2-Bromothiazole

• Catalog No.: A14838
• CAS Number: 3034-53-5
• M. F.: C3H2BrNS
• M. W.: 164.02368
• Purity: 99%

SYNONYMS

• Title: 2-溴噻唑
• IUPAC name: 2-bromo-1,3-thiazole
• IUPAC Traditional name: thiazole, 2-bromo-

DATABASE IDS

• EC Number: 221-229-4
• MDL Number: MFCD00005316
• Beilstein Number: 105724
• CAS Number: 3034-53-5

PROPERTIES

• Purity: 99%
• Boiling Point: 171°C
• Density: 1.836
• Flash Point: 63°C(145°F)
• Refractive Index: 1.5930
• GHS Hazard statements: H315-H319-H335-H227
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是

REFERENCES

• 2-Lithiothiazole can be obtained by direct lithiation of thiazole or, more conveniently, by exchange with 2-bromothiazole using n-BuLi: J. Org. Chem., 53, 1748 (1988). It behaves as a valuable formyl anion equivalent, and as such has been applied, mainly by Dondoni's group, in the syntheses of a variety of products; see, e.g.: Tetrahedron Lett., 34, 7319, 7323, 7327 (1993). See also 2-(Trimethylsilyl)thiazole, B21903. Reaction of 2-lithiothiazole with nitrones gives ɑ-aminoaldehydes: Tetrahedron Lett., 33, 4221 (1992); stereocontrolled addition to C-galacto-pyranosylnitrone has been used in syntheses of destomic acid, a component of the antibiotics destomycin and hygromycin, and of lincosamine, the sugar component of the anticancer antibiotic lincomycin: Synlett, 78 (1993). For applications of 2-lithiothiazole in the synthesis of the aza-sugar (+)-galactostsin, see: J. Org. Chem., 60, 4749 (1995). The Thiazole Aldehyde Synthesis has been reviewed by Dondoni: Synthesis, 1681 (1998).