2,6-bis(propan-2-yl)aniline

• ChemBase ID: 123311
• Molecular Formular: C12H19N
• Molecular Mass: 177.28596
• Monoisotopic Mass: 177.15174961
• SMILES: c1(c(C(C)C)cccc1C(C)C)N
• Canonical SMILES: CC(c1cccc(c1N)C(C)C)C
• InChI: InChI=1S/C12H19N/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9H,13H2,1-4H3
• InChIKey: WKBALTUBRZPIPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-bis(propan-2-yl)aniline
• IUPAC Traditional name: 2,6-diisopropylaniline
• Synonyms: 2,6-Diisopropylaniline; 2,6-diisopropylaniline; 2,6-二异丙基苯胺

Database IDs

• CAS Number: 24544-04-5
• EC Number: 246-305-4
• MDL Number: MFCD00008887
• Beilstein Number: 2208763
• PubChem SID: 24863333; 24863968; 162217664; 24849695
• PubChem CID: 32484

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.6208081
• LogD (pH = 7.4): 3.634165
• Log P: 3.6343381
• Molar Refractivity: 59.14 cm^3
• Polarizability: 22.41357 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -45 °C(lit.); -54°C
• Boiling Point: 254-257°C; 257 °C(lit.)
• Flash Point: 117 °C; 125°C(257°F); 242.6 °F
• Density: 0.94 g/mL at 25 °C(lit.); 0.940
• Refractive Index: 1.5330; n20/D 1.532; n20/D 1.532(lit.)
• Vapor Pressure: <0.01 mmHg ( 20 °C)

Safety Information

• RTECS: BX4025000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36-52/53; 52/53
• Safety Statements: 26-61; 61
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H319-H402-H412
• GHS Precautionary statements: P280-P273-P264-P305+P351+P338-P337+P313-P501A
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ~90% (GC); 90%; 90+%; 95+%; 97%
• Grade: technical; technical grade
• Linear Formula: [(CH3)2CH]2C6H3NH2

DETAILS

Sigma Aldrich - 374733

Application
Used to prepare N-heterocyclic carbene complexes for α-arylation of acyclic ketones,1 amination of haloarenes,1 and aqueous Suzuki coupling.2
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 157716

Packaging
100, 500 mL in glass bottle

REFERENCES

• This hindered amine has been converted to the nitrile in 52% yield by treatment with alkyl nitrite and copper(I) cyanide in DMSO, as an alternative to the classical Sandmeyer conditions: Tetrahedron, 52, 7137 (1996).