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Sigma-Aldrich

Jones reagent

Synonym(s):

Jone′s reagent, Chromium trioxide solution in sulfuric acid, Sulfuric acid-chromium trioxide mixture

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About This Item

CAS Number:
MDL number:
UNSPSC Code:
12352000
PubChem Substance ID:
NACRES:
NA.22

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

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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

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.

Signal Word

Danger

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

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH SVHC Candidate List

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EU REACH Annex XVII (Restriction List)

CAS No.

EU REACH Annex XIV (Authorisation List)

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Heilbron, I. M.; et al.
Journal of the Chemical Society, 604-604 (1949)
Oxidative coupling of 2-substituted 1, 2-dihydro-1-naphthols using Jones reagent: a simple entry into 3, 3?-disubstituted 1, 1?-binaphthyl-4, 4?-diols
Fillion E, et al.
Tetrahedron Letters, 46(7), 1091-1094 (2005)
A convenient, mild method for oxidative cleavage of alkenes with Jones reagent/osmium tetraoxide
Henry JR and Weinreb SM
The Journal of Organic Chemistry, 58(17), 4745-4745 (1993)
Jones, E. R. H.
Journal of the Chemical Society, 2548-2548 (1953)
Jones, E. R. H.
Journal of the Chemical Society, 3019-3019 (1953)

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