3-Nitrobenzoic acid

3-Nitrobenzoic acid Basic information
Product Name:3-Nitrobenzoic acid
Synonyms:RARECHEM AL BO 0229;3-NITRODRACYLIC ACID;3-NITROBENZOIC ACID;LABOTEST-BB LT00795102;3-nitro-benzoicaci;Benzoic acid, m-nitro-;Benzoicacid,3-nitro-;m-NITROBENZOIC ACID extrapure AR
CAS:121-92-6
MF:C7H5NO4
MW:167.12
EINECS:204-508-5
Product Categories:Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organics;Organic acids;Dyestuff Intermediates;C7;Carbonyl Compounds;Carboxylic Acids
Mol File:121-92-6.mol
3-Nitrobenzoic acid Structure
3-Nitrobenzoic acid Chemical Properties
Melting point 139-141 °C(lit.)
Boiling point 295.67°C (rough estimate)
density 1,494 g/cm3
vapor density 5.76 (vs air)
vapor pressure 0.005Pa at 25℃
refractive index 1.6280 (estimate)
Fp 190 °C
storage temp. no restrictions.
solubility water: soluble3g/L at 25°C
form Crystals or Powder
pka3.47(at 25℃)
color Slightly green to light yellow
PH Range3
PH3 (5g/l, H2O, 20℃)(aqueous suspension)
Water Solubility <0.01 g/100 mL at 18 ºC
Merck 14,6588
BRN 908644
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyAFPHTEQTJZKQAQ-UHFFFAOYSA-N
LogP1.1 at 25℃
CAS DataBase Reference121-92-6(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 3-nitro-(121-92-6)
EPA Substance Registry Systemm-Nitrobenzoic acid (121-92-6)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37-33-36/37/38
Safety Statements 26-24/25
WGK Germany 3
RTECS DH5000000
Autoignition Temperature490 °C
Hazard Note Irritant
TSCA Yes
HS Code 29163900
Hazardous Substances Data121-92-6(Hazardous Substances Data)
MSDS Information
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3-Nitrobenzoic acid English
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3-Nitrobenzoic acid Usage And Synthesis
Chemical PropertiesWhite or light yellow monoclinic leaf-like crystal. Soluble in acetone, chloroform, ethanol and ether, slightly soluble in benzene, water, carbon disulfide and petroleum ether, more soluble in hot water. It smells like almonds. 3-nitrobenzoic acid is quite a strong acid, it is soluble in a relatively weak base. It is about ten times more acidic than benzoic acid.The conjugate base of benzoic acid is stabilised by the presence of the electron withdrawing nitro group which explains its increased acidity in comparison to unsubstituted benzoic acid.
Uses3-Nitrobenzoic acid was used to investigated the role of ozone as additional decomposition or finishing reagent in the degradation of o-, m- and p-nitobenzoic acids
Application3-Nitrobenzoic acid is an intermediate of photosensitive materials, functional pigments and drugs. In the pharmaceutical industry, it is used to produce bile acid, acetic acid and so on.
m-nitrobenzoic acid is a reagent used in the coupling of allyl acetate to allylic, aliphatic and benzylic alcohols. It is also used as a chemoattractant against Pseudomonas strains.
Preparation3-Nitrobenzoic acid is prepared by nitrating benzoic acid at low temperature. Approximately 20% of the 2-nitro isomer and 1.5% of the 4-nitro isomer are co-produced. The 3-nitrobenzoic acid can be purified by recrystallization of the sodium salt. The oxidation of 3-nitrobenzaldehyde, prepared by the controlled oxidation of benzaldehyde, gives a higher yield.
Synthesis Reference(s)Organic Syntheses, Coll. Vol. 1, p. 391, 1941
The Journal of Organic Chemistry, 46, p. 3056, 1981 DOI: 10.1021/jo00328a013
General DescriptionOff white to yellowish-white crystals. Bitter taste. Melts in hot water.
Air & Water ReactionsInsoluble in water.
Reactivity Profile3-Nitrobenzoic acid is incompatible with strong oxidizers. 3-Nitrobenzoic acid is also incompatible with strong bases. 3-Nitrobenzoic acid may react with cyanides.
Fire HazardFlash point data for 3-Nitrobenzoic acid are not available but 3-Nitrobenzoic acid is probably combustible.
Flammability and ExplosibilityNonflammable
Purification MethodsCrystallise the acid from *benzene, H2O, EtOH (charcoal), glacial acetic acid or MeOH/H2O. Dry and store it in a vacuum desiccator. The amide has m 143o (from H2O or *C6H6). [Beilstein 9 III 1489, 9 IV 1055.]
4-(4-METHYLPIPERAZIN-1-YL)-3-NITROBENZOIC ACID 4-[(4-CHLOROPHENYL)THIO]-3-NITROBENZOIC ACID 4-ANILINO-3-NITROBENZOIC ACID Ethyl 2-(Chlorosulfonyl)acetate 4-BROMO-5-FLUORO-2-NITROBENZOIC ACID 4-[3-(ETHOXYCARBONYL)PIPERIDIN-1-YL]-3-NITROBENZOIC ACID Ascoric Acid 2[(2-AMINOETHYL)AMINO]-3-NITROBENZOIC ACID ETHYLENEDIAMINE TETRAKIS(PROPOXYLATE-BLOCK-ETHOXYLATE) TETROL 3-NITROBENZOIC ACID, [RING-14C(U)] Diphenolic acid 4-[(2,5-DICHLOROPHENYL)SULFONYL]-3-NITROBENZOIC ACID 5-Chlorovaleric acid 4-(BOC-PIPERAZIN-1-YL)-3-NITROBENZOIC ACID 4-BROMO-3-NITROBENZOIC ACID 3-IODO-5-NITROBENZOIC ACID 3-METHOXY-2-NITROBENZOIC ACID METHYL ESTER 3-NITROBENZOIC ACID SODIUM SALT

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