2-Amino-3-methoxybenzonitrile

Base Information

• Chemical Name: 2-Amino-3-methoxybenzonitrile
• CAS No.: 148932-68-7
• Molecular Formula: C8H8 N2 O
• Molecular Weight: 148.164
• Hs Code.: 2926909090
• European Community (EC) Number: 834-055-4
• DSSTox Substance ID: DTXSID70473681
• Wikidata: Q72438678
• Mol file: 148932-68-7.mol

Synonyms:2-amino-3-methoxybenzonitrile;148932-68-7;2-Amino-3-Methoxy benzonitrile;MFCD09744022;Benzonitrile, 2-amino-3-methoxy-;2-amino-3-methoxy-benzonitrile;SCHEMBL1622431;DTXSID70473681;KLCPAKMBBMVXMD-UHFFFAOYSA-N;AKOS006331883;CS-W021551;GS-4535;SY035950;FT-0715531;EN300-188391;A808825;Z1198221994

Chemical Property of 2-Amino-3-methoxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 286.928 °C at 760 mmHg
• PKA: 1.75±0.10(Predicted)
• Flash Point: 127.33 °C
• PSA: 59.04000
• Density: 1.176 g/cm³
• LogP: 1.73028
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 148.063662883
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Amino-3-methoxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1N)C#N
• Uses: 2-Amino-3-methoxybenzonitrile is used to prepare cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands. It is also used to prepare 2- and 3-aminobenzo[b]thiophenes as antimitotic agents.

Technology Process of 2-Amino-3-methoxybenzonitrile

There total 5 articles about 2-Amino-3-methoxybenzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.5%

3-methoxy-2-nitrobenzonitrile (142596-50-7) → 3-methoxy-2-aminobenzonitrile (148932-68-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; under 760 Torr;

DOI:10.1248/cpb.44.547

Reference yield:

3-methoxy-2-nitro-benzamide (99595-85-4) → 3-methoxy-2-aminobenzonitrile (148932-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 74.5 percent / SOCl₂ / tetrahydrofuran / Ambient temperature

2: 87.5 percent / H₂ / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr

With thionyl chloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1248/cpb.44.547

Reference yield:

3-methoxy-2-nitrobenzoic acid (4920-80-3) → 3-methoxy-2-aminobenzonitrile (148932-68-7)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂ / CH₂Cl₂ / 2 h / Heating

2: aq. NH₃ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 74.5 percent / SOCl₂ / tetrahydrofuran / Ambient temperature

4: 87.5 percent / H₂ / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr

With ammonium hydroxide; thionyl chloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1248/cpb.44.547

upstream raw materials:

3-methoxy-2-nitrobenzonitrile

3-methoxy-2-nitro-benzamide

3-methoxy-2-nitrobenzoic acid

2-nitro-3-methoxybenzoyl chloride

Downstream raw materials:

1-(2-Cyano-6-methoxy-phenyl)-3-pentyl-urea

(2-cyano-6-methoxy-phenyl)-carbamic acid ethyl ester

2-amino-5-(isopropylsulfonyl)-3-{[5-(methylthio)pyridin-2-yl]methoxy}benzonitrile

2-amino-5-(isopropylsulfonyl)-3-[3-(methylsulfonyl)propoxy]benzonitrile

Refernces

• 1、 Goto,Nakamura,Morioka,Kondo,Naito,Tsutsumi. "Synthesis and biological activity of the metabolites of diethyl 4-[(4- bromo-2-cyanophenyl)carbamoyl]benzylphosphonate (NO-1886)". . p. 547 - 551. Retrieved 2007/10/03.