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20425

Sigma-Aldrich

tert-Butoxy bis(dimethylamino)methane

technical

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/REAXYS Number:
1901973
EC Number:
227-383-9
MDL number:
MFCD00042858
UNSPSC Code:
12352100
PubChem Substance ID:
57647837
NACRES:
NA.22

grade

technical

Quality Level

200

refractive index

n20/D 1.422 (lit.)
n20/D 1.422

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

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

Analysis Note

mixture of tert-Butoxy bis(dimethylamino)methane, tris(dimethylamino)methane and N,N-Dimethylformamide di-tert-butyl acetal

Other Notes

Review; Mild condensation 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)

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W. Haefliger et al.
Tetrahedron Letters, 25, 285-285 (1984)
R.F. Abdulla et al.
Tetrahedron, 35, 1675-1675 (1979)

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