299920-65-3

Basic information

• Product Name: methyl 3-amino-4,6-dinitro-1-benzothiophene-2-carboxylate
• Synonyms: methyl 3-amino-4,6-dinitro-1-benzothiophene-2-carboxylate
• CAS NO: 299920-65-3
• Molecular Formula: C₁₀H₇N₃O₆S
• Molecular Weight: 297.24408
• Mol File: 299920-65-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 3-amino-4,6-dinitro-1-benzothiophene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-amino-4,6-dinitro-1-benzothiophene-2-carboxylate(299920-65-3)
• EPA Substance Registry System: methyl 3-amino-4,6-dinitro-1-benzothiophene-2-carboxylate(299920-65-3)

Safety Data

• Hazardous Substances Data: 299920-65-3(Hazardous Substances Data)

Upstream product

• 309272-29-5 methyl 2-(2-cyano-3,5-dinitrophenylthio)acetate 
• 51226-42-7 2,4,6-Trinitrobenzamide 
• 309272-25-1 2-(methoxycarbonylmethylthio)-4,6-dinitrobenzamide 
• 37841-25-1 1-cyano-2,4,6-trinitrobenzene 
• 2365-48-2 Methyl thioglycolate 

Relevant articles and documents

Synthetic utilization of polynitroaromatic compounds. 4. Synthesis of nitro-free 4,6-disubstituted 3-aminobenzothiophene derivatives based on 2,4,6-trinitrobenzamide

A convenient synthesis of nitro-free 4,6-disubstituted 3-aminobenzothiophenes, their S-oxides and S,S-dioxides based on the available 2,4,6-trinitrobenzamide has been developed. The synthesis entails stepwise nucleophilic substitution of all nitro groups in the starting compound by S-, N-, and O-nucleophiles followed by Thorpe-Ziegler cyclization.

Chemistry of 2,4,6-trinitrobenzonitrile 1. Nitro group substitution in 2,4,6-trinitrobenzonitrile under the action of anionic nucleophiles. Factors favoring substitution of the ortho-nitro group

The direction of the nitro group substitution (the ratio of the ortho/para substitution) in 2,4,6-trinitrobenzonitrile under the action of anionic nucleophiles (MeO-, RS-, and N3-) as well as of HCl was studied.

Regiospecific substitution of the 4-nitro group in 3-amino-4,6-dinitrobenzo[b]thiophene-2-carboxylates: Unexpected activating effect of the amino group

The cyclocondensation of 2,4,6-trinitrobenzonitrile with the esters of thioglycolic acid results in the formation of 3-amino-4,6-dinitrobenzo[b]thiophene-2-carboxylates 3. The interaction of 3 with anionic nucleophiles RO- (R=CF3CH2, CH≡CCH2), RS- (R=Ph, PhCH2, (CH3)2CHCH2), N3- in NMP or DMF leads to the substitution of only the 4-NO2 group. The replacement of the electron-donating NH2 group in 3 with hydrogen unexpectedly and significantly hampers nucleophilic substitution of the nitro group. It is assumed that increased reactivity of the 4-NO2 in 3 is connected with the twist of this group with respect to the plane of the aromatic ring under the influence of the NH2 group as indicated by semi-empirical quantum chemical calculations.