102871-91-0

Basic information

• Product Name: 1-(β-methoxyethyl)2-nitrobenzene
• Synonyms: 1-(β-methoxyethyl)2-nitrobenzene
• CAS NO: 102871-91-0
• Molecular Weight: 181.191
• Mol File: 102871-91-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(β-methoxyethyl)2-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(β-methoxyethyl)2-nitrobenzene(102871-91-0)
• EPA Substance Registry System: 1-(β-methoxyethyl)2-nitrobenzene(102871-91-0)

Safety Data

• Hazardous Substances Data: 102871-91-0(Hazardous Substances Data)

Upstream product

• 3558-60-9 1-methoxy-2-phenylethane 
• 15121-84-3 2-nitro-benzeneethanol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 31553-11-4 2-(2-Methoxyethyl)-aniline 
• 161368-65-6 3-(β-methoxyethyl) p-aminophenol 

Relevant articles and documents

Experiments on the Chaperon effect in the nitration of aromatics

A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.

Synthesis of 2-(2-Methoxyethyl)- and 2-(2-Thiomethoxyethyl)-aniline and Related Compounds

2-(2-Nitrophenyl)-ethanol (2) was methylated with dimethyl sulfate to give 2-(2-methoxyethyl)-1-nitrobenzene (3a) which then was reduced with hydrazine hydrate in the presence of Raney nickel to 2-(2-methoxyethyl)-aniline (1a).Compound 1a can be transformed into the N-monosilylated derivative 4 by lithiation with n-butyllithium and subsequent reaction with chlorotrimethylsilane.Reaction of 2 with p-toluenesulfonyl chloride yields 2-(2-nitrophenyl)-ethyl p-toluenesulfonate (5), which reacts with sodium thiomethoxide to give 2-(2-thiomethoxyethyl)-1-nitrobenzene (3b). 3b was reduced with hydrazine hydrate in the presence of Raney nickel to yield 2-(2-thiomethoxyethyl)-aniline (1b).Ethyl (2-nitrophenyl)-acetate (6) could be dimethylated with methyl iodide in the presence of potassium tert-butoxide and 18-crown-6 to give ethyl 2-methyl-2-(2-nitrophenyl)-propionate (7).Reduction of 7 with lithium borohydride yields 2,3-dihydro-3,3-dimethyl-1H-indole (9) and 2--aniline (10). - Keywords: 2-Functionalized anilines; Hemilabile ligands; Imido ligands