Production Method 1

89760-77-0

876-03-9

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  rt → reflux; overnight, reflux

Reference

Synthesis and evaluation of novel aromatic substrates and competitive inhibitors of GABA aminotransferase

Clift, Michael D.; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(10), 3122-3125

Production Method 2

876-03-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  0 °C; 24 h
2.1 Reagents: Hydrochloric acid Solvents: Water ;  rt → reflux; overnight, reflux

Reference

Synthesis and evaluation of novel aromatic substrates and competitive inhibitors of GABA aminotransferase

Clift, Michael D.; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(10), 3122-3125

Production Method 3

905973-32-2

876-03-9

Reaction Conditions

1.1 Reagents: 1,3-Diphenyldisiloxane Catalysts: Triphenylphosphine Solvents: Cyclopentyl methyl ether ;  24 h, 22 °C
1.2 Reagents: Water ;  22 °C
1.3 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ;  22 °C

Reference

Catalytic Staudinger Reduction at Room Temperature

Lenstra, Danny C.; et al, Journal of Organic Chemistry, 2019, 84(10), 6536-6545

Production Method 4

31719-77-4

876-03-9

Reaction Conditions

1.1 Reagents: Sodium azide Solvents: Acetone ,  Water ;  overnight, 60 °C
1.2 Reagents: Sodium chloride Solvents: Water ;  60 °C
2.1 Reagents: 1,3-Diphenyldisiloxane Catalysts: Triphenylphosphine Solvents: Cyclopentyl methyl ether ;  24 h, 22 °C
2.2 Reagents: Water ;  22 °C
2.3 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ;  22 °C

Reference

Catalytic Staudinger Reduction at Room Temperature

Lenstra, Danny C.; et al, Journal of Organic Chemistry, 2019, 84(10), 6536-6545

Production Method 5

180863-54-1

876-03-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  24 h, rt
1.2 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  0 °C; 17 h, 0 °C → rt
2.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  0 °C; 24 h
3.1 Reagents: Hydrochloric acid Solvents: Water ;  rt → reflux; overnight, reflux

Reference

Synthesis and evaluation of novel aromatic substrates and competitive inhibitors of GABA aminotransferase

Clift, Michael D.; et al, Bioorganic & Medicinal Chemistry Letters, 2008, 18(10), 3122-3125

3-(Aminomethyl)benzoic acid hydrochloride Raw materials

• 3-(Azidomethyl)benzoic acid
• 3-(Chloromethyl)benzoic acid
• 3-({(benzyloxy)carbonylamino}methyl)benzoic acid
• methyl 3-(azidomethyl)benzoate

3-(Aminomethyl)benzoic acid hydrochloride Preparation Products

• 3-(Aminomethyl)benzoic acid hydrochloride (876-03-9)

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• 5. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzoic acids

Research Brief on 3-(Aminomethyl)benzoic acid hydrochloride (CAS: 876-03-9): Recent Advances and Applications

3-(Aminomethyl)benzoic acid hydrochloride (CAS: 876-03-9) is a key intermediate in the synthesis of various pharmaceuticals and bioactive compounds. Recent studies have highlighted its significance in drug development, particularly in the design of enzyme inhibitors and receptor modulators. This research brief consolidates the latest findings on its chemical properties, synthetic applications, and therapeutic potential, providing a comprehensive overview for researchers in the chemical, biological, and pharmaceutical fields.

Recent advancements in synthetic methodologies have enabled more efficient production of 3-(Aminomethyl)benzoic acid hydrochloride, with improved yields and purity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility as a building block for novel GABA_A receptor ligands, showcasing its role in developing treatments for neurological disorders. The study emphasized the compound's structural versatility, which allows for diverse modifications to enhance binding affinity and selectivity.

In addition to its pharmacological applications, 3-(Aminomethyl)benzoic acid hydrochloride has been investigated for its role in peptide synthesis. A recent Organic & Biomolecular Chemistry article (2024) detailed its use as a coupling agent in solid-phase peptide synthesis, enabling the efficient assembly of complex peptides with high fidelity. This application is particularly relevant for the development of peptide-based therapeutics, where precise control over molecular structure is critical.

Further research has explored the compound's potential in cancer therapy. A 2024 preclinical study in Bioorganic & Medicinal Chemistry Letters reported the synthesis of derivatives of 3-(Aminomethyl)benzoic acid hydrochloride that exhibit potent inhibitory activity against histone deacetylases (HDACs), a class of enzymes implicated in tumor progression. These findings suggest promising avenues for the development of new anticancer agents.

Despite these advancements, challenges remain in optimizing the pharmacokinetic properties of derivatives derived from 3-(Aminomethyl)benzoic acid hydrochloride. Future research directions may focus on structural modifications to improve bioavailability and reduce off-target effects. Collaborative efforts between chemists, biologists, and pharmacologists will be essential to translate these discoveries into clinically viable therapies.

In conclusion, 3-(Aminomethyl)benzoic acid hydrochloride continues to be a valuable scaffold in medicinal chemistry, with emerging applications in neurology, oncology, and peptide therapeutics. Its versatility and synthetic accessibility make it a cornerstone for innovation in drug discovery. Ongoing studies are expected to further elucidate its mechanisms of action and expand its therapeutic repertoire.

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