1,4-萘二甲酸

1,4-萘二甲酸
英文名	1,4-Naphthalenedicarboxylic acid
别名	萘-1,4-二甲酸
识别
CAS号	605-70-9
PubChem	69065
SMILES	C1=CC=C2C(=C1)C(=CC=C2C(=O)O)C(=O)O;
InChI	1S/C12H8O4/c13-11(14)9-5-6-10(12(15)16)8-4-2-1-3-7(8)9/h1-6H,(H,13,14)(H,15,16);
InChIKey	ABMFBCRYHDZLRD-UHFFFAOYSA-N
性质
化学式	C12H8O4
摩尔质量	216.19 g·mol−1
密度	1.54 g·cm−3
熔点	325 °C（598 K）
结构
空间群	P1
晶格常数	a = 13.309, b = 9.591, c = 3.709
晶格常数	α = 97.38°, β = 80.56°, γ = 89.67°
危险性
	GHS危险性符号;
GHS提示词	警告
H-术语	H315, H319, H335
P-术语	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1,4-萘二甲酸是一种有机化合物，化学式为C₁₂H₈O₄，它是萘二甲酸的同分异构体之一。

合成

1-甲基萘在三氯化铝催化下和乙酰氯反应，得到1-甲基-4-乙酰基萘，它经溴化、氧化得到1-甲酰基-4-乙酰基萘，再在酸性条件下被高锰酸钾氧化，得到1,4-萘二甲酸。^[3]它也可由1,4-二甲基萘在乙酸钴-乙酸锰-溴化钾催化剂的催化下被氧气氧化^[4]，或直接由重铬酸钠氧化制得。^[5]以萘为原料，可先将其溴化，得到1,4-二溴萘，再于二甲基甲酰胺中和氰化亚铜反应，得到1,4-二氰基萘，它在硫酸中水解，得到1,4-萘二甲酸。^[5]

反应

1,4-萘二甲酸可以和二甲基甲酰胺在过氧化叔丁醇的存在下、氧化铜催化下于80 °C水中反应，得到N,N,N',N'-四甲基萘-1,4-二甲酰胺。^[6]

1,4-萘二甲酸在二甲基甲酰胺催化下，和氯化亚砜回流反应，可以得到1,4-萘二甲酰氯。^[7]它在四氢呋喃中可以被氢化铝锂还原为1,4-萘二甲醇。^[7]它和甲醇在硫酸催化下于65 °C反应，可以得到1,4-萘二甲酸二甲酯。^[8]它和四氟化硫在氟化氢中反应，可以得到1,4-二(三氟甲基)萘。^[9]

它和金属盐反应，可以得到金属有机框架材料。^[10]^[11]

参考文献

^ ^1.0 ^1.1 Derissen, J. L.; Timmermans, C.; Schoone, J. C. 1,4-Naphthalenedicarboxylic acid, C₁₂H₈O₄. Crystal Structure Communications. 1979, 8 (3): 533-536 [2021-08-16]. ISSN 0302-1742. （原始内容存档于2021-08-16）（英语）.
^ Lock, G. 1-Ethyl- and 1,4-diethylnaphthalene. Monatshefte für Chemie. 1952, 83: 865-869. ISSN 0026-9247 （德语）.
^ 嚴星一, 姜龍漢, 咸慶宇, 梁正信, 李潤坤. Napthalene-1,4-dicarboxylic acid의 새로운 합성법에 관한 연구. 대한화학회지. 2000, 44 (2): 170-172 [2021-08-16]. ISSN 1017-2548. （原始内容存档于2021-08-16）（韩语）.
^ JP 06345685,伊藤育夫, 横田圭一, 佐藤利雄,「1,4−ナフタレンジカルボン酸の製造方法」,发表于1993-06-04,发行于1994-12-20
^ ^5.0 ^5.1 Balaban, Alexandru T.; Schiketanz, Iosif; Gheorghiu, Mircea D.; Schiketanz, Ana. Aminoketone and oxazole synthesis. IX. 2,2'-(p-Phenylene)-bis-(5-aryloxazoles) and 2,2'-(1,4-naphthalenediyl)-bis-(5-aryloxazoles) via acylaminoacylation of aromatic hydrocarbons. Revue Roumaine de Chimie. 1985, 30 (11-12): 977-984. ISSN 0035-3930 （英语）.
^ Mohammad, Akbar; Chandra, Prakash; Ghosh, Topi; Carraro, Mauro; Mobin, Shaikh M. Facile Access to Amides from Oxygenated or Unsaturated Organic Compounds by Metal Oxide Nanocatalysts Derived from Single-Source Molecular Precursors. Inorganic Chemistry (American Chemical Society (ACS)). 2017-08-21, 56 (17): 10596–10608. ISSN 0020-1669. doi:10.1021/acs.inorgchem.7b01576 （英语）.
^ ^7.0 ^7.1 Kang, Mei Ting; Meng, Miao; Tan, Ying Ning; Cheng, Tao; Liu, Chun Y. Tuning the Electronic Coupling and Electron Transfer in Mo2Donor-Acceptor Systems by Variation of the Bridge Conformation. Chemistry - A European Journal (Wiley). 2016-01-25, 22 (9): 3115–3126. ISSN 0947-6539. doi:10.1002/chem.201504033 （英语）.
^ Vailonis, Kristina M.; Gnanasekaran, Karthikeyan; Powers, Xian B.; Gianneschi, Nathan C.; Jenkins, David M. Elucidating the Growth of Metal–Organic Nanotubes Combining Isoreticular Synthesis with Liquid-Cell Transmission Electron Microscopy. Journal of the American Chemical Society (American Chemical Society (ACS)). 2019-06-24, 141 (26): 10177–10182. ISSN 0002-7863. doi:10.1021/jacs.9b04586 （英语）.
^ Wang, Chia-Lin J. Fluorination by Sulfur Tetrafluoride. Organic Reactions. Hoboken, NJ, USA: John Wiley & Sons, Inc. 1985-02-20: 319–400. doi:10.1002/0471264180.or034.02 （英语）.
^ Rabe, Timo; Pewe, Harm; Reinsch, Helge; Willhammar, Tom; Svensson Grape, Erik; Stock, Norbert. Influence of the substitution pattern of four naphthalenedicarboxylic acids on the structures and properties of group 13 metal–organic frameworks and coordination polymers. Dalton Transactions (Royal Society of Chemistry (RSC)). 2020, 49 (15): 4861–4868. ISSN 1477-9226. doi:10.1039/d0dt00387e （英语）.
^ Kanoo, Prakash; Gurunatha, K. L.; Maji, Tapas Kumar. Versatile functionalities in MOFs assembled from the same building units: interplay of structural flexibility, rigidity and regularity. J. Mater. Chem. (Royal Society of Chemistry (RSC)). 2010, 20 (7): 1322–1331. ISSN 0959-9428. doi:10.1039/b917029d （英语）.

