . 69, No. 5, May 1, 1971, pp. 893-899. doi : 10.1093 / oxfordjournals.jbchem.a129540 . PMID 5577153 .

[Sigma-1] Datasheet Benzamidine from Sigma-Aldrich , accessed on June 28, 2020 ( PDF ).

[W._L._F._Armarego,_Christina_Li_Lin_Chai-2] WLF Armarego, Christina Li Lin Chai: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2003, ISBN 978-0-7506-7571-0 , pp. 596 ( limited preview in Google Book search).

[3] External identifiers of or database links for benzamidine hydrochloride hydrate : CAS number: 206752-36-5, EC number: 606-598-5, ECHA InfoCard: 100.132.412 , PubChem : 16219042 , ChemSpider : 11348235 , Wikidata : Q72445010 .

[OS1-4] A ^b Bryan Li, Charles KF Chiu, Richard F. Hank, Jerry Murry, Joshua Roth, Harry Tobiassen: Preparation of 2,4-Disubstituted Imidazoles: 4- (4-Methoxyphenyl) -2-Phenyl-1H-Imidazoles . In: Organic Syntheses . 81, 2005, p. 105. doi : 10.15227 / orgsyn.081.0105 .

[5] J. Barker, PR Phillips, MGH Wallbridge, HR Powell: Benzamidine . In: Acta Crystallographica Section C Crystal Structure Communications . 52, No. 10, 1996, pp. 2617-2619. doi : 10.1107 / S0108270196006282 .

[6] Kazutaka Tanizawa, Shin-ichi Ishii, Kazo Hamaguchi, Yuichi Kanaoka: Proteolytic EnzymesVI. Aromatic Amidines as Competitive Inhibitors of Trypsin . In: The Journal of Biochemistry . 69, No. 5, May 1, 1971, pp. 893-899. doi : 10.1093 / oxfordjournals.jbchem.a129540 . PMID 5577153 .