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Merck

274623

Dess-Martin periodinane

97%

Sinonimo/i:

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

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CHF 128.00

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Informazioni su questo articolo

Formula empirica (notazione di Hill):
C13H13IO8
Numero CAS:
87413-09-0
Peso molecolare:
424.14
NACRES:
NA.22
PubChem Substance ID:
24856593
UNSPSC Code:
12352005
MDL number:
MFCD00130127

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Nome del prodotto

Dess-Martin periodinane, 97%

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

Categorie correlate

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Questo articolo
559873696641394963
Dess-Martin periodinane 97%

Sigma-Aldrich

274623

Dess-Martin periodinane

Dess-Martin periodinane solution 0.3 M in methylene chloride

Sigma-Aldrich

559873

Dess-Martin periodinane solution

3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole 95%

Sigma-Aldrich

696641

3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole

N,N-Dimethylformamide dimethyl acetal derivatization grade (GC derivatization), LiChropur™

Supelco

394963

N,N-Dimethylformamide dimethyl acetal

assay

97%

assay

-

assay

95%

assay

>95%

reaction suitability

reagent type: oxidant

reaction suitability

reagent type: oxidant

reaction suitability

-

reaction suitability

reagent type: derivatization reagent
reaction type: Acylations, reagent type: derivatization reagent
reaction type: Esterifications

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

130-133 °C (lit.)

mp

-

mp

75-79 °C

mp

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

functional group

iodo

functional group

iodo

functional group

fluoro, iodo

functional group

-

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

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.

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

Classe di stoccaggio

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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Certificati d'analisi (COA)

Lot/Batch Number
0000496553
0000496553
0000495561
0000495561
0000464579

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Articoli

Dess–Martin Periodinane

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

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/418/501/product-dating-information-06-25-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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