6850-57-3

Basic information

• Product Name: 2-Methoxybenzylamine
• Synonyms: (2-Methoxyphenyl)methanamine;Benzenemethanamine, 2-methoxy-;RARECHEM AL BW 0150;O-ANISYLAMINE;O-METHOXYBENZYLAMINE;2-METHOXYBENZYLAMINE;2-AMINOMETHYL-ANISOLE;AKOS BBS-00003620
• CAS NO: 6850-57-3
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 229-941-7
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amine;Amines;C8;Nitrogen Compounds;Amines, Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 6850-57-3.mol
• Article Data: 42

Chemical Properties

• Melting Point: 60 °C
• Boiling Point: 227 °C724 mm Hg(lit.)
• Flash Point: 212 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.051 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0712mmHg at 25°C
• Refractive Index: n20/D 1.548(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 9.15±0.10(Predicted)
• Water Solubility: slightly soluble
• Sensitive: Air Sensitive
• BRN: 1100448
• CAS DataBase Reference: 2-Methoxybenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxybenzylamine(6850-57-3)
• EPA Substance Registry System: 2-Methoxybenzylamine(6850-57-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-37
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6850-57-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 6850-57-3 differently. You can refer to the following data:
1. 2-Methoxybenzylamine is a 2-methoxy derivative of benzylamine. 2-Methoxybenzylamine is one the the metabolites detected in urine after metabolism of dopamine analogues. 2-Methoxybenzylamine is used in the preparation of GABAA receptor ligands as analgesic agents.
2. 2-Methoxybenzylamine was used in the preparation of 6-substituted purines.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 109, 1955 DOI: 10.1021/ja01606a035Tetrahedron Letters, 33, p. 3599, 1992 DOI: 10.1016/S0040-4039(00)92512-7

InChI:InChI=1/C8H11NO/c1-10-8-5-3-2-4-7(8)6-9/h2-5H,6,9H2,1H3/p+1

Synthetic route

2-methoxy-benzonitrile (6609-56-9) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With ammonia; hydrogen In water; isopropyl alcohol at 100℃; under 15001.5 Torr; for 24h; Autoclave;	99%
With C19H34Cl2CoN2P; hydrogen; sodium ethanolate; sodium triethylborohydride In benzene at 135℃; under 22502.3 Torr; for 36h; Autoclave;	88%
With borane-ammonia complex; C15H30Cl2CoN3P In hexane at 50℃; for 16h; Sealed tube; Inert atmosphere; chemoselective reaction;	88%

2-Methoxy-benzaldehyde oxime (29577-53-5) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With (pyridine)(tetrahydroborato)zinc In tetrahydrofuran for 6h; Heating;	95%
With sodium hydrogensulfate monohydrate; molybdenum(V) chloride; sodium cyanoborohydride In N,N-dimethyl-formamide for 1.1h; Reflux;	95%
With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Heating;	6.3 g
With acetic acid; zinc at 60 - 70℃; for 1h;

N-trityl-2-methoxybenzylamine → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With hydrogenchloride In ethanol Hydrolysis;	95%
With ammonium cerium (IV) nitrate; water; acetic acid In dichloromethane at 20℃; for 13h; Inert atmosphere;

2-(2-methoxybenzyl)isoindoline-1,3-dione (172372-20-2) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With hydrazine hydrate In ethanol for 2.5h; Inert atmosphere; Reflux;	83%

(2-methoxyphenyl)methanol (612-16-8) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With ammonia In toluene at 110℃; under 5250.53 Torr; for 20h;	81%
Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: hydrazine hydrate / ethanol / 2.5 h / Inert atmosphere; Reflux View Scheme

2-methoxy-benzonitrile (6609-56-9) → 2-methoxybenzylamine (6850-57-3) + bis(2-methoxybenzyl)amine

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In ethanol at 20℃; for 0.0833333h;	A 77% B 6%

