4-Aminobenzamidine dihydrochloride Chemical Properties

Melting point:

>300 °C(lit.)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Water

form 

Fine Crystalline Powder

color 

White to yellow

Sensitive 

Hygroscopic

BRN 

3692927

Stability:

Hygroscopic

InChI

InChI=1S/C7H9N3.2ClH/c8-6-3-1-5(2-4-6)7(9)10;;/h1-4H,8H2,(H3,9,10);2*1H

InChIKey

GHEHNICLPWTXJC-UHFFFAOYSA-N

SMILES

C1(C=CC(N)=CC=1)C(=N)N.Cl.Cl

CAS DataBase Reference

2498-50-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39-36

WGK Germany 

3

RTECS 

CV6126500

F 

3-10-21

HS Code 

29252900

MSDS

• Language:English Provider:4-Aminobenzamidine dihydrochloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Aminobenzamidine dihydrochloride Usage And Synthesis

Chemical Properties

white to yellowish fine crystalline powder

Uses

4-Aminobenzamidine dihydrochloride is a synthetic diamidine derivative that acts as a urokinase inhibitor as well as trypsin inhibitor. It is used as a ligand in affinity chromatography for purification and immobilization of enzymes.

Application

4-Aminobenzamidine dihydrochloride can be used to synthesize:
Orally active fibrinogen receptor antagonists based on benzamidines.
Benzamidine derivatives that are selective and potent serine protease inhibitors.
Novel pyrrolo [3,2-c] quinolines that are structural analogs of topoisomerase inhibitors such as coralyne and fagaronine.
Synthesis of a selective inhibitor of PRMT1 (SKLB-639)

Preparation

4-Aminobenzamididine dihydrochloride is obtained by cyanation, addition, amination and reduction of 4-nitrobenzoic acid.

Definition

ChEBI: P-Aminobenzamidine dihydrochloride is an organic molecular entity.

Synthesis

In a three-necked flask equipped with a reflux condenser tube and a mechanical stirring device, 15.0 g of 4-nitrobenzenecarboximidamide (IV) prepared from Example 2, 20 mL of acetic acid, 45 mL of water, and 45 mL of ethanol (V water: V ethanol=1:1) were added, and the reaction was stirred and refluxed at 60° C. until complete dissolution. Subsequently, 20.3 g of iron powder (n4-nitrobenzenecarboximidamide IV: n iron powder = 1:4) was added to the reaction system, and the reaction was warmed up to 80 °C and continued to be stirred and refluxed for 4 hours. After completion of the reaction, it was filtered while hot. The filtrate was adjusted to pH 11~12 with 20% NaOH solution, at which time a large amount of flocculent precipitation was generated, and after filtration, the filtrate was adjusted to pH 1~2 with concentrated hydrochloric acid. the solution was concentrated until the crystals precipitated, and the resulting crystals were dried in vacuum at 100 ℃ to obtain 17.9 g of 4-nitrobenzenecarboximidamide dihydrochloride (I), as a white solid with 94.7% yield and 99.51% HPLC purity.

References

[1] Patent: CN104163778, 2016, B. Location in patent: Paragraph 0056; 0057

4-Aminobenzamidine dihydrochloride(2498-50-2)Related Product Information

• Amitraz
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• BENZAMIDINE
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• P-AMINOBENZAMIDE GLUTAMIC ACID
• Formamidine acetate
• 4-Dimethylaminobenzoic acid
• 4-Aminobenzaldehyde
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• Benzamidine hydrochloride
• 4-Aminophenylacetic acid
• 4-Amino-benzenesulfonic acid monosodium salt
• Formamidine hydrochloride
• Dihydrochloride
• Itraconazole
• 3-AMINOBENZAMIDINE DIHYDROCHLORIDE,3-AMINOBENZAMIDINE DIHYDROCHLORIDE HYDRATE,M-AMINOBENZAMIDINE DIHYDROCHLORIDE,M-AMINOBENZAMIDINE DIHYDROCHLORIDE HYDRATE, 98%