4837-88-1

Basic information

• Product Name: 2-Methyl-3-nitroanisole
• Synonyms: 6-METHOXY-2-NITROTOLUENE;2-METHOXY-6-NITROTOLUENE;2-METHYL-3-NITROANISOLE;1-METHOXY-2-METHYL-3-NITROBENZENE;BUTTPARK 52\11-31;Anisole, 2-methyl-3-nitro-;Nitrobenzene, 3-methoxy-2-methyl-;3-Methoxy-2-methyl-1-nitrobenzene~6-Methoxy-2-nitrotoluene
• CAS NO: 4837-88-1
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• EINECS: 225-424-5
• Product Categories: Drug Intermediates;Multisubstituted Benzene;Aromatic Ethers;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Alpha sort;H-MAlphabetic;M;META - METH;Pesticides&Metabolites;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4837-88-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 94-96°C 0,5mm
• Flash Point: >230 °F
• Appearance: Yellow to pale brown/Powder or Crystalline Powder
• Density: 1.18 g/cm³
• Vapor Pressure: 0.0194mmHg at 25°C
• Refractive Index: 1.538
• Solubility: soluble in Methanol
• BRN: 2328599
• CAS DataBase Reference: 2-Methyl-3-nitroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-nitroanisole(4837-88-1)
• EPA Substance Registry System: 2-Methyl-3-nitroanisole(4837-88-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-36/37-36-26
• RIDADR: 2811
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 4837-88-1(Hazardous Substances Data)

Usage

Uses

2-Methyl-3-nitroanisole may be used in chemical synthesis studies.

Purification Methods

2-Methyl-5-nitroanisole crystallises from MeOH (yellow needles) and sublimes in vacuo. [Kuffner Monatsh Chem 91 1152 1960, Beilstein 6 I 178.]

InChI:InChI=1/C8H9NO3/c1-6-7(9(10)11)4-3-5-8(6)12-2/h3-5H,1-2H3

Upstream product

• 5460-31-1 3-nitro-o-cresol 
• 77-78-1 dimethyl sulfate 
• 18102-30-2 2-methoxy-3-methylaniline 
• 861548-37-0 acetic acid-(2-methoxy-3-methyl-4-nitro-anilide) 
• 67-56-1 methanol 
• 83-42-1 6-chloro-2-nitrotoluene 
• 603-83-8 3-nitro-o-tolylamine 
• 74-88-4 methyl iodide 
• 861609-40-7 2-methoxy-3-methyl-4-nitro-aniline 
• 606-20-2 2,6-dinitrotoluene 
• 143359-98-2 acetic acid-(2-methoxy-3-methyl-anilide) 

Downstream Products

• 4837-89-2 pyruvic acid 
• 4837-90-5 4-methoxy-1H-indole 
• 117609-03-7 1-[(E)-2-(2-Methoxy-6-nitro-phenyl)-vinyl]-piperidine 
• 301155-92-0 3-(2-Methoxy-6-nitro-phenyl)-2-oxo-propionic acid ethyl ester 
• 20876-28-2 2-(2-methoxy-6-nitrophenyl)acetic acid 
• 78179-09-6 2-methyl-1-(2'-amino-6'-methoxybenzyl)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 
• 19532-68-4 2,2'-dithiobis(6-methoxybenzoic acid) 
• 53600-33-2 6-methoxyanthranilic acid 
• 50868-74-1 acetic acid-(3-methoxy-2-methyl-anilide) 
• 19689-87-3 (2-methoxy-6-nitrophenyl)methanol 
• 50608-38-3 ethyl (6-methoxy-2-nitrobenzyl)aminoacetate 
• 1000068-23-4 [1-(tert-butoxycarbonyl)-4-methoxy-1H-indol-2-yl]boronic acid 
• 1443151-84-5 1-[(E)-2-(2-methoxy-6-nitrophenyl)vinyl]pyrrolidine 
• 1567350-97-3 N-(2-(3-bromopropoxy)-7-(((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)oxy)-8-methylquinolin-3-yl)-3',6-dimethoxy-[1,1'-biphenyl]-3-carboxamide 

Relevant articles and documents

Synthetic method of 4-hydroxyindole

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of 4-hydroxyindole. Aiming at the problems existing in industrial production of 4-hydroxyindole in the prior art, the technical scheme of the invention is as follows: the method comprises the following steps: (1) protecting hydroxyl in a compound 3 by using a protective group to obtaina compound 4; (2) reacting the compound 4 with N, N-dimethylformamide dimethyl acetal to obtain a compound 5; (3) mixing the compound 5 with NH2NH2.H2O and MeOH, and carrying out a reaction to obtaina compound 6; and (4) removing the protective group of the compound 6 to obtain 4-hydroxyindole. According to the method for synthesizing 4-hydroxyindole, the cost of starting materials is low, the reaction conditions in the synthesis process are mild, operation is convenient, aftertreatment is simple, and the yield is high.

Synthesis and biological evaluation of coumarin replacements of novobiocin as Hsp90 inhibitors

Since Hsp90 modulates all six hallmarks of cancer simultaneously, it has become an attractive target for the development of cancer chemotherapeutics. In an effort to develop more efficacious compounds for Hsp90 inhibition, novobiocin analogues were prepared by replacing the central coumarin core with naphthalene, quinolinone, and quinoline surrogates. These modifications allowed for modification of the 2-position, which was previously unexplored. Biological evaluation of these compounds suggests a hydrophobic pocket about the 2-position of novobiocin. Anti-proliferative activities of these analogues against multiple cancer cell lines identified 2-alkoxyquinoline derivatives to exhibit improved activity.

Structure-activity relationships in the acronycine and benzo[b]acronycine series: Role of the pyran ring

In order to explore the structure-activity relationships in the acronycine series, simplified analogues of cis-1,2-diacetoxy-1,2-dihydroacronycine and cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1, under clinical trials) lacking the fused pyran ring, but possessing an acetoxymethyl leaving group at position 4 were prepared. These new analogues only displayed marginal antiproliferative activity compared to the parent compounds. The presence of the angularly fused dimethylpyran ring appears as an indispensable structural requirement to observe significant cytotoxic activity in this series.