758035
Jones reagent
Synonym(s):
Jone′s reagent, Chromium trioxide solution in sulfuric acid, Sulfuric acid-chromium trioxide mixture
About This Item
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form
liquid
Quality Level
composition
2 M CrO3 in aqueous H2SO4
reaction suitability
core: chromium
reagent type: catalyst
reagent type: oxidant
density
1.298 g/mL at 25 °C
SMILES string
O=[Cr](=O)=O.OS(O)(=O)=O
InChI
1S/Cr.H2O4S.3O/c;1-5(2,3)4;;;/h;(H2,1,2,3,4);;;
InChI key
HNPXHFOTGAXAJY-UHFFFAOYSA-N
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General description
- Jones reagent is a solution of chromium trioxide in aqueous sulfuric acid.
- Using acetone as a reaction solvent, the reagent is usually used for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively.
- The oxidation is very rapid and exothermic.
- The reagent tolerates a variety of functionalities, such as, for example, unsaturated bonds, which are rarely oxidized.
For a comprehensive review of chromium-based reagents, see "Oxidation of Alcohols to Aldehydes and Ketones" by Tojo and Fernández, Springer Berlin, 2006, 1-97.
Application
- In the oxidative cleavage of various alkenes into carboxylic acids and ketones using a catalytic amount of osmium tetroxide.
- To prepare symmetrical binaphthols by oxidative dehydrodimerization of substituted naphthols.
- To synthesize acyl-naphthols and substituted isocoumarins from 2-(4-hydroxy-but-1-ynyl)benzaldehydes.
Signal Word
Danger
Precautionary Statements
Hazard Classifications
Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Eye Dam. 1 - Met. Corr. 1 - Muta. 1B - Ox. Liq. 1 - Repr. 2 - Resp. Sens. 1 - Skin Corr. 1A - Skin Sens. 1 - STOT RE 1 Inhalation - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Listings
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EU REACH SVHC Candidate List
EU REACH Annex XVII (Restriction List)
EU REACH Annex XIV (Authorisation List)
Certificates of Analysis (COA)
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