758035

Jones reagent

• Synonym(s): Jone′s reagent, Chromium trioxide solution in sulfuric acid, Sulfuric acid-chromium trioxide mixture
• CAS Number: 65272-70-0
• MDL number: MFCD22199316
• UNSPSC Code: 12352000
• PubChem Substance ID: 329766706
• NACRES: NA.22

Properties

• form: liquid
• 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

Description

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

Jones reagent can be used:

• 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.

Safety Information

• Pictograms: GHS03,GHS06,GHS08,GHS05,GHS09
• Signal Word: Danger
• Hazard Statements: H271,H290,H301,H312,H314,H317,H330,H334,H335,H340,H350,H361f,H372,H410
• Precautionary Statements: P210 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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