Production Method 1

99-36-5

93071-65-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Carbon tetrachloride ;  6 h, reflux; reflux → rt
1.2 Reagents: Potassium phthalimide Solvents: Dimethylformamide ;  10 h, 90 °C
1.3 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  9 h, reflux

Reference

The development of a novel transforming growth factor-β (TGF-β) inhibitor that disrupts ligand-receptor interactions

Wu, Han; Sun, Yu; Wong, Wee Lin; Cui, Jiajia; Li, Jingyang; et al, European Journal of Medicinal Chemistry, 2020, 189,

Production Method 2

180863-54-1

93071-65-9

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Tetrahydrofuran ,  Water ;  24 h, rt

Reference

Bromination by means of sodium monobromoisocyanurate (SMBI)

Okada, Yukihiro; Yokozawa, Masanori; Akiba, Miwa; Oishi, Kazuhiko; Okawa, Kyoji; et al, Organic & Biomolecular Chemistry, 2003, 1(14), 2506-2511

Production Method 3

863703-13-3

93071-65-9

Reaction Conditions

1.1 Reagents: Piperidine Solvents: Dimethylformamide ;  30 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  pH 9, rt

Reference

Preparation of N-substituted (hetero)aryl, particularly furan-2-yl, carboxamides and related compounds as prostanoid EP2 receptor agonists

, World Intellectual Property Organization, , ,

Production Method 4

13531-48-1

93071-65-9

Reaction Conditions

1.1 Reagents: Hydrogen ,  Hydrochloric acid Catalysts: Palladium Solvents: Methanol ,  Water ;  24 h, rt

Reference

Pd(II)-Catalyzed Direct Sulfonylation of Benzylamines Using Sodium Sulfinates

Karmakar, Ujjwal; Samanta, Rajarshi, Journal of Organic Chemistry, 2019, 84(5), 2850-2861

Production Method 5

17841-68-8

93071-65-9

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  30 min

Reference

Novel symmetrical ureas as modulators of protein arginine methyl transferases

Fontan, Noelia; Garcia-Dominguez, Patricia; Alvarez, Rosana; de Lera, Angel R., Bioorganic & Medicinal Chemistry, 2013, 21(7), 2056-2067

Production Method 6

180863-54-1

93071-65-9

Reaction Conditions

Reference

Sulfonamide-benzoic acid derivatives as GPAT inhibitors and their preparation, pharmaceutical compositions and use in the treatment of obesity

, World Intellectual Property Organization, , ,

Production Method 7

93071-65-9

Reaction Conditions

Reference

1,2,3-Triazole derivatives as histone deacetylase inhibitors and their preparation and use for the treatment of HDAC-related diseases

, India, , ,

Production Method 8

93071-65-9

Reaction Conditions

Reference

Heterocyclic naphthalene amides having leukotriene-antagonistic action

, World Intellectual Property Organization, , ,

Production Method 9

13531-48-1

93071-65-9

208450-86-6

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  16 h, rt

Reference

Synthesis of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas and evaluation as modulators of the isoforms of nitric oxide synthase

Goodyer, Claire L. M.; Chinje, Edwin C.; Jaffar, Mohammed; Stratford, Ian J.; Threadgill, Michael D., Bioorganic & Medicinal Chemistry, 2003, 11(19), 4189-4206

Production Method 10

781632-38-0

93071-65-9

Reaction Conditions

1.1 Reagents: Hydrazine Solvents: Tetrahydrofuran ,  Water ;  overnight, reflux
1.2 Reagents: Sodium carbonate

Reference

Tripodal Tris-tacn and Tris-dpa Platforms for Assembling Phosphate-Templated Trimetallic Centers

Cao, Rui; Muller, Peter; Lippard, Stephen J., Journal of the American Chemical Society, 2010, 132(49), 17366-17369

Production Method 11

52178-50-4

93071-65-9

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene ,  Sulfuric acid magnesium salt (1:1) ,  Benzeneacetic acid, α-amino-α-methyl-, potassium salt (1:1) Solvents: 1,4-Dioxane ;  36 h, 50 °C
1.2 Reagents: Hydroxylamine Solvents: Water ;  15 min, rt

Reference

Transamination of Aromatic Aldehydes to Primary Arylmethylamines

Cai, Weiqi; Yang, Yue; Ma, Jiguo; Cao, Jing; Ren, Xinyi; et al, Organic Letters, 2023, 25(21), 3876-3880

Production Method 12

180863-54-1

93071-65-9

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Tetrahydrofuran ;  5 min, rt → 0 °C; 15 h, 0 °C → rt; rt
1.2 Reagents: Water ;  1 h, rt

Reference

Cation-Transporting Peptides: Scaffolds for Functionalized Pores?

