[(2S)-oxiran-2-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 74255
• Molecular Formular: C10H12O4S
• Molecular Mass: 228.26488
• Monoisotopic Mass: 228.04562986
• SMILES: S(=O)(=O)(c1ccc(cc1)C)OC[C@@H]1CO1
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@H]1OC1
• InChI: InChI=1S/C10H12O4S/c1-8-2-4-10(5-3-8)15(11,12)14-7-9-6-13-9/h2-5,9H,6-7H2,1H3/t9-/m0/s1
• InChIKey: NOQXXYIGRPAZJC-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-oxiran-2-yl]methyl 4-methylbenzene-1-sulfonate; (2S)-oxiran-2-ylmethyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: (2S)-oxiran-2-ylmethyl 4-methylbenzenesulfonate
• Synonyms: (S)-(+)-Glycidyl p-toluenesulfonate; (S)-(+)-Oxirane-2-methanol p-toluenesulfonate; (2S)-(+)-Glycidyl tosylate; (S)-Oxiran-2-ylMethyl 4-Methylbenzenesulfonate; (2S)-2-Oxiranemethanol 2-(4-Methylbenzenesulfonate); (+)-Glycidyl Tosylate; (S)-(+)-Oxiran-2-ylmethyl 4-Methylbenzenesulfonate; (S)-Oxiran-2-ylmethyl Toluene-4-sulfonate; (S)-Toluene-4-sulfonic Scid Oxiranylmethyl Ester; (S)-(2,3-Epoxypropan-1-yl) 4-Methylbenzenesulfonate; (2S)-(+)-Glycidyl Tosylate; (2S)-(+)-Glycidyl tosylate; (2S)-Oxiran-2-ylmethyl 4-methylbenzenesulphonate; (S)-(+)-对甲苯磺酸缩水甘油酯; (S)-(+)-环氧乙烷-2-甲醇对甲苯磺酸酯; (2S)-(+)-缩水甘油对甲苯磺酸酯

Database IDs

• CAS Number: 70987-78-9
• EC Number: 417-210-7
• MDL Number: MFCD00064489
• Beilstein Number: 3592143
• PubChem SID: 162039174; 24878443
• PubChem CID: 153296

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8868012
• LogD (pH = 7.4): 1.8868012
• Log P: 1.8868012
• Molar Refractivity: 54.9487 cm^3
• Polarizability: 22.457752 Å^3
• Polar Surface Area: 55.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dioxane; DMSO; Methanol
• Apperance: Off-White SOlid
• Melting Point: 41-43°C; 46-49 °C(lit.); 47-49°C
• Flash Point: 113 °C; 235.4 °F

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant
• RTECS: RR0510050
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 45-41-43-51/53-68
• Safety Statements: 53-45-61
• GHS Pictograms: GHS05; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H318-H341-H350-H411
• GHS Precautionary statements: P201-P273-P280-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C10H12O4S

DETAILS

Sigma Aldrich - 540129

Application
Used in the first enantioselective synthesis of (R)- and (S)-4-acetyl-3-(hydroxymethyl)-3,4-dihydro-2H-pyrido[3,2-b]oxazines.1
Packaging
5, 25 g in glass bottle
Legal Information
Manufactured under license by Shasun Chemicals and Drugs Limited, using Jacobsen HKR technology.

Toronto Research Chemicals - G616001

Protected Glycidol, used as an intermediate in the preparation of neurochemicals.

REFERENCES

• Wang, J., et al.: J. Med. Chem., 48, 6271 (2005)
• Qian, L., et al.: ChemMedChem, 1, 376 (2005)
• Li, Y., et al.: Bioorg. Med. Chem. Lett., 19, 5037 (2005)