methyl[(1R)-1-phenylethyl]amine

• ChemBase ID: 148888
• Molecular Formular: C9H13N
• Molecular Mass: 135.20622
• Monoisotopic Mass: 135.10479942
• SMILES: C[C@H](c1ccccc1)NC
• Canonical SMILES: CN[C@@H](c1ccccc1)C
• InChI: InChI=1S/C9H13N/c1-8(10-2)9-6-4-3-5-7-9/h3-8,10H,1-2H3/t8-/m1/s1
• InChIKey: RCSSHZGQHHEHPZ-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl[(1R)-1-phenylethyl]amine
• IUPAC Traditional name: methyl[(1R)-1-phenylethyl]amine
• Synonyms: (R)-(+)-N-Methyl-1-phenylethylamine; (R)-(+)-N,α-Dimethylbenzylamine; (R)-(+)-N-甲基-1-苯乙胺; R-N-甲基-苯乙胺

Database IDs

• CAS Number: 5933-40-4
• MDL Number: MFCD00044966
• Beilstein Number: 4350160
• PubChem SID: 24885695; 162243060; 24864558
• PubChem CID: 2060888

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.2559385
• LogD (pH = 7.4): -0.37916717
• Log P: 1.9481697
• Molar Refractivity: 43.7248 cm^3
• Polarizability: 17.443655 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 74-76 °C/11 mmHg(lit.)
• Flash Point: 141.8 °F; 61 °C
• Density: 0.924 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.511; n20/D 1.511(lit.)
• Optical Rotation: [α]20/D +70°, c = 2 in chloroform; [α]20/D +74±4°, c = 2% in chloroform

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 2619
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 20/21/22-34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H314-H332
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2619 8/PG 2

Product Information

• Purity: ≥96.0% (sum of enantiomers, GC); 98%
• Grade: purum
• Linear Formula: C6H5CH(CH3)NHCH3

DETAILS

Sigma Aldrich - 394009

Packaging
1, 5 g in glass bottle
Application
Used to make asymmetric organometallic catalysts (e.g., for conjugate additions to enones).1

Sigma Aldrich - 68620

Other Notes
Chiral secondary amine used as auxiliary, e.g. detn. of absolute configuration of carboxylic acids1; Asymmetric addition of cuprates to enones2; Preparation of chiral thiophosphonate3