Skip to Content
MilliporeSigma
All Photos(1)

Documents

384216

Sigma-Aldrich

tert-Butoxy bis(dimethylamino)methane

Synonym(s):

Bredereck’s reagent

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
(CH3)3COCH[N(CH3)2]2
CAS Number:
5815-08-7
Molecular Weight:
174.28
Beilstein/REAXYS Number:
1901973
EC Number:
227-383-9
MDL number:
MFCD00042858
UNSPSC Code:
12352100
PubChem Substance ID:
24863653
NACRES:
NA.22

form

liquid

refractive index

n20/D 1.422 (lit.)

bp

50-55 °C/15 mmHg (lit.)

density

0.844 g/mL at 25 °C (lit.)

SMILES string

CN(C)C(OC(C)(C)C)N(C)C

InChI

1S/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3

InChI key

HXRAMSFGUAOAJR-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

tert-Butoxy bis(dimethylamino)methane (Bredereck′s reagent) may be used in the following studies:
  • Enamination of active methylene and methyl groups.
  • As condensation reagent in the synthesis of benz[c,d]indoles.
  • Preparation of methyl and ethyl 3-dimethylamino-2-(indol-3-yl)propenoate.
  • Synthesis of the macrolide natural product (-)-gloeosporone.
  • Preparation of new bioactive naphthyridine alkaloids lophocladine A and B.
  • Preparation of (E/Z)-ethyl 6,7-dichloro-3-[1-cyano-2-(dimethylamino)vinyl]-1-methyl-1H-indole-2-carboxylate.
  • Preparation of (E)-ethyl 3-(dimethylamino)-2-(1H-indol-3-yl)acrylate.
  • α-Enamination of ketones and esters.
Reactant for:
  • Preparation of pyrroloquinazolines as photochemotherapeutic agents
  • Enanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical addition
  • Synthesis of camptothecin via intramolecular isomuenchnone cycloaddition reaction
  • Aminomethylenation reactions

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

105.8 °F - closed cup

flash_point_c

41 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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?

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

Visit the Document Library

Benz [c, d] indoles-I. The use of tert-butoxy-bis (dimethylamino) methane as condensation reagent.
Hafliger W and Knecht H.
Tetrahedron Letters, 25(3), 285-288 (1984)
Synthetic access to benzazolyl (pyrazoles, thiazoles, or triazoles).
Abdel Wahab BF and Mohamed HA.
Turkish Journal of Chemistry, 36(6), 805-826 (2012)
Journal of Heterocyclic Chemistry, 28, 1043-1043 (1991)
Application of alkyl 3-dimethylamino-2-(1H-indol-3-yl) propenoates in the synthesis of 3-heteroarylindoles.
Jakse R, et al.
Tetrahedron, 60(21), 4601-4608 (2004)
Matthias Lotter et al.
Archiv der Pharmazie, 339(12), 677-679 (2006-11-17)
The one-pot reaction of 4-benzylpyridine-3-carbonitrile with Bredereck's reagent and subsequent treatment with either glacial acetic acid and sulfuric acid or ammonium acetate provided the new bioactive naphthyridine alkaloids lophocladine A and B, respectively.
View All Related Papers

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