tert-Butoxy bis(dimethylamino)methane Chemical Properties

Boiling point:

50-55 °C/15 mmHg (lit.)

Density 

0.844 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.422(lit.)

Flash point:

106 °F

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly)

pka

5.46±0.38(Predicted)

form 

Liquid

color 

Clear pale yellow

Specific Gravity

0.844

BRN 

1901973

Stability:

Hygroscopic

InChI

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

InChIKey

HXRAMSFGUAOAJR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5815-08-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

26

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

10

HazardClass 

3

PackingGroup 

III

HS Code 

29221990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

tert-Butoxy bis(dimethylamino)methane Usage And Synthesis

Description

Bredereck's reagent, chemically known as tert-Butoxy bis(dimethylamino)methane, is a versatile reagent. It can be used for a-methylation, a-methylenation, and a-amidation of multiple carbonyl systems or compounds with active CH groups. The advantage is the in situ generation of strongly basic alkanes (t-BuO-) and the generation of the corresponding iminium ions by thermal decomposition. After the Mannich reaction of the carbonyl substrate with the in situ generated iminium ion, the dimethylamine is eliminated from the adduct B- in the final step to give the condensation product, which can be converted into various types of compounds.

Chemical Properties

Clear pale yellow liquid

Uses

Reactant for:• ;Preparation of pyrroloquinazolines as photochemotherapeutic agents1• ;Enanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical addition2• ;Synthesis of camptothecin via intramolecular isomuenchnone cycloaddition reaction3• ;Aminomethylenation reactions4

Uses

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

Uses

Mild enamination reagent; catalyst in ring-opening polymerization reactions.

tert-Butoxy bis(dimethylamino)methane(5815-08-7)Related Product Information

• TERT-BUTYL 4-(2-HYDROXYETHYL)PIPERAZINE-1-CARBOXYLATE
• tert-Butyldimethylsilyl chloride
• TERT-BUTYL VINYL ETHER
• Poly(vinyl alcohol)
• Selenium dioxide
• Trisodium citrate dihydrate
• 2,6-DIMETHYL-4-NITROSOPHENOL
• BREDERECK'S REAGENT
• METHOXY-BIS(DIMETHYLAMINO)METHANE