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758035

Sigma-Aldrich

Jones reagent

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Synonym(s):
Jone′s reagent, Chromium trioxide solution in sulfuric acid, Sulfuric acid-chromium trioxide mixture
CAS Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
236470373680273031
vibrant-m

758035

Jones reagent

-
vibrant-m

236470

Chromium(VI) oxide

Essential Grade
vibrant-m

273031

3-Chloroperbenzoic acid

-
form

liquid

form

powder or crystals

form

-

form

solid

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

density

1.298 g/mL at 25 °C

density

-

density

-

density

-

composition

2 M CrO3 in aqueous H2SO4

composition

-

composition

-

composition

-

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.

signalword

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

Storage Class

5.1A - Strongly oxidizing hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Customers Also Viewed

Tunable Synthesis of 3-Acyl-2-naphthols and 3-Substituted Isocoumarins via Jones Reagent Promoted Cascade Reactions of 2-(4-Hydroxy-but-1-ynyl) benzaldehydes
He Y, et al.
The Journal of Organic Chemistry, 78(20), 10178-10191 (2013)
Jones, E. R. H.
Journal of the Chemical Society, 2548-2548 (1953)
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)
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)
Heilbron, I. M.; et al.
Journal of the Chemical Society, 604-604 (1949)

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