Behera, Harekrushna; Ramkumar, Venkatachalam; Madhavan, Nandita, Chemistry - A European Journal, 2015, 21(28), 10179-10184

Production Method 13

52178-50-4

93071-65-9

Reaction Conditions

1.1 Reagents: Zinc ,  Hydrochloric acid Solvents: Ethanol ,  Water ;  4 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  pH 7

Reference

Preparation of aromatic amides as kv2.1 inhibitors

, World Intellectual Property Organization, , ,

Production Method 14

2393-20-6

93071-65-9

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  cooled; 6 h, reflux

Reference

Preparation of pyrazolylalkylamide derivatives for use as 5-lipoxygenase inhibitors

, World Intellectual Property Organization, , ,

Production Method 15

781632-38-0

93071-65-9

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Methanol ;  25 °C; 4 h, reflux; reflux → 25 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

1,2,3-Triazole derivatives as histone deacetylase inhibitors and their preparation and use for the treatment of HDAC-related diseases

, World Intellectual Property Organization, , ,

Production Method 16

180863-54-1

93071-65-9

Reaction Conditions

Reference

Design and Synthesis of Small Molecule Glycerol 3-Phosphate Acyltransferase Inhibitors

Wydysh, Edward A.; Medghalchi, Susan M.; Vadlamudi, Aravinda; Townsend, Craig A., Journal of Medicinal Chemistry, 2009, 52(10), 3317-3327

Production Method 17

180863-55-2

93071-65-9

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Dichloromethane ,  1,4-Dioxane ;  4.5 h, rt
1.2 Solvents: Dichloromethane ;  overnight, rt

Reference

N-benzyl sulfonamides and related derivatives as 11β-HSD1 inhibitors, their preparation, pharmaceutical compositions, and use in therapy

, World Intellectual Property Organization, , ,

Production Method 18

93071-65-9

Reaction Conditions

Reference

Histone deacetylase inhibitors

, United States, , ,

Production Method 19

93071-65-9

Reaction Conditions

Reference

Molecular meccano. 34. Combining different hydrogen-bonding motifs to self-assemble interwoven superstructures

Ashton, Peter R.; Fyfe, Matthew C. T.; Hickingbottom, Sarah K.; Menzer, Stephan; Stoddart, J. Fraser; et al, Chemistry - A European Journal, 1998, 4(4), 577-589

Production Method 20

93071-65-9

Reaction Conditions

Reference

Aminoalkylbenzamide peptidomimetic compounds for inhibiting farnesyl-protein transferase, and their preparation

, United States, , ,

Methyl 3-(aminomethyl)benzoate Raw materials

• Methyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzoate
• Benzoic acid, 3-[[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]methyl]-, methyl ester
• Methyl 3-(aminomethyl)benzoate Hydrochloride
• 3-(Aminomethyl)benzoic acid
• Methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate
• Methyl 3-formylbenzoate
• 3-Cyanobenzoic Acid Methyl Ester
• Methyl 3-methylbenzoate
• methyl 3-(azidomethyl)benzoate

Methyl 3-(aminomethyl)benzoate Preparation Products

• Benzoic acid, 3,3'-[iminobis(methylene)]bis-, dimethyl ester (208450-86-6)
• Methyl 3-(aminomethyl)benzoate (93071-65-9)

• 1. An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems
  RabailGul,MariamMir,MurtazaNAli
• 2. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 3. An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS?
  Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” Kim Lab Chip, 2006,6, 1213-1219
• 4. Aluminium complexes with thio-phosphorus ligands: syntheses and characterisations of [Al2(CyPS3)2(CyPHS2)2] and [Al(S2PPh2)3]?
  Robert P. Davies,Maria A. Giménez,Laura Patel,Andrew J. P. White Dalton Trans., 2008, 5705-5707
• 5. An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction?
  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200

Methyl 3-(Aminomethyl)Benzoate: A Comprehensive Overview

Methyl 3-(aminomethyl)benzoate, also known by its CAS number 93071-65-9, is a compound of significant interest in the fields of organic chemistry and pharmaceutical research. This compound, with the molecular formula C₁₀H₁₃NO₂, belongs to the class of benzoate esters and is characterized by its unique structure, which includes a benzoate group substituted with an aminomethyl group at the third position. The compound's structure makes it a versatile molecule with potential applications in drug design, agrochemicals, and materials science.

