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ChemicalBook >  Product Catalog >  Flavors and fragrances >  Synthetic fragrances >  Oxygen-containing heterocyclic compounds >  Thiazole, thiophene, and pyridine >  2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine

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2,2,6,6-Tetramethylpiperidine Basic information

Product Name:
2,2,6,6-Tetramethylpiperidine
Synonyms:
  • HTMP
  • 2,2,6,6-TETRAMETHYLPIPERIDINE
  • 2,2,6,6-TetramethyL
  • 2,2,6,6-Teteamethyl-piperidine
  • 2,2,6,6-Tetramethylpiperidine(Tmp)
  • 2,2,6,6-tetramethyl-piperidin
  • Norpempidine
  • 2,2,6,6-Tetramethylpiperidine (HTMP)
CAS:
768-66-1
MF:
C9H19N
MW:
141.25
EINECS:
212-199-3
Product Categories:
  • Fine Chemical
  • Industrial/Fine Chemicals
  • Piperidines, Piperidones, Piperazines
  • Piperidine
  • API intermediates
  • Organic BasesBuilding Blocks
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • Piperidines
  • Synthetic Reagents
  • 768-66-1
  • bc0001
Mol File:
768-66-1.mol
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2,2,6,6-Tetramethylpiperidine Chemical Properties

Melting point:
-59°C
Boiling point:
152 °C (lit.)
Density 
0.837 g/mL at 25 °C (lit.)
vapor pressure 
14 hPa (39 °C)
refractive index 
n20/D 1.445(lit.)
Flash point:
76 °F
storage temp. 
Store below +30°C.
solubility 
MISCIBLE
pka
11.07(at 25℃)
form 
Liquid
Specific Gravity
0.837
color 
Clear colorless to yellow
Water Solubility 
MISCIBLE
Sensitive 
Air Sensitive
BRN 
103296
InChIKey
RKMGAJGJIURJSJ-UHFFFAOYSA-N
CAS DataBase Reference
768-66-1(CAS DataBase Reference)
NIST Chemistry Reference
Piperidine, 2,2,6,6-tetramethyl-(768-66-1)
EPA Substance Registry System
Piperidine, 2,2,6,6-tetramethyl- (768-66-1)
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Safety Information

Hazard Codes 
Xn,F,C
Risk Statements 
10-22-36/37/38
Safety Statements 
26-37/39-16
RIDADR 
UN 1992 3/PG 3
WGK Germany 
2
RTECS 
TN4220000
Autoignition Temperature
290 °C
TSCA 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29333999
Toxicity
LD50 orally in Rabbit: 500 mg/kg

MSDS

  • Language:English Provider:HTMP
  • Language:English Provider:SigmaAldrich
  • Language:English Provider:ACROS
  • Language:English Provider:ALFA
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2,2,6,6-Tetramethylpiperidine Usage And Synthesis

Chemical Properties

clear colorless to light yellow-green liquid

Uses

2,2,6,6-Tetramethylpiperidine is a hindered base used to prepare metallo-amide bases and selective generation of silylketene acetals. It is used in the preparation of hibarimicinone, (Z)-silylketene acetal and 4-substituted quinazoline. It acts as a precursor to Lithium tetramethylpiperidide and (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl radical.

Uses

2,2,6,6-Tetramethylpiperidine is used in the syntheses of HMP-Y1, Hibarimicinone and HMP-P1, tyrosine kinase inhibitors.

Uses

The lithium amide has been used to efficiently ortho deprotonate pyridine-3-carboxamides.

Preparation

Many routes for the synthesis of TMP have been reported. One method starts with a conjugate addition reaction of ammonia to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction.

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