2-Methoxy-5-nitrophenol

Base Information

• Chemical Name: 2-Methoxy-5-nitrophenol
• CAS No.: 636-93-1
• Molecular Formula: C7H7NO4
• Molecular Weight: 169.137
• Hs Code.: 29095090
• European Community (EC) Number: 211-269-0
• UNII: E5T11I2JUB
• DSSTox Substance ID: DTXSID1047021
• Nikkaji Number: J60.116K
• Wikidata: Q27155007
• Mol file: 636-93-1.mol

Synonyms:2-Methoxy-5-nitrophenol;636-93-1;5-Nitroguaiacol;Phenol, 2-methoxy-5-nitro-;2-methoxy-5-nitro-phenol;3-Hydroxy-4-methoxynitrobenzene;MFCD00015561;2-hydroxy-4-nitroanisole;2-methoxy-5-nitro phenol;UNII-E5T11I2JUB;E5T11I2JUB;EINECS 211-269-0;2-Methyloxy-5-nitrophenol;Cambridge id 5108253;GUAIACOL, 5-NITRO-;SCHEMBL443353;ghl.PD_Mitscher_leg0.1131;3-NITRO-6-METHOXYPHENOL;DTXSID1047021;2-Methoxy-5-nitrophenol, 98%;CHEBI:81049;4-NITRO-2-HYDROXYANISOLE;CS-B1762;2-Hydroxy-1-methoxy-4-nitrobenzene;3-Hydroxy-4-methoxy-1-nitrobenzene;STL411904;AKOS000121448;PS-4080;AC-10141;BP-21455;SY017638;AM20050145;FT-0620707;N0498;EN300-21138;C17385;A868062;AE-641/00127024;W-104886;Q27155007;L8Q

Chemical Property of 2-Methoxy-5-nitrophenol

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0.00115mmHg at 25°C
• Melting Point: 103-107 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 291 °C at 760 mmHg
• PKA: 8.31±0.19(Predicted)
• Flash Point: 147.1 °C
• PSA: 75.28000
• Density: 1.367 g/cm³
• LogP: 1.83220
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 169.03750770
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

2-Methoxy-5-nitrophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)[N+](=O)[O-])O
• Uses: 2-Methoxy-5-nitrophenol is used in the synthesis of potent VEGF and tyrosine kinase inhibitors. Also used in the synthesis of GABA analogues and phosphodiesterase inhibitors such as rolipram.

Technology Process of 2-Methoxy-5-nitrophenol

There total 73 articles about 2-Methoxy-5-nitrophenol 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: 96.0%

3,4-dimethoxynitrobenzene (709-09-1) → 5-nitroguaiacol (636-93-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; for 2h; Irradiation;

DOI:10.1016/S0040-4020(01)81712-9

Reference yield: 94.6%

5-nitro-1,3-benzodioxole (2620-44-2) → 5-nitroguaiacol (636-93-1)

Guidance literature:

With sodium methylate; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; at 150 ℃; for 0.15h;

DOI:10.1248/cpb.40.1691

Reference yield: 91.0%

1,2-dihydroxy-4-nitrobenzene (3316-09-4) + dimethyl sulfate (77-78-1) → 5-nitroguaiacol (636-93-1)

Guidance literature:

With poly(ethylene glycol) 400; sodium hydroxide; at 110 ℃; for 6h;

DOI:10.1080/00397910008087221

upstream raw materials:

methanol

2,2-dimethyl-5-nitro-1,3-benzodioxole

sodium methylate

5-nitro-1,3-benzodioxole

Downstream raw materials:

2-isopropyloxy-1-methoxy-4-nitrobenzene

2-butoxy-1-methoxy-4-nitro-benzene

2-ethoxy-4-nitroanisole

3,4-dimethoxynitrobenzene

Refernces

• 1、 Wubbels, Gene G.,Tamura, Ryo,Gannon, Emmett J.. "Temperature-dependent regioselectivity of nucleophilic aromatic photosubstitution. Evidence that activation energy controls reactivity". . p. 4834 - 4839. Retrieved 2013/07/11.
• 2、 Hatanaka, Yasumaru,Kaneda, Masaki,Tomohiro, Takenori. "Photochemical nucleophile mapping: Identification of Tyr311 within the catalytic domain of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase". . p. 213 - 217. Retrieved 2008/02/01.