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4-Nitrobenzoic acid

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4-Nitrobenzoic acid Basic information
Product Name:4-Nitrobenzoic acid
Synonyms:4-nitrodracylicacid;acide4-nitrobenzoique;Benzoic acid, p-nitro-;Benzoicacid,4-nitro-;Kyselina p-nitrobenzoova;kyselinap-nitrobenzoova;kyselinap-nitrobenzoova(czech);Nitrodracylic acid
CAS:62-23-7
MF:C7H5NO4
MW:167.12
EINECS:200-526-2
Product Categories:C7;Carbonyl Compounds;Carboxylic Acids;Absolute Configuration Determination (Exciton Chirality CD Method);Analytical Chemistry;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Method (for Hydroxyl Groups);Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Dyestuff Intermediates;62-23-7
Mol File:62-23-7.mol
4-Nitrobenzoic acid Structure
4-Nitrobenzoic acid Chemical Properties
Melting point 237-240 °C(lit.)
Boiling point 295.67°C (rough estimate)
density 1.61
refractive index 1.6280 (estimate)
Fp 237 °C
storage temp. Store below +30°C.
solubility 0.42g/l
pka3.41(at 25℃)
form Crystalline Powder
color Light yellow
PH3.1 (0.42g/l, H2O, 20℃)(saturated solution)
Water Solubility <0.1 g/100 mL at 26 ºC
Merck 14,6589
BRN 973593
Specific Activity50-60 mCi/mmol
Concentration0.1 mCi/ml
SolventEthanol
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, cyanides, strong bases.
InChIKeyOTLNPYWUJOZPPA-UHFFFAOYSA-N
LogP1.890
CAS DataBase Reference62-23-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 4-nitro-(62-23-7)
EPA Substance Registry Systemp-Nitrobenzoic acid (62-23-7)
Safety Information
Hazard Codes Xn
Risk Statements 22-41-36
Safety Statements 26-39-24/25
WGK Germany 1
RTECS DH5075000
TSCA Yes
HS Code 29163900
Hazardous Substances Data62-23-7(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1960 mg/kg
MSDS Information
ProviderLanguage
4-Nitrobenzoic acid English
SigmaAldrich English
ACROS English
ALFA English
4-Nitrobenzoic acid Usage And Synthesis
Chemical Propertieslight yellow crystalline powder
Uses4-Nitrobenzoic Acid is used in the synthesis of anti-Trypanosoma cruzi agents in the treatment of chagas disease.
DefinitionChEBI: A nitrobenzoic acid having the nitro group at the 4-position.
Production Methodsp-Nitrobenzoic acid is produced commercially by the oxidation of 4-nitrotoluene with molecular oxygen. Oxidation with 15 % nitric acid at 175 ℃ produces the acid in 88.5 % yield. An interesting method involves the nitration and subsequent oxidation of polystyrene. This method uses the steric hindrance of the polymer chain to improve the para to ortho ratio of the product.
Synthesis Reference(s)Tetrahedron Letters, 26, p. 2387, 1985 DOI: 10.1016/S0040-4039(00)94834-2
Journal of the American Chemical Society, 72, p. 5012, 1950 DOI: 10.1021/ja01167a051
General DescriptionOdorless pale yellow crystals.
Air & Water ReactionsInsoluble in water.
Reactivity Profilep-Nitrobenzoic acid is incompatible with strong oxidizers. p-Nitrobenzoic acid is also incompatible with strong bases (potassium hydroxide). p-Nitrobenzoic acid may react with cyanides.
Fire Hazardp-Nitrobenzoic acid is combustible.
ToxicologyAmong various nitroaromatics, 4-nitrobenzoic acid (4-NBA) is one of the simplest and basic derivates of the explosives. Moreover, 4-NBA harms human health and causes severe water and atmosphere pollution. 4-Nitrobenzoic acid is stable, toxic, and non-biodegradable. US/Zn0 was found to degrade more than 85% of 4-nitrobenzoic acid in 30 min. There was an apparent synergistic effect between ultrasound and Zn[1-2].
Purification MethodsPurify it as for 3-nitrobenzoic acid above. The amide has m 201.6o (from H2O). [Beilstein 9 III 1537, 9 IV 1072.]
References [1] Shan Chong. “Ultrasound/Zn0 for aqueous 4-nitrobenzoic acid degradation.” Desalination and Water Treatment 322 1 (2016): 24990–24998.
[2] Xue-Huan Xin . “A luminescent barium-based metal-organic framework: Synthesis, structure and efficient detection of 4-nitrobenzoic acid.” Inorganic Chemistry Communications 97 (2018): Pages 129-133.
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