N-methylaniline; trifluoroacetic acid

• ChemBase ID: 153068
• Molecular Formular: C9H10F3NO2
• Molecular Mass: 221.1764096
• Monoisotopic Mass: 221.06636323
• SMILES: CNc1ccccc1.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CNc1ccccc1
• InChI: InChI=1S/C7H9N.C2HF3O2/c1-8-7-5-3-2-4-6-7;3-2(4,5)1(6)7/h2-6,8H,1H3;(H,6,7)
• InChIKey: TXXJGCVOHDSYBC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methylaniline; trifluoroacetic acid
• IUPAC Traditional name: methylaniline; trifluoroacetic acid
• Synonyms: Trifluoroacetic acid N-methylanilinium salt; N-Methylanilinium trifluoroacetate; TAMA; Trifluoroacetic acid N-methylaniline salt; N-Methylaniline trifluoroacetate; N-甲基三氟乙酸苯胺; 三氟乙酸 N-甲基苯胺盐; 氮甲基苯胺三氟乙酸

Database IDs

• CAS Number: 29885-95-8
• EC Number: 249-927-4
• MDL Number: MFCD00043278
• Beilstein Number: 3638133
• PubChem SID: 162247208; 24852614
• PubChem CID: 11806238

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.3845329
• LogD (pH = 7.4): 1.4451928
• Log P: 1.446024
• Molar Refractivity: 36.2518 cm^3
• Polarizability: 13.344026 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 63-67 °C; 64-68°C; 65-66 °C(lit.)

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Nature polluting (N); X
• UN Number: UN3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: III
• Risk Statements: 20/21/22-33-51/53
• Safety Statements: 28-36/37-61
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Hazard statements: H301-H311-H332-H373-H411-H401
• GHS Precautionary statements: P260-P301+P310-P361-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (NT); 99%
• Grade: puriss.
• Linear Formula: C6H5NH2+(CH3)CF3COO-

DETAILS

Sigma Aldrich - 210080

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 65765

Other Notes
Catalyst for a direct α-methylenation of ketones with paraformaldehyde1,2; Activator used in oligonucleotide synthesis3

REFERENCES

• In combination with Paraformaldehyde, A11313, ketones undergo direct ɑ-methylenation in high yield: Tetrahedron Lett., 2111 (1978). The reaction proceeds via the Mannich intermediate. For an example (1-tetralone to its 2-methylene derivative), see: Org. Synth. Coll., 7, 332 (1990).