34259-99-9

Basic information

• Product Name: 4-Bromothiazole
• Synonyms: 4-BROMOTHIAZOLE;4-Bromo-1,3-thiazole;4-BroMothiazole 97%
• CAS NO: 34259-99-9
• Molecular Formula: C₃H₂BrNS
• Molecular Weight: 164.02
• EINECS: 1308068-626-2
• Product Categories: pharmacetical;Thiazole series;Halogenated;Organohalides;Thiazole;Thiazoles;ThiazolesHeterocyclic Building Blocks;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Building Blocks;C3 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 34259-99-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 190°C(lit.)
• Flash Point: 102 °C
• Appearance: Clear to slightly turbid colorless to yellow-brownish to pink/Solution
• Density: 1.839 g/mL at 25 °C
• Vapor Pressure: 0.535mmHg at 25°C
• Refractive Index: n20/D 1.602
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -0.05±0.10(Predicted)
• CAS DataBase Reference: 4-Bromothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromothiazole(34259-99-9)
• EPA Substance Registry System: 4-Bromothiazole(34259-99-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 34259-99-9(Hazardous Substances Data)

Usage

General Description

4-Bromothiazole is a chemical compound that belongs to the class of thiazole derivatives. It is a clear, colorless to pale yellow liquid that is mainly used as a building block in the synthesis of pharmaceuticals and agrochemicals. 4-Bromothiazole exhibits strong nucleophilic characteristics due to the presence of a bromine atom, making it useful in the formation of carbon-carbon and carbon-heteroatom bonds. It also has potential applications in the development of new materials and in the field of organic synthesis. However, it is important to handle 4-Bromothiazole with caution due to its hazardous nature and potential health effects.

InChI:InChI=1/C3H2BrNS/c4-3-1-6-2-5-3/h1-2H

Upstream product

• 4175-77-3 2,4-dibromo-1,3-thiazole 
• 57314-13-3 2,4,5-tribromothiazole 
• 108306-53-2 4-Bromo-2-trimethylsilylthiazole 
• 1613393-51-3 (3aR,5S)-5-methyl-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1 ,2]oxazole 
• 20731-74-2 3-(methylthio)thiophene 
• 173978-99-9 4-bromo-2-lithiothiazole 

Downstream Products

• 162704-76-9 4-(pyridin-3-yl)thiazole 
• 1083180-00-0 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiazole 
• 3364-80-5 1,3-thiazole-4-carbaldehyde 
• 148-79-8 thiabendazole 
• 1826-12-6 4-phenyl-thiazole 

Relevant articles and documents

Synthesis of thiazole compounds via lithiation: An unexpected rearrangement

A novel rearrangement was discovered during an investigation of the lithium-bromine exchange reactions of bromothiazole derivatives and their subsequent reactions with various electrophiles.

An Approach to Nonsymmetric Bis(tertiary phosphine oxides) Comprising Heterocyclic Fragments via the Pd-Catalyzed Phosphorylation

Nonsymmetric tertiary phosphine oxides with different five- and six-membered heterocyclic fragments such as pyridine, 2,2′-bipyridine, 1,10-phenantroline, quinoline, imidazole, and thiazole were synthesized in good yields via the successive introduction of phosphine oxide groups into the initial dihalogenated heterocycles by means of Pd-catalyzed phosphorylation reaction. The synthesis of pyridine-type compounds is hindered by competing double coupling, while for five-membered heterocycles the principal difficulty is the dehalogenation. Both side processes were successfully suppressed by the use of an excess of a dihalide (which can be easily recovered during the product purification step), proper phosphine ligand for palladium, and nonpolar solvent such as toluene.

Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods

The synthesis of the full family of bromothiazoles has been revisited in order to update and optimize their production. The species reported include 2-bromothiazole, 4-bromothiazole, 5-bromothiazole, 2,4-dibromothiazole, 2,5-dibromothiazole, 4,5-dibromothiazole, and 2,4,5-tribromothiazole, the majority of which are produced via sequential bromination and debromination steps. This complete family can now be produced without the use of elemental bromine, and the presented methods have allowed the physical and NMR spectroscopic characterization of the full family to be reported for the first time.