邻二甲苯

邻二甲苯
IUPAC名
1,2-Xylene[1]
系统名
1,2-Dimethylbenzene[1]
1,2-二甲基苯
别名 邻二甲基苯、o-二甲苯
识别
CAS号 95-47-6  checkY
SMILES
 
  • CC1=C(C)C=CC=C1
RTECS ZE2450000
性质
化学式 C8H10
摩尔质量 106.16 g·mol⁻¹
外观 无色液体
熔点 -24 °C（249 K）
沸点 144.4 °C（418 K）
溶解性（水） 0.2 g/L (20℃)[2]
溶解性（其他溶剂） 可溶于乙醇和乙醚
蒸氣壓 7 mmHg (20°C)[2]
折光度n
D 		1.50545
黏度 11.049 cP, 0 ℃
8.102 cP, 20 ℃
结构
偶极矩 0.64 D[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”）中腐蚀性物质的标签图案《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《全球化学品统一分类和标签制度》（简称“GHS”）中对人体有害物质的标签图案
GHS提示词 Danger
H-术语 H225, H226, H304, H312, H312, H315, H319, H332, H335, H412
P-术语 P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+310, P302+352, P303+361+353
NFPA 704
3
2
0
 
爆炸極限 0.9%-6.7%[2]
PEL TWA 100 ppm (435 mg/m3)[2]
TLV {{{TLV}}}, 100 ppm[4] (TWA), 150 ppm[4] (STEL)
致死量或浓度：
LCLo（最低）
 6125 ppm (rat, 12 hr)
6125 ppm (human, 12 hr)[5]
相关物质
相关芳香烃 间二甲苯、对二甲苯、甲苯
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

邻二甲苯是苯邻位的两个氢被甲基取代后形成的化合物，化学式 C
6H
4(CH
3)
2。它是一种无色，微油状的可燃液体。[6]

生产和用处

石油含有约 1%（重量计）的二甲苯。大多数的邻二甲苯是通过裂化石油生产的，裂化提供了芳香化合物，包括二甲苯的各种异构体。间二甲苯也会异构化为邻二甲苯。2000年，邻二甲苯的净产量约为50万吨。

邻二甲苯被大量用来制造苯酐，后者是许多材料、药物和其它化学品的前体。[6]由于容易氧化，邻二甲苯的甲基很容易被卤化。当它和溴反应时，这些甲基被溴化成1,2-二(溴甲基)苯：[7]

C6H4(CH3)2 + 2 Br2 → C6H4(CH2Br)2 + 2 HBr

毒性和暴露

二甲苯的LD50（大鼠，口服）为 4300 mg/kg，效果因动物和二甲苯的异构体种类而异。人们对二甲苯的关注集中在其麻醉作用上。[6]

参见

参考资料

  1. ^ 1.0 1.1 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 121, 139, 653. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069. 
  2. ^ 2.0 2.1 2.2 2.3 NIOSH Pocket Guide to Chemical Hazards. #0668. NIOSH. 
  3. ^ Rudolph, H.D.; Walzer, K.; Krutzik, Irmhild. Microwave spectrum, barrier for methyl rotation, methyl conformation, and dipole moment of ortho-xylene. Journal of Molecular Spectroscopy. 1973, 47 (2): 314. Bibcode:1973JMoSp..47..314R. doi:10.1016/0022-2852(73)90016-7. 
  4. ^ 4.0 4.1 o-Xylene. International Chemical Safety Cards. ICSC/NIOSH. July 1, 2014 [2021-10-13]. （原始内容存档于2018-06-27）. 
  5. ^ Xylene (o-, m-, p-isomers). Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 
  6. ^ 6.0 6.1 6.2 Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A., Xylenes, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a28_433 
  7. ^ Emily F. M. Stephenson. o-Xylylene Dibromide. Organic Syntheses. 1954, 34: 100. doi:10.15227/orgsyn.034.0100. 

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