tert-Butoxy bis(dimethylamino)methane

ALDRICH/384216

Synonym: Bredereck’s reagent

CAS Number: 5815-08-7
Empirical Formula (Hill Notation): C₉H₂₂N₂O
Molecular Weight: 174.28
EC Number: 227-383-9
MDL Number: MFCD00042858
Linear Formula: (CH₃)₃COCH[N(CH₃)₂]₂
Product Type: Chemical

Catalog Number	PKG Qty.	Price	Quantity


45-384216-1G	1 g	$57.60 1/EA		Add To Favorites
45-384216-10G	10 g	$254.00 1/EA		Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

bp	50-55 °C/15 mmHg (lit.)
density	0.844 g/mL at 25 °C (lit.)
form	liquid
functional group	amine
	ether
InChI	1S/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3
InChI key	HXRAMSFGUAOAJR-UHFFFAOYSA-N
Quality Level	200
refractive index	n20/D 1.422 (lit.)
SMILES string	CN(C)C(OC(C)(C)C)N(C)C

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.
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
Packaging:	1, 10 g in glass bottle

Symbol	GHS02,GHS07
Signal word	Warning
Hazard statements	H226 - H315 - H319 - H335
Precautionary statements	P210 - P302 + P352 - P305 + P351 + P338
Hazard Codes	Xi
Risk Statements	10-36/37/38
Safety Statements	26
RIDADR	UN 1993C 3 / PGIII
WGK Germany	WGK 3
Flash Point(F)	105.8 °F - closed cup
Flash Point(C)	41 °C - closed cup

bp	50-55 °C/15 mmHg (lit.)
Density	0.844 g/mL at 25 °C (lit.)
Refractive Index	n20/D 1.422 (lit.)
UNSPSC	12352100

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