45438-77-5

Basic information

• Product Name: 5-Chloromethylthiazole
• Synonyms: 5-(chloroMethyl)-1,3-thiazole;5-(chloromethyl)-1,3-thiazole hydrochloride;5-thiazolylmethyl chloride
• CAS NO: 45438-77-5
• Molecular Formula: C₄H₄ClNS
• Molecular Weight: 133.5993
• Product Categories: Thiazoles
• Mol File: 45438-77-5.mol

Chemical Properties

• Boiling Point: 214.9 °C at 760 mmHg
• Flash Point: 83.8 °C
• Appearance: /
• Density: 1.338 g/cm³
• CAS DataBase Reference: 5-Chloromethylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloromethylthiazole(45438-77-5)
• EPA Substance Registry System: 5-Chloromethylthiazole(45438-77-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 45438-77-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloromethylthiazole is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Chloromethylthiazole is utilized as an intermediate in the production of agrochemicals, aiding in the creation of compounds that can protect crops from pests and diseases.
Used in Antimicrobial Applications:
5-Chloromethylthiazole is studied for its potential as an antimicrobial agent, leveraging its ability to combat harmful microorganisms, which can be beneficial in various medical and industrial settings.
Used in Antifungal Applications:
5-Chloromethylthiazole is also being investigated for its antifungal properties, making it a candidate for use in treatments and products designed to prevent fungal infections.

Upstream product

• 38585-74-9 thiazol-5-yl-methanol 
• 105827-91-6 α-Cl-β-thiazolyl chloride 
• 124-63-0 methanesulfonyl chloride 
• 3581-89-3 5-methylthiazole 

Downstream Products

• 1442476-78-9 methyl (S)-2-((tert-butoxycarbonyl)(thiazol-5-ylmethyl)amino)-3-phenylpropanoate 
• 937662-70-9 N-(thiazol-5-yl-methyl)ethylamine 
• 933751-05-4 N-(thiazol-5-ylmethyl)methylamine 
• 172649-44-4 (1S,2R,2'R,4'S,2S)-1-((2-Benzyl-5-(((2-(t-butyl)amino)carbonyl)-4-((thiazol-5-yl)methyl)piperazin-1-yl)-4-hydroxypentanoyl)amino)indan-2-ol 
• 181040-44-8 2-Fluoro-4-(thiazol-5-ylmethoxy)benzonitrile 

Relevant articles and documents

Synthesis of Arylethylamines via C(sp3)-C(sp3) Palladium-Catalyzed Cross-Coupling

Substituted arylethylamines represent a key structural motif in natural, pharmaceutical, and agrochemical compounds. Access to such scaffolds has been the subject of long-standing synthetic interest. Herein, we report the synthesis of such scaffolds via a palladium-catalyzed C(sp3)-C(sp3) coupling between (chloromethyl)aryls and air-/moisture-stable N,N-dialkylaminomethyltrifluoroborate salts. Rapid hit identification was achieved using microscale high-throughput experimentation and was followed by millimolar-scale reaction parameter optimization. A range of structurally and electronically varied arylethylamine products were obtained in moderate to excellent yields (27-96%, >60 examples). The reaction mechanism is proposed to proceed via formation of a trialkylbenzylammonium species prior to oxidative addition.

Antitubercular and Antiparasitic 2-Nitroimidazopyrazinones with Improved Potency and Solubility

Following the approval of delamanid and pretomanid as new drugs to treat drug-resistant tuberculosis, there is now a renewed interest in bicyclic nitroimidazole scaffolds as a source of therapeutics against infectious diseases. We recently described a nitroimidazopyrazinone bicyclic subclass with promising antitubercular and antiparasitic activity, prompting additional efforts to generate analogs with improved solubility and enhanced potency. The key pendant aryl substituent was modified by (i) introducing polar functionality to the methylene linker, (ii) replacing the terminal phenyl group with less lipophilic heterocycles, or (iii) generating extended biaryl side chains. Improved antitubercular and antitrypanosomal activity was observed with the biaryl side chains, with most analogs achieved 2- to 175-fold higher activity than the monoaryl parent compounds, with encouraging improvements in solubility when pyridyl groups were incorporated. This study has contributed to understanding the existing structure-activity relationship (SAR) of the nitroimidazopyrazinone scaffold against a panel of disease-causing organisms to support future lead optimization.

