2-丁炔酸

2-丁炔酸
	IUPAC名; But-2-ynoic acid; 丁-2-炔酸
识别
CAS号	590-93-2
PubChem	68535
ChemSpider	61810
InChI	1S/C4H4O2/c1-2-3-4(5)6/h1H3,(H,5,6);
InChIKey	LUEHNHVFDCZTGL-UHFFFAOYSA-N
性质
化学式	C4H4O2
摩尔质量	84.07 g·mol−1
密度	0.9641 g/cm3
熔点	75—76 °C（348—349 K）; 77 °C（350 K）
沸点	203 °C（476 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

2-丁炔酸（英語：Tetrolic acid，2-butynoic acid）是一种不饱和羧酸，化学式C₄H₄O₂。

历史

普遍认为2-丁炔酸是由德国化学家Johann Georg Anton Geuther于1871年在研究乙酰乙酸乙酯衍生物中首次合成^[3]。

工业生产

2-丁炔酸的商业量级的生产是通过用强碱处理丙炔形成金属炔化物，然后用二氧化碳处理得到^[4]：

采用的强碱有正丁基锂^[5]和氨基钠^[6]等。

性质

2-丁炔酸在水、乙醇等极性溶液高度可溶，也可以在庚烷、己烷、甲苯等非极性溶剂中进行重结晶。其为白色晶体，并且存在两种晶型^[7]。2-丁炔酸升华温度为20 °C,因此可以在冰箱中密封保存^[8]。

其氘代二甲基亚砜（DMSO-D6）溶液的核磁共振氢谱(¹H-NMR)显示，在δ=1.99 ppm处显现出甲基氢特征峰。

加速量热仪显2-丁炔酸初始放热温度为135 °C，因此无法通过短程蒸馏进行提纯^[8]。

参考文献

^ Fleming, Ian; Ramarao, Chandrashekar. Decarboxylative elimination of enol triflates as a general synthesis of acetylenes. Org. Biomol. Chem. 2004, 2 (10): 1504-1510 [2025-04-05]. ISSN 1477-0520. doi:10.1039/B401435A （英语）.
^ Simmross, Frank-Michael; Weyerstahl, Peter. Ein einfacher Weg zu 2-Butynsäure (Tetrolsäure). Synthesis. 1981, 1981 (01): 72 [2025-04-05]. ISSN 0039-7881. doi:10.1055/s-1981-29345 （英语）.
^ Organic chemistry. Journal of the Chemical Society. 1871-01-01, 24 (0): 812-837 [2025-04-05]. ISSN 0368-1769. doi:10.1039/JS8712400808 （英语）.
^ US3752848A,Smith, W.,「Preparation of tetrolic acid」,发行于1973-08-14
^ Hartzoulakis, Basil; Gani, David. Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid. Journal of the Chemical Society, Perkin Transactions 1. 1994, (18): 2525-2531 [2025-04-05]. ISSN 0300-922X. doi:10.1039/p19940002525 （英语）.
^ (1962) "Tetrolic Acid (2-Butynoic Acid)". Org. Synth. 42: 97; Coll. Vol. 5: 1043.
^ Flakus, Henryk T.; Hachuła, Barbara. Effects of “excessive” exciton interactions in polarized IR spectra of the hydrogen bond in 2-butynoic acid crystals: Proton transfer induced by dynamical co-operative interactions involving hydrogen bonds. Chemical Physics. 2008-04-03, 345 (1): 49-64 [2025-04-05]. Bibcode:2008CP....345...49F. ISSN 0301-0104. doi:10.1016/j.chemphys.2008.01.035.
^ ^8.0 ^8.1 Ashton, Hannah; Bethel, Paul A.; Cantlie, Sarah-Kate; Churchill, Trevor; Cooper, Katie; Dobson, Benjamin; Golden, Michael; Hoyle, Mark. Thermal Stability of 2-Butynoic Acid (Tetrolic Acid). Organic Process Research & Development. 2019-05-17, 23 (5): 1101-1104 [2025-04-05]. ISSN 1083-6160. S2CID 146028375. doi:10.1021/acs.oprd.9b00106.

[1] Fleming, Ian; Ramarao, Chandrashekar. Decarboxylative elimination of enol triflates as a general synthesis of acetylenes. Org. Biomol. Chem. 2004, 2 (10): 1504-1510 [2025-04-05]. ISSN 1477-0520. doi:10.1039/B401435A （英语）.

[2] Simmross, Frank-Michael; Weyerstahl, Peter. Ein einfacher Weg zu 2-Butynsäure (Tetrolsäure). Synthesis. 1981, 1981 (01): 72 [2025-04-05]. ISSN 0039-7881. doi:10.1055/s-1981-29345 （英语）.

[3] Organic chemistry. Journal of the Chemical Society. 1871-01-01, 24 (0): 812-837 [2025-04-05]. ISSN 0368-1769. doi:10.1039/JS8712400808 （英语）.

[4] US3752848A,Smith, W.,「Preparation of tetrolic acid」,发行于1973-08-14

[5] Hartzoulakis, Basil; Gani, David. Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid. Journal of the Chemical Society, Perkin Transactions 1. 1994, (18): 2525-2531 [2025-04-05]. ISSN 0300-922X. doi:10.1039/p19940002525 （英语）.

[6] (1962) "Tetrolic Acid (2-Butynoic Acid)". Org. Synth. 42: 97; Coll. Vol. 5: 1043.

[7] Flakus, Henryk T.; Hachuła, Barbara. Effects of “excessive” exciton interactions in polarized IR spectra of the hydrogen bond in 2-butynoic acid crystals: Proton transfer induced by dynamical co-operative interactions involving hydrogen bonds. Chemical Physics. 2008-04-03, 345 (1): 49-64 [2025-04-05]. Bibcode:2008CP....345...49F. ISSN 0301-0104. doi:10.1016/j.chemphys.2008.01.035.

[stability-8] 8.0 ^8.1 Ashton, Hannah; Bethel, Paul A.; Cantlie, Sarah-Kate; Churchill, Trevor; Cooper, Katie; Dobson, Benjamin; Golden, Michael; Hoyle, Mark. Thermal Stability of 2-Butynoic Acid (Tetrolic Acid). Organic Process Research & Development. 2019-05-17, 23 (5): 1101-1104 [2025-04-05]. ISSN 1083-6160. S2CID 146028375. doi:10.1021/acs.oprd.9b00106.

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