3-Nitrobenzene-1,2-diol

Base Information

• Chemical Name: 3-Nitrobenzene-1,2-diol
• CAS No.: 6665-98-1
• Molecular Formula: C6H5 N O4
• Molecular Weight: 155.11
• Hs Code.: 2908999090
• ChEMBL ID: CHEMBL288446
• DSSTox Substance ID: DTXSID90901759
• Nikkaji Number: J801.899E
• NSC Number: 407241
• Mol file: 6665-98-1.mol

Synonyms:nitrocatechol

Chemical Property of 3-Nitrobenzene-1,2-diol

Chemical Property:

• Vapor Pressure: 0.00461mmHg at 25°C
• Refractive Index: 1.5423 (estimate)
• Boiling Point: 268.6°C at 760 mmHg
• Flash Point: 123.7°C
• PSA: 86.28000
• Density: 1.58g/cm³
• LogP: 1.52920
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: 14.88g/L(20.5 oC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 155.02185764
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)O)[N+](=O)[O-]
• Uses: 3-Nitrobenzene-1,2-diol is a possible inhibitor of neuronal nitric oxide synthase. It is also used to synthesize serotonin 5HT1A antagonists.

Technology Process of 3-Nitrobenzene-1,2-diol

There total 24 articles about 3-Nitrobenzene-1,2-diol 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: 78.0%

1-nitro-1-phenylmethane (622-42-4) + sodium carbonate monohydrate → 3-nitrobenzene-1,2-diol (6665-98-1) + 2-nitro-2-phenyl-propane-1,3-diol (5428-02-4)

Guidance literature:

With formaldehyd; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; toluene;

Reference yield: 75.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 3-nitrobenzene-1,2-diol (6665-98-1)

Guidance literature:

With uronium nitrate; In water; acetonitrile; at 80 ℃; for 0.5h; regioselective reaction; Microwave irradiation;

DOI:10.1016/j.tetlet.2013.12.114

Reference yield: 40.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 3-nitrobenzene-1,2-diol (6665-98-1) + 1,2-dihydroxy-4-nitrobenzene (3316-09-4)

Guidance literature:

With nitric acid; In diethyl ether; for 22h; Ambient temperature;

DOI:10.1016/0022-328X(95)05717-4

upstream raw materials:

meta-nitrophenol

4-hydroxy-3-methoxy-2-nitro-benzoic acid

2-benzoyloxy-6-nitrophenol

3-nitroveratrole

Downstream raw materials:

3-nitroveratrole

o-bromanil

Tetrabromocatechol

oxalic acid

Refernces

• 1、 Elgaher, Walid A. M.,Hamed, Mostafa M.,Baumann, Sascha,Herrmann, Jennifer,Siebenbürger, Lorenz,Krull, Jana,Cirnski, Katarina,Kirschning, Andreas,Br?nstrup, Mark,Müller, Rolf,Hartmann, Rolf W.. "Cystobactamid 507: Concise Synthesis, Mode of Action, and Optimization toward More Potent Antibiotics". supporting information. p. 7219 - 7225. Retrieved 2020/05/08.
• 2、 Verma, Sanny,Pandita, Sangeeta,Jain, Suman L.. "Microwave assisted synthesis of nitro phenols from the reaction of phenols with urea nitrate under acid-free conditions". . p. 1320 - 1322. Retrieved 2014/03/21.