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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.)

functional group

amine
ether

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

384216-BULK:
384216-VAR:
384216-10G:
384216-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD5390
BCCB9391
BCBS6882V
BCBL4004V
BCBK3378V

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Tetrahedron Asymmetry, 17, 1217-1217 (2006)
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)
Tetrahedron Letters, 31, 2105-2105 (1990)
Tetrahedron Letters, 48, 613-613 (2007)
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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