[crystal-1] 1.0 ^1.1 Derissen, J. L.; Timmermans, C.; Schoone, J. C. 1,4-Naphthalenedicarboxylic acid, C₁₂H₈O₄. Crystal Structure Communications. 1979, 8 (3): 533-536 [2021-08-16]. ISSN 0302-1742. （原始内容存档于2021-08-16）（英语）.

[2] Lock, G. 1-Ethyl- and 1,4-diethylnaphthalene. Monatshefte für Chemie. 1952, 83: 865-869. ISSN 0026-9247 （德语）.

[3] 嚴星一, 姜龍漢, 咸慶宇, 梁正信, 李潤坤. Napthalene-1,4-dicarboxylic acid의 새로운 합성법에 관한 연구. 대한화학회지. 2000, 44 (2): 170-172 [2021-08-16]. ISSN 1017-2548. （原始内容存档于2021-08-16）（韩语）.

[4] JP 06345685,伊藤育夫, 横田圭一, 佐藤利雄,「1,4−ナフタレンジカルボン酸の製造方法」,发表于1993-06-04,发行于1994-12-20

[RevRoumChim-5] 5.0 ^5.1 Balaban, Alexandru T.; Schiketanz, Iosif; Gheorghiu, Mircea D.; Schiketanz, Ana. Aminoketone and oxazole synthesis. IX. 2,2'-(p-Phenylene)-bis-(5-aryloxazoles) and 2,2'-(1,4-naphthalenediyl)-bis-(5-aryloxazoles) via acylaminoacylation of aromatic hydrocarbons. Revue Roumaine de Chimie. 1985, 30 (11-12): 977-984. ISSN 0035-3930 （英语）.

[6] Mohammad, Akbar; Chandra, Prakash; Ghosh, Topi; Carraro, Mauro; Mobin, Shaikh M. Facile Access to Amides from Oxygenated or Unsaturated Organic Compounds by Metal Oxide Nanocatalysts Derived from Single-Source Molecular Precursors. Inorganic Chemistry (American Chemical Society (ACS)). 2017-08-21, 56 (17): 10596–10608. ISSN 0020-1669. doi:10.1021/acs.inorgchem.7b01576 （英语）.

[#1-7] 7.0 ^7.1 Kang, Mei Ting; Meng, Miao; Tan, Ying Ning; Cheng, Tao; Liu, Chun Y. Tuning the Electronic Coupling and Electron Transfer in Mo2Donor-Acceptor Systems by Variation of the Bridge Conformation. Chemistry - A European Journal (Wiley). 2016-01-25, 22 (9): 3115–3126. ISSN 0947-6539. doi:10.1002/chem.201504033 （英语）.

[8] Vailonis, Kristina M.; Gnanasekaran, Karthikeyan; Powers, Xian B.; Gianneschi, Nathan C.; Jenkins, David M. Elucidating the Growth of Metal–Organic Nanotubes Combining Isoreticular Synthesis with Liquid-Cell Transmission Electron Microscopy. Journal of the American Chemical Society (American Chemical Society (ACS)). 2019-06-24, 141 (26): 10177–10182. ISSN 0002-7863. doi:10.1021/jacs.9b04586 （英语）.

[9] Wang, Chia-Lin J. Fluorination by Sulfur Tetrafluoride. Organic Reactions. Hoboken, NJ, USA: John Wiley & Sons, Inc. 1985-02-20: 319–400. doi:10.1002/0471264180.or034.02 （英语）.

[10] Rabe, Timo; Pewe, Harm; Reinsch, Helge; Willhammar, Tom; Svensson Grape, Erik; Stock, Norbert. Influence of the substitution pattern of four naphthalenedicarboxylic acids on the structures and properties of group 13 metal–organic frameworks and coordination polymers. Dalton Transactions (Royal Society of Chemistry (RSC)). 2020, 49 (15): 4861–4868. ISSN 1477-9226. doi:10.1039/d0dt00387e （英语）.

[11] Kanoo, Prakash; Gurunatha, K. L.; Maji, Tapas Kumar. Versatile functionalities in MOFs assembled from the same building units: interplay of structural flexibility, rigidity and regularity. J. Mater. Chem. (Royal Society of Chemistry (RSC)). 2010, 20 (7): 1322–1331. ISSN 0959-9428. doi:10.1039/b917029d （英语）.

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