4175-77-3

Basic information

• Product Name: 2,4-Dibromothiazole
• Synonyms: 2,4-DIBROMOTHIAZOLE;2,4-BROMOTHIAZOLE;2,4-Dibromo-1,3-thiazole;2,4-DIBROMOTHIAZOLE 98%;2,4-Dibromothiazole ,98%;2,4-DIBROMOTHIAZOLE, 97+%;2,4-Dibrmothiazole;2,4-dibormothiazole
• CAS NO: 4175-77-3
• Molecular Formula: C₃HBr₂NS
• Molecular Weight: 242.92
• EINECS: 1308068-626-2
• Product Categories: blocks;Bromides;Thiazoles;Thiazole;Halogenated;Organohalides;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiazolesHeterocyclic Building Blocks
• Mol File: 4175-77-3.mol

Chemical Properties

• Melting Point: 80-84°C
• Boiling Point: 242.8 °C at 760 mmHg
• Flash Point: 100.6 °C
• Appearance: Off-white crystalline powder
• Density: 2.324 g/cm³
• Storage Temp.: Keep Cold
• Solubility: soluble in Methanol
• PKA: -1.93±0.10(Predicted)
• CAS DataBase Reference: 2,4-Dibromothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dibromothiazole(4175-77-3)
• EPA Substance Registry System: 2,4-Dibromothiazole(4175-77-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-39-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 4175-77-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dibromothiazole is used as an intermediate for the preparation of 2,4-disubstituted thiazole derivatives with biologically active properties, such as survival motor neuron (SMN) protein modulators. These modulators play a crucial role in the development of therapeutic agents for various diseases and conditions.
Used in Organic Synthesis:
2,4-Dibromothiazole is used as a building block in the synthesis of Melithiazole C, employing a highly (E)-selective cross-metathesis between the derived 4-vinylthiazole and a dienone side-chain. This application highlights its importance in the development of complex organic molecules with potential applications in various fields, including pharmaceuticals and materials science.

Upstream product

• 57314-13-3 2,4,5-tribromothiazole 
• 2295-31-0 thiazoline-2,4-dione 
• 2682-49-7 thiazolidine-2-one 
• 21295-51-2 phosphoryl(III) bromide 

Downstream Products

• 108306-53-2 4-Bromo-2-trimethylsilylthiazole 
• 139669-97-9 (2,4-Dibromo-thiazol-5-yl)-diphenyl-methanol 
• 139669-96-8 2,4-dibromo-1,3-thiazole-5-carboxylic acid 
• 88982-82-5 4-bromo-1,3-thiazole-2-carboxylic acid 
• 139669-95-7 2,4-dibromo-1,3-thiazole-5-carbaldehyde 
• 34259-99-9 4-bromo-1,3-thiazole 
• 204513-61-1 2-(piperidin-1-yl)-4-bromothiazole 
• 208264-53-3 1-(4-bromo-1,3-thiazol-2-yl)ethanone 
• 204513-62-2 4-bromo-2-(methylsulfanyl)-1,3-thiazole 
• 167366-05-4 4-bromo-1,3-thiazole-2-carbaldehyde 
• 240816-34-6 2-ethoxy-4-bromothiazole 
• 209260-74-2 2-vinyl-4-bromothiazole 
• 271601-01-5 4-bromo-2-[5-chloro-2-(methoxymethoxy)phenyl]thiazole 
• 271601-02-6 4-bromo-2-[4-(tert-butyl)-2-(methoxymethoxy)phenyl]thiazole 

Relevant articles and documents

The X-ray Structures of 2,4-Dibromothiazole and 2,4-Diacetyl-5-bromothiazole

2,4-Dibromothiazole [orthorhombic, a = 6.700 (10), b = 16.21 (3), c = 5.516 (8) ?, space group Fmm2] shows a disordered crystal structure with molecules randomly oriented with respect to the direction of the Br-C(2)-N-C(2)-Br unit and the remaining ring atoms S(3) and C(3)H showing mixed occupancy. 2,4-Diacetyl-5-bromothiazole [triclinic, a = 4.040 (2), b = 8.254 (5), c = 13.208 (8) ?, α = 96.191 (17), β = 93.865 (16), γ = 94.067 (11)°, space group P-1] shows a structure dominated by halogen bonding, intramolecular between 4-COMe and 5-Br and intermolecular between 2-COMe of one molecule and 5-Br of the next. Graphical Abstract: 2,4-Dibromothiazole is disordered in the crystal structure with molecules randomly oriented either way round as shown. There is evidence for unusual intramolecular, and perhaps also intermolecular, halogen bonding between Br and C = O in the structure of 2,4-diacetyl-5-bromothiazole.[Figure not available: see fulltext.]

