1,4-二乙炔基苯

1,4-二乙炔基苯
別名	對二乙炔基苯
識別
CAS號	935-14-8
PubChem	120463
ChemSpider	107543
SMILES	C#Cc1ccc(C#C)cc1;
InChI	1S/C10H6/c1-3-9-5-7-10(4-2)8-6-9/h1-2,5-8H;
InChIKey	MVLGANVFCMOJHR-UHFFFAOYSA-N
性質
化學式	C10H6
摩爾質量	126.15 g·mol−1
外觀	無色固體
密度	1.202 g/cm3（預測）
熔點	96.5 °C（205.7 °F；369.6 K）
結構
晶體結構	單斜晶系
空間群	P21/c（No. 14）
晶格常數	a = 3.887(1) Å, b = 5.931(2) Å, c = 15.114(6) Å
晶格常數	α = 90°, β = 90.84(3)°, γ = 90°
危險性
	GHS危險性符號;
H-術語	H317
P-術語	P261, P272, P280, P302+352, P333+313, P362+364
相關物質
相關化學品	苯乙炔; 1,4-二乙基苯（日語：1,4-ジエチルベンゼン）; 1,4-二乙烯基苯
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1,4-二乙炔基苯是化學式為C₁₀H₆的炔烴，外觀呈無色固體。

合成與反應[編輯]

1,4-二乙烯基苯在氯仿里溴化後會產生1,4-二(1,2-二溴乙基)苯，後者與叔丁醇鉀在叔丁醇里反應即可得到1,4-二乙炔基苯。^[1]

1,4-二乙炔基苯的氫化反應會產生1,4-二乙烯基苯。^[5]在氯化亞銅、氯化銨、氧氣存在下，1,4-二乙炔基苯可發生縮合反應，生成低聚物。其外觀為橙紅色粉末，不溶於水和有機溶劑。^[6]它還可與鎳、鈀形成配合物。^[7]

應用研究[編輯]

目前有研究將1,4-二乙炔基苯用作火箭燃料分散劑。^[8]

參考資料[編輯]

^ ^1.0 ^1.1 ^1.2 Hay, Allan. Notes- Preparation of m- and p-Diethynylbenzenes. The Journal of Organic Chemistry. 1960, 25 (4): 637–638. ISSN 0022-3263. doi:10.1021/jo01074a603.
^ Weiss, Hans-Christoph; Bläser, Dieter; Boese, Roland; Doughan, Brandon M.; Haley, Michael M. C–H···π interactions in ethynylbenzenes: the crystal structures of ethynylbenzene and 1,3,5-triethynylbenzene, and a redetermination of the structure of 1,4-diethynylbenzene. Chemical Communications. 1997, (18): 1703–1704. doi:10.1039/a704070i.
^ Weiss, H.-C.; Blaser, D.; Boese, R.; Doughan, B.M.; Haley, M.M., CCDC 740314: Experimental Crystal Structure Determination, 1998, doi:10.5517/CCSVC32
^ 來源：Sigma-Aldrich Co., 1,4-Diethynylbenzene （2024-07-13查閱）.
^ Wienhöfer, Gerrit; Westerhaus, Felix A.; Jagadeesh, Rajenahally V.; Junge, Kathrin; Junge, Henrik; Beller, Matthias. Selective iron-catalyzed transfer hydrogenation of terminal alkynes. Chemical Communications. 2012, 48 (40): 4827. ISSN 1359-7345. doi:10.1039/c2cc31091k.
^ Kotlyarevskii, I.L.; Fisher, L.B.; Dulov, A.A.; Slinkin, A.A.; Rubinshtein, A.M. The synthesis and some physical properties of poly-p-diethynylbenzene. Polymer Science U.S.S.R. 1963, 4 (1): 58–68. doi:10.1016/0032-3950(63)90544-6.
^ Ballester, L.; Cano, M.; Santos, A. New nickel(II), palladium(II) and palladium(0) derivatives of p-diethynylbenzene. Journal of Organometallic Chemistry. 1982, 229 (1): 101–107. doi:10.1016/S0022-328X(00)89121-4.
^ Yanovskii, L. S.; Lempert, D. B.; Raznoschikov, V. V.; Averkov, I. S.; Zyuzin, I. N.; Zholudev, A. F.; Kislov, M. B. Prospects for the use of diethynylbenzene as a fuel dispersant for rocket ramjet engines. Russian Chemical Bulletin. 2019, 68 (10): 1848–1855. ISSN 1066-5285. doi:10.1007/s11172-019-2634-9.

[Hay-1] 1.0 ^1.1 ^1.2 Hay, Allan. Notes- Preparation of m- and p-Diethynylbenzenes. The Journal of Organic Chemistry. 1960, 25 (4): 637–638. ISSN 0022-3263. doi:10.1021/jo01074a603.

[2] Weiss, Hans-Christoph; Bläser, Dieter; Boese, Roland; Doughan, Brandon M.; Haley, Michael M. C–H···π interactions in ethynylbenzenes: the crystal structures of ethynylbenzene and 1,3,5-triethynylbenzene, and a redetermination of the structure of 1,4-diethynylbenzene. Chemical Communications. 1997, (18): 1703–1704. doi:10.1039/a704070i.

[3] Weiss, H.-C.; Blaser, D.; Boese, R.; Doughan, B.M.; Haley, M.M., CCDC 740314: Experimental Crystal Structure Determination, 1998, doi:10.5517/CCSVC32

[4] 來源：Sigma-Aldrich Co., 1,4-Diethynylbenzene （2024-07-13查閱）.

[5] Wienhöfer, Gerrit; Westerhaus, Felix A.; Jagadeesh, Rajenahally V.; Junge, Kathrin; Junge, Henrik; Beller, Matthias. Selective iron-catalyzed transfer hydrogenation of terminal alkynes. Chemical Communications. 2012, 48 (40): 4827. ISSN 1359-7345. doi:10.1039/c2cc31091k.

[6] Kotlyarevskii, I.L.; Fisher, L.B.; Dulov, A.A.; Slinkin, A.A.; Rubinshtein, A.M. The synthesis and some physical properties of poly-p-diethynylbenzene. Polymer Science U.S.S.R. 1963, 4 (1): 58–68. doi:10.1016/0032-3950(63)90544-6.

[7] Ballester, L.; Cano, M.; Santos, A. New nickel(II), palladium(II) and palladium(0) derivatives of p-diethynylbenzene. Journal of Organometallic Chemistry. 1982, 229 (1): 101–107. doi:10.1016/S0022-328X(00)89121-4.

[8] Yanovskii, L. S.; Lempert, D. B.; Raznoschikov, V. V.; Averkov, I. S.; Zyuzin, I. N.; Zholudev, A. F.; Kislov, M. B. Prospects for the use of diethynylbenzene as a fuel dispersant for rocket ramjet engines. Russian Chemical Bulletin. 2019, 68 (10): 1848–1855. ISSN 1066-5285. doi:10.1007/s11172-019-2634-9.

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