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013714

013714-1g



TEMPO


CAS Number: 2564-83-2
   
Molecular Formula: C9H18NO
   
Molecular Weight: 156.25
   
MDL Number: MFCD00009599


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013714-1g
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013714-5g
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013714-25g
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013714-100g
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013714-250g
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013714-500g
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Purity:99%
Mp:36-38°
 
Pictograms:
Signal Word:Danger
Hazard Statements:H314, H318
Precautionary Statements:P260, P264, P280, P310, P301 + P330 + P331, P303 + P361 + P353, P304 + P340, P305 + P351 + P338
UN#:UN3263
Packing Group:II
Hazard Class:8
Flash Point:67°
RTECS:TN8991900
SDS: See MSDS
 
Limited Quantities:1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities:Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

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A stable nitroxyl radical serving as a catalytic oxidant. Applied in catalytic oxidation of nerol to neral,1 catalytic oxidation of primary and secondary alcohols to aldehydes and ketones,2 catalytic oxidation of 1,2-diols to α-hydroxy ketones or α-diketones,3 aerobic oxidation of benzylic alcohols in water,4 catalytic oxidative amidation-diketonization reaction of terminal alkynes to give α-ketoamides,5 mono-oxidation of unprotected glycosides in combination with trichloroisocyanuric acid to afford dialdo-glycosides,6 oxidative conversion of primary amines to the corresponding nitriles,7 oxidatively cleavage of benzylic ethers to give the corresponding aromatic aldehydes and alcohols,8 oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated carbonyl compounds,9 and cross coupling of ortho-substituted aryl Grignard reagents with alkynyl Grignard reagents.10


Reference

1.        Org. Synth. 200683, 18.
2.        Synlett 2006, 2055.
3.        Synthesis 2007, 551.
4.        J. Org. Chem. 200570, 239.
5.        J. Am. Chem. Soc. 2010132, 28.
6.        Eur. J. Org. Chem. 2006, 4323.
7.        Synthesis 2003, 2629.
8.        J. Org. Chem. 200974, 9501.
9.        J. Org. Chem. 200873, 4750.
10.        Org. Lett. 201012, 3878.

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