Diphenyl diselenide 二苯基二硒醚

CAS 1666-13-3 MFCD00003001

化学结构图

1666-13-3
SMILES: c1ccc([Se][Se]c2ccccc2)cc1

化学属性

Mol. FormulaC12H10Se2
Mol. Weight312
Density1.422
Melting Point60.0 to 63.0 deg-C
TSCAYes
Solubility溶于热乙醇、乙醚、二甲苯。
Boiling Point202°C/11mmHg(lit.)

别名和识别编码

Chemical NameDiphenyl diselenide
Synonym diphenylselenide Bis(phenylselenide)
CAS Number1666-13-3
EC Number216-780-2
Beilstein Registry Number6,346
MDL NumberMFCD00003001
PubChem Substance ID15460
Chemical Name Translation二苯基二硒醚
Reaxys-RN2047179
InChIKeyYWWZCHLUQSHMCL-UHFFFAOYSA-N
Wiswesser Line NotationR-SE--SE-R
LabNetwork Molecule IDLN00197902
InChIInChI=1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
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分类

  • {SNA} Building Blocks, Chemical Synthesis, Organic Building Blocks, Selenium Compounds
  • {uni_hamburg} no charge; carbocycle; aromatic; 6RingOnly; 6ring; 1fragment

产品应用

  • 用于合成烯丙基醇、烯丙基醚、乙酸酯和α,β-不饱和羰基化合物。

相关文献及参考

  • For introduction of the phenylseleno group by Michael addition, phenylselenol can be generated in situ by borohydride cleavage: Synthesis, 664 (1980).
  • For a comprehensive review of the preparation of ɑß-unsaturated carbonyl compounds and nitriles by selenoxide elimination, see: Org. React., 44, 1 (1993). Compare also Phenyl­selenenyl­ bromide, A11906 and Phenyl­selenenyl­ chloride, A12751.
  • Reagent for ɑ-phenylselenation of enolates. The products are readily oxidized to the selenoxides which undergo ambient temperature Cope-type elimination, providing a mild method for the introduction of ɑß-unsaturation into, e.g. ketones: J. Am. Chem. Soc., 97, 5434 (1975):
  • Short: EINECS
  • Short: III/5a
  • Beilstein:6,346
  • Oxidation of diphenyl diselenide by persulfate in the absence of a nucleophilic counter-ion generates the phenylselenium cation, which adds to alkenes. Molecules with a suitably placed nucleophilic site (alkene, hydroxyl, carbonyl, carboxyl, etc.) can then undergo intramolecular cyclization: J. Org. Chem., 55, 429 (1990); J. Chem. Soc. Perkin 1, 1989 (1993); Synlett, 373 (1994):
  • Short: III/35G
  • For reviews of the application of organoselenium reagents in organic synthesis, see: Tetrahedron, 34, 1049 (1978); Acc. Chem. Res., 12, 22 (1979); 17, 28 (1984). Monograph: Organoselenium Chemistry, D. Liotta, ed., Wiley, N.Y. (1987).

安全信息

Signal word
GHS Symbol
WGK Germany3
Safety Statements
Risk Statements
  • R33 Danger of cumulative effects 有累积作用的危险
  • R50/53
  • R23/25 Toxic by inhalation and if swallowed 吸入及吞食都有毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P301+P310
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • P301+P310+P330
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P305+P351+P338
  • P304+P340+P310
  • P405 Store locked up. 上锁保管。
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P403+P233
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
Hazard statements
  • H300+H330
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
  • H301+H331
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
  • H331 Toxic if inhaled 吸入中毒
  • H301 Toxic if swallowed 吞食有毒
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
RTECSJM9152500
Packing GroupII
UN Number 3283
Hazard Codes T,N
Hazard Class6.1
Storage condition Store at 0-5°C
Warnings 危化品目录(2015)
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 28 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#05657

Restrict 危险品

其他信息

  • 职业标准:TLV-TWA 0.2 (硒) 毫克/ 立方米; STEL 0.3 (硒) 毫克/ 立方米
  • TCI Shanghai:二苯基二硒醚 Diphenyl Diselenide,>;96.0%(GC)(1666-13-3)
  • 二苯基二硒醚价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 XW16661331 二苯二硒醚 5g 216元 2011/08/23 XW16661332 二苯二硒醚 25g 659元 2011/08/23 XW16661333 二苯二硒醚 100g 1996元
  • 外观性质:黄色固体, 无气味。
  • 可燃性危险特性:明火可燃;高热分解有毒硒化物;与酸起作用
  • 毒性分级:剧毒
  • 方法一:溴苯和镁屑在绝对乙醚中制成苯基溴化镁,然后分批加入硒粉,使反应物维持激烈的回流状态。半小时后,加水破坏剩余的格氏试剂,冷却,搅拌下向混合物滴加溴,再慢慢加入氯化铵水溶液。过滤,滤饼用乙醚用乙醚洗涤。合并滤液和洗涤液,蒸除溶剂,使析出的固体溶于热己烷,滤去不溶物,滤液冷至6℃,过滤,干燥,得二硒二苯
  • Acros Organics:二苯基联二硒 Diphenyl diselenide, 99%(1666-13-3)
  • 急性毒性:静注- 小鼠 LD50: 28 毫克/ 公斤
  • 溶于热醇、醚和二甲苯。不溶于水。
  • MSDS 信息:二苯基二硒(1666-13-3).msds
  • Sigma Aldrich:1666-13-3(sigmaaldrich)
  • 储运特性:库房通风低温干燥; 与氧化剂、食品添加剂、酸类分开存放
  • Alfa Aesar:二苯基二硒醚,98% Diphenyl diselenide, 98%(1666-13-3)
  • 用途一:用于合成烯丙基醇、烯丙基醚、乙酸酯和α,β-不饱和羰基化合物。
  • 灭火剂:泡沫、雾状水、砂土
  • MOL 文件:1666-13-3.mol
  • 上游原料:溴苯 --> 格氏试剂 --> 硒
  • 类别:有毒物品

系列性分类


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