115754

2,2,6,6-Tetramethylpiperidine

≥99%

• Synonym(s): 2,2,6,6-tetramethylpiperidide, 2,2,6,6-tetramethylpiperidine, Norpempidine, TEMP, TMPH
• Empirical Formula (Hill Notation): C₉H₁₉N
• CAS Number: 768-66-1
• Molecular Weight: 141.25
• Beilstein/REAXYS Number: 103296
• EC Number: 212-199-3
• MDL number: MFCD00005985
• UNSPSC Code: 12352005
• PubChem Substance ID: 24847237
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS05,GHS07
• signalword: Danger
• hcodes: H226,H290,H302,H314,H335
• pcodes: P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• 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: 3 - Flammable liquids
• wgk_germany: WGK 2
• flash_point_f: 98.6 °F - closed cup
• flash_point_c: 37 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter