Skip to Content
Merck
CN
All Photos(2)

Documents

758035

Sigma-Aldrich

Jones reagent

Sign Into View Organizational & Contract Pricing
All Photos(2)
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

form

liquid

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service