Pyrrolo[2,3-d:5,4-d′]bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-Ring Bithiophenes

New synthetic methods have been developed for the preparation of 4-alkyl- and 4-aryl-pyrrolo[2,3-d:5,4-d′]bisthiazole (PBTz) building blocks from 2,4-thiazolidinedione. The resulting PBTz products have been fully characterized via structural, electronic, and optical methods, thus allowing full comparison to the previously reported dithieno[3,2-b:2′,3′-d]pyrrole (DTP) analogues. Such comparisons then allow a detailed discussion of the relative electronic effects of the various methods utilized to tune the properties of the parent DTP building block.

Synthesis, molecular docking, antimicrobial, antioxidant and anticonvulsant assessment of novel S and C-linker thiazole derivatives

In medicinal chemistry, the searching for new anticonvulsants with greater selectivity and reduced toxicity is still active. Therefore, multistep reaction sequence has been explored to obtained novel series of S and C-linker thiazole derivatives (7a-h and 8a-d). The final compounds were screened for antimicrobial activity against different microbial strains. The DPPH and hydroxyl radical scavenging methods were evaluated to assess their antioxidant capabilities. The anticonvulsant activity was established in MES and PTZ seizure models and the most active compound was 7b and 7 g which showed 100% protection. A computational study was also carried out including drug likeness and docking studies.

Composite tetraheteroarylenes and related higher cyclic oligomers of heteroarenes produced by palladium-catalyzed direct coupling

Substantial research interests have been focused on cyclic π-conjugated molecules owing to their unique chemical and physical properties. By constructing hybrid aromatic arrays within these cyclic systems, new series of composite macrocycles would be prov

Novel 4,8-benzobisthiazole copolymers and their field-effect transistor and photovoltaic applications

A series of copolymers containing the benzo[1,2-d:4,5-d′]bis(thiazole) (BBT) unit has been designed and synthesised with bisthienyl-diketopyrrolopyrrole (DPP), dithienopyrrole (DTP), benzothiadiazole (BT), benzodithiophene (BDT) or 4,4′-dialkoxybithiazole (BTz) comonomers. The resulting polymers possess a conjugation pathway that is orthogonal to the more usual substitution pathway through the 2,6-positions of the BBT unit, facilitating intramolecular non-covalent interactions between strategically placed heteroatoms of neighbouring monomer units. Such interactions enable a control over the degree of planarity through altering their number and strength, in turn allowing for tuning of the band gap. The resulting 4,8-BBT materials gave enhanced mobility in p-type organic field-effect transistors of up to 2.16 × 10-2 cm2 V-1 s-1 for pDPP2ThBBT and good solar cell performance of up to 4.45% power conversion efficiency for pBT2ThBBT.

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.

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

Convenient preparation of halo-1,3-thiazoles: Important building blocks for materials and pharmaceutical synthesis

Convenient, scalable and high-yielding approaches to 2,5- and 2,4-dibromo-1,3-thiazole are reported that offer significant improvements over previously reported approaches. 2,5-Dibromo-1,3-thiazole was generated in two steps from commercially inexpensive 2-amino-1,3-thiazole, whereas 2,4-dibromo-1,3-thiazole was generated in a single step from commercially inexpensive 1,3-thiazolidine-2,4-dione. As part of this study, convenient approaches to 2-bromo- and 2-iodo-1,3-thiazole were also developed. Georg Thieme Verlag Stuttgart · New York.

Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities

The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.

Compounds and Methods of Treatment

A derivative, which is useful as a ret kinase inhibitor is described herein. The described invention also includes methods of using the same in the treatment of diseases mediated by inappropriate ret kinase activity.