MilliporeSigma
All Photos(1)

Documents

11625

Sigma-Aldrich

Di-tert-butyl azodicarboxylate

purum, ≥98.0% (GC)

Sign Into View Organizational & Contract Pricing

Synonym(s):
Bis(1,1-dimethylethyl)azodicarboxylate, DBAD, Di-tert-butyl azodiformate, NSC 109889
Linear Formula:
(CH3)3COCON=NCOOC(CH3)3
CAS Number:
Molecular Weight:
230.26
Beilstein/REAXYS Number:
1911434
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

assay

≥98.0% (GC)

form

solid

mp

89-92 °C (lit.)
89-92 °C

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

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
135992270822419885
Di-tert-butyl azodicarboxylate purum, ≥98.0% (GC)

11625

Di-tert-butyl azodicarboxylate

Di-tert-butyl azodicarboxylate 98%

135992

Di-tert-butyl azodicarboxylate

tert-Butyl propiolate 98%

419885

tert-Butyl propiolate

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

mp

89-92 °C (lit.)

mp

89-92 °C (lit.)

mp

33-37 °C (lit.)

mp

18-20 °C (lit.)

form

solid

form

solid

form

solid

form

liquid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

grade

purum

grade

-

grade

-

grade

-

General description

Di-tert-butyl azodicarboxylate is a an acid labile reagent for Mitsunobu reactions allowing facile isolation of products and for the electrophilic amination and hydrazination of enolates and lithium alkyls.

Application

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 3

1 of 3

D.A. Evans et al.
Journal of the American Chemical Society, 108, 6395-6395 (1986)
C. Gennari et al.
Journal of the American Chemical Society, 108, 6394-6394 (1986)
J.L. Vicario et al.
Tetrahedron Letters, 40, 7123 -7123 (1999)
Masaru Kondo et al.
Angewandte Chemie (International ed. in English), 54(28), 8198-8202 (2015-05-28)
The catalytic enantioselective reaction of diphenylmethylidene-protected α-aminoacetonitriles with imines has been developed. Good yields and diastereo- and enantioselectivities were observed for the reaction of various imines using chiral bis(imidazoline)/Pd catalysts. The reaction of α-aminonitriles with di-tert-butyl azodicarboxylate afforded chiral α,α-diaminonitriles
M. Kiankarimi et al.
Tetrahedron Letters, 40, 4497 -4497 (1999)

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