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758035

Sigma-Aldrich

Jones reagent

Sinónimos:

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

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About This Item

Número de CAS:
65272-70-0
Número MDL:
MFCD22199316
Código UNSPSC:
12352000
ID de la sustancia en PubChem:
329766706
NACRES:
NA.22
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Formulario

liquid

Nivel de calidad

100

composición

2 M CrO3 in aqueous H2SO4

idoneidad de la reacción

core: chromium
reagent type: catalyst
reagent type: oxidant

densidad

1.298 g/mL at 25 °C

cadena SMILES

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);;;

Clave InChI

HNPXHFOTGAXAJY-UHFFFAOYSA-N

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Descripción general

  • 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.

Aplicación

Jones reagent can be used:
  • In the oxidative cleavage of various alkenes into carboxylic acids and ketones using a catalytic amount of osmium tetroxide.[1]
  • To prepare symmetrical binaphthols by oxidative dehydrodimerization of substituted naphthols.[2]
  • To synthesize acyl-naphthols and substituted isocoumarins from 2-(4-hydroxy-but-1-ynyl)benzaldehydes.[3]

Palabra de señalización

Danger

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
MKCX1819
MKCW0888
MKCW0757
MKCT8298
MKCT2029

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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)
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)
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)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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