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1-萘硫酚

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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
 
  • C1=CC=C2C(=C1)C=CC=C2S
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
《全球化学品统一分类和标签制度》(简称“GHS”)中有害物质的标签图案
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2-萘硫酚英语2-Naphthalenethiol

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,在和乙二硫醇的催化下反应制得。[4]

1-萘酚二硫化物用/氯化铵乙醇中回流,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

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ Dittmer, Donald C. Hydrogen sulfide. e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001. pp 1-5. CODEN: 69KUHI.
  9. ^ 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. 
  10. ^ 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
  11. ^ 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. 
  12. ^ 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.