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Merck
CN

115754

2,2,6,6-Tetramethylpiperidine

≥99%

Synonym(s):

2,2,6,6-tetramethylpiperidide, 2,2,6,6-tetramethylpiperidine, Norpempidine, TEMP, TMPH

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About This Item

Empirical Formula (Hill Notation):
C9H19N
CAS Number:
768-66-1
Molecular Weight:
141.25
Beilstein:
103296
EC Number:
212-199-3
MDL number:
MFCD00005985
UNSPSC Code:
12352005
PubChem Substance ID:
24847237
NACRES:
NA.22

Key Documents

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Quality Level

200

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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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 Statements

H226,H290,H302,H314,H335

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 - closed cup

Flash Point(C)

37 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0725
STBL1140
0000181359
0000172914
0000151507

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S Doruk Cezan et al.
Nature communications, 10(1), 276-276 (2019-01-19)
Triboelectric charging of insulators, also known as contact charging in which electrical charges develop on surfaces upon contact, is a significant problem that is especially critical for various industries such as polymers, pharmaceuticals, electronics, and space. Several methods of tribocharge
Guangwei Geng et al.
ACS nano, 11(5), 4866-4876 (2017-04-18)
Metal-free catalytic materials have recently received broad attention as promising alternatives to metal-involved catalysts. This is owing to their inherent capability to overcome the inevitable limitations of metal-involved catalysts, such as high sensitivity to poisoning, the limited reserves, high cost
David Joram Mendoza et al.
Carbohydrate polymers, 226, 115292-115292 (2019-10-05)
TEMPO/NaClO/NaBr and sodium periodate were combined in a one-shot reaction to oxidise cellulose from bleached pulp. Oxidation of cellulose forms two fractions: a highly-carboxylated water-insoluble (up to 1.9 mmol COO-/g, DS = 0.39) and a water-soluble fraction (up to 4 mmol COO-/g, DS = 1.1). Results
Kasper Wigh Lipsø et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 274, 65-72 (2016-11-28)
We demonstrate a method for the preparation of hyperpolarized water by dissolution Dynamic Nuclear Polarization at high magnetic field. Protons were polarized at 6.7T and 1.1K to >70% with frequency modulated microwave irradiation at 188GHz. 97.2±0.7% of the radical was
Gaku Akimoto et al.
The Journal of organic chemistry, 83(21), 13498-13506 (2018-10-23)
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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