1-(isothiocyanatomethyl)-2-methoxybenzene (17608-09-2) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With 3,4-dimercaptotoluene In methanol	66%

ortho-anisaldehyde (135-02-4) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With ammonia; nickel In methanol at 120℃; under 83600 Torr; Catalytic hydrogenation;	62.4%
With methanol; ammonia; nickel under 58840.6 Torr; Hydrogenation;
With L-alanin; pyridoxal 5'-phosphate; halomonas elongatatransaminase W56G mutant In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 24h; pH=8; Reagent/catalyst; Enzymatic reaction;

sodium [(1,3-dioxoisoindolin-2-yl)methyl]trifluoroborate + 2-bromoanisole (578-57-4) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
Stage #1: sodium [(1,3-dioxoisoindolin-2-yl)methyl]trifluoroborate; 2-bromoanisole With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; water; caesium carbonate; palladium diacetate In 1,4-dioxane at 95℃; Stage #2: With hydrazine In 1,4-dioxane; methanol at 20℃; for 1h; Heating / reflux;	19%

methanol (67-56-1) + N-acetyl-2-methoxybenzylamine (63452-53-9) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With sodium hydroxide at 140 - 150℃;

α'-amino-2,2'-dimethoxy-bibenzyl-α-ol (860567-26-6) → 2-methoxybenzylamine (6850-57-3) + ortho-anisaldehyde (135-02-4)

Conditions	Yield
With hydrogenchloride

ammonium formate (540-69-2) + ortho-anisaldehyde (135-02-4) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
anschliessend mit wss.HCl;

2-methoxybenzamide (2439-77-2) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
Yield given. Multistep reaction;

2-(2-Methoxy-benzyl)-1,1,1,3,3,3-hexamethyl-disilazane (94807-37-1) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With toluene-4-sulfonic acid In methanol Heating;

2-methoxy-benzaldoxime → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With sodium amalgam; ethanol; acetic acid

ethanol (64-17-5) + 2-methoxy-benzonitrile (6609-56-9) + ethyl acetate (141-78-6) + nickel → 2-methoxybenzylamine (6850-57-3) + bis(2-methoxybenzyl)amine + ortho-anisaldehyde (135-02-4)

Conditions	Yield
at 130℃; under 73550.8 Torr; Hydrogenation;

O-benzoyl-N-[(2-methoxy-phenyl)-acetyl]-hydroxylamine + ammonium hydroxide → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
Erhitzen des mit wss. Salzsaeure angesaeuerten Reaktionsgemisches;

ortho-anisaldehyde (135-02-4) → 2-methoxybenzylamine (6850-57-3) + (2-methoxyphenyl)methanol (612-16-8)

Conditions	Yield
With ammonium hydroxide; ammonium acetate; hydrogen; [Ru(cod)Cl]2; trisodium tris(3-sulfophenyl)phosphine In tetrahydrofuran at 135℃; under 48754.9 Torr; for 2h;	A 85 % Chromat. B 3 % Chromat.
With triethylsilane; ammonium hydroxide; hydrio-iridium(III) complex at 20℃;	A 16 % Spectr. B 84 % Spectr.

1-(azidomethyl)-2-methoxybenzene (300823-47-6) → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With ammonium chloride; zinc In ethanol; water

C20H23NOSi2 → 2-methoxybenzylamine (6850-57-3)

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;

2-methoxybenzylamine (6850-57-3) + acrylonitrile (107-13-1) → N,N-bis(2-cyanoethyl)-2-methoxybenzylamine (368862-89-9)

Conditions	Yield
In methanol for 48h; Heating;	100%
With p-benzoquinone at 140℃; for 144h;	56%

2-methoxybenzylamine (6850-57-3) + methanesulfonyl chloride (124-63-0) → N-(2-methoxy-benzyl)-methanesulfonamide (346695-60-1)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	100%

