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
• Article Data: 12

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

General Description

5-Chloromethylthiazole is a chemical compound with the molecular formula C4H4ClNS. It is a thiazole derivative with a chlorine atom attached to the methyl group. 5-Chloromethylthiazole is commonly used as an intermediate for the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential antimicrobial and antifungal properties. 5-Chloromethylthiazole is a clear, colorless to slightly yellow liquid at room temperature and is soluble in organic solvents. It is important to handle this compound with care, as it may be harmful if ingested or inhaled, and can cause skin irritation upon contact.

Upstream product

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

Downstream Products

• 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 
• 937662-70-9 N-(thiazol-5-yl-methyl)ethylamine 
• 933751-05-4 N-(thiazol-5-ylmethyl)methylamine 
• 1442476-78-9 methyl (S)-2-((tert-butoxycarbonyl)(thiazol-5-ylmethyl)amino)-3-phenylpropanoate 
• 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.

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.