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Merck
CN

758035

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:
65272-70-0
NACRES:
NA.22
PubChem Substance ID:
329766706
UNSPSC Code:
12352000
MDL number:
MFCD22199316

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InChI

1S/Cr.H2O4S.3O/c;1-5(2,3)4;;;/h;(H2,1,2,3,4);;;

SMILES string

O=[Cr](=O)=O.OS(O)(=O)=O

InChI key

HNPXHFOTGAXAJY-UHFFFAOYSA-N

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

Quality Level

100

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.

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4892
MKCZ4262
MKCX7140
MKCX4595
MKCX4572

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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)
Heilbron, I. M.; et al.
Journal of the Chemical Society, 604-604 (1949)
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)
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