4-(Aminomethyl)benzoic acid

Base Information

• Chemical Name: 4-(Aminomethyl)benzoic acid
• CAS No.: 56-91-7
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• Hs Code.: 29224999
• European Community (EC) Number: 200-297-9
• NSC Number: 41629
• UNII: 68WG9JKC7L
• DSSTox Substance ID: DTXSID20204568
• Nikkaji Number: J36.120H
• Wikipedia: Aminomethylbenzoic acid
• Wikidata: Q695442
• Pharos Ligand ID: 674H44ZMBTJ8
• Metabolomics Workbench ID: 154073
• ChEMBL ID: CHEMBL328875
• Mol file: 56-91-7.mol

Synonyms:p-Toluicacid, a-amino- (6CI,8CI);4-(Aminomethyl)benzoic acid;4-Carboxybenzylamine;Aminomethylbenzoic acid;Benzylamine-4-carboxylic acid;Gumbix;NSC 41629;PAMBA;Styptopur;p-(Aminomethyl)benzoic acid;p-Carboxybenzylamine;a-Amino-p-toluic acid;

Chemical Property of 4-(Aminomethyl)benzoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: ≥300 °C(lit.)
• Refractive Index: 1.5810 (estimate)
• Boiling Point: 323.1 °C at 760 mmHg
• PKA: 3.75±0.10(Predicted)
• Flash Point: 149.2 °C
• PSA: 63.32000
• Density: 1.239 g/cm³
• LogP: 1.54380
• Storage Temp.: Store at 0-5°C
• Solubility.: Aqueous Base (Slightly), Water (Slightly, Heated, Sonicated)
• Water Solubility.: Slightly soluble in water. Insoluble in ethanol, benzene and chloroform.
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

4-(Aminomethyl)benzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-26,37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Aminobenzoic Acids
• Canonical SMILES: C1=CC(=CC=C1CN)C(=O)O
• Description: 4-(Aminomethyl)benzoic acid is a organic compound that can serve as a type 2 antifibrinolytic agent used in the treatment of fibrotic skin disorders, such as Peyronie's disease. It is believed that 4-(Aminomethyl)benzoic acid is effective to increase the oxygen uptake at the tissue level and enhance activity of monoamine oxidase, thus to promote the degradation of serotonin, which in excess, may lead to fibrotic changes. It is also administrated by mouth to treat several skin conditions including vitiligo, pemphigus, dermatomyositis, morphea, lymphoblastoma cutis and scleroderma. It is sometimes used in pill form by patients suffering from irritable bowel syndrome to treat the relevant gastrointestinal symptoms and applied in nutritional epidemiological studies to assess the completeness of 24-hour urine collection for the determination of urinary sodium, potassium, or nitrogen levels. Besides, it can also serve as nutritional supplements to darken gray hair, prevent hair loss, make skin look younger and prevent sunburn and its benefits are claimed for people with fatigue, irritability, depression, weeping eczema, scleroderma, patchy pigment loss in skin, and premature grey hair.
• Uses: 4-(Aminomethyl)benzoic Acid is a type 2 antifibrinolytic agent. 4-(Aminomethyl)benzoic acid acts as an unnatural amino acid derivative. It is also used as a type 2 antifibrinolytic agent. Further, it reacts with 2-methyl-isothiourea sulfate to prepare 4-guanidinomethylbenzoic acid. 4-(Aminomethyl)benzoic acid (PAMBA) can be used in the synthesis of:Cobalt carboxy phosphonates.Apoptozole (Az), which has cellular potency to promote membrane trafficking of mutant cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel activity.Cyclopeptide composed of L-glutamic acid and 3-aminobenzoic acid that can be used as receptors for a variety of cations and anions.A bioactive peptide which has potent GPR54 (a G protein-coupled receptor) agonistic activity.

Technology Process of 4-(Aminomethyl)benzoic acid

There total 30 articles about 4-(Aminomethyl)benzoic 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: 98.0%

p-Toluic acid (99-94-5) → p-aminomethylbenzoic acid (56-91-7)

Guidance literature:

With ammonium peroxydisulfate; 2,2'-azobis-(2,4-dimethylvaleronitrile); hydrogen bromide; In tetrachloromethane; at 45 ℃; for 15h; Solvent; Reagent/catalyst; Temperature;

Reference yield: 95.8%

4-(hydroxyiminomethyl)benzoic acid methyl ester (53148-13-3) → p-aminomethylbenzoic acid (56-91-7)

Guidance literature:

4-(hydroxyiminomethyl)benzoic acid methyl ester; With water; hydrogen; sodium hydroxide; 5%-palladium/activated carbon; at 20 ℃; for 3.5h; under 7355.72 Torr;

With hydrogenchloride; In water; pH=7;

Reference yield: 95.32%

4-bromomethylbenzoic Acid (6232-88-8) → p-aminomethylbenzoic acid (56-91-7)

Guidance literature:

With potassium carbonate; triethylamine; In tetrachloromethane; at 25 ℃; for 4h; Temperature;

upstream raw materials:

4-cyanobenzoic Acid

4-bromomethylbenzoic Acid

p-carboxybenzaldehyde oxime

4-[(2-carboxy-benzoylamino)-methyl]-benzoic acid

Downstream raw materials:

4-(tert-Butoxycarbonylaminomethyl)benzoic acid

N-(cholesteryloxycarbonyl)-4-aminomethylbenzoic acid

N-(Nicotinoyl)-p-aminomethylbenzoic acid

p-guanidinomethyl benzoic acid

Refernces

• 1、 -. "P-aminomethyl benzoic acid and preparation method thereof". Paragraph 0020; 0033-0034; 0038-0040; 0044-0046; 0049; 0057. . Retrieved 2020/09/09.
• 2、 -. "Method for preparing aminomethylbenzoic acid by cyclically using bromine element". Paragraph 0048-0084. . Retrieved 2019/07/01.