23784-96-5

Basic information

• Product Name: 2-Chloro-5-chloromethylthiophene
• Synonyms: 2-CHLORO-5-(CHLOROMETHYL)THIOPHENE;2-CHLORO-5-CHLOROMETHYLTHIOPHENE 98+%;5-Chloro-2-thenyl chloride;2-Chloro-5-(chloromethyl)thiophene,97%
• CAS NO: 23784-96-5
• Molecular Formula: C₅H₄Cl₂S
• Molecular Weight: 167.06
• Product Categories: Sulphur Derivatives;Sulfur;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks
• Mol File: 23784-96-5.mol

Chemical Properties

• Boiling Point: 83-85 °C8 mm Hg(lit.)
• Flash Point: 213 °F
• Appearance: Colorless to brown/Liquid
• Density: 1.385 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.211mmHg at 25°C
• Refractive Index: n20/D 1.575(lit.)
• Storage Temp.: ?20°C
• CAS DataBase Reference: 2-Chloro-5-chloromethylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-5-chloromethylthiophene(23784-96-5)
• EPA Substance Registry System: 2-Chloro-5-chloromethylthiophene(23784-96-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 23784-96-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-5-chloromethylthiophene is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the synthesis of complex molecules with potential therapeutic applications.
2-Chloro-5-chloromethylthiophene is used as a building block for the synthesis of 1-(1,1′-biphenyl-4-yl)-3-(5-chloro-thiophen-2-yl)-2-(1H-imidazol-1-yl)propane and 1-(5-chlorothiophen-2-yl)-2-(1H-imidazol-1-yl)-3-phenylpropane. These compounds may have potential applications in the development of new drugs targeting specific biological pathways or receptors.
Used in Chemical Research:
2-Chloro-5-chloromethylthiophene can be utilized as a research compound in academic and industrial laboratories. Its unique properties make it a valuable tool for studying the effects of structural modifications on the chemical and biological properties of thiophene derivatives.
Used in Material Science:
The compound may also find applications in the field of material science, where its chemical properties could be exploited to develop new materials with specific characteristics, such as improved stability, reactivity, or selectivity in various chemical processes.

InChI:InChI=1/C5H4Cl2S/c6-3-4-1-2-5(7)8-4/h1-2H,3H2

Upstream product

• 96-43-5 2-thienyl chloride 
• 50-00-0 formaldehyd 
• 79387-71-6 (5-bromothien-2-yl)methanol 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 74168-69-7 5-chloro-2-thiophenemethanol 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 636-72-6 2-thiophenemethanol 

Downstream Products

• 90797-71-0 (5-chloro-thiophen-2-ylmethyl)-pyridin-2-yl-amine 
• 148-65-2 Chlorothen 
• 101581-65-1 N-(5-chloro-[2]thienylmethyl)-N-(1-methyl-[4]piperidyl)-aniline 
• 92650-92-5 N-(5-chloro-[2]thienylmethyl)-N',N'-dimethyl-N-phenyl-ethylenediamine 
• 42520-90-1 (5-chlorothiophen-2-yl)acetonitrile 
• 74168-69-7 5-chloro-2-thiophenemethanol 
• 112758-76-6 N-benzoyl-N'-[2-[(5-chloro-2-thenyl)thio]ethyl]-thiourea 
• 94966-03-7 1-{3-[3-(5-chloro-[2]thienylmethyl)-4-methoxy-phenyl]-2-methyl-propyl}-piperidine 
• 94686-35-8 4-{3-[3-(5-chloro-thiophen-2-ylmethyl)-4-methoxy-phenyl]-2-methyl-propyl}-morpholine 
• 945027-70-3 C₁₀H₁₅N₂SCl 
• 214759-22-5 C-(5-Chloro-thiophen-2-yl)-methylamine 

Relevant articles and documents

Novel M2-selective, Gi-biased agonists of muscarinic acetylcholine receptors

Background and Purpose: More than 30% of currently marketed medications act via GPCRs. Thus, GPCRs represent one of the most important pharmacotherapeutic targets. In contrast to traditional agonists activating multiple signalling pathways, agonists activating a single signalling pathway represent a new generation of drugs with increased specificity and fewer adverse effects. Experimental Approach: We have synthesized novel agonists of muscarinic ACh receptors and tested their binding and function (on levels of cAMP and inositol phosphates) in CHO cells expressing individual subtypes of muscarinic receptors, primary cultures of rat aortic smooth muscle cells and suspensions of digested native tissues from rats. Binding of the novel compounds to M2 receptors was modelled in silico. Key Results: Two of the tested new compounds (1-(thiophen-2-ylmethyl)-3,6-dihydro-2H-pyridinium and 1-methyl-1-(thiophen-2-ylmethyl)-3,6-dihydro-2H-pyridinium) only inhibited cAMP synthesis in CHO cells, primary cultures, and native tissues, with selectivity for M2 muscarinic receptors and displaying bias towards the Gi signalling pathway at all subtypes of muscarinic receptors. Molecular modelling revealed interactions with the orthosteric binding site in a way specific for a given agonist followed by agonist-specific changes in the conformation of the receptor. Conclusions and Implications: The identified compounds may serve as lead structures in the search for novel non-steroidal and non-opioid analgesics acting via M2 and M4 muscarinic receptors with reduced side effects associated with activation of the phospholipase C signalling pathway.

Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors

Production of metallo-β-lactamases (MBLs) in bacterial pathogens is an important cause of resistance to the ‘last-resort’ carbapenem antibiotics. Development of effective MBL inhibitors to reverse carbapenem resistance in Gram-negative bacteria is still needed. We herein report X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives by considering how to engage with the active-site flexible loops and improve penetration into Gram-negative bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallographic analyses. Of the tested ICA inhibitors, 55 displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clinically isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphologic and internal structural changes of bacterial cells after treatment further demonstrated that 55 crossed the outer membrane and reversed the activity of meropenem. Moreover, 55 showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-negative carbapenem resistance.

MUSCARINIC AGONISTS AS NON-STEROIDAL AND NON-OPIOID ANALGESICS AND METHODS OF USE THEREOF

Novel Gi/o-biased muscarinic agonists selectively activate only one specific signaling pathway and are novel pharmacophores for development of new painkillers (analgesics). Methods of making and using these agonists are also described.

Benzoxazine compound and its preparation methods and application

The invention relates to a benzoxazine compound represented in the following formula 1. The benzoxazine compound can serve as a beta 2 receptor agonist. The formula can be seen from the description.

Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane

Palladium-catalyzed allylation reactions of 2-(chloromethyl)thiophenes, 2-(chloromethyl)furans, and N-protected 2-(chloromethyl)-1H-pyrroles with allyltributylstannane were described in this study. This type of allylation reaction regioselectively occurred on the heteroarene rings to produce allylated dearomