402499-05-2

Basic information

• Product Name: ethyl 4,6-dinitrobenzothiophene-2-carboxylate
• Synonyms: ethyl 4,6-dinitro-1-benzothiophene-2-carboxylate; Ethyl-4,6-dinitro-1-benzothiophen-2-carboxylat
• CAS NO: 402499-05-2
• Molecular Formula: C₁₁H₈N₂O₆S
• Molecular Weight: 296.26
• Mol File: 402499-05-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 462°C at 760 mmHg
• Flash Point: 233.2°C
• Density: 1.55g/cm³
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: ethyl 4,6-dinitrobenzothiophene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4,6-dinitrobenzothiophene-2-carboxylate(402499-05-2)
• EPA Substance Registry System: ethyl 4,6-dinitrobenzothiophene-2-carboxylate(402499-05-2)

Safety Data

• Hazardous Substances Data: 402499-05-2(Hazardous Substances Data)

Upstream product

• 285553-56-2 ethyl 3-amino-4,6-dinitrobenzo[b]thiophene-2-carboxylate 

Relevant articles and documents

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.