1,4-萘二甲酸

1,4-萘二甲酸
英文名	1,4-Naphthalenedicarboxylic acid
別名	萘-1,4-二甲酸
識別
CAS號	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
性質
化學式	C12H8O4
摩爾質量	216.19 g·mol−1
密度	1.54 g·cm−3
熔點	325 °C（598 K）
結構
空間群	P1
晶格常數	a = 13.309, b = 9.591, c = 3.709
晶格常數	α = 97.38°, β = 80.56°, γ = 89.67°
危險性
	GHS危險性符號;
GHS提示詞	警告
H-術語	H315, H319, H335
P-術語	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1,4-萘二甲酸是一種有機化合物，化學式為C₁₂H₈O₄，它是萘二甲酸的同分異構體之一。

合成

1-甲基萘在三氯化鋁催化下和乙酰氯反應，得到1-甲基-4-乙酰基萘，它經溴化、氧化得到1-甲酰基-4-乙酰基萘，再在酸性條件下被高錳酸鉀氧化，得到1,4-萘二甲酸。^[3]它也可由1,4-二甲基萘在乙酸鈷-乙酸錳-溴化鉀催化劑的催化下被氧氣氧化^[4]，或直接由重鉻酸鈉氧化製得。^[5]以萘為原料，可先將其溴化，得到1,4-二溴萘，再於二甲基甲酰胺中和氰化亞銅反應，得到1,4-二氰基萘，它在硫酸中水解，得到1,4-萘二甲酸。^[5]

反應

1,4-萘二甲酸可以和二甲基甲酰胺在過氧化叔丁醇的存在下、氧化銅催化下於80 °C水中反應，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，和氯化亞碸回流反應，可以得到1,4-萘二甲酰氯。^[7]它在四氫呋喃中可以被氫化鋁鋰還原為1,4-萘二甲醇。^[7]它和甲醇在硫酸催化下於65 °C反應，可以得到1,4-萘二甲酸二甲酯。^[8]它和四氟化硫在氟化氫中反應，可以得到1,4-二(三氟甲基)萘。^[9]

它和金屬鹽反應，可以得到金屬有機框架材料。^[10]^[11]

參考文獻

^ ^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. （原始內容存檔於2021-08-16）（英語）.
^ Lock, G. 1-Ethyl- and 1,4-diethylnaphthalene. Monatshefte für Chemie. 1952, 83: 865-869. ISSN 0026-9247 （德語）.
^ 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. （原始內容存檔於2021-08-16）（韓語）.
^ JP 06345685,伊藤育夫, 橫田圭一, 佐藤利雄,「1,4−ナフタレンジカルボン酸の製造方法」,發表於1993-06-04,發行於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 （英語）.
^ 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 （英語）.
^ ^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 （英語）.
^ 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 （英語）.
^ 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 （英語）.
^ 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 （英語）.
^ 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 （英語）.

[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. （原始內容存檔於2021-08-16）（英語）.

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

[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. （原始內容存檔於2021-08-16）（韓語）.

[4] JP 06345685,伊藤育夫, 橫田圭一, 佐藤利雄,「1,4−ナフタレンジカルボン酸の製造方法」,發表於1993-06-04,發行於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 （英語）.

[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 （英語）.

[#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 （英語）.

[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 （英語）.

[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 （英語）.

[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 （英語）.

[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 （英語）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]