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5-Nitroisophthalic acid

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CAS:618-88-2
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5-Nitroisophthalic acid Basic information
Uses
Product Name:5-Nitroisophthalic acid
Synonyms:NITROISOPHTHALIC-5 ACID;NITRO ISOPHTHALIC ACID;5-NIPA;5-NITRO-ISO-PHTHALIC ACID PESTANAL;1,3-BENZENEDICARBOXYLIC ACID,5-NITRO;5-NITROISOPHTHALIC ACID 99+%;5-NITROISOPHTHALIC ACID5-NITRO-PHENYL-1,3-DICARBOXYLIC ACID;5-Nitro-m-phthalic acid
CAS:618-88-2
MF:C8H5NO6
MW:211.13
EINECS:210-568-3
Product Categories:Building Blocks;C8;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Organic acids;Phthalic Acids, Esters and Derivatives;1
Mol File:618-88-2.mol
5-Nitroisophthalic acid Structure
5-Nitroisophthalic acid Chemical Properties
Melting point 259-261 °C(lit.)
Boiling point 350.79°C (rough estimate)
density 1.6342 (rough estimate)
vapor pressure 0Pa at 25℃
refractive index 1.5282 (estimate)
Fp 120°C
storage temp. Sealed in dry,Room Temperature
solubility Acetonitrile (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
form Solid
pka2.81±0.10(Predicted)
color White to Off-White
Water Solubility Soluble in water.1.5 g/L at 20°C
BRN 1976587
LogP1.1 at 25℃
CAS DataBase Reference618-88-2(CAS DataBase Reference)
EPA Substance Registry System5-Nitroisophthalic acid (618-88-2)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-40
Safety Statements 26-36-22
RIDADR 2811
WGK Germany 3
TSCA Yes
HS Code 29173990
MSDS Information
ProviderLanguage
5-Nitroisophthalic acid English
ACROS English
SigmaAldrich English
ALFA English
5-Nitroisophthalic acid Usage And Synthesis
Uses5-Nitrobenzene-1,3-Dicarboxylic Acid is used in the synthesis of Glycopyrrolate, a novel pharmaceutical compound based on PDE IV inhibitors; used in the treatment of respiratory complaints. Also used in the synthesis of coordination polymers.
Chemical PropertiesLIGHT CREAM CRYSTALLINE POWDER
Usespharmaceutical intermediate
Uses5-Nitroisophthalic acid is used as an intermediate of medicine compound and as a disperser in dyes. It is used as an intermediate in organic synthesis,agrochemical,pharmaceutical and dyestuffs etc,.
Flammability and ExplosibilityNon flammable
Synthesis
Isophthalic acid

121-91-5

5-Nitroisophthalic acid

618-88-2

The general procedure for the synthesis of 5-nitroisophthalic acid from isophthalic acid is as follows: concentrated sulfuric acid (120 mL, 2.21 mol) was added to a three-neck flask, followed by isophthalic acid (80 g, 0.48 mol). The mixture was heated to 75 °C and maintained at this temperature for 0.5 h under stirring conditions. 60% nitric acid (73.5 g, 0.70 mol) was slowly added dropwise, with the rate of acceleration of the drop being controlled to ensure completion of the drop within 2 to 2.5 hours. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 75 °C for 2 hours. Subsequently, the temperature was raised to 90 °C and the reaction continued for 1 hour. Upon completion of the reaction, the mixture was cooled to below 50 °C and 120 mL of water was slowly added dropwise. The mixture was further cooled to room temperature, filtered, and the spent acid was removed by filtration. The filter cake was washed three times with pure water to remove the wash water. Pure water (120 mL) was added to the filter cake, stirred and heated until dissolved, stirring the mixture thoroughly. Hot filtration was carried out, cooled and crystallized, and the filter cake was dried to give a white crystalline solid 5-nitroisophthalic acid (89.6 g) in 88.3% yield.

References[1] Patent: CN107721859, 2018, A. Location in patent: Paragraph 0025; 0027; 0029; 0031; 0033; 0034; 0035; 0036
[2] RSC Advances, 2016, vol. 6, # 10, p. 8495 - 8502
[3] Journal fuer Praktische Chemie (Leipzig), 1986, vol. 328, # 4, p. 497 - 514
[4] Langmuir, 2016, vol. 32, # 36, p. 9301 - 9312
[5] Acta Crystallographica Section C: Crystal Structure Communications, 1999, vol. 55, # 11, p. 1845 - 1847
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