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8.22288

Sigma-Aldrich

Periodic acid

for synthesis

Synonym(s):

Periodic acid

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About This Item

Empirical Formula (Hill Notation):
H5IO6
CAS Number:
10450-60-9
Molecular Weight:
227.94
MDL number:
MFCD00011344
UNSPSC Code:
12352301
EC Index Number:
233-937-0
NACRES:
NA.22

Quality Level

200

assay

≥98% (iodometric)

form

solid

reaction suitability

reagent type: oxidant

pH

1.2 (20 °C, 100 g/L in H2O)

mp

122 °C

solubility

ethanol: soluble at 20 °C
water: soluble at 20 °C

bulk density

1400 kg/m3

storage temp.

15-25°C

InChI

1S/H5IO6/c2-1(3,4,5,6)7/h(H5,2,3,4,5,6,7)

InChI key

TWLXDPFBEPBAQB-UHFFFAOYSA-N

Application

Periodic acid can be used as a reagent for the oxidative cleavage of 1,2 diols to ketones or aldehydes, and epoxides to aldehydes. It is also used in the oxidative cleavage of various protecting groups such as acetonide, tetrahydropyranyl ether (THP), ethoxyethyl acetals, cyclic acetals, dithioacetals, and oxathioacetals.
It can also be used:
  • In the selective N-nitrosation of secondary amines in the presence of sodium nitrite, and wet silica gel.
  • As a stoichiometric oxidant with chromium (IV) acetate for the oxidation of tertiary C−H bonds to tertiary alcohols.
  • In combination with chromium oxide to oxidize primary alcohols to carboxylic acids; alkylbenzenes to benzoic acids; and cyclic benzyl ethers to the corresponding lactones.
  • In the iodination of bulky polyalkyl benzenes in the presence of iodine.
  • In the oxidative coupling of polycyclic aromatic hydrocarbons in the presence of aqueous acetic acid.
  • In the selective oxidation of sulfides to sulfoxides using FeCl3 as a catalyst.

Analysis Note

Assay (iodometric): ≥ 98.0 %
Melting range (lower value): ≥ 124 °C
Melting range (upper value): ≤ 129 °C

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Ox. Sol. 1 - Skin Corr. 1B - STOT RE 1 Oral

target_organs

Thyroid

Storage Class

5.1A - Strongly oxidizing hazardous materials

wgk_germany

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’.

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Periodic Acid
Stengel JH, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis), 1-6 (2001)
One-pot hydrothermal synthesis and characterization of CoFe2O4 nanoparticles and its application as magnetically recoverable catalyst in oxidation of alcohols by periodic acid
Paul B, et al.
Materials Chemistry and Physics, 181, 99-105 (2016)
A mild and highly efficient oxidation of sulfides to sulfoxides with periodic acid catalyzed by FeCl3
Kim SS, et al.
Synthesis, 2002(17), 2484-2486 (2002)

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