4393-09-3

Basic information

• Product Name: 2,3-Dimethoxybenzylamine
• Synonyms: (2,3-Dimethoxyphenyl)methanamine;RARECHEM AL BW 0151;2,3-DIMETHOXYBENZYLAMINE;2,3-Dimethoxybenzenemethanamine;2,3-Dimethoxybenzylamine ,99%;2,3-Dimethoxybenzyla;(2,3-Dimethoxyphenyl)methylamine;4393/9/3
• CAS NO: 4393-09-3
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.21
• EINECS: 224-515-7
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amine;Amines;C9 to C10;Nitrogen Compounds
• Mol File: 4393-09-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 229-230 °C(Solv: N,N-dimethylformamide (68-12-2))
• Boiling Point: 137 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00709mmHg at 25°C
• Refractive Index: n20/D 1.54(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.12±0.10(Predicted)
• CAS DataBase Reference: 2,3-Dimethoxybenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethoxybenzylamine(4393-09-3)
• EPA Substance Registry System: 2,3-Dimethoxybenzylamine(4393-09-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 2735
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 4393-09-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellowliqui

Uses

2,3-Dimethoxybenzylamine was used in the synthesis of di-,tri- and tetrapeptide linked dicatechol derivatives and 1-aryl-2,3-dihydro-1H-isoindoles (isoindolines).

InChI:InChI=1/C9H13NO2/c1-11-8-5-3-4-7(6-10)9(8)12-2/h3-5H,6,10H2,1-2H3

Synthetic route

oxime of 2,3-dimethoxy-benzaldehyde (5470-95-1) → 2,3-dimethoxybenzyl amine (4393-09-3)

Conditions	Yield
With sodium amalgam; acetic acid at 40 - 50℃;
With lithium aluminium tetrahydride

2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-dimethoxybenzyl amine (4393-09-3)

Conditions	Yield
With sodium hydroxide; hydrogen; sodium chloride; platinum(IV) oxide 1.) ethanol, chloroform, 40 psi, 3 h; Yield given. Multistep reaction;

2,3-dimethyoxybenzaldehyde (86-51-1) → 2,3-dimethoxybenzyl amine (4393-09-3)

Conditions	Yield
Stage #1: 2,3-dimethyoxybenzaldehyde In trimethyl orthoformate at 25℃; Stage #2: With lithium borohydride In tetrahydrofuran at 65℃; for 5h; Stage #3: With trifluoroacetic acid In dichloromethane at 25℃; for 5h;

C9H12NO2Pol → 2,3-dimethoxybenzyl amine (4393-09-3)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 25℃; for 5h; ((9-(amino)xanthen-2-yl)oxy)butanoic acid handle, p-methylbenzhydrylamine resin (H2N-XAL-MBHA resin);

C9H10NO2Pol → 2,3-dimethoxybenzyl amine (4393-09-3)

Conditions	Yield
Stage #1: C9H10NO2Pol With lithium borohydride In tetrahydrofuran at 65℃; for 5h; Stage #2: With trifluoroacetic acid In dichloromethane at 25℃; for 5h;

boc-β-methoxyalanine dicyclohexylamine (69912-63-6) + 2,3-dimethoxybenzyl amine (4393-09-3) → tert-butyl (S)-(1-((2,3-dimethoxybenzyl)amino)-3-methoxy-1-oxopropan-2-yl)carbamate

Conditions	Yield
In ethyl acetate	100%

2,3-dimethoxybenzyl amine (4393-09-3) + Fmoc-Pro-OH (71989-31-6) → 2-(2,3-dimethoxy-benzylcarbamoyl)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (866824-06-8)

Conditions	Yield
Stage #1: Fmoc-Pro-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,3-dimethoxybenzyl amine In acetonitrile at 20℃;	99%

2,3-dimethoxybenzyl amine (4393-09-3) + α-bromoacetophenone → 2-(2,3-dimethoxyphenyl)-5-phenyloxazole

Conditions	Yield
With iodine; potassium carbonate In N,N-dimethyl-formamide for 18h; Heating;	99%

8-(2,3-dimethoxy-benzoylamino)-octanoic acid (209961-35-3) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-[7-(2,3-dimethoxy-benzylcarbamoyl)-heptyl]-2,3-dimethoxy-benzamide (773156-68-6)

Conditions	Yield
Stage #1: 8-(2,3-dimethoxy-benzoylamino)-octanoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile for 0.5h; Stage #2: 2,3-dimethoxybenzyl amine In acetonitrile	96%

2,3-dimethoxybenzyl amine (4393-09-3) + Fmoc-Asn-OH (71989-16-7) → [2-carbamoyl-1-(2,3-dimethoxy-benzylcarbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (857064-44-9)

Conditions	Yield
Stage #1: Fmoc-Asn-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,3-dimethoxybenzyl amine In acetonitrile at 20℃;	95%

2,3-dimethoxybenzyl amine (4393-09-3) + 2-Bromo-2'-acetonaphthone (613-54-7) → 2-(2,3-dimethoxyphenyl)-5-(naphthalen-2-yl)oxazole

