1-萘硫酚
| 1-萘硫酚 | |
|---|---|
| |
| IUPAC名 Naphthalene-1-thiol | |
| 别名 | 1-巯基萘 1-硫代萘酚 |
| 识别 | |
| CAS号 | 529-36-2 |
| PubChem | 68259 |
| ChemSpider | 61557 |
| SMILES |
|
| 性质 | |
| 化学式 | C10H8S |
| 摩尔质量 | 160.23 g·mol⁻¹ |
| 外观 | 无色油状液体 |
| 密度 | 1.189 g/mL（20 °C）[1] |
| 熔点 | 15 °C（288 K）[2] |
| 沸点 | 285 °C（558 K）[3] |
| 危险性 | |
GHS危险性符号
| |
| GHS提示词 | 警告 |
| H-术语 | H302 |
| P-术语 | P264, P270, P301+312, P330, P501 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
1-萘硫酚是一种有机硫化合物，化学式为C10H8S。它的另一种同分异构体是2-萘硫酚。
合成
1-萘硫酚可由1-碘萘和硫酸铜、过量的乙二硫醇在碱性条件下反应得到，也可以九水合硫化钠作为硫源，在铜和乙二硫醇的催化下反应制得。[4]
1-萘酚二硫化物用铟/氯化铵在乙醇中回流，可以将其还原为1-萘硫酚。[5]1-萘磺酰氯在1,2-二氯乙烷中与二甲基二氯硅烷和N,N-二甲基乙酰胺反应，经锌还原，也能得到1-萘硫酚，副产物二硫化物仅占痕量。[6]其它方法还有1-溴萘和甲硫醇钠反应、[7]1-氯萘在600 °C和硫化氢反应[8]等。
性质
1-萘硫酚的化学性质体现在其巯基上，如在碱性条件下和有机卤化物反应生成硫醚。如碱为氢氧化钠时，和2-氯乙醇反应，生成2-(1-萘硫基)乙醇；[9]碱使用碳酸钠，在N,N-二甲基甲酰胺中和溴化苄反应，生成1-萘基苄基硫醚；[10]和邻二卤苯反应则发生成环反应。[11]它和4-二甲氨基苯基氯化锌发生偶联反应，脱硫后生成N,N-二甲基-4-(1-萘基)苯胺。[12]
参考文献
- ^ Kuliev, A. M.; Arabova, A. S.; Mamedova, Z. A. Synthesis of alkylnaphthalenethiols. Uchenye Zapiski Azerbaidzhanskogo Gosudarstvennogo Universiteta, Seriya Khimicheskikh Nauk, 1964. 4: 35-38. CODEN: UAKKAU. ISSN: 0408-2508.
- ^ Palmer, Keith W. Hydroxy aryl mercapto compounds and processes for preparing the same （页面存档备份，存于互联网档案馆） [P]. US 2004728. 1935. CAN29: 39399.
- ^ Taboury, F. Contribution to the Study of Sulphur and Selenium Compounds of the Aromatic Series. Annales de Chimie et de Physique, 1908. 15: 5-66. CODEN: ACPHAA. ISSN: 0365-1444.
- ^ Liu, Yajun; Chae, Junghyun; Xue, Hongyu; Jing, Bing; Liu, Shasha. Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol. Synlett. 2017, 28 (17): 2272–2276. ISSN 0936-5214. doi:10.1055/s-0036-1588482.
- ^ Reddy, G. Vidya Sagar; Rao, G. Venkat; Iyengar, D. S. A Novel, Practical and Highly Chemoselective Methodology for Reduction of Disulphides to Thiols. Synthetic Communications. 2000, 30 (5): 859–862. ISSN 0039-7911. doi:10.1080/00397910008087097.
- ^ Uchiro, Hiromi; Kobayashi, Susumu. Non-aqueous reduction of aromatic sulfonyl chlorides to thiols using a dichlorodimethylsilane-zinc-dimethylacetamide system. Tetrahedron Letters. 1999, 40 (16): 3179–3182. ISSN 0040-4039. doi:10.1016/S0040-4039(99)00408-6.
- ^ Testaferri, L.; Tingoli, M.; Tiecco, M. A convenient synthesis of aromatic thiols from unactivated aryl halides. Tetrahedron Letters. 1980, 21 (32): 3099–3100. ISSN 0040-4039. doi:10.1016/S0040-4039(00)77418-1.
- ^ Dittmer, Donald C. Hydrogen sulfide. e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001. pp 1-5. CODEN: 69KUHI.
- ^ Daub, Guido H.; Whaley, Thomas W. Synthesis of 4-(2-hydroxyethylsulfonyl)-1-naphthalenesulfonamide. The Journal of Organic Chemistry. 1978, 43 (24): 4659–4662. ISSN 0022-3263. doi:10.1021/jo00418a030.
- ^ Gege, Christian; Steeneck, Christoph; Kinzel, Olaf; Kleymann, Gerald; Hoffmann, Thomas. Substituted thiazoles and related derivatives as modulators for the retinoid-receptor related orphan nuclear receptor RORγ. WO 2013178362 A1, 2013. (WO 2013-EP1593; CN 2013-80028983). CODEN: PIXXD2
- ^ Song, Juan; Wu, Hao; Sun, Wei; Wang, Songjiang; Sun, Haisen; Xiao, Kang; Qian, Yan; Liu, Chao. A Pd-catalyzed optional approach for the synthesis of dibenzothiophenes. Organic & Biomolecular Chemistry. 2018, 16 (12): 2083–2087. ISSN 1477-0520. doi:10.1039/C8OB00235E.
- ^ Yang, Bo; Wang, Zhong-Xia. Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents. Organic Letters. 2017, 19 (22): 6220–6223. ISSN 1523-7060. doi:10.1021/acs.orglett.7b03145.