3-硝基苯甲酸

3-硝基苯甲酸是一种有机化合物，化学式为C₇H₅NO₄，它是苯甲酸苯环间位上的氢被硝基取代的产物，是硝基苯甲酸的同分异构体之一。

3-硝基苯甲酸
Skeletal formula Ball-and-stick model
IUPAC名 3-Nitrobenzoic acid
别名	间硝基苯甲酸 m-硝基苯甲酸
识别
CAS号	121-92-6
PubChem	8497
ChemSpider	8183
SMILES	O=[N+]([O-])c1cc(C(=O)O)ccc1
InChI	1/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)
InChIKey	AFPHTEQTJZKQAQ-UHFFFAOYAS
性质
化学式	C7H5NO4
摩尔质量	167.12 g·mol^−1
外观	浅黄色透明晶体^[1]
密度	1.498 g·cm^−3^[1]
熔点	140 °C（413 K）^[2]
溶解性（水）	0.24 g/100 mL（15 °C）
pKa	3.48±0.10（25 °C）^[3]
磁化率	-80.22·10^−6 cm^3/mol
相关物质
相关化学品	苯甲酸、硝基苯 2-硝基苯甲酸、4-硝基苯甲酸 3-硝基甲苯
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

制备

3-硝基苯甲酸可由苯甲酸在较低温度下的硝化反应制备，其副产物为2-硝基苯甲酸（20%）和4-硝基苯甲酸（1.5%）。^[4]苯甲酸甲酯硝化后水解也可得到3-硝基苯甲酸，但产率较低。^[5]

 

其它制备方法还包括3-硝基苯甲醇（英语：3-Nitrobenzyl alcohol）^[6]、3-硝基苯甲醛^[7]或3-硝基甲苯^[8]的氧化反应及3-硝基苯甲腈的水解反应^[9]。

反应

3-硝基苯甲酸具有酸的通性，如和氢氧化钾反应，得到3-硝基苯甲酸钾。^[10]

3-硝基苯甲酸和氯化亚砜回流反应，得到3-硝基苯甲酰氯。^[11]它和甲醇在酸催化下反应，得到3-硝基苯甲酸甲酯。^[12]它被还原剂（如氢等）还原，可以得到3-氨基苯甲酸。^[13]

参考文献

1. Dhaneshwar, N. N.; Kulkarni, A. G.; Tavale, S. S.; Pant, L. M. Crystal structure of a second modification of m-nitrobenzoic acid. Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry, 1975. B31 (7): 1978-1980. ISSN: 0567-7408. DOI: 10.1107/S0567740875006620.
2. Mayuranathan, P. S. Thermal decomposition of the mercuric and silver salts of the isomeric methyl hydrogen 3-nitrophthalates. Journal of the Chemical Society, 1957. 493-495. ISSN: 0368-1769.
3. Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02. Retrieved from SciFinder. [2020-07-13]
4. Takao Maki, Kazuo Takeda (2002). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. DOI: 10.1002/14356007.a03_555
5. Oliver Kamm and J. B. Segur. m-Nitrobenzoic Acid. Org. Synth. 1923, 3 (73).DOI: 10.15227/orgsyn.003.0073.
6. Banerjee, Amalendu; Dutt, Sachchidananda; Banerjee, Gopal Chandra; Hazra, Banasri; Datta, Hasi; Banerjee, Santanu. Studies on the oxidation of aromatic aldehydes and arylmethanols by vanadate and dichromate in dilute perchloric acid. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1990. 29B (3): 257-262. ISSN: 0376-4699.
7. Hunsen, Mo. Carboxylic acids from primary alcohols and aldehydes by a pyridinium chlorochromate-catalyzed oxidation. Synthesis, 2005, 15. 2487-2490. ISSN: 0039-7881. DOI: 10.1055/s-2005-872085
8. Yamazaki, Shigekazu. Chromium(VI) Oxide-Catalyzed Benzylic Oxidation with Periodic Acid. Organic Letters, 1999. 1 (13): 2129-2132. ISSN: 1523-7060. DOI: 10.1021/ol991175k.
9. Meth-Cohn, Otto; Wang, Mei-Xiang. An in-depth study of the biotransformation of nitriles into amides and/or acids using Rhodococcus rhodochrous AJ270. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 1997. 8. 1099-1104. ISSN: 0300-922X.
10. Rouhi-Saadabad, Hamed; Akhlaghinia, Batool. Facile and direct synthesis of symmetrical acid anhydrides using a newly prepared powerful and efficient mixed reagent. Chemical Papers, 2015. 69 (3). 479-485. ISSN: 0366-6352. DOI: 10.1515/chempap-2015-0042.
11. Xu, Yiming; Liang, Pengyun; Rashid, Haroon ur; Wu, Lichuan; Xie, Peng; Wang, Haodong; Zhang, Shuyan; Wang, Lisheng; Jiang, Jun. Design, synthesis, and biological evaluation of matrine derivatives possessing piperazine moiety as antitumor agents. Medicinal Chemistry Research, 2019. 28 (10): 1618-1627. ISSN: 1054-2523. DOI: 10.1007/s00044-019-02398-2.
12. Zaheer, Muhammad; Zia-Ur-Rehman, Muhammad; Rahman, Salma; Ahmed, Naveed; Chaudhary, Muhammad Nawaz. Microwave assisted synthesis of biologically active 4-hydroxy-N'-(phenylcarbonyl)-2H-1,2-benzothiazine-3-carbohydrazide 1,1-dioxide derivatives. Journal of the Chilean Chemical Society, 2012. 57 (4). 1492-1496. ISSN: 0717-9324. DOI: 10.4067/S0717-97072012000400031
13. Rahman, Md. Taifur; Wharry, Scott; Smyth, Megan; Manyar, Haresh; Moody, Thomas S. FAST Hydrogenations as a Continuous Platform for Green Aromatic Nitroreductions. Synlett, 2020. 31 (6). 581-586. ISSN: 0936-5214. DOI: 10.1055/s-0037-1610751.