N-[(3S)-2,5-dioxooxolan-3-yl]-2,2,2-trifluoroacetamide

• ChemBase ID: 139970
• Molecular Formular: C6H4F3NO4
• Molecular Mass: 211.0954696
• Monoisotopic Mass: 211.00924227
• SMILES: C1[C@@H](C(=O)OC1=O)NC(=O)C(F)(F)F
• Canonical SMILES: O=C1OC(=O)[C@H](C1)NC(=O)C(F)(F)F
• InChI: InChI=1S/C6H4F3NO4/c7-6(8,9)5(13)10-2-1-3(11)14-4(2)12/h2H,1H2,(H,10,13)/t2-/m0/s1
• InChIKey: ABTJOHYOWBAGTP-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3S)-2,5-dioxooxolan-3-yl]-2,2,2-trifluoroacetamide
• IUPAC Traditional name: N-[(3S)-2,5-dioxooxolan-3-yl]-2,2,2-trifluoroacetamide
• Synonyms: (S)-(-)-2-Trifluoroacetamidosuccinic anhydride; N-Trifluoroacetyl-L-aspartic acid anhydride; (S)-(-)-2-(Trifluoroacetamido)succinic anhydride; (S)-(-)-2-三氟乙酰氨基琥珀酸酐; N-三氟乙酰-L-天冬氨酸酐; (S)-(-)-2-(三氟乙酰胺)琥珀酸酐

Database IDs

• CAS Number: 777-33-3
• MDL Number: MFCD00012332
• PubChem SID: 24858416; 162234216
• PubChem CID: 12197622

CALCULATED PROPERTIES

• Acid pKa: 4.412915
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.87736714
• LogD (pH = 7.4): -1.074662
• Log P: -0.13517597
• Molar Refractivity: 33.7813 cm^3
• Polarizability: 13.241734 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 131-132 °C(lit.)
• Optical Rotation: [α]20/D -28.0°, c = 1 in THF

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C6H4F3NO4

DETAILS

Sigma Aldrich - 305251

Packaging
1 g in glass bottle
Application
Useful in the synthesis of 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene, a potent dopamine agonist.1 Used in the synthesis of sweetening agents, such as N-trifluoroacetyl-L-aspartic acid α-amides and α-anilides.2