Cornforth reagent

Cornforth reagent
Names
Other names
Pyridinium dichromate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.039.511 Edit this at Wikidata
EC Number
  • 243-478-8
UNII
  • InChI=1S/2C5H5N.2Cr.7O/c2*1-2-4-6-5-3-1;;;;;;;;;/h2*1-5H;;;;;;;;;/q;;;;;;;;;2*-1/p+2 ☒N
    Key: LMYWWPCAXXPJFF-UHFFFAOYSA-P ☒N
  • InChI=1/2C5H5N.2Cr.7O/c2*1-2-4-6-5-3-1;;;;;;;;;/h2*1-5H;;;;;;;;;/q;;;;;;;;;2*-1/p+2/r2C5H5N.Cr2O7/c2*1-2-4-6-5-3-1;3-1(4,5)9-2(6,7)8/h2*1-5H;/q;;-2/p+2
    Key: LMYWWPCAXXPJFF-OXLJHMOQAP
  • [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.c1cc[nH+]cc1.[nH+]1ccccc1
Properties
C10H12N2Cr2O7
Molar mass 376.2 g/mol
Appearance orange to brown solid[1]
Boiling point 145 to 147 °C (293 to 297 °F; 418 to 420 K)[1]
soluble in water[1]
Hazards
GHS labelling:
GHS02: FlammableGHS03: OxidizingGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H228, H272, H314, H315, H317, H319, H350, H410
P201, P202, P210, P220, P221, P240, P241, P260, P261, P264, P272, P273, P280, P281, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

The Cornforth reagent (pyridinium dichromate or PDC) is a pyridinium salt of dichromate with the chemical formula [C5H5NH]2[Cr2O7]. This compound is named after the Australian-British chemist Sir John Warcup Cornforth (b. 1917) who introduced it in 1962.[2][3] The Cornforth reagent is a strong oxidizing agent which can convert primary and secondary alcohols to aldehydes and ketones respectively. In its chemical structure and functions it is closely related to other compounds made from hexavalent chromium oxide, such as pyridinium chlorochromate and Collins reagent. Because of their toxicity, these reagents are rarely used nowadays.[4]

  1. ^ a b c Pyridinium dichromate, MSDS, Alfa Caesar
  2. ^ Alexander Senning Elsevier's dictionary of chemoetymology: the whies and whences of chemical nomenclature and terminology, Elsevier, 2007, ISBN 0-444-52239-5 p. 94
  3. ^ Cornforth, R.H.; Cornforth, J.W.; Popjak, G. (1962). "Preparation of R-and S-mevalonolactones". Tetrahedron. 18 (12): 1351–4. doi:10.1016/S0040-4020(01)99289-0.
  4. ^ G. Tojo; M. Fernâandez (2006). Oxidation of alcohols to aldehydes and ketones: a guide to current common practice. New York: Springer. pp. 28, 29, 86. ISBN 0-387-23607-4.