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384216

Sigma-Aldrich

tert-Butoxy bis(dimethylamino)methane

Synonym(s):

Bredereck’s reagent

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About This Item

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

form

liquid

Quality Level

200

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

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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

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

105.8 °F - closed cup

Flash Point(C)

41 °C - closed cup

Personal Protective Equipment

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’.

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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)
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)
Journal of Heterocyclic Chemistry, 28, 1043-1043 (1991)
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.
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