Conditions	Yield
With iodine; potassium carbonate In N,N-dimethyl-formamide for 18h; Heating;	95%

(R)-6-oxo-1,2-dithia-5-azacyclodecane-4-carboxylic acid (945031-68-5) + 2,3-dimethoxybenzyl amine (4393-09-3) → (R)-N-(2,3-dimethoxybenzyl)-6-oxo-1,2,5-dithiazecane-4-carboxamide

Conditions	Yield
Stage #1: (R)-6-oxo-1,2-dithia-5-azacyclodecane-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2,3-dimethoxybenzyl amine In tetrahydrofuran at 20℃; for 18h; Further stages.;	94%

2,3-dimethoxybenzyl amine (4393-09-3) + acetic anhydride (108-24-7) → N-(2,3-dimethoxybenzyl)acetamide (861523-11-7)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	93%

2,3-dimethoxybenzyl amine (4393-09-3) + 2-bromo-3'-methoxyacetophenone (5000-65-7) → 2-(2,3-dimethoxyphenyl)-5-(3-methoxyphenyl)oxazole

Conditions	Yield
With iodine; potassium carbonate In N,N-dimethyl-formamide for 18h; Heating;	93%

phthalic anhydride (85-44-9) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-(2,3-dimethoxybenzyl)phthalamide

Conditions	Yield
In dichloromethane	90%

2,3-dimethoxybenzyl amine (4393-09-3) + Fmoc-(tBu)Asp-OH (71989-14-5) → N-(2,3-dimethoxy-benzyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester (773156-70-0)

Conditions	Yield
Stage #1: Fmoc-(tBu)Asp-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 2h; Stage #2: 2,3-dimethoxybenzyl amine In dichloromethane; N,N-dimethyl-formamide	90%

2,3-dimethoxybenzyl amine (4393-09-3) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → 2-(2,3-dimethoxyphenyl)-5-(4-methoxyphenyl)oxazole

Conditions	Yield
With iodine; potassium carbonate In N,N-dimethyl-formamide for 18h; Heating;	90%

BOC-glycine (4530-20-5) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-t-butoxycarbonylglycine(2,3-dimethoxybenzyl)amide (591207-56-6)

Conditions	Yield
Stage #1: BOC-glycine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: 2,3-dimethoxybenzyl amine In dichloromethane; N,N-dimethyl-formamide	88%

Fmoc-His(Mtt)-OH + 2,3-dimethoxybenzyl amine (4393-09-3) → {1-(2,3-dimethoxy-benzylcarbamoyl)-2-[1-(2,2,2-triphenyl-ethyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions	Yield
Stage #1: Fmoc-His(Mtt)-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,3-dimethoxybenzyl amine In acetonitrile at 20℃;	87%

2,3-dimethoxybenzyl amine (4393-09-3) + N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) → [3-carbamoyl-1-(2,3-dimethoxy-benzylcarbamoyl)-propyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (857064-45-0)

Conditions	Yield
Stage #1: N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,3-dimethoxybenzyl amine In acetonitrile at 20℃;	87%

2-Picolinic acid (98-98-6) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-(2,3-dimethoxybenzyl)pyridine-2-amide

Conditions	Yield
Inert atmosphere;	84%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;

2,3-dimethoxybenzyl amine (4393-09-3) + methyl 5-(N,N-dimethylamino)-2,4-pentadienoate (187808-48-6) → methyl 5-(2,3-dimethoxybenzylamino)-2,4-pentadienoate

Conditions	Yield
In tetrahydrofuran for 85h; Heating;	83%

Hippuric Acid (495-69-2) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-benzoylglycine(2,3-dimethoxybenzyl)amide

Conditions	Yield
Stage #1: Hippuric Acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: 2,3-dimethoxybenzyl amine In dichloromethane; N,N-dimethyl-formamide	82%

2,3-dimethoxybenzyl amine (4393-09-3) + N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine (77128-72-4) → [1-(2,3-dimethoxy-benzylcarbamoyl)-2-(4-methoxy-phenyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (857064-46-1)

Conditions	Yield
Stage #1: N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,3-dimethoxybenzyl amine In acetonitrile at 20℃;	82%

2-Bromobenzamide (4001-73-4) + 2,3-dimethoxybenzyl amine (4393-09-3) → 2-(2,3-dimethoxyphenyl)quinazolin-4(3H)-one

Conditions	Yield
With potassium carbonate; dimethyl sulfoxide at 80℃; for 2h;	82%

2,3-dimethoxybenzyl amine (4393-09-3) + cyanomethyl bromide (590-17-0) → 2-((2,3-dimethoxybenzyl)amino)acetonitrile

Conditions	Yield
Stage #1: 2,3-dimethoxybenzyl amine With triethylamine In tetrahydrofuran at 0℃; for 0.25h; Stage #2: cyanomethyl bromide In tetrahydrofuran at 0 - 20℃; for 16h;	82%

