3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride

• ChemBase ID: 90581
• Molecular Formular: C13H16ClNOS
• Molecular Mass: 269.79024
• Monoisotopic Mass: 269.06411282
• SMILES: [n+]1(csc(c1C)CCO)Cc1ccccc1.[Cl-]
• Canonical SMILES: OCCc1sc[n+](c1C)Cc1ccccc1.[Cl-]
• InChI: InChI=1S/C13H16NOS.ClH/c1-11-13(7-8-15)16-10-14(11)9-12-5-3-2-4-6-12;/h2-6,10,15H,7-9H2,1H3;1H/q+1;/p-1
• InChIKey: IWSVLBKHBJGMAA-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride
• IUPAC Traditional name: 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride
• Synonyms: 3-Benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride; 3-苄基-5-(2-羟基乙基)-4-甲基噻唑鎓氯化物; 3-苄基-5-(2-羟乙基)-4-甲基氯化噻唑

Database IDs

• CAS Number: 4568-71-2
• EC Number: 224-947-6
• MDL Number: MFCD00011959
• Beilstein Number: 3788921
• PubChem SID: 24848161; 24855509; 162077377
• PubChem CID: 2833352

CALCULATED PROPERTIES

• Acid pKa: 15.505245
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.3549578
• LogD (pH = 7.4): -1.3549578
• Log P: -1.3549578
• Molar Refractivity: 67.0971 cm^3
• Polarizability: 25.672298 Å^3
• Polar Surface Area: 24.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 142-144 °C(lit.); 142-144°C; 142-145°C

Safety Information

• Storage Warning: Hygroscopic; Irritant/Hygroscopic/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (AT); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C13H16ClNOS

DETAILS

Sigma Aldrich - 256234

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 13453

Other Notes
Catalyst for the addition of aliphatic and heterocyclic aldehydes to α,β-unsaturated ketones, nitriles and esters1,2,3

REFERENCES

• For reviews, see: Angew. Chem. Int. Ed., 15, 639 (1976); Org. React., 40, 407 (1991). For a further example, see Phenyl vinyl sulfone, A14794.
• Aliphatic aldehydes undergo the acyloin condensation in the presence of this catalyst and mild base. For example (butyraldehyde to butyroin), see: Org. Synth. Coll., 7, 95 (1990).
• The same system is effective in catalyzing the addition of aldehydes to electron-deficient alkenes, including ɑ?-unsaturated ketones, esters and nitriles (Stetter reaction), providing a non-toxic alternative to cyanide in these reactions; e.g. in the synthesis of dihydrojasmone: Org. Synth. Coll., 8, 620 (1993):