7-Nitrobenzoxadiazole-6-aminohexanoic acid

Base Information

• Chemical Name: 7-Nitrobenzoxadiazole-6-aminohexanoic acid
• CAS No.: 88235-25-0
• Molecular Formula: C12H14N4O5
• Molecular Weight: 294.267
• Hs Code.: 2934999090
• European Community (EC) Number: 635-833-4
• DSSTox Substance ID: DTXSID20236920
• Nikkaji Number: J535.346G
• Wikidata: Q27123278
• Metabolomics Workbench ID: 58136
• Mol file: 88235-25-0.mol

Synonyms:7-nitrobenzoxadiazole-6-aminohexanoic acid;N(7-nitro-2,1,3-benzoxadiazol-4-yl)-6-aminocaproic acid;N-(7-nitro-2,1,3-benzoxadiazol-4-yl)-6-aminohexanoic acid;NBD-AMHA

Chemical Property of 7-Nitrobenzoxadiazole-6-aminohexanoic acid

Chemical Property:

• Vapor Pressure: 2.38E-13mmHg at 25°C
• Refractive Index: 1.65
• Boiling Point: 559.4 °C at 760 mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 292.1 °C
• PSA: 134.07000
• Density: 1.462 g/cm³
• LogP: 2.78410
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 294.09641956
• Heavy Atom Count: 21
• Complexity: 375

Purity/Quality:

97% ^*data from raw suppliers

NBDHexanoicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 22-26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C2=NON=C2C(=C1)[N+](=O)[O-])NCCCCCC(=O)O
• Uses: 6-(7-NITRO-2,1,3-BENZOXADIAZOL-4-YLAMINO)HEXANOIC ACID is used for investigation of binding sites of fatty acid and sterol carrier proteins, also used for cell membrane staining. 6-(7-NITRO-2,1,3-BENZOXADIAZOL-4-YLAMINO)HEXANOIC ACID is used as a fluorescent probes for studying the fat globule (membrane) of bovine and human. NBD Hexanoic Acid is used as a fluorescent probes for studying the fat globule (membrane) of bovine and human.

Technology Process of 7-Nitrobenzoxadiazole-6-aminohexanoic acid

There total 6 articles about 7-Nitrobenzoxadiazole-6-aminohexanoic 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: 100.0%

NBD chloride (10199-89-0) + 6-aminohexanoic acid (60-32-2,93208-38-9) → 6-(7-nitrobenzofurazan-4-ylamino)hexanoic acid (88235-25-0)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 0 - 50 ℃; for 3.5h;

DOI:10.1055/s-0034-1378537

Reference yield: 89.0%

tert-butyl 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanoate → 6-(7-nitrobenzofurazan-4-ylamino)hexanoic acid (88235-25-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 25 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.202109967

Reference yield:

NBD chloride (10199-89-0) → 6-(7-nitrobenzofurazan-4-ylamino)hexanoic acid (88235-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 940 mg / NaHCO₃ / methanol / 24 h

2: 325 mg / NaOH / H₂O; tetrahydrofuran / 3 h / 20 °C

With sodium hydroxide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water;

DOI:10.1021/ol0501931

upstream raw materials:

NBD chloride

6-aminohexanoic acid

methyl 6-aminocaproate hydrochloride

6-aminohexanoic acid tert-butyl ester

Downstream raw materials:

N-(4-hydroxy-4-(2-nitrophenyl)butyl)-6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanamide

N-[4-(1,3,2-dithiarsolan-2-yl)phenyl]-6-[(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino]hexanamide

Refernces

• 1、 Kope?ná, Monika,Ková?ik, Andrej,Ku?era, Ond?ej,Machá?ek, Miloslav,Sochorová, Michaela,Audrlická, Pavla,Vávrová, Kate?ina. "Fluorescent Penetration Enhancers Reveal Complex Interactions among the Enhancer, Drug, Solvent, and Skin". . p. 886 - 897. Retrieved 2019.
• 2、 Arenz, Christoph,Basu, Shibom,Bechara, Cherine,Bossis, Guillaume,Cong, Xiaojing,Del Nero, Elise,Drapeau, Marion,Fontanel, Simon,Gabellier, Ludovic,Golebiowski, Jér?me,Granier, Sebastien,Healey, Robert D.,Hornemann, Thorsten,Jeannot, Sylvain,Karsai, Gergely,Leyrat, Cedric,Maurel, Damien,Saied, Essa M.,Saint-Paul, Julie. "Discovery and Mechanism of Action of Small Molecule Inhibitors of Ceramidases**". . . Retrieved 2021/12/09.