4-Guanidinobenzoic acid

Base Information

• Chemical Name: 4-Guanidinobenzoic acid
• CAS No.: 16060-65-4
• Molecular Formula: C8H9 N3 O2
• Molecular Weight: 179.178
• Hs Code.: 2925290090
• European Community (EC) Number: 813-388-9
• DSSTox Substance ID: DTXSID90936349
• Nikkaji Number: J26.916F
• Wikidata: Q27093453
• Pharos Ligand ID: Y82LMTYXNY82
• Metabolomics Workbench ID: 52723
• ChEMBL ID: CHEMBL20767
• Mol file: 16060-65-4.mol

Synonyms:4-guanidinobenzoate;4-guanidinobenzoate, monohydrobromide;4-guanidinobenzoate, monohydrochloride;p-guanidinobenzoic acid;para-guanidinobenzoate

Chemical Property of 4-Guanidinobenzoic acid

Chemical Property:

• Melting Point: 260-270 oC
• Boiling Point: 361.3±44.0 °C(Predicted)
• PKA: 3.76±0.10(Predicted)
• PSA: 99.20000
• Density: 1.42
• LogP: 1.56320
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 179.069476538
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

99.9% ^*data from raw suppliers

4-GUANIDINOBENZOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)O)N=C(N)N

Technology Process of 4-Guanidinobenzoic acid

There total 13 articles about 4-Guanidinobenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

aminoiminomethanesulfonic acid (1184-90-3) + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-guanidinobenzoic acid (16060-65-4)

Guidance literature:

With potassium carbonate; In water; for 24h; Ambient temperature;

DOI:10.1055/s-1986-31777

Reference yield: 47.0%

CYANAMID (420-04-2) + 4-methoxycarbonyl aniline (619-45-4) → 4-guanidinobenzoic acid (16060-65-4) + N-(p-methoxycarbonylphenyl)guanidine (122228-09-5)

Guidance literature:

With water; scandium tris(trifluoromethanesulfonate); at 100 ℃; for 48h; Overall yield = 63 %;

DOI:10.1055/s-0033-1341080

Reference yield:

4'-Nitrophenyl 4-guanidinobenzoate (21658-26-4) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-guanidinobenzoic acid (16060-65-4)

Guidance literature:

In water; at 25 ℃; Rate constant; Equilibrium constant; reaction with human serum albumin at pH=7.4; pH dependency of the reaction;

DOI:10.1248/cpb.39.1292

upstream raw materials:

4-((imino(methylthio)methyl)amino)benzoic acid

CYANAMID

4-amino-benzoic acid

aminoiminomethanesulfonic acid

Downstream raw materials:

4-guanidino-benzoic acid ethyl ester

4-Guanidino-benzoic acid {[(carbamoylmethyl-carbamoyl)-methyl]-carbamoyl}-methyl ester

4-Guanidino-benzoic acid ((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl ester

4-Guanidino-benzoic acid 1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-ethyl ester

Refernces

• 1、 Nishihata,Saitoh,Sakai. "Intestinal absorption of N,N'-dimethylcarbamoylmethyl 4-(4-guanidinobenzoyloxy) phenylacetate methanesulfonate in rats". . p. 2544 - 2550. Retrieved 1988.
• 2、 Takai, Satomi,Matsuda, Ayuka,Usami, Yoshiko,Adachi, Tetsuo,Sugiyama, Tadashi,Katagiri, Yoshihiro,Tatematsu, Masae,Hirano, Kazuyuki. "Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver". . p. 869 - 873. Retrieved 2007/10/03.