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2,2,6,6-Tetramethylpiperidine

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
Mol File:768-66-1.mol
2,2,6,6-Tetramethylpiperidine Structure
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.)
Fp 76 °F
storage temp. Store below +30°C.
solubility MISCIBLE
pka11.07(at 25℃)
form Liquid
color Clear colorless to yellow
Specific Gravity0.837
Water Solubility MISCIBLE
Sensitive Air Sensitive
BRN 103296
InChIKeyRKMGAJGJIURJSJ-UHFFFAOYSA-N
CAS DataBase Reference768-66-1(CAS DataBase Reference)
NIST Chemistry ReferencePiperidine, 2,2,6,6-tetramethyl-(768-66-1)
EPA Substance Registry SystemPiperidine, 2,2,6,6-tetramethyl- (768-66-1)
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 Temperature290 °C
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29333999
ToxicityLD50 orally in Rabbit: 500 mg/kg
MSDS Information
ProviderLanguage
HTMP English
ACROS English
SigmaAldrich English
ALFA English
2,2,6,6-Tetramethylpiperidine Usage And Synthesis
Chemical Propertiesclear colorless to light yellow-green liquid
Uses2,2,6,6-Tetramethylpiperidine is used in the syntheses of HMP-Y1, Hibarimicinone and HMP-P1, tyrosine kinase inhibitors.
Uses2,2,6,6-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.
UsesThe 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.
Preparation of 2,2,6,6-Tetramethylpiperidine
2,2,6,6-Tetramethylpiperidine Preparation Products And Raw materials
Preparation Products2-(TRIFLUOROMETHYL)-4-ISOCYANATOPYRIDINE-->5-FLUORO-2-PICOLINIC ACID-->2-CHLOROPYRIDINE-3,4-DICARBOXYLIC ACID-->2,2,6,6-Tetramethylpiperidinooxy-->3-BROMO-2-((CYCLOPROPYLAMINO)METHYL)BENZALDEHYDE-->6-CHLOROPYRIDINE-3,4-DICARBOXYLIC ACID-->4-(TRIFLUOROMETHYL)-2-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->2-CHLORO-6-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->2-BROMO-6-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->3-FLUORO-2-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->2-(3-METHOXYPHENYL)CYCLOHEXANONE-->5-(TRIFLUOROMETHYL)-2-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->2-CYANO-5-BROMOPHENYLBORONIC ACID PINACOL ESTER-->2-(TRIFLUOROMETHYL)-6-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->(E)-5-(2-CARBOXYVINYL)-2,4-DIMETHOXYPYRIMIDINE-->2-Chloro-4-methoxypyrimidine-5-carbaldehyde-->4-CHLORO-2-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->2-METHOXY-6-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->3-METHOXY-2-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZONITRILE-->5-FORMYL-2,4-DIMETHOXYPYRIMIDINE-->3-CYANOPYRIDIN-4-YLBORONIC ACID-->4-CYANOPYRIDIN-3-YLBORONIC ACID-->2-CYANOPYRIDIN-3-YLBORONIC ACID
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE PURUM 97%,4-Amine-2,2,6,6-Tetramethylpiperidine Diphenoxylate 2,2,6,6-Tetramethylpiperidine 4-(DIMETHYLAMINO)-1,2,2,6,6-PENTAMETHYLPIPERIDINE 2,2,6,6-Tetramethyl-4-piperidone hydrochloride Triacetonamine 1,2,2,6,6-PENTAMETHYLPIPERIDINE 4-Oxo-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical 3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidin-1-yl 4-MALEIMIDO-TEMPO PHENCYCLIDINE-D5 HYDROCHLORIDE 2,2,6,6-Tetramethylpiperidinooxy LITHIUM TETRAMETHYLPIPERIDIDE 2,6-Lutidine Haloperidol 2,2,6,6-Tetramethyl-4-piperidinol 4-ETHOXYFLUOROPHOSPHINYLOXY TEMPO DROPERIDOL
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