The synthesis of methyl 3-(aminomethyl)benzoate involves several methods, including nucleophilic substitution and esterification reactions. Recent studies have explored the use of green chemistry approaches to synthesize this compound, such as using microwave-assisted synthesis or enzymatic catalysis. These methods not only enhance the efficiency of the synthesis process but also reduce environmental impact, aligning with current trends in sustainable chemical manufacturing.

One of the most promising areas of research involving methyl 3-(aminomethyl)benzoate is its application in drug design. The compound's structure allows for functionalization at multiple sites, making it a valuable scaffold for developing bioactive molecules. For instance, researchers have investigated its potential as a precursor for anti-inflammatory agents and anticancer drugs. In a recent study published in Journal of Medicinal Chemistry, scientists demonstrated that derivatives of methyl 3-(aminomethyl)benzoate exhibit potent inhibitory activity against certain enzymes associated with cancer progression.

In addition to its pharmaceutical applications, methyl 3-(aminomethyl)benzoate has shown potential in agrochemicals. Its ability to act as a plant growth regulator has been explored in recent agricultural studies. For example, field trials conducted in controlled environments have indicated that this compound can enhance crop yield by improving nutrient uptake and stress resistance in plants. These findings suggest that methyl 3-(aminomethyl)benzoate could play a role in sustainable agriculture practices.

The physical and chemical properties of methyl 3-(aminomethyl)benzoate are well-documented. It is a white crystalline solid with a melting point of approximately 85°C and a boiling point around 250°C under standard conditions. The compound is sparingly soluble in water but dissolves readily in organic solvents such as dichloromethane and ethyl acetate. Its stability under various conditions has been tested, and it has been found to be stable under normal storage conditions but may degrade under strong acidic or basic environments.

Recent advancements in computational chemistry have enabled researchers to predict the behavior of methyl 3-(aminomethyl)benzoate in various chemical reactions with high accuracy. For instance, density functional theory (DFT) calculations have been used to study the electronic structure of this compound, providing insights into its reactivity and selectivity in different reaction pathways. These computational studies have significantly accelerated the development of new synthetic routes and applications for this compound.

In terms of safety considerations, methyl 3-(aminomethyl)benzoate is generally considered non-toxic when handled appropriately. However, like all chemicals, it should be stored and used according to standard laboratory safety protocols. Occupational exposure limits (OELs) have been established based on its physical properties and toxicological data, ensuring safe handling practices in industrial settings.

The future outlook for methyl 3-(aminomethyl)benzoate is bright, with ongoing research exploring its potential in emerging fields such as nanotechnology and biotechnology. For example, researchers are investigating its use as a building block for constructing nanostructured materials with specific functionalities. Additionally, advancements in biocatalysis may pave the way for more efficient and scalable production methods for this compound.

In conclusion, methyl 3-(aminomethyl)benzoate (CAS No.93071-65-9) is a versatile compound with diverse applications across multiple disciplines. Its unique structure and chemical properties make it an invaluable tool in drug discovery, agrochemical development, and materials science. As research continues to uncover new possibilities for this compound, it is likely to play an increasingly important role in advancing modern chemistry and technology.

• 6232-11-7(Methyl 4-(aminomethyl)benzoate hydrochloride)
• 17841-68-8(Methyl 3-(aminomethyl)benzoate Hydrochloride)
• 6757-31-9(Methyl 4-carbamoylbenzoate)
• 91843-34-4(Ethyl 3-(aminomethyl)benzoate hydrochloride)
• 1260853-77-7(methyl 5-(aminomethyl)naphthalene-2-carboxylate)
• 18469-52-8(Methyl 4-(aminomethyl)benzoate)
• 366-84-7(Ethyl 4-(aminomethyl)benzoate)
• 6232-12-8(Ethyl 4-(aminomethyl)benzoate hydrochloride)
• 105995-42-4(Benzoic acid, 3,5-bis(aminomethyl)-, methyl ester)
• 922163-35-7(methyl 3-(methylamino)methylbenzoate)