Methyl 4-amino-3-chloro-5-methylbenzoate

Base Information

• Chemical Name: Methyl 4-amino-3-chloro-5-methylbenzoate
• CAS No.: 202146-16-5
• Molecular Formula: C9H10ClNO2
• Molecular Weight: 199.637
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID90371610
• Wikidata: Q82158997
• Mol file: 202146-16-5.mol

Synonyms:methyl 4-amino-3-chloro-5-methylbenzoate;202146-16-5;Benzoic acid, 4-amino-3-chloro-5-methyl-, methyl ester;SCHEMBL8060962;DTXSID90371610;SDBXHTMFAXKDML-UHFFFAOYSA-N;CIA14616;MFCD01313708;AKOS027252568;AS-8597;methyl4-amino-3-chloro-5-methylbenzoate;CS-0061260;EN300-205310;A856756;Z1255465551

Chemical Property of Methyl 4-amino-3-chloro-5-methylbenzoate

Chemical Property:

• Melting Point: 80-82
• PSA: 52.32000
• LogP: 2.59840
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 199.0400063
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

99%min. ^*data from raw suppliers

methyl4-amino-3-chloro-5-methylbenzoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1N)Cl)C(=O)OC

Technology Process of Methyl 4-amino-3-chloro-5-methylbenzoate

There total 3 articles about Methyl 4-amino-3-chloro-5-methylbenzoate 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: 82.0%

methyl 4-amino-3-methylbenzoate (18595-14-7) → methyl 4-amino-3-chloro-5-methylbenzoate (202146-16-5)

Guidance literature:

With N-chloro-succinimide; In dichloromethane; at 20 ℃;

Reference yield: 55.0%

methyl 4-amino-3-chloro-5-methylthiomethylbenzoate (569344-33-8) → methyl 4-amino-3-chloro-5-methylbenzoate (202146-16-5)

Guidance literature:

With hydrogen; nickel; In ethanol; at 20 ℃; for 1h;

DOI:10.1021/jm020597o

Reference yield:

methyl 4-amino-3-chlorobenzoate (84228-44-4) → methyl 4-amino-3-chloro-5-methylbenzoate (202146-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-chlorosuccinimide / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 49 percent / Et₃N / 5 h / Heating

2.1: 55 percent / H₂ / Raney Ni / ethanol / 1 h / 20 °C

With N-chloro-succinimide; hydrogen; nickel; In ethanol; dichloromethane; 1.1: Gassman reaction;

DOI:10.1021/jm020597o

upstream raw materials:

methyl 4-amino-3-chloro-5-methylthiomethylbenzoate

methyl 4-amino-3-chlorobenzoate

methyl 4-amino-3-methylbenzoate

Downstream raw materials:

3-chloro-5-methyl-4-propionylamino-benzoic acid

Refernces

• 1、 Teramoto, Shuji,Tanaka, Michinori,Shimizu, Hiroshi,Fujioka, Takafumi,Tabusa, Fujio,Imaizumi, Takashi,Yoshida, Kenji,Fujiki, Hiroyuki,Mori, Toyoki,Sumida, Takumi,Tominaga, Michiaki. "Novel selective hindlimb vasodilators: Synthesis and biological activity of 1-acyl-4-aminopiperidine derivatives". . p. 3033 - 3044. Retrieved 2007/10/03.