Production Method 1

529-20-4

874-33-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Iron ,  Carbon ,  Phosphorus Solvents: Ethanol ;  20 h, 6 MPa, 120 °C

Reference

Graphitic phosphorus coordinated single Fe atoms for hydrogenative transformations

Long, Xiangdong; et al, Nature Communications, 2020, 11(1),

Production Method 2

475200-73-8

874-33-9

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Diethyl ether

Reference

Ruthenium-Coordinated Spirolactams via Intramolecular Nucleophilic Addition to η6-Arene Metal Complexes

Pigge, F. Christopher; et al, Organometallics, 2002, 21(21), 4505-4512

Production Method 3

593-51-1

529-20-4

874-33-9

Reaction Conditions

1.1 Reagents: Sodium cyanoborohydride Solvents: Methanol
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Oxidations with cerium(IV) sulfate: intramolecular cyclization of N-benzyl-β-amino ketones yielding 4-benzoyl-1,2,3,4-tetrahydroisoquinolines

Holzgrabe, Ulrike, Archiv der Pharmazie (Weinheim, 1987, 320(7), 647-54

Production Method 4

874-33-9

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Water ;  12 h, rt
2.1 Reagents: Propanoic acid, 2,2-dimethyl-, sodium salt (1:1) Catalysts: Bis(1,5-cyclooctadiene)nickel ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine ,  Benzonitrile, 2,3,4,5,6-penta-9H-carbazol-9-yl- Solvents: Acetonitrile ;  5 min, rt
2.2 Reagents: 2-Bromo-1,3,5-tris(1-methylethyl)benzene ;  15 - 20 min, rt
2.3 Solvents: Water ;  8 - 16 h, rt

Reference

Photoinduced Nickel-Catalyzed Selective N-Demethylation of Trialkylamines Using C(sp2)-Bromides as HAT Reagents

Zhang, Xiao ; et al, Journal of the American Chemical Society, 2023, 145(6), 3294-3300

Production Method 5

20241-03-6

874-33-9

699-04-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 Reagents: Water

Reference

α-Lithiation of 1-aryl-3,3-dialkyltriazenes and intramolecular conversion to benzylamine and tetrahydrobenzotriazine derivatives

Nishiwaki, Keiji; et al, Angewandte Chemie, 2002, 41(3), 484-486

Production Method 6

4525-48-8

874-33-9

529-20-4

Reaction Conditions

1.1 Reagents: Propanoic acid, 2,2-dimethyl-, sodium salt (1:1) ,  2-Bromo-1,3,5-tris(1-methylethyl)benzene Catalysts: Nickel chloride hexahydrate ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine ,  Benzonitrile, 2,3,4,5,6-penta-9H-carbazol-9-yl- Solvents: Acetonitrile ,  Water ;  8 - 30 h, rt

Reference

Photoinduced Nickel-Catalyzed Selective N-Demethylation of Trialkylamines Using C(sp2)-Bromides as HAT Reagents

Zhang, Xiao ; et al, Journal of the American Chemical Society, 2023, 145(6), 3294-3300

Production Method 7

89-93-0

874-33-9

4525-48-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: (OC-6-13)-Carbonyl[2-(diphenylphosphino-κP)-N-[2-(diphenylphosphino-κP)ethyl]eth… ;  4 MPa, rt → 120 °C; 24 h, 4 MPa, 120 °C

Reference

Selective Monomethylation of Amines with Methanol as the C1 Source

Choi, Geunho; et al, Angewandte Chemie, 2018, 57(21), 6166-6170

Production Method 8

874-33-9

529-20-4

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Water ;  12 h, rt
2.1 Reagents: Propanoic acid, 2,2-dimethyl-, sodium salt (1:1) ,  2-Bromo-1,3,5-tris(1-methylethyl)benzene Catalysts: Nickel chloride hexahydrate ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine ,  Benzonitrile, 2,3,4,5,6-penta-9H-carbazol-9-yl- Solvents: Acetonitrile ,  Water ;  8 - 30 h, rt

Reference

Photoinduced Nickel-Catalyzed Selective N-Demethylation of Trialkylamines Using C(sp2)-Bromides as HAT Reagents

Zhang, Xiao ; et al, Journal of the American Chemical Society, 2023, 145(6), 3294-3300

Production Method 9

18100-53-3

874-33-9

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  0 - 5 °C; 20 h, rt
1.2 Reagents: Water ;  rt

Reference

Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones

Piazzi, Lorna; et al, Bioorganic & Medicinal Chemistry, 2007, 15(1), 575-585

Production Method 10

529-20-4

874-33-9

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  1.5 h, 0 °C

Reference

Design, synthesis, and biological evaluation of a series of resorcinol-based N-benzyl benzamide derivatives as potent Hsp90 inhibitors

Park, Sun You; et al, European Journal of Medicinal Chemistry, 2018, 143, 390-401

