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384216

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863653
EC Number:
227-383-9
Beilstein/REAXYS Number:
1901973
MDL number:
MFCD00042858
Form:
liquid
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form

liquid

Quality Segment

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

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

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pictograms

FlameExclamation mark
GHS02,GHS07

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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

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

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