N,N-Diethyl-1,1,1-trimethylsilylamine

Synonym(s):(Diethylamino)trimethylsilane;N-(Trimethylsilyl)diethylamine;TMSDEA

CAS NO.：996-50-9
Empirical Formula: C7H19NSi
Molecular Weight: 145.32
MDL number: MFCD00009040
EINECS: 213-637-6
SAFETY DATA SHEET (SDS)
Update Date: 2024-04-25 17:59:01

N,N-Diethyl-1,1,1-trimethylsilylamine Structural

What is N,N-Diethyl-1,1,1-trimethylsilylamine?

Chemical properties

Colorless liquid

The Uses of N,N-Diethyl-1,1,1-trimethylsilylamine

Trimethylsilyldiethylamine is a reagent used as an electrophilic trimethylsilyl source for cleavage of cyclic ethers, esters, oxazolidines, and cyclic acetals; also as a nucleophilic source of the diethylamino group, participating in the following synthesis reactions: Trimethylsilyl Group Transfer, Diethylamino Group Transfer, Trimethylsilyldiethylamine as Halosilane Equivalent, Silylation of Alcohols, Mild Generation of Phosphonochloridates, Silylation of Amines, Diethylamino Group Transfer, Conjugate Addition, Aminoalkylation of Aldehydes, Enamine and Silyl Enol Ether Preparation, Mediation of 1,4-Conjugate Additions, etc.

The Uses of N,N-Diethyl-1,1,1-trimethylsilylamine

It is used to derivative polar organic compounds. N,N-Diethyl(trimethylsilyl)amine is a chemical reagent with wide application in organic chemistry and used in stereo specific addition reactions as well as in SN2 nucleophilic substitutions.

Definition

ChEBI: An N-silyl compound that is diethylamine in which the amino hydrogen is replaced by a trimethylsilyl group. N-(trimethylsilyl)diethylamine is a derivatisation agent used in gas chromatography/mass spectrometry applicat ons.

General Description

N,N-Diethyltrimethylsilylamine is a silylating agent used to derivatize polar organic compounds.

Purification Methods

Fractionate it through a 2ft vacuum-jacketed column containing Helipak packing with a reflux ratio of 10:1. [Sauer & Hasek J Am Chem Soc 68 241 1946, Langer et al. J Org Chem 23 50 1958, Rühlmann J Prakt Chem 9 315 1959, Beilstein 4 IV 4010.]

Properties of N,N-Diethyl-1,1,1-trimethylsilylamine

Melting point:	-10°C
Boiling point:	125-126 °C(lit.)
Density	0.767 g/mL at 25 °C(lit.)
vapor density	>1 (vs air)
refractive index	n20/D 1.411(lit.)
Flash point:	50 °F
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
solubility	Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly)
pka	11.27±0.70(Predicted)
form	clear liquid
Specific Gravity	0.763
color	Colorless to Light yellow
Water Solubility	decomposes
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
BRN	635718
CAS DataBase Reference	996-50-9(CAS DataBase Reference)
NIST Chemistry Reference	N,N-Diethyl-1,1,1-trimethylsilylamine(996-50-9)
EPA Substance Registry System	Silanamine, N,N-diethyl-1,1,1-trimethyl- (996-50-9)

Safety information for N,N-Diethyl-1,1,1-trimethylsilylamine

Signal word	Danger
Pictogram(s)	Flame Flammables GHS02 Corrosion Corrosives GHS05
GHS Hazard Statements	H225:Flammable liquids H314:Skin corrosion/irritation
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.