(2S,3S,4R,5R)-4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate

• ChemBase ID: 158114
• Molecular Formular: C12H15NO7S
• Molecular Mass: 317.315
• Monoisotopic Mass: 317.05692283
• SMILES: CC(=O)O[C@@H]1CO[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)N=C=S
• Canonical SMILES: S=C=N[C@H]1OC[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C12H15NO7S/c1-6(14)18-9-4-17-12(13-5-21)11(20-8(3)16)10(9)19-7(2)15/h9-12H,4H2,1-3H3/t9-,10-,11+,12+/m1/s1
• InChIKey: RCHZRAFPHKCWRI-WYUUTHIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate
• IUPAC Traditional name: (2S,3S,4R,5R)-4,5-bis(acetyloxy)-2-isothiocyanatooxan-3-yl acetate
• Synonyms: AITC; 2,3,4-Tri-O-acetyl-α-D-arabinopyranosyl isothiocyanate; 2,3,4-三-邻-乙酰基-α-D-吡喃阿拉伯糖异硫氰酸酯

Database IDs

• CAS Number: 62414-75-9
• MDL Number: MFCD00142781
• Beilstein Number: 1690031
• PubChem SID: 24889335; 162252250
• PubChem CID: 3080889

CALCULATED PROPERTIES

• Acid pKa: 15.064769
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.6093991
• LogD (pH = 7.4): 0.6093991
• Log P: 0.6093991
• Molar Refractivity: 70.4832 cm^3
• Polarizability: 29.17503 Å^3
• Polar Surface Area: 100.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +50±1°, c = 1% in chloroform stab. with amylenes

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-42
• Safety Statements: 23-26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0%; ≥98.0% (sum of enantiomers, HPLC)
• Grade: for chiral derivatization
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C12H15NO7S

DETAILS

Sigma Aldrich - 90245

Other Notes
Chiral derivatizing agent for amines, amino acids and amino alcohols; det. of enantiomeric purity by HPLC1,2,3