2,4,6-tris(propan-2-yl)benzene-1-sulfonyl azide

• ChemBase ID: 143344
• Molecular Formular: C15H23N3O2S
• Molecular Mass: 309.42702
• Monoisotopic Mass: 309.15109799
• SMILES: CC(C)c1cc(c(c(c1)C(C)C)S(=O)(=O)N=[N+]=[N-])C(C)C
• Canonical SMILES: [N-]=[N+]=NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C
• InChI: InChI=1S/C15H23N3O2S/c1-9(2)12-7-13(10(3)4)15(14(8-12)11(5)6)21(19,20)18-17-16/h7-11H,1-6H3
• InChIKey: AEMWUHCKKDPRSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4,6-tris(propan-2-yl)benzene-1-sulfonyl azide
• IUPAC Traditional name: 2,4,6-triisopropylbenzenesulfonyl azide
• Synonyms: Trisyl azide solution; 2,4,6-Triisopropylbenzenesulfonyl azide solution; 2,4,6-Triisopropylphenylsulfonyl azide; 2,4,6-Tris(1-methylethyl)-benzenesulfonyl azide; 2,4,6-Triisopropylbenzenesulfonyl azide; Trisyl azide; 2,4,6-三异丙基苯磺酰叠氮化物 溶液; 2,4,6-三异丙基苯磺酰叠氮化物; 2,4,6-三异丙基苯磺酰基叠氮化物

Database IDs

• CAS Number: 36982-84-0
• MDL Number: MFCD00859286
• Beilstein Number: 2391566
• PubChem SID: 162237564
• PubChem CID: 371707

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.845143
• LogD (pH = 7.4): 4.845143
• Log P: 4.9591885
• Molar Refractivity: 85.3454 cm^3
• Polarizability: 33.06464 Å^3
• Polar Surface Area: 63.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 39-44 °C; 40-44°C
• Flash Point: 110 °C; 230 °F; 39.2 °F; 4 °C
• Refractive Index: n20/D 1.499

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 5-36/37/38; 63-11-22-38-48/20-65-67
• Safety Statements: 16-36/37-62; 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H304-H315-H336-H361d-H373; H315-H319-H335
• GHS Precautionary statements: P210-P261-P281-P301 + P310-P331; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 97%; 98%, stab. with ca 10% water
• Concentration: 10%±2% in toluene
• Impurities: ≤0.015% water
• Contains: 15 wt. % water as stabilizer
• Empirical Formula (Hill Notation): C15H23N3O2S

DETAILS

Sigma Aldrich - 723045

Packaging
1, 5 g in glass bottle
Application
Reagent for:
• Stereoselective diversity-oriented synthesis of functionalized saccharides1
• Meyer′s lactamization2Reagent for synthesis of:
• Antidote to anthrax lethal factor intoxication3
• Bacterial RNA polymerase inhibitor4
• Bicyclic extended dipeptide surrogates5
• Single enantiomers of mycobacterial keomycolic acids6

REFERENCES

• Reagent for diazo transfer to ketones, e.g. under phase-transfer conditions, giving better yields of sterically-hindered ɑ-diazo ketones than other methods: Synthesis, 368 (1980); J. Am. Chem. Soc., 102, 6626 (1980); 113, 2598 (1991); Tetrahedron, 43, 5677 (1987).
• Also used for azide transfer to potassium enolates (KHMDS) to form the ɑ-azido derivatives: J. Am. Chem. Soc., 109, 6881 (1987); 112, 4011 (1990); Tetrahedron Lett., 28, 6141 (1987). Other bases tend to favor diazo transfer. For further discussion and examples, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 5174.