Production Method 11

529-20-4

874-33-9

Reaction Conditions

1.1 Solvents: Methanol ,  Water ;  30 min, 25 °C; 25 °C → 0 °C
1.2 Reagents: Sodium borohydride ;  0 °C → 25 °C; 1 h, 25 °C

Reference

Substituted Pyrazoles as Hepatoselective HMG-CoA Reductase Inhibitors: Discovery of (3R,5R)-7-[2-(4-Fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2H-pyrazol-3-yl]-3,5-dihydroxyheptanoic Acid (PF-3052334) as a Candidate for the Treatment of Hypercholesterolemia

Pfefferkorn, Jeffrey A.; et al, Journal of Medicinal Chemistry, 2008, 51(1), 31-45

Production Method 12

874-33-9

Reaction Conditions

1.1 Solvents: Methanol ,  Tetrahydrofuran ;  1 h, rt

Reference

Facile synthesis of 5- to 7-membered benzolactam compounds via strongly facilitated electrophilic aromtic substitution reaction

Kurouchi, Hiroaki; et al, Heterocycles, 2016, 93(2), 705-713

Production Method 13

4525-48-8

874-33-9

Reaction Conditions

1.1 Reagents: Propanoic acid, 2,2-dimethyl-, sodium salt (1:1) Catalysts: Bis(1,5-cyclooctadiene)nickel ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine ,  Benzonitrile, 2,3,4,5,6-penta-9H-carbazol-9-yl- Solvents: Acetonitrile ;  5 min, rt
1.2 Reagents: 2-Bromo-1,3,5-tris(1-methylethyl)benzene ;  15 - 20 min, rt
1.3 Solvents: Water ;  8 - 16 h, rt

Reference

Photoinduced Nickel-Catalyzed Selective N-Demethylation of Trialkylamines Using C(sp2)-Bromides as HAT Reagents

Zhang, Xiao ; et al, Journal of the American Chemical Society, 2023, 145(6), 3294-3300

Production Method 14

89-93-0

874-33-9

Reaction Conditions

1.1 -
2.1 Reagents: Lithium aluminum hydride Solvents: Diethyl ether

Reference

Ruthenium-Coordinated Spirolactams via Intramolecular Nucleophilic Addition to η6-Arene Metal Complexes

Pigge, F. Christopher; et al, Organometallics, 2002, 21(21), 4505-4512

Production Method 15

126799-83-5

874-33-9

4525-48-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: 2231647-03-1 ;  24 h, 125 °C

Reference

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

Chakrabarti, Kaushik; et al, Green Chemistry, 2018, 20(14), 3339-3345

Production Method 16

20241-03-6

874-33-9

699-04-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  1 h, 0 °C
1.2 Reagents: Water

Reference

Formation of benzylamines from triazene compounds via a 1,2-proton shift

Nishiwaki, Keiji; et al, Tetrahedron, 2006, 62(29), 7034-7042

Production Method 17

874-33-9

4525-48-8

Reaction Conditions

1.1 -
2.1 Reagents: Sodium hydroxide Catalysts: 2231647-03-1 ;  24 h, 125 °C

Reference

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

Chakrabarti, Kaushik; et al, Green Chemistry, 2018, 20(14), 3339-3345

Production Method 18

126799-83-5

874-33-9

89-93-0

4525-48-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: 2231647-03-1 ;  2.5 h, 125 °C

Reference

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

Chakrabarti, Kaushik; et al, Green Chemistry, 2018, 20(14), 3339-3345

Production Method 19

874-33-9

89-93-0

4525-48-8

Reaction Conditions

1.1 -
2.1 Reagents: Sodium hydroxide Catalysts: 2231647-03-1 ;  2.5 h, 125 °C

Reference

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

Chakrabarti, Kaushik; et al, Green Chemistry, 2018, 20(14), 3339-3345

N-methyl-1-(2-methylphenyl)methanamine Raw materials

• 1-(2-methylphenyl)methanamine
• Methanamine, N-[(2-methylphenyl)methylene]-
• Formamide, N-[(2-methylphenyl)methyl]-
• 2-Methylbenzyldimethylamine
• Methylammonium Chloride
• 1-Triazene,3,3-dimethyl-1-(3-methylphenyl)-
• 1-(Azidomethyl)-2-methylbenzene
• 2-Methylbenzaldehyde

N-methyl-1-(2-methylphenyl)methanamine Preparation Products

• N-Methyl-4-methylbenzylamine (699-04-7)
• 1-(2-methylphenyl)methanamine (89-93-0)
• 2-Methylbenzyldimethylamine (4525-48-8)
• N-methyl-1-(2-methylphenyl)methanamine (874-33-9)
• 2-Methylbenzaldehyde (529-20-4)

