1,4-二乙炔基苯

1,4-二乙炔基苯
别名	对二乙炔基苯
识别
CAS号	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
性质
化学式	C10H6
摩尔质量	126.15 g·mol−1
外观	无色固体
密度	1.202 g/cm3（预测）
熔点	96.5 °C（205.7 °F；369.6 K）
结构
晶体结构	单斜晶系
空间群	P21/c（No. 14）
晶格常数	a = 3.887(1) Å, b = 5.931(2) Å, c = 15.114(6) Å
晶格常数	α = 90°, β = 90.84(3)°, γ = 90°
危险性
	GHS危险性符号;
H-术语	H317
P-术语	P261, P272, P280, P302+352, P333+313, P362+364
相关物质
相关化学品	苯乙炔; 1,4-二乙基苯（日语：1,4-ジエチルベンゼン）; 1,4-二乙烯基苯
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1,4-二乙炔基苯是化学式为C₁₀H₆的炔烃，外观呈无色固体。

合成与反应

1,4-二乙烯基苯在氯仿里溴化后会产生1,4-二(1,2-二溴乙基)苯，后者与叔丁醇钾在叔丁醇里反应即可得到1,4-二乙炔基苯。^[1]

1,4-二乙炔基苯的氢化反应会产生1,4-二乙烯基苯。^[5]在氯化亚铜、氯化铵、氧气存在下，1,4-二乙炔基苯可发生缩合反应，生成低聚物。其外观为橙红色粉末，不溶于水和有机溶剂。^[6]它还可与镍、钯形成配合物。^[7]

应用研究

目前有研究将1,4-二乙炔基苯用作火箭燃料分散剂。^[8]

参考资料

^ ^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
^ 来源：Sigma-Aldrich Co., 1,4-Diethynylbenzene （2024-07-13查阅）.
^ 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] 来源：Sigma-Aldrich Co., 1,4-Diethynylbenzene （2024-07-13查阅）.

[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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