2-bromo-1,3-thiazole

• ChemBase ID: 21406
• Molecular Formular: C3H2BrNS
• Molecular Mass: 164.02368
• Monoisotopic Mass: 162.90913207
• SMILES: c1(sccn1)Br
• Canonical SMILES: Brc1nccs1
• InChI: InChI=1S/C3H2BrNS/c4-3-5-1-2-6-3/h1-2H
• InChIKey: RXNZFHIEDZEUQM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-1,3-thiazole
• IUPAC Traditional name: thiazole, 2-bromo-
• Synonyms: 2-Bromo-1,3-thiazole; 2-Bromothiazole; 2-Bromo-1,3-thiazole; NSC 91532; 2-Bromothiazole; 2-溴噻唑

Database IDs

• CAS Number: 3034-53-5
• EC Number: 221-229-4
• MDL Number: MFCD00005316
• Beilstein Number: 105724
• PubChem SID: 160984713; 24849873
• PubChem CID: 76430

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.6960974
• LogD (pH = 7.4): 1.6961056
• Log P: 1.6961057
• Molar Refractivity: 28.8912 cm^3
• Polarizability: 11.275743 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Brown Oil
• Boiling Point: 170.5-171.5°C; 171 °C(lit.); 171°C; 171°C; 70-71°C/20mm
• Flash Point: 152.6 °F; 63°C(145°F); 67 °C; 67°C
• Density: 1.82 g/mL at 25 °C(lit.); 1.820; 1.836
• Refractive Index: 1.5930; n20/D 1.593(lit.)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT, FLAMMABLE; Irritant/Light Sensitive/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 95+%; 97%; 98%; 99%
• Empirical Formula (Hill Notation): C3H2BrNS

DETAILS

MP Biomedicals - 05224233

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 160474

Application
Aryl halide used to N-arylate 5- and 7-azaindoles.1 Copper-catalyzed cyanation provides 2-cyanothiazole.2
Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - B688160

2-Bromothiazole is a heterocyclic S compound to induce base-pair substitution and having mutagenic activity.

REFERENCES

• Voogd, C.E., et al.: Mutation Research, Genetic Toxicology Testing, 118, 153 (1983)
• 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).