Synthesis method of ritonavir intermediate 5-hydroxymethylthiazole

The invention discloses a synthetic method of a ritonavir intermediate 5-hydroxymethyl thiazole. The synthetic method includes following steps: adding 200 g of 2-chloro-5-chloromethylthiazole, 240 g of an acid-binding agent, 600 g of methanol, 120 g of a Raney nickel catalyst and water into a hydrogenation kettle, performing nitrogen replacementfor three times and hydrogen replacement for three times, pressurizing the kettle to 1.0-1.4 PA, heating the kettle to 67.5 DEG C, and carrying out heat preservation 32-38 h; taking 2-chloro-5-chloromethylthiazole which is less than or equal to 0.3%, after the reaction is finished, relieving pressure, filtering the reaction product, recovering Raney nickel, drying an organic layer for 1 hour under reduced pressure, washing the organic layer with EA,blending the organic layer, recovering the organic layer under reduced pressure, and rectifying the semi-product to obtain 5-chloromethylthiazole. The method is simple in process step, short in production period, high in yield, low in process three-waste amount, capable of effectively considering the cost of industrial production, safe and suitable for industrial large-scale production.

Hetero-aromatic compound and its use in medicine (by machine translation)

The invention discloses heteroaromatic compound and its use in medicine, in particular, the invention provides a hetero-aromatic compound or its stereoisomers, geometric isomers, tautomers, racemate, nitrogen oxide, hydrate, solvate, metabolite, pharmaceutically acceptable salt or prodrug, and containing said pharmaceutical composition; the invention also discloses the compound or its pharmaceutical compositions in use for preparing a medicament, and in the treatment of autoimmune diseases or proliferative diseases of application. (by machine translation)

Thiazole alkyl pyridylamine compound and preparation method and application thereof

The present invention discloses a thiazole alkyl pyridylamine compound shown in formula (I) and a preparation method and application thereof, wherein R, R ', Z, R1 and R2 are as defined in the specification. The thiazole alkyl pyridylamine compound shown in formula (I) has bactericidal, acaricidal or herbicidal biologically activity, and has high activity on pathogenic bacteria such as sclerotinia sclerotiorum, botrytis cinerea pers, and the like.

HEPATITIS B CORE PROTEIN ALLOSTERIC MODULATORS

ABSTRACT The present disclosure provides, in part, compounds having allosteric effector properties against Hepatitis B virus Cp. Also provided herein are methods of treating viral infections, such as hepatitis B, comprising administering to a patient in need thereof a disclosed compound.

Structure-activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers. Part II: P2/P3 region and discovery of cobicistat (GS-9350)

The HIV protease inhibitor (PI) ritonavir (RTV) has been widely used as a pharmacoenhancer for other PIs, which are substrates of cytochrome P450 3A (CYP3A). However the potent anti-HIV activity of ritonavir may limit its use as a pharmacoenhancer with other classes of anti-HIV agents. Ritonavir is also associated with limitations such as poor physicochemical properties. To address these issues a series of compounds with replacements at the P2 and/or P3 region was designed and evaluated as novel CYP3A inhibitors. Through these efforts, a potent and selective inhibitor of CYP3A, GS-9350 (cobicistat) with improved physiochemical properties was discovered.

ANTIPROLIFERATIVE BENZO [B] AZEPIN- 2 - ONES

Disclosed are compounds of Formula (I) or pharmaceutically acceptable salts thereof, wherein W, X, Y, Z, R1, R2, R3 and R4 are described in this application, and methods of using said compounds in the treatment of cancer.

Synthesis and properties of NLO chromophores with fine-tuned gradient electronic structures

A novel series of heterocycle-based NLO chromophores based on different combinations of auxiliary donor (i.e., benzene, thiophene and pyrrole) and auxiliary acceptor (i.e., thiazole with different regiochemistries) were designed and synthesized. Due to the different electron-rich and poor nature of the auxiliary donors and acceptors, respectively, the resulting NLO chromophores have systematically varied ground-state electronic structures, as evidenced by the 1H NMR, CV and UV-vis investigations. The nonlinear optical properties of the resulting NLO chromophores were studied by UV-vis spectroscopy, Hyper-Rayleigh scattering (HRS), and semi-empirical computations. All the chromophores have very large molecular hyperpolarizabilities (β1000 nm) in the range of 704-1500 × 10-30 esu (or β0, 318-768 × 10-30 esu), which showed a great sensitivity to the gradient electronic structures. Upon increasing the electron density from benzene to thiophene and to pyrrole, substantial increases in β0 were observed; significantly larger β0 values were also observed for NLO chromophores based on "matched" thiazole (C2 is connected to the acceptor) than those based on "un-matched" thiazole (C5 is connected to the acceptor). TGA investigations showed good thermal stability for the resulting NLO chromophores. However, with the increase of electron density of the auxiliary donor, a decrease in thermal and photochemical stability was observed. It is interesting to note that NLO chromophores based on triarylamine as the donor and thiazole as the auxiliary acceptor exhibited not only high thermal stability but also very large β0 values.

Use of 2-aminothiazoline derivatives as inhibitors of inducible no-synthase

The present invention relates to the use of 2-aminothiazoline derivatives of formula: in which either R1 is a hydrogen atom or an alkyl radical and R2 is an alkyl, -alk-NH2, —CH2—R3, —CH2—S