Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

135992

Sigma-Aldrich

Di-tert-butyl azodicarboxylate

greener alternative

98%

Synonym(s):

Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
(CH3)3COCON=NCOOC(CH3)3
CAS Number:
870-50-8
Molecular Weight:
230.26
Beilstein:
1911434
EC Number:
212-796-9
MDL number:
MFCD00015001
UNSPSC Code:
12352108
PubChem Substance ID:
24848251
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

200

Assay

98%

form

solid

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

89-92 °C (lit.)

functional group

azo

greener alternative category

Aligned,

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)\N=N\C(=O)OC(C)(C)C

InChI

1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3/b12-11+

InChI key

QKSQWQOAUQFORH-VAWYXSNFSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalysis.

Automate your Mitsunobu reactions with Synple Automated Synthesis Platform (SYNPLE-SC002)

Application

Co-oxidant in copper-catalyzed greener oxidation of alcohols under aerobic conditions.

Modified Markó′s aerobic oxidation of alcohols under atmospheric pressure with air or molecular oxygen at room temperature
Reactant for:
  • Preparation of hexapeptide key fragments via stereoselective selenocyclization/oxidative deselenylation or hydrazination/cyclization reactions
  • Asymmetric Michael addition reactions
  • Preparation of dipeptidyl peptidase IV dependent water-soluble prodrugs via Mitsunobu reaction
  • Synthesis of pyrroloisoquinoline template via stereoselective N-acyliminium-mediated cyclization and enolate amination for synthesis of peptidomimetic compounds
  • Barbier-type propargylation reactions
  • Synthesis of bacterial peptide deformylase (PDF) inhibitor fumimycin
  • Asymmetric amination of glycine Schiff bases
Reagent employed in the electrophilic amination of ß-keto esters catalyzed by an axially chiral guanidine.[1] Building block in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such a L-proline or (S)-2-pyrrolidinyl tetrazole.[2]
Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.[3]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCM3760
BCCK6330
BCCJ6259
BCBL6517V
1380161

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Chirally aminated 2-naphthols--organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination.
Sebastian Brandes et al.
Angewandte Chemie (International ed. in English), 45(7), 1147-1151 (2006-01-04)
Synlett, 2548-2548 (2006)
Masahiro Terada et al.
Journal of the American Chemical Society, 128(50), 16044-16045 (2006-12-15)
A newly designed axially chiral guanidine is found to function as an effective platform for asymmetric induction at the alpha-carbon of unsymmetrically substituted 1,3-dicarbonyl compounds. Highly efficient and enantioselective electrophilic amination of various 1,3-dicarbonyl compounds with azodicarboxylate was successfully achieved

Questions

1–2 of 2 Questions  

  1. 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

      Helpful?

  2. 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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service