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Merck
CN

8.00653

Selenium dioxide

(sublimed) for synthesis

别名:

Selenium dioxide, Selenious anhydride, Selenium(IV) oxide

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关于此项目

经验公式(希尔记法):
O2Se
化学文摘社编号:
分子量:
110.96
MDL number:
UNSPSC Code:
12352303
EC Index Number:
231-194-7
NACRES:
NA.22
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产品名称

Selenium dioxide, (sublimed) for synthesis

SMILES string

[Se](=O)=O

InChI

1S/O2Se/c1-3-2

InChI key

JPJALAQPGMAKDF-UHFFFAOYSA-N

vapor pressure

<1 Pa ( 20 °C)

form

crystals

potency

68.1 mg/kg LD50, oral (Rat)

reaction suitability

reagent type: oxidant

pH

2 (20 °C, 10 g/L in H2O)

mp

340 °C

solubility

1353 g/L

density

3.95 g/cm3 at 20 °C

storage temp.

2-30°C

Quality Level

Analysis Note

Assay (iodometric): ≥ 98.0 %

Application

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.

signalword

Danger

Hazard Classifications

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

存储类别

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

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

危险化学品
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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
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%)

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