2,3-dimethoxybenzyl amine (4393-09-3) + 4-{3,5-bis-[3-carboxy-1,1-bis-(2-carboxy-ethyl)-propylcarbamoyl]-benzoylamino}-4-(2-carboxy-ethyl)-heptanedioic acid → C120H150N12O30

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 48h;	81%

2,3-dimethoxybenzyl amine (4393-09-3) + 2-bromo-1-o-tolylethanone (51012-65-8) → 2-(2,3-dimethoxyphenyl)-5-(2-methylphenyl)oxazole

Conditions	Yield
With iodine; potassium carbonate In N,N-dimethyl-formamide for 18h; Heating;	80%

8-chloro-2,2-dimethyl-5-pyrrolidin-1-yl-1,4-dihydro-2H-pyrano[4'',3":4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine (371224-33-8) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-(2,3-dimethoxybenzyl)-5-(pyrrolidin-1-yl)-2,2-dimethyl-1,4-dihydro-2H-pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine-8-amine (889657-56-1)

Conditions	Yield
In ethanol for 24h; Heating / reflux;	79%

2,3-dimethoxybenzyl amine (4393-09-3) + N-2,3-Dimethoxybenzoyl-glycine (78217-83-1) → 2-(2,3-Dimethoxyphenyl)carbonyl amino-N-(2,3-dimethoxybenzyl) acetamide

Conditions	Yield
Stage #1: N-2,3-Dimethoxybenzoyl-glycine With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 16h; Stage #2: 2,3-dimethoxybenzyl amine With sodium hydrogencarbonate In water for 20h;	77%

azelaic acid (123-99-9) + 2,3-dimethoxybenzyl amine (4393-09-3) → azelic acid bis(2,3-dimethoxybenzylamide)

Conditions	Yield
Stage #1: azelaic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile for 0.25h; Stage #2: 2,3-dimethoxybenzyl amine In acetonitrile for 2h;	77%

4-(benzyloxy)-5-methoxy-2-nitrobenzaldehyde (2426-84-8) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-(4-benzyloxy-5-methoxy-2-nitrobenzyl)-1-(2,3-dimethoxyphenyl)methanamine

Conditions	Yield
With sodium tris(acetoxy)borohydride In chloroform for 48h; Reflux;	76%

2-(4-hydroxy-3,5-dimethoxyphenyl)acetic acid (4385-56-2) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-(2,3-dimethoxybenzyl)-2-(4-hydroxy-3,5-dimethoxyphenyl)acetamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 10h;	75%

2-bromo-2',5'-dimethoxyacetophenone (1204-21-3) + 2,3-dimethoxybenzyl amine (4393-09-3) → 2-(2,3-dimethoxyphenyl)-5-(2,5-dimethoxyphenyl)oxazole

Conditions	Yield
With iodine; potassium carbonate In N,N-dimethyl-formamide for 18h; Heating;	75%

N-dodecanoylglycine (7596-88-5) + 2,3-dimethoxybenzyl amine (4393-09-3) → N-dodecanoylglycine(2,3-dimethoxybenzyl)amide

Conditions	Yield
Stage #1: N-dodecanoylglycine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: 2,3-dimethoxybenzyl amine In dichloromethane; N,N-dimethyl-formamide	74%

Upstream product

• 5653-62-3 2,3-dimethoxybenzonitrile 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 5470-95-1 oxime of 2,3-dimethoxy-benzaldehyde 

Downstream Products

• 100253-84-7 N-(2,3-dimethoxy-benzyl)-β-alanine nitrile 
• 116120-11-7 N-(2,3-Dimethoxy-benzyl)-2-(6-hydroxymethyl-benzo[1,3]dioxol-5-yl)-acetamide 
• 408349-44-0 N-{(S)-1-[(S)-1-(2,3-Dimethoxy-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-ethyl}-2,3-dimethoxy-benzamide 
• 591207-56-6 N-t-butoxycarbonylglycine(2,3-dimethoxybenzyl)amide 
• 525607-05-0 6-(2,3-dimethoxybenzylamino)purine 
• 229627-44-5 3-[(2,3-dimethoxy-benzyl)-({2-[3-methoxy-4-(3-o-tolylureido)phenyl]-acetylamino}-acetyl)-amino]-propionic acid 
• 889657-56-1 N-(2,3-dimethoxybenzyl)-5-(pyrrolidin-1-yl)-2,2-dimethyl-1,4-dihydro-2H-pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine-8-amine 
• 904310-81-2 4-amino-5-cyano-N-(2,3-dimethoxybenzyl)-6-ethoxypyridine-2-carboxamide 
• 410544-34-2 5-cyano-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide 
• 410544-41-1 5-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide 
• 410544-43-3 N-(2,3-dimethoxybenzyl)-8-hydroxy-5-(methylsulfonyl)-1,6-naphthyridine-7-carboxamide 
• 122670-45-5 N-(2,3-Dimethoxybenzyl)diethoxyacetamide 

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