2,2,6,6-tetramethylpiperidine

• ChemBase ID: 22369
• Molecular Formular: C9H19N
• Molecular Mass: 141.25386
• Monoisotopic Mass: 141.15174961
• SMILES: CC1(C)NC(C)(C)CCC1
• Canonical SMILES: CC1(C)CCCC(N1)(C)C
• InChI: InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3
• InChIKey: RKMGAJGJIURJSJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,6,6-tetramethylpiperidine
• IUPAC Traditional name: 2,2,6,6-tetramethylpiperidine
• Synonyms: 2,2,6,6-Tetramethylpiperidine; Norpempidine; 2,2,6,6-Tetramethylpiperidine 99+%; 2,2,6,6-Tetramethylpiperidine; Tetramethylpiperidine; 2,2,6,6-TETRAMETHYL PIPERIDINE; 2,2,6,6-四甲基哌啶

Database IDs

• CAS Number: 768-66-1
• EC Number: 212-199-3
• MDL Number: MFCD00005985
• Beilstein Number: 103296
• PubChem SID: 160985676; 24888966; 24847237
• PubChem CID: 13035
• Chemspider ID: 12493
• Wikipedia Title: 2,2,6,6-Tetramethylpiperidine

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.1858974
• LogD (pH = 7.4): -0.9358902
• Log P: 2.051791
• Molar Refractivity: 44.9494 cm^3
• Polarizability: 18.13941 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Clear liquid
• Melting Point: -59°C; -59°C
• Boiling Point: 151-152°C; 152 °C(lit.); 152°C; 152-154°C; 155-157°C
• Flash Point: 24 °C; 24°C; 34°C(93°F); 75.2 °F
• Density: 0.83 g/mL; 0.832; 0.832 g/ml; 0.837; 0.837 g/mL at 25 °C(lit.)
• Refractive Index: 1.4440; 1.4450; n20/D 1.445; n20/D 1.445(lit.)

Safety Information

• Storage Warning: FLAMMABLE; Flammable/Toxic/Irritant
• RTECS: TN4220000
• European Hazard Symbols: Corrosive (C); Flammable (F); X; Irritant (Xi); Harmful (Xn)
• UN Number: 1992; UN2733
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-22-34; 10-22-36/37/38; R:10-36/37/38; R10 R22 R36/37/38
• Safety Statements: 26; 26-36/37/39-45; S:9-16-25-26; S16 S26 S37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H301-H315-H319-H335; H314-H318-H226-H302
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1992 3/PG 3

Product Information

• Purity: ≥97.0% (GC); ≥99%; 97%; 98%; 98+%
• Grade: purum
• Empirical Formula (Hill Notation): C9H19N

DETAILS

MP Biomedicals - 05225654

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 115754

Application
The lithium amide has been used to efficiently ortho deprotonate pyridine-3-carboxamides.1
Packaging
5, 10, 25 g in glass bottle

Sigma Aldrich - 87900

Other Notes
The lithium amide is a base promoting stereoselective enolate formation1,2

REFERENCES

• Lithiation gives a highly-hindered, non-nucleophilic strong base; see, e.g. Org. Synth. Coll., 6, 571 (1988);9, 426 (1998); Tetrahedron, 50, 3099 (1994). For use in selective isomerization of epoxides to aldehydes, see: J. Chem. Soc., Chem. Commun., 2103 (1994). For a study of the influence of TMEDA and related chelating ligands on the solution structure of the lithiated base, see: J. Org. Chem., 62, 5748 (1997). The Mg derivative, obtained by reaction with n-BuMgCl, is also an effective strong base which has been used in the regioselective ortho-metallation of pyridine carbamates and carboxamides: J. Org. Chem., 60,8414 (1995).