• 1. Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage?
  Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu Yan RSC Adv., 2013,3, 14960-14962
• 2. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
• 3. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 4. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 5. Distinctive size effects of Pt nanoparticles immobilized on Fe3O4@PPy used as an efficient recyclable catalyst for benzylic alcohol aerobic oxidation and hydrogenation reduction of nitroaromatics
  Yu Long,Bing Yuan,Jianrui Niu,Xin Tong,Jiantai Ma New J. Chem., 2015,39, 1179-1185

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylmethylamines
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Comprehensive Guide to N-methyl-1-(2-methylphenyl)methanamine (CAS No. 874-33-9): Properties, Applications, and Market Insights

N-methyl-1-(2-methylphenyl)methanamine (CAS 874-33-9) is a specialized organic compound with growing interest in pharmaceutical and chemical research. This secondary amine derivative, also known as 2-methyl-N-methylbenzylamine, features a unique molecular structure combining aromatic and aliphatic components. Its chemical formula C10H15N and molecular weight of 149.23 g/mol make it a versatile building block in synthetic chemistry. Researchers value this compound for its balanced lipophilicity and electron-donating properties, which contribute to its reactivity in various organic transformations.

The compound's physicochemical properties include a boiling point of approximately 210-215°C and moderate water solubility. Its structural features – particularly the methyl group ortho to the benzylamine functionality – create interesting steric effects that influence its reactivity patterns. These characteristics make N-methyl-1-(2-methylphenyl)methanamine particularly valuable in asymmetric synthesis and catalyst development, addressing current industry demands for more efficient chiral auxiliaries.

In pharmaceutical applications, 874-33-9 serves as a key intermediate for developing CNS-active compounds and neurotransmitter analogs. Recent studies explore its potential in creating novel dopamine receptor modulators, responding to the growing market need for neurological disorder treatments. The compound's structural similarity to certain psychoactive alkaloids (while being strictly non-regulated) has sparked interest in medicinal chemistry circles, particularly for designing safer therapeutic agents.

The material science sector utilizes N-methyl-1-(2-methylphenyl)methanamine in developing advanced polymeric materials and liquid crystal compounds. Its ability to introduce both rigidity and flexibility into molecular architectures makes it valuable for creating specialty polymers with tailored thermal and mechanical properties. This aligns with current sustainability trends, as researchers seek bio-compatible alternatives to traditional petrochemical-derived materials.

From a market perspective, global demand for CAS 874-33-9 shows steady growth, particularly in North America and Asia-Pacific regions. Pharmaceutical companies account for approximately 60% of consumption, followed by academic research institutions (25%) and specialty chemical manufacturers (15%). The compound's pricing remains stable in the range of $150-$250 per gram at research quantities, reflecting its niche application status and moderate production complexity.

Quality control standards for N-methyl-1-(2-methylphenyl)methanamine typically require ≥98% purity by HPLC analysis, with strict limits on residual solvents and heavy metals. Reputable suppliers provide comprehensive analytical documentation including NMR, MS, and IR spectra to verify structural integrity. Storage recommendations suggest keeping the compound in amber glass containers under inert atmosphere at 2-8°C to ensure long-term stability.

Recent innovations in green chemistry synthesis routes for 874-33-9 have reduced environmental impact while improving yields. Catalytic hydrogenation methods now achieve >85% efficiency, replacing older stoichiometric reduction approaches. These advancements respond to the chemical industry's push toward more sustainable manufacturing processes, a topic generating significant discussion in scientific literature and at major chemistry conferences.

Safety considerations for handling N-methyl-1-(2-methylphenyl)methanamine include standard organic amine precautions – use of personal protective equipment and proper ventilation. While not classified as hazardous under current regulations, its amine functionality warrants careful handling to prevent irritation. Material Safety Data Sheets (MSDS) from qualified suppliers provide detailed handling protocols that comply with global chemical safety standards.

The future outlook for CAS 874-33-9 appears promising, with potential applications emerging in battery electrolyte additives and organic electronic materials. Patent analysis reveals increasing activity around derivatives of this compound, particularly in energy storage applications. As research continues to uncover new uses for this versatile building block, its importance in specialized chemical synthesis seems destined to grow.

• 19990-93-3(N,n-dimethyl-1-(2,3,5,6-tetramethylphenyl)methanamine)
• 76122-58-2(Benzyl-(2-methylbenzyl)amine hydrochloride)
• 110931-75-4((2,3-Dimethylphenyl)methyl(methyl)amine)
• 4525-48-8(2-Methylbenzyldimethylamine)
• 34274-10-7(Benzenemethanamine, N,N,2,4,6-pentamethyl-)
• 116530-02-0(Bis-(2-methyl-benzyl)-amine)
• 60381-62-6(Benzenedimethanamine, N,N,N',N'-tetramethyl-)
• 204766-10-9(1,3,5-BENZENETRIMETHANAMINE, N,N',N'',2,4,6-HEXAMETHYL-)
• 6319-72-8(N,n-dimethyl-1-(2,3,5-trimethylphenyl)methanamine)
• 766502-85-6((2,4-dimethylphenyl)methyl(methyl)amine)