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Merck

274623

Dess-Martin periodinane

97%

Synonym(s):

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one

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About This Item

Empirical Formula (Hill Notation):
C13H13IO8
CAS Number:
87413-09-0
Molecular Weight:
424.14
NACRES:
NA.22
PubChem Substance ID:
24856593
UNSPSC Code:
12352005
MDL number:
MFCD00130127
Assay:
97%

Key Documents

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InChI

1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3

SMILES string

CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc12

InChI key

NKLCNNUWBJBICK-UHFFFAOYSA-N

assay

97%

reaction suitability

reagent type: oxidant

mp

130-133 °C (lit.)

functional group

iodo

storage temp.

−20°C

Quality Level

100

Related Categories

General description

Dess-Martin periodinane (DMP) is a hypervalent iodine compound widely used as a mild reagent for the oxidation of primary/secondary alcohols to aldehydes/ketones; oxidation of amides into imides; the dehydrogenation of amines to nitriles, and disulfides to sulfones. It is also used to selectively oxidize alkenes to epoxides. This is a useful reaction for generating three-membered cyclic ethers. Additionally, DMP is used to oxidatively cleave 1,2-diols to form aldehydes or ketones and in the synthesis of lactones.

Application

Dess–Martin periodinane is used as an oxidizing agent:
  • For 1° and 2° alcohols to aldehydes and ketones.
  • In the synthesis of N-protected α-amino aldehydes from the corresponding N-protected β-amino alcohols.
  • To synthesize alkynyl oxoaldehyde probe (AlkMGO).
Used for the oxidation of hydroxychlorins to chlorin-α-diones and tetraones.

Features and Benefits

Benefits of using DMP as an oxidizing reagent:
  • milder reaction conditions (room temperature, neutral pH)
  • shorter reaction times and higher yields      
  • high chemoselectivity     
  • tolerance of sensitive functional groups, and a long shelf life
  • simplified workups

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH044

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000496553
0000496553
0000495561
0000495561
0000464579

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Synthesis of highly epimerizable N-protected $\alpha$-amino aldehydes of high enantiomeric excess
Andrew GM,et al.
Tetrahedron Letters, 41, 1359-1362 (2000)
The Journal of Organic Chemistry, 48, 4155-4155 (1983)
Iman Al-Saleh et al.
The Science of the total environment, 578, 440-451 (2016-11-12)
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Advanced Synthesis & Catalysis, 346, 111-124 (2004)
Brittany A Weldon et al.
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