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Merck
CN
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安全信息

8.00653

Sigma-Aldrich

Selenium dioxide

(sublimed) for synthesis

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别名:
Selenium dioxide, Selenious anhydride, Selenium(IV) oxide
经验公式（希尔记法）:
O2Se
CAS号:
7446-08-4
分子量:
110.96
UNSPSC代码:
12352303
EC索引号:
231-194-7
NACRES:
NA.22

蒸汽压

<1 Pa ( 20 °C)

质量水平

200

形式

crystals

效能

68.1 mg/kg LD50, oral (Rat)

反应适用性

reagent type: oxidant

pH值（酸碱度）

2 (20 °C, 10 g/L in H2O)

mp

340 °C

溶解性

1353 g/L

密度

3.95 g/cm3 at 20 °C

储存温度

2-30°C

InChI

1S/O2Se/c1-3-2

InChI key

JPJALAQPGMAKDF-UHFFFAOYSA-N

相关类别

应用

Selenium dioxide (SeO2) is mainly used to oxidize the activated carbon-bearing positions (α-methylene carbon atoms), particularly at allylic or propargylic sites. The more substituted end of the double bond undergoes oxidation.
It can also be used as an oxidizing reagent to synthesize:
  • Amides by oxidative amidation of aldehydes with amines.
  • Tropone from cycloheptatriene in the presence of potassium dihydrogen phosphate.
  • Acetyltetrahydrobenzofurans by oxidation of conjugated dienones.
  • 9-hydroxy-undec-10-ynoate from methyl undec-10-ynoate.

分析说明

Assay (iodometric): ≥ 98.0 %

警示用语：

Danger

危险分类

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

储存分类代码

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 2

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

危险化学品

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Selenium (IV) Oxide
Hoekstra WJ, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2017)
M S Jie et al.
Lipids, 32(10), 1119-1123 (1997-11-14)
Reaction of methyl undec-10-ynoate (1) with selenium dioxide/tert-butyl hydroperoxide (TBHP) in aqueous dioxane gave methyl 9-oxo-undec-10-ynoate (2, 9%) and 9-hydroxy-undec-10-ynoate (3, 60%), while methyl octadec-9-ynoate (4) yielded mixtures of positional isomers of mono-keto (viz. methyl 8-oxo- and 11-oxo-octadec-9-ynoate, 5, 5%)
Jacek Młochowski et al.
Molecules (Basel, Switzerland), 20(6), 10205-10243 (2015-06-06)
A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as

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