4-碘苯甲酸

4-碘苯甲酸
英文名	4-iodobenzoic acid
別名	對碘苯甲酸
識別
CAS號	619-58-9
PubChem	12085
SMILES	C1=CC(=CC=C1C(=O)O)I;
InChIKey	GHICCUXQJBDNRN-UHFFFAOYSA-N
性質
化學式	C7H5IO2
莫耳質量	248.02 g·mol⁻¹
外觀	白色固體
密度	1.999±0.06 g·cm−3
熔點	269—270 °C（542—543 K）
溶解性	可溶於丙酮
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

4-碘苯甲酸是一種有機化合物，化學式為C₇H₅IO₂，它是2-碘苯甲酸和3-碘苯甲酸（葡萄牙語：Ácido 3-iodobenzoico）的同分異構體。

合成

4-碘苯甲酸可以通過重氮化反應來製備：^[1]

也可由碘在二甲基亞碸中於60 °C氧化4-肼基苯甲酸鹽酸鹽得到：^[3]

乙酸碘(I)直接氧化苯甲酸，也會生成4-碘苯甲酸。^[4]

其它的合成方法還包括碘和對氯汞苯甲酸的反應等。^[5]

結構及性質

4-碘苯甲酸和其它4-鹵苯甲酸同構，屬單斜晶系P2₁/n空間群，在固相以二聚體的形式存在。^[2]

4-碘苯甲酸可以發生Suzuki反應，如和苯硼酸反應在鈀催化劑的存在下，生成聯苯-4-甲酸。^[6]它也能發生羧酸的特徵反應，如和甲醇反應，生成4-碘苯甲酸甲酯；^[7]和氯化亞碸回流反應，得到4-碘苯甲醯氯。^[8]

它可以和Mn²⁺、Co²⁺和Ni²⁺等金屬離子形成配合物。^[9]

參考文獻

^ ^1.0 ^1.1 Gorlushko, Dmitry A.; Filimonov, Victor D.; Krasnokutskaya, Elena A.; Semenischeva, Nadya I.; Go, Bong Seong; Hwang, Ho Yun; Cha, Eun Hye; Chi, Ki-Whan. Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates. Tetrahedron Letters. 2008, 49 (6): 1080–1082. ISSN 0040-4039. doi:10.1016/j.tetlet.2007.11.192. Supplementary data (doc)
^ ^2.0 ^2.1 Nygren, Cara L.; Wilson, Chick C.; Turner, John F. C. On the Solid State Structure of 4-Iodobenzoic Acid. The Journal of Physical Chemistry A. 2005, 109 (11): 2586–2593. ISSN 1089-5639. doi:10.1021/jp047189b.
^ Dong, Chun-ping; Nakamura, Kentaro; Taniguchi, Toshihide; Mita, Soichiro; Kodama, Shintaro; Kawaguchi, Shin-ichi; Nomoto, Akihiro; Ogawa, Akiya; Mizuno, Takumi. Synthesis of Aryl Iodides from Arylhydrazines and Iodine. ACS Omega. 2018, 3 (8): 9814–9821. ISSN 2470-1343. doi:10.1021/acsomega.8b01559.
^ Giri, Ramesh; Yu, Jin-Quan. Iodine monoacetate. e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd., 2008. pp 1-10. CODEN: 69KUHI. ISBN 978-0-470-84289-8
^ Frank C. Whitmore and Gladys E. Woodward. p-IODOBENZOIC ACID [Benzoic acid, p-iodo-] （頁面存檔備份，存於網際網路檔案館）. Org. Synth. 1927, 7, 58. doi:10.15227/orgsyn.007.0058
^ Jebali, Zayneb; Granados, Albert; Nabili, Abdelkader; Boufi, Sami; do Rego, Ana Maria B.; Majdoub, Hatem; Vallribera, Adelina. Cationic cellulose nanofibrils as a green support of palladium nanoparticles: catalyst evaluation in Suzuki reactions. Cellulose. 2018, 25 (12): 6963–6975. ISSN 0969-0239. doi:10.1007/s10570-018-2085-8.
^ Chisholm, David R.; Tomlinson, Charles W. E.; Zhou, Garr-Layy; Holden, Claire; Affleck, Valerie; Lamb, Rebecca; Newling, Katherine; Ashton, Peter; Valentine, Roy; Redfern, Christopher; Erostyák, János; Makkai, Geza; Ambler, Carrie A.; Whiting, Andrew; Pohl, Ehmke. Fluorescent Retinoic Acid Analogues as Probes for Biochemical and Intracellular Characterization of Retinoid Signaling Pathways. ACS Chemical Biology. 2019, 14 (3): 369–377. ISSN 1554-8929. doi:10.1021/acschembio.8b00916.
^ Wang, Qun; Liu, Long; Dong, Jianyu; Tian, Zhibin; Chen, Tieqiao. Metal-free thioesterification of amides generating acyl thioesters. New Journal of Chemistry. 2019, 43 (24): 9384–9388. ISSN 1144-0546. doi:10.1039/C9NJ01748H.
^ Churagov, F. M.; Gambarov, D. G.; Mamedov, Kh. S. Several properties and structure of manganese(II), cobalt(II) and nickel(II) complexes with p-derivatives of benzoic acid. Koordinatsionnaya Khimiya, 1991. 17 (10): 1404-1411. ISSN: 0132-344X.

