4-Nitro-3-(octanoyloxy)benzoic acid

Base Information

• Chemical Name: 4-Nitro-3-(octanoyloxy)benzoic acid
• CAS No.: 55894-52-5
• Molecular Formula: C15H19NO6
• Molecular Weight: 309.319
• DSSTox Substance ID: DTXSID80602602
• Nikkaji Number: J786.341A
• Wikidata: Q82499729
• Mol file: 55894-52-5.mol

Synonyms:4-nitro-3-(octanoyloxy)benzoic acid;4-nitro-3-octanoyloxybenzoic acid;4-NOOBA

Chemical Property of 4-Nitro-3-(octanoyloxy)benzoic acid

Chemical Property:

• Melting Point: 146 - 148°C
• PSA: 109.42000
• LogP: 4.08210
• Storage Temp.: RT
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 309.12123733
• Heavy Atom Count: 22
• Complexity: 392

Purity/Quality:

99% ^*data from raw suppliers

4-Nitro-3-[(1-oxooctyl)oxy]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCC(=O)OC1=C(C=CC(=C1)C(=O)O)[N+](=O)[O-]
• Description: NOBA (55894-52-5) is a chromogenic substrate for phospholipases such as PLA2. Read absorbance at 425 nm.
• Uses: 4-Nitro-3-[(1-oxooctyl)oxy]benzoic acid is used to acrylate ε-amino groups of Lysine (L468895) in order to immobilize phospholipase A2 in snake venom.

Technology Process of 4-Nitro-3-(octanoyloxy)benzoic acid

There total 5 articles about 4-Nitro-3-(octanoyloxy)benzoic acid 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: 90.0%

3-hydroxy-4-nitro-benzoic acid (619-14-7) + n-octanoic acid chloride (111-64-8) → 4-nitro-3-(octanoyloxy)-benzoic acid (55894-52-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 0 deg C then r.t., overnight;

DOI:10.1021/ja00223a043

Reference yield:

Octanoic acid (124-07-2) + 3-hydroxy-4-nitro-benzoic acid (619-14-7) → 4-nitro-3-(octanoyloxy)-benzoic acid (55894-52-5) + 4-nitro-3-<<4'-nitro-3'-(octanoyloxy)benzoyl>oxy>-benzoic acid (115162-20-4)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; Multistep reaction. Yields of byproduct given; 1.) THF, 0 deg C, 30 min; 2.) THF, r.t., overnight;

DOI:10.1021/ja00223a043

Reference yield:

undecanoyl chloride (17746-05-3) + 3-hydroxy-4-nitro-benzoic acid (619-14-7) → 4-nitro-3-(octanoyloxy)-benzoic acid (55894-52-5) + 4-nitro-3-(undecanoyloxy)benzoic acid (115162-24-8)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; Yield given. Multistep reaction; 1.) THF, 0 deg C, 30 min; THF, r.t., overnight;

DOI:10.1021/ja00223a043

upstream raw materials:

Octanoic acid

3-hydroxy-4-nitro-benzoic acid

undecanoyl chloride

n-octanoic acid chloride

Downstream raw materials:

Octanoic acid

3-hydroxy-4-nitro-benzoic acid

Refernces

• 1、 Cho, Wonhwa,Markowitz, Michael A.,Kezdy, Ferenc J.. "A New Class of Phospholipase A2 Substrates: Kinetics of the Phospholipase A2 Catalyzed Hydrolysis of 3-(Acyloxy)-4-nitrobenzoic Acids". . p. 5166 - 5171. Retrieved 2007/10/02.