13661-34-2

Upstream product

• 186581-53-3 diazomethane 
• 4097-63-6 2-methoxy-4,6-dinitrophenol 
• 7539-25-5 1-methoxy-2,3,5-trinitrobenzene 
• 124-41-4 sodium methylate 
• 77-78-1 dimethyl sulfate 
• 63975-57-5 4.6-Dinitro-guajacol 
• 116668-84-9 3-nitroveratrole 
• 7697-37-2 nitric acid 
• 5327-44-6 3,5-dinitroanisole 
• 865-33-8 potassium methanolate 
• 861800-46-6 carbonic acid bis-(5-nitro-2-methoxy-phenyl ester) 
• 861293-19-8 carbonic acid bis-(2-methoxy-3,5-dinitro-phenyl ester) 
• 553-17-3 bis(2-methoxy-phenyl)carbonate 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 13660-96-3 2-ethoxy-1-methoxy-3,5-dinitro-benzene 
• 13077-75-3 2,3-dimethoxy-1,6-dihydroxybenzene 
• 17418-07-4 1,2-dimethoxy-3,4,5-trinitrobenzene 
• 408328-35-8 2,3-dimethoxy-5-nitro-aniline 
• 21268-85-9 2-amino-1-methoxy-3,5-dinitrobenzene 
• 101252-48-6 2,4-diamino-1,6-dimethoxybenzene 
• 98488-57-4 N-methyl-2'-methoxy-4',6'-dinitroaniline 
• 189622-86-4 (3-Amino-4,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester 
• 189622-88-6 (3,4-Dimethoxy-5-methylamino-phenyl)-carbamic acid tert-butyl ester 
• 189622-78-4 (3-Amino-4,5-dimethoxy-phenyl)-carbamic acid benzyl ester 
• 189622-80-8 (3-Benzylamino-4,5-dimethoxy-phenyl)-carbamic acid benzyl ester 
• 189622-82-0 (1-Benzyl-4-benzyloxycarbonylamino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid ethyl ester 
• 100059-77-6 1-(2,6-dihydroxy-3,4-dimethoxy-phenyl)-2-methoxy-ethanone 

Relevant academic research and scientific papers

Direct methoxylation of nitroarenes and nitroazaarenes with alkaline methoxides via nucleophilic displacement of an aromatic hydrogen atom

Treatment of 1,3-dinitrobenzene and 5-substituted derivatives with excess potassium or sodium methoxide in 1,3-dimethylimidazolidin-2-one (DMI) at room temperature results in the displacement of an aromatic hydrogen at the 4-position by methoxide, affording 2,4-dinitroanisole and its 6-substituted derivatives, respectively, in low to moderate yield. In contrast, an equimolar reaction under similar conditions leads to the replacement of the nitro group in preference to the ring hydrogen. The reaction does not take place with lithium methoxide as a base. Mono- and dinitronaphthalenes and nitroquinolines undergo similar displacement of a hydrogen atom at the position ortho or para to the nitro group, giving the corresponding methoxy derivatives in moderate yield. A slow addition of the nitro compound to a large excess of potassium methoxide under an oxygen atmosphere has been found to enhance the conversion and improve the product yield. On the basis of the product distribution as well as the kinetic isotope effect kH/kD = 2.1, direct displacement of a ring hydrogen atom by methoxide ion has been interpreted in terms of the rate-determining release of an ipso-hydrogen atom as a proton from the initially formed Meisenheimer adduct.

Influence of the Heterocyclic Side Ring on Orientation During Nitrations of 1,2-Alkylenedioxy-annelated Benzenes and Their Mononitro Derivatives

Nitration of 1,2-alkylenedioxybenzenes 1 furnished the respective nitro derivatives 3 and 4 in the relative ratios: 4a:3a/100:trace, 4b:3b/98:2.4, 4c:3c/86:14, 4e:3e/91:9, 4f:3f/99:1.3.Nitration of 4 gave 5a:6a:8a/0:0:100, 5b:6b:8b/7.7:3.2:89, 5c:6c:8c/23:12:65, 5d:6d:8d/14:74:12, 5e:6e:8e/27:18:55 and 5f:6f:8f/23:7.0:70.Nitration of the isomeric 3 afforded the dinitroproducts 5, 6 and 7 in the following relative ratios: 5a:6a:7a/92:8:0, 5b:6b:7b/80:20:0, 5c:6c:7c/69:20:11, 5d:6d:7d/45:19:36, 5e:6e:7e/37:57:5.9 and 5f:6f:7f/64:36:0.Nitration of 3-nitro-1,2-dimethoxybenzene (9) furnished: 10:11/63:37.Orientation as a function of the h eterocyclic ring-size is discussed.