拓展閱讀

Grineva, Olga V.; Zorky, Petr M.; Rostov, Evgenij S. Crystal structures of monohalogenated benzoic acids. Structural Chemistry. 2007, 18 (4): 443–448. ISSN 1040-0400. doi:10.1007/s11224-007-9161-2.
Lewandowski, W.; Barańska, H.; Mościbroda, P.; Dasiewicz, B. Effects of halogens on the aromatic system of benzoic acid. Journal of Molecular Structure. 1993, 293: 89–92. ISSN 0022-2860. doi:10.1016/0022-2860(93)80022-N.

[Gorlushko-1] 1.0 ^1.1 Gorlushko, Dmitry A.; Filimonov, Victor D.; Krasnokutskaya, Elena A.; Semenischeva, Nadya I.; Go, Bong Seong; Hwang, Ho Yun; Cha, Eun Hye; Chi, Ki-Whan. Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates. Tetrahedron Letters. 2008, 49 (6): 1080–1082. ISSN 0040-4039. doi:10.1016/j.tetlet.2007.11.192. Supplementary data (doc)

[Nygren-2] 2.0 ^2.1 Nygren, Cara L.; Wilson, Chick C.; Turner, John F. C. On the Solid State Structure of 4-Iodobenzoic Acid. The Journal of Physical Chemistry A. 2005, 109 (11): 2586–2593. ISSN 1089-5639. doi:10.1021/jp047189b.

[3] Dong, Chun-ping; Nakamura, Kentaro; Taniguchi, Toshihide; Mita, Soichiro; Kodama, Shintaro; Kawaguchi, Shin-ichi; Nomoto, Akihiro; Ogawa, Akiya; Mizuno, Takumi. Synthesis of Aryl Iodides from Arylhydrazines and Iodine. ACS Omega. 2018, 3 (8): 9814–9821. ISSN 2470-1343. doi:10.1021/acsomega.8b01559.

[4] Giri, Ramesh; Yu, Jin-Quan. Iodine monoacetate. e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd., 2008. pp 1-10. CODEN: 69KUHI. ISBN 978-0-470-84289-8

[5] Frank C. Whitmore and Gladys E. Woodward. p-IODOBENZOIC ACID [Benzoic acid, p-iodo-] （頁面存檔備份，存於網際網路檔案館）. Org. Synth. 1927, 7, 58. doi:10.15227/orgsyn.007.0058

[6] Jebali, Zayneb; Granados, Albert; Nabili, Abdelkader; Boufi, Sami; do Rego, Ana Maria B.; Majdoub, Hatem; Vallribera, Adelina. Cationic cellulose nanofibrils as a green support of palladium nanoparticles: catalyst evaluation in Suzuki reactions. Cellulose. 2018, 25 (12): 6963–6975. ISSN 0969-0239. doi:10.1007/s10570-018-2085-8.

[7] Chisholm, David R.; Tomlinson, Charles W. E.; Zhou, Garr-Layy; Holden, Claire; Affleck, Valerie; Lamb, Rebecca; Newling, Katherine; Ashton, Peter; Valentine, Roy; Redfern, Christopher; Erostyák, János; Makkai, Geza; Ambler, Carrie A.; Whiting, Andrew; Pohl, Ehmke. Fluorescent Retinoic Acid Analogues as Probes for Biochemical and Intracellular Characterization of Retinoid Signaling Pathways. ACS Chemical Biology. 2019, 14 (3): 369–377. ISSN 1554-8929. doi:10.1021/acschembio.8b00916.

[8] Wang, Qun; Liu, Long; Dong, Jianyu; Tian, Zhibin; Chen, Tieqiao. Metal-free thioesterification of amides generating acyl thioesters. New Journal of Chemistry. 2019, 43 (24): 9384–9388. ISSN 1144-0546. doi:10.1039/C9NJ01748H.

[9] Churagov, F. M.; Gambarov, D. G.; Mamedov, Kh. S. Several properties and structure of manganese(II), cobalt(II) and nickel(II) complexes with p-derivatives of benzoic acid. Koordinatsionnaya Khimiya, 1991. 17 (10): 1404-1411. ISSN: 0132-344X.

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