2,4-Dibromothiazole

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CAS:4175-77-3
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2,4-Dibromothiazole Basic information
Product Name:2,4-Dibromothiazole
Synonyms:2,4-DIBROMOTHIAZOLE;2,4-BROMOTHIAZOLE;2,4-DIBROMOTHIAZOLE 98%;2,4-Dibromothiazole ,98%;2,4-DIBROMOTHIAZOLE, 97+%;2,4-Dibrmothiazole;2,4-dibormothiazole;Thiazole, 2,4-dibroMo-
CAS:4175-77-3
MF:C3HBr2NS
MW:242.92
EINECS:629-026-6
Product Categories:Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiazolesHeterocyclic Building Blocks;Halogenated;Organohalides;Thiazole;Thiazoles;blocks;Bromides
Mol File:4175-77-3.mol
2,4-Dibromothiazole Structure
2,4-Dibromothiazole Chemical Properties
Melting point 80-84 °C
Boiling point 242.8±13.0 °C(Predicted)
density 2.324±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Methanol[soluble in]
solubility soluble in Methanol
form powder to crystal
pka-1.93±0.10(Predicted)
color White to Light yellow
InChIInChI=1S/C3HBr2NS/c4-2-1-7-3(5)6-2/h1H
InChIKeyMKEJZKKVVUZXIS-UHFFFAOYSA-N
SMILESS1C=C(Br)N=C1Br
CAS DataBase Reference4175-77-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-37/38-41-36/37/38
Safety Statements 26-39-36-37/39
WGK Germany 3
Hazard Note Harmful
HazardClass IRRITANT, KEEP COLD
HS Code 29349990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3
MSDS Information
2,4-Dibromothiazole Usage And Synthesis
Chemical PropertiesOff-white crystalline powder
UsesBuilding block in a synthesis of Melithiazole C employing a highly (E)-selective cross-metathesis between the derived 4-vinylthiazole and a dienote side-chain.
Uses2,4-Dibromothiazole is an intermediate used in the preparation of various 2,4-disubstituted thiazole derivatives with biologically active properties such as survival motor neuron (SMN) protein modula tors.
Uses2,4-Dibromothiazole is applied as a building block in a synthesis of Melithiazole C employing a highly (E)-selective cross-metathesis between the derived 4-vinylthiazole and a dienote side-chain. It is also used as an intermediate in the preparation of various 2,4-disubstituted thiazole derivatives with biologically active properties such as survival motor neuron (SMN) protein modulators.
Synthesis
2,4-Thiazolidinedione

2295-31-0

2,4-Dibromothiazole

4175-77-3

General procedure for the synthesis of 2,4-dibromothiazoles from 2,4-thiazolidinediones: Example 41: Preparation of 2-amino-3-methyl-5-(3-pyrimidin-5-ylphenyl)-5-(1,3-thiazol-4-yl)-3,5-dihydro-4H-imidazol-4-one Step a) Preparation of compound 2 A mixture of 2,4-thiazolidinedione 1 (2.28 g, 19.5 mmol) with phosphorus tribromide (25.0 g, 87.0 mmol) was heated at 130°C for 30 min and subsequently cooled to room temperature. The reaction mixture was diluted with ice water (300 mL) and neutralized by batchwise addition of solid sodium carbonate. After neutralization was complete, the mixture was extracted with dichloromethane (3 x 150 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by fast column chromatography (silica gel, elution gradient: 0:100 to 5:95 ethyl acetate/hexane) to afford compound 2 (3.34 g, 71%) as light yellow crystals.1H NMR (500 MHz, CDCl3) δ 7.21 (s, 1H).

References[1] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3754 - 3761
[2] Synthesis, 2012, vol. 44, # 7, p. 1026 - 1029
[3] Journal of Materials Chemistry C, 2017, vol. 5, # 45, p. 11927 - 11936
[4] Patent: US2007/4786, 2007, A1. Location in patent: Page/Page column 21
[5] Tetrahedron, 2006, vol. 62, # 38, p. 9017 - 9037
Tag:2,4-Dibromothiazole(4175-77-3) Related Product Information
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