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115754

Sigma-Aldrich

2,2,6,6-Tetramethylpiperidine

≥99%

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Synonym(s):
2,2,6,6-tetramethylpiperidide, 2,2,6,6-tetramethylpiperidine, Norpempidine, TEMP, TMPH
Empirical Formula (Hill Notation):
C9H19N
CAS Number:
Molecular Weight:
141.25
Beilstein:
103296
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99%

refractive index

n20/D 1.445 (lit.)

bp

152 °C (lit.)

density

0.837 g/mL at 25 °C (lit.)

SMILES string

CC1(C)CCCC(C)(C)N1

InChI

1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3

InChI key

RKMGAJGJIURJSJ-UHFFFAOYSA-N

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1 of 4

This Item
1761418.18132115746
4-Hydroxy-TEMPO 95%

Sigma-Aldrich

176141

4-Hydroxy-TEMPO

refractive index

n20/D 1.445 (lit.)

refractive index

-

refractive index

-

refractive index

-

bp

152 °C (lit.)

bp

-

bp

-

bp

212-215 °C (lit.)

density

0.837 g/mL at 25 °C (lit.)

density

-

density

0.83 g/cm3 at 20 °C

density

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

General description

2,2,6,6-Tetramethylpiperidineis a hindered secondary amine that is used to prepare metallo-amide bases and selective generation of silylketene acetals.

Application

2,2,6,6-Tetramethylpiperidine can be used as a reactant to synthesize:
  • Allylated tertiary amines via allylic amination of allylic chlorides.
  • Hydroxylamines via oxidation in the presence of oxone as an oxidant.
  • Sulfenamide compounds by reacting with heterocyclic thiols in the presence of iodine as an oxidant.
  • N-methylated amines via N-methylation by reacting with CO2 and phenylsilane.
  • Propargylamines via three-component Mannich coupling reaction with aldehydes and alkynes.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Met. Corr. 1 - Skin Corr. 1A - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

98.6 °F

Flash Point(C)

37 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The reaction pathways of lithium 2,2,6,6-tetramethylpiperidide (LiTMP)-mediated deprotonative metalation of methoxy-substituted arenes were investigated. Importantly, it was experimentally observed that, whereas TMEDA has no effect on the course of the reactions, the presence of more than the stoichiometric amount of

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