552-16-9 Usage
Description
2-Nitrobenzoic acid, also known as ChEBI, is a nitrobenzoic acid derivative with the nitro substituent at the 2nd position. It is characterized by its yellowish-white crystalline appearance and an intensely sweet taste. This organic compound is known for its chemical properties as an off-white powder.
Uses
Used in Chemical Synthesis:
2-Nitrobenzoic acid is used as a reagent in the synthesis of various organic compounds. It plays a crucial role in the production of novel triazoles and a tetrazole of escitalopram, which are known to act as cholinesterase inhibitors. Additionally, it is utilized in the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles, contributing to the development of new chemical entities with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Nitrobenzoic acid serves as an NH2-protecting reagent. This application is essential for the synthesis of certain drugs and pharmaceutical compounds, where the protection of the amine group is necessary to prevent unwanted reactions during the synthesis process. The use of 2-Nitrobenzoic acid as a protecting reagent ensures the successful synthesis of target molecules with desired properties and functionalities.
Synthesis Reference(s)
The Journal of Organic Chemistry, 56, p. 5924, 1991 DOI: 10.1021/jo00020a040Tetrahedron Letters, 35, p. 219, 1994 DOI: 10.1016/S0040-4039(00)76515-4
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2-Nitrobenzoic acid is incompatible with strong oxidizing agents. Also incompatible with strong bases. May react with cyanides .
Health Hazard
ACUTE/CHRONIC HAZARDS: When 2-Nitrobenzoic acid is heated to decomposition it emits very toxic fumes.
Fire Hazard
Flash point data concerning 2-Nitrobenzoic acid are not available, however, 2-Nitrobenzoic acid is probably combustible.
Purification Methods
Crystallise the acid from *benzene (twice), n-butyl ether (twice), then water (twice). Dry and store it in a vacuum desiccator. [Le Noble & Wheland J Am Chem Soc 80 5397 1958.] It has also been crystallised from EtOH/H2O. The amide has m 176.5o (from H2O). [Beilstein 9 III 1466, 9 IV 1046.]
Check Digit Verification of cas no
The CAS Registry Mumber 552-16-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 2 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 552-16:
(5*5)+(4*5)+(3*2)+(2*1)+(1*6)=59
59 % 10 = 9
So 552-16-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)/p-1
552-16-9Relevant articles and documents
Direct C–H Carboxylation Forming Polyfunctionalized Aromatic Carboxylic Acids by Combined Br?nsted Bases
Hanasaka, Kazuya,Izumi, Koki,Kondo, Yoshinori,Kwon, Eunsang,Nozawa-Kumada, Kanako,Shigeno, Masanori,Tohara, Itsuki,Yamakoshi, Hiroyuki
supporting information, p. 809 - 814 (2022/02/05)
CO2 fixation into electron-deficient aromatic C–H bonds proceeds with the combined Br?nsted bases LiO-t-Bu and LiO-t-Am/CsF/18-crown-6 (t-Am = CEtMe2) under a CO2 atmosphere to afford a variety of polyfunctionalized aromat
Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives
Bernard, Josephine,Capilato, Joseph N.,Hoy, Erik P.,Mattiucci, Joseph,Pellegrinelli, Peter J.,Perez, Lark J.,Philippi, Shane,Schnorbus, Logan
, p. 5298 - 5302 (2021/06/30)
The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.
Continuous production method of benzoic acid derivative
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Paragraph 0032-0034, (2021/11/14)
The invention relates to the technical field of preparation of benzoic acid derivatives. The invention particularly relates to a continuous production method of a benzoic acid derivative. The continuous reaction device is characterized by comprising a small-diameter sleeve, wherein the small-diameter sleeve is sleeved with a large-diameter sleeve, and a small pipeline is arranged between the small-diameter sleeve and the large-diameter sleeve, and a plurality of small holes are arranged on the small pipeline. The small-diameter casing is rotated, the large-diameter casing is fixed, and the reaction liquid composed of the nitric acid and the toluene derivative is between a small-diameter casing pipe and a large-diameter casing pipe.