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274623

Sigma-Aldrich

Dess-Martin periodinane

97%

Synonym(s):

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

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5 G
€128.00
25 G
€445.00
50 G
€671.00
250 G
€1,870.00

About This Item

Empirical Formula (Hill Notation):
C13H13IO8
CAS Number:
Molecular Weight:
424.14
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

€128.00


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Quality Level

Assay

97%

reaction suitability

reagent type: oxidant

mp

130-133 °C (lit.)

functional group

iodo

storage temp.

−20°C

SMILES string

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

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

InChI key

NKLCNNUWBJBICK-UHFFFAOYSA-N

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.[1]
  • To synthesize alkynyl oxoaldehyde probe (AlkMGO). [2]
Used for the oxidation of hydroxychlorins to chlorin-α-diones and tetraones.[3]

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Jun Wang et al.
Journal of endodontics, 43(1), 109-115 (2016-11-17)
Mutations in the proteinase bone morphogenetic protein-1 (BMP1) were recently identified in patients with osteogenesis imperfecta, which can be associated with type 1 dentinogenesis imperfecta. BMP1 is co-expressed in various tissues and has overlapping activities with the closely related proteinase
Synthesis of an alkynyl methylglyoxal probe to investigate nonenzymatic histone glycation
Qingfei Z,et al.
The Journal of Organic Chemistry, 85, 1691-1697 (2019)
Hui Chen et al.
Environmental science and pollution research international, 26(24), 24609-24619 (2019-06-27)
Phthalates (PAEs) in drinking water sources such as the Yangtze River in developing countries had aroused widespread concern. Here, the water, suspended particulate matter (SPM), and sediment samples were collected from 15 sites in wet and dry seasons in Zhenjiang
Yajing Chen et al.
Journal of immunology (Baltimore, Md. : 1950), 197(10), 3982-3998 (2016-11-07)
Elicitation of broadly neutralizing Ab (bNAb) responses to the conserved elements of the HIV-1 envelope glycoproteins (Env), including the primary receptor CD4 binding site (CD4bs), is a major focus of vaccine development yet to be accomplished. However, a large number
Journal of Porphyrins and Phthalocyanines, 9, 444-444 (2005)

Articles

Dess-Martin Periodinane enables mild oxidation of alcohols to aldehydes and ketones suitable for synthesizing complex intermediates.

Questions

1–2 of 2 Questions  
  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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