1-N-Boc-4-(3-Carboxy-4-nitrophenyl)piperazine

Base Information

• Chemical Name: 1-N-Boc-4-(3-Carboxy-4-nitrophenyl)piperazine
• CAS No.: 183622-36-8
• Molecular Formula: C16H21 N3 O6
• Molecular Weight: 351.359
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID90472939
• Wikidata: Q82302129
• Mol file: 183622-36-8.mol

Synonyms:183622-36-8;1-N-Boc-4-(3-Carboxy-4-nitrophenyl)piperazine;5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)-2-nitrobenzoic acid;5-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]-2-nitrobenzoic acid;MFCD09878788;1-Piperazinecarboxylic acid, 4-(3-carboxy-4-nitrophenyl)-, 1-(1,1-dimethylethyl) ester;4-(3-CARBOXY-4-NITRO-PHENYL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;SCHEMBL5863471;DTXSID90472939;5-{4-[(tert-butoxy)carbonyl]piperazin-1-yl}-2-nitrobenzoic acid;AKOS022172429;AB54004;MD-0048;SY239656;CS-0171796;5-(4-Boc-1-piperazinyl)-2-nitrobenzoic Acid;5-(4-(tert-Butoxycarbonyl)piperazin-1-yl)-2-nitrobenzoicacid

Chemical Property of 1-N-Boc-4-(3-Carboxy-4-nitrophenyl)piperazine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.583
• Boiling Point: 555.6°Cat760mmHg
• Flash Point: 289.8°C
• PSA: 115.90000
• Density: 1.329g/cm³
• LogP: 2.87620
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 351.14303540
• Heavy Atom Count: 25
• Complexity: 519

Purity/Quality:

98% ^*data from raw suppliers

1-N-Boc-4-(3-Carboxy-4-nitrophenyl)piperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)[N+](=O)[O-])C(=O)O

Technology Process of 1-N-Boc-4-(3-Carboxy-4-nitrophenyl)piperazine

There total 3 articles about 1-N-Boc-4-(3-Carboxy-4-nitrophenyl)piperazine 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: 86.0%

5-bromo-2-nitrobenzoic acid (6950-43-2) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → 5-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2-nitrobenzoic acid (183622-36-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 70 ℃;

Reference yield:

5-chloro-2-nitrobenzoic acid (2516-95-2) → 5-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2-nitrobenzoic acid (183622-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: neat (no solvent) / 2 h / 110 °C

2: aq. NaOH / dioxane / 16 h

With sodium hydroxide; In 1,4-dioxane;

DOI:10.1021/jm9604787

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 2-nitro-5-piperazin-1-ylbenzoic acid (183622-35-7) → 5-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2-nitrobenzoic acid (183622-36-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 16h;

DOI:10.1021/jm9604787

upstream raw materials:

di-tert-butyl dicarbonate

2-nitro-5-piperazin-1-ylbenzoic acid

5-chloro-2-nitrobenzoic acid

5-bromo-2-nitrobenzoic acid

Downstream raw materials:

2-amino-5-(4-(tert-butoxycarbonyl)piperazin-1-yl)benzoic acid

4-(3-Ethoxycarbonylmethyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester

4-[4-Amino-3-(ethoxycarbonylmethyl-carbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

4-(3-Carboxymethyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Hutchinson, John H.,Cook, Jacquelynn J.,Brashear, Karen M.,Breslin, Michael J.,Glass, Joan D.,Gould, Robert J.,Halczenko, Wasyl,Holahan, Marie A.,Lynch, Robert J.,Sitko, Gary R.,Stranieri, Maria T.,Hartman, George D.. "Non-peptide glycoprotein IIb/IIIa antagonists. 11. Design and in vivo evaluation of 3,4-dihydro-1(1H)-isoquinolinone-based antagonists and ethyl ester prodrugs". . p. 4583 - 4591. Retrieved 2007/10/03.