Upstream product

• 540-69-2 ammonium formate 
• 135-02-4 ortho-anisaldehyde 
• 64-17-5 ethanol 
• 6609-56-9 2-methoxy-benzonitrile 
• 141-78-6 ethyl acetate 
• 300823-47-6 1-(azidomethyl)-2-methoxybenzene 
• 172372-20-2 2-(2-methoxybenzyl)isoindoline-1,3-dione 
• 612-16-8 (2-methoxyphenyl)methanol 
• 578-57-4 2-bromoanisole 
• 29577-53-5 2-Methoxy-benzaldehyde oxime 
• 94807-37-1 2-(2-Methoxy-benzyl)-1,1,1,3,3,3-hexamethyl-disilazane 
• 17608-09-2 1-(isothiocyanatomethyl)-2-methoxybenzene 
• 2439-77-2 2-methoxybenzamide 
• 860567-26-6 α'-amino-2,2'-dimethoxy-bibenzyl-α-ol 

Downstream Products

• 626216-36-2 N'-(2-methoxy-benzyl)-N,N-dimethyl-ethylenediamine 
• 105909-52-2 3-chloro-propionic acid-(2-methoxy-benzylamide) 
• 112088-70-7 6-Chloro-N⁴-(2-methoxy-benzyl)-pyrimidine-4,5-diamine 
• 827012-76-0 2-amino-N-(2-methoxybenzyl)benzamide 
• 368862-89-9 N,N-bis(2-cyanoethyl)-2-methoxybenzylamine 
• 6609-56-9 2-methoxy-benzonitrile 
• 159817-18-2 1,2-Dihydro-N-(2-methoxybenzyl)-2-methyl-4-(2-methylphenyl)-1-oxo-3-isoquinolinecarboxamide 

Relevant articles and documents

Method for preparing primary amine by catalytically reducing nitrile compounds through nano-porous palladium catalyst

The invention belongs to the technical field of heterogeneous catalysis, and provides a method for preparing primary amine by catalytically reducing nitrile compounds with a nano-porous palladium catalyst. According to the invention, aromatic and aliphatic nitrile compounds are adopted as raw materials, nano-porous palladium is adopted as a catalyst, ammonia borane is adopted as a hydrogen source, no additional additive is added, and selective hydrogenation is performed to prepare the corresponding primary amine. The method provided by the invention has the beneficial effects of mild reaction conditions, no additive, environmental protection, no need of hydrogen, simple operation, stable hydrogen source, safety, harmlessness, high conversion rate, high selectivity and good catalyst stability, and makes industrialization possible.

Benzimidazole fragment containing Mn-complex catalyzed hydrosilylation of ketones and nitriles

The synthesis of a new bidentate (NN)–Mn(I) complex is reported and its catalytic activity towards the reduction of ketones and nitriles is studied. On comparing the reactivity of various other Mn(I) complexes supported by benzimidazole ligand, it was observed that the Mn(I) complexes bearing 6-methylpyridine and benzimidazole fragments exhibited the highest catalytic activity towards monohydrosilylation of ketones and dihydrosilylation of nitriles. Using this protocol, a wide range of ketones were selectively reduced to the corresponding silyl ethers. In case of unsaturated ketones, the chemoselective reduction of carbonyl group over olefinic bonds was observed. Additionally, selective dihydrosilylation of several nitriles were also achieved using this complex. Mechanistic investigations with radical scavengers suggested the involvement of radical species during the catalytic reaction. Stoichiometric reaction of the Mn(I) complex with phenylsilane revealed the formation of a new Mn(I) complex.

Effects of ruthenium hydride species on primary amine synthesis by direct amination of alcohols over a heterogeneous Ru catalyst

Heterogeneously catalysed synthesis of primary amines by direct amination of alcohols with ammonia has long been an elusive goal. In contrast to reported Ru-based catalytic systems, we report that Ru-MgO/TiO2 acts as an effective heterogeneous catalyst for the direct amination of a variety of alcohols to primary amines at low temperatures of ca. 100 °C without the introduction of H2 gas. The present system could be applied to a variety of alcohols and provides an efficient synthetic route for 2,5-bis(aminomethyl)furan (BAMF), an attention-getting biomonomer. The high catalytic performance can be rationalized by the reactivity tuning of Ru-H species using MgO. Spectroscopic measurements suggest that MgO enhances the reactivity of hydride species by electron donation from MgO to Ru.