Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

Base Information

• Chemical Name: Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate
• CAS No.: 89481-87-8
• Molecular Formula: C13H12ClNO4
• Molecular Weight: 281.696
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10442215
• Nikkaji Number: J2.635.664D
• Wikidata: Q82259373
• Mol file: 89481-87-8.mol

Synonyms:89481-87-8;Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate;methyl 5-chloro-4-acetamido-2-(prop-2-yn-1-yloxy)benzoate;methyl 4-acetamido-5-chloro-2-prop-2-ynoxybenzoate;SCHEMBL5321109;DTXSID10442215;WKSGTEJRMLXGEG-UHFFFAOYSA-N;AKOS022188130;FT-0758210;methyl 4-(acetylamino)-5-chloro-2-(2-propynoxy)benzoate;methyl 4-acetylamino-5-chloro-2-(prop-2-ynyloxy)benzoate;Methyl4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate;Methyl 4-(acetylamino)-5-chloro-2-(2-propyn-1-yloxy)benzoate;Methyl 4-acetamido-5-chloro-2-[(prop-2-yn-1-yl)oxy]benzoate;2-(Propargyloxy)-4-(acetylamino)-5-chlorobenzoic acid methyl ester

Chemical Property of Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

Chemical Property:

• PSA: 68.12000
• LogP: 2.74650
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 281.0454856
• Heavy Atom Count: 19
• Complexity: 389

Purity/Quality:

98% ^*data from raw suppliers

Methyl 5-chloro-4-acetamido-2-(prop-2-yn-1-yloxy)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=C(C=C(C(=C1)OCC#C)C(=O)OC)Cl

Technology Process of Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

There total 5 articles about Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate 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: 96.5%

methyl 4-acetylamino-2-propargyloxybenzoate (152880-16-5) → methyl 4-(acetylamino)-5-chloro-2-(2-propynyloxy)benzoate (89481-87-8)

Guidance literature:

With N-chloro-succinimide; In N,N-dimethyl-formamide; at 70 ℃; for 3h;

DOI:10.1248/cpb.46.42

Reference yield: 88.64%

methyl 4-acetylamino-5-chloro-2-hydroxybenzoate (24190-77-0) + propargyl bromide (106-96-7) → methyl 4-(acetylamino)-5-chloro-2-(2-propynyloxy)benzoate (89481-87-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 28h;

Reference yield:

methyl 4-acetamido-2-hydroxybenzoate (4093-28-1) → methyl 4-(acetylamino)-5-chloro-2-(2-propynyloxy)benzoate (89481-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78.8 percent / K₂CO₃ / acetonitrile / 24 h / Heating

2: 96.5 percent / NCS / dimethylformamide / 3 h / 70 °C

With N-chloro-succinimide; potassium carbonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.46.42

upstream raw materials:

methyl 4-acetylamino-2-propargyloxybenzoate

methyl 4-acetamido-2-hydroxybenzoate

methyl 4-acetylamino-5-chloro-2-hydroxybenzoate

propargyl bromide

Downstream raw materials:

methyl 5-acetylamino-6-chloro-2H-1-benzopyran-8-carboxylate

methyl 4-acetylamino-5-chloro-2-hydroxybenzoate

methyl 4-acetylamino-5-chloro-2-methylbenzofuran-7-carboxylate

methyl 4-acetylamino-5-chloro-2-methylbenzofuran-7-carboxylate