14289-24-8

Basic information

• Product Name: 5-nitrothiophen-2-ylmethylene diacetate
• Synonyms: 5-nitrothiophen-2-ylmethylene diacetate;(5-Nitro-2-thienyl)methanediol diacetate;2-(Diacetoxymethyl)-5-nitrothiophene;5-Nitro-2-thenylidene diacetate;Diacetic acid 5-nitro-2-thenylidene ester;(5-nitro-2-thienyl)methylene diacetate
• CAS NO: 14289-24-8
• Molecular Formula: C₉H₉NO₆S
• Molecular Weight: 259.23586
• EINECS: 238-211-7
• Mol File: 14289-24-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 72-73 °C
• Boiling Point: 372.4°Cat760mmHg
• Flash Point: 179°C
• Appearance: /
• Density: 1.433g/cm³
• Vapor Pressure: 9.62E-06mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 5-nitrothiophen-2-ylmethylene diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-nitrothiophen-2-ylmethylene diacetate(14289-24-8)
• EPA Substance Registry System: 5-nitrothiophen-2-ylmethylene diacetate(14289-24-8)

Safety Data

• Hazardous Substances Data: 14289-24-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H9NO6S/c1-5(11)15-9(16-6(2)12)7-3-4-8(17-7)10(13)14/h3-4,9H,1-2H3

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 108-24-7 acetic anhydride 
• 63011-97-2 2-thiophenecarboxaldehyde diacetate 
• 7697-37-2 nitric acid 

Downstream Products

• 167106-56-1 2,3-Dibromo-3-(5-nitro-thiophen-2-yl)-1-phenyl-propan-1-one 
• 167106-60-7 3-(5-Nitro-thiophen-2-yl)-1-phenyl-propynone 
• 167106-61-8 3-(5-Nitro-thiophen-2-yl)-1-p-tolyl-propynone 
• 167106-64-1 (Z)-2-Bromo-3-(5-nitro-thiophen-2-yl)-1-phenyl-propenone 
• 167106-62-9 1-(4-Chloro-phenyl)-3-(5-nitro-thiophen-2-yl)-propynone 
• 167106-63-0 1-(4-Methoxy-phenyl)-3-(5-nitro-thiophen-2-yl)-propynone 
• 167106-57-2 2,3-Dibromo-3-(5-nitro-thiophen-2-yl)-1-p-tolyl-propan-1-one 
• 167106-59-4 2,3-Dibromo-1-(4-methoxy-phenyl)-3-(5-nitro-thiophen-2-yl)-propan-1-one 

Relevant articles and documents

NITRO DERIVATIVES OF THE THIOPHENE SERIES. 4. NITRATION OF THIOPHENE DERIVATIVES WITH METAL NITRATES IN ACETIC ANHYDRIDE

The nitration of 2-formylthiophene, 2-acetothienone, and unsaturated ketones of the thiophene series with copper and aluminum nitrates in acetic anhydride at various temperatures was studied.At low temperatures 2-acetothienone gives a mixture of 4- and 5-nitro isomers, while 2-formylthiphene gives only a 5-nitro-substituted compound in the diacetate form; α,β-unsaturated ketones are not nitrated under these conditions.When the reaction is carried out at 70-90 degC, one can obtain mixtures of nitro ketones in the case of unsaturated ketones; 2-formylthiophene is oxidized to thiophene-2-carboxylic acid, while 2-acetothienone gives a substance, the structure of which could not be established.The reaction of copper and aluminum nitrates with acetic anhydride was investigated by means of thermal and X-ray diffraction analysis.It is shown that the reaction is accompanied by the formation of free nitric acid, and the nitrating agent in these mixtures is consequently the nitronium cation.

Synthesis method of 5-nitrothiophene-2-formaldehyde

The invention relates to the technical field of chemistry, in particular to a synthesis method of 5-nitrothiophene-2-formaldehyde. The method comprises the steps of mixing 2-thiophenecarboxaldehyde and acetic anhydride, carrying out nucleophilic addition reaction to generate (acetyloxy) (2-thiophene) methyl acetate, and adding a nitrating agent to carry out nitration reaction to prepare 5-nitrothiophene-2-yl methylene diacetate; and carrying out a hydrolysis reaction on the obtained 5-nitrothiophene-2-yl methylene diacetate in a solvent to prepare 5-nitrothiophene-2-formaldehyde. The method has the beneficial effects that (1) cheap and easily available raw materials are used, the process is simple, the production cost is low, and the method is suitable for industrial production; and (2) the total yield and the total purity of the product are high.