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3-硝基苯甲酸

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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  checkY
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 cm3/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。

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。

制备

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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

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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

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  1. ^ 1.0 1.1 Dhaneshwar, N. N.; Kulkarni, A. G.; Tavale, S. S.; Pant, L. M. The crystal structure of a second modification of m -nitrobenzoic acid. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 1975-07-01, 31 (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. ^ Ullmann's Encyclopedia of Industrial Chemistry. Wiley. 2000-06-15. ISBN 978-3-527-30385-4. doi:10.1002/14356007.a03_555. 
  5. ^ m-NITROBENZOIC ACID. Organic Syntheses. 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. 2005-07-20, 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. 2015-01-01, 69 (3). ISSN 1336-9075. 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 0717-9707. 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 (06): 581–586. ISSN 0936-5214. doi:10.1055/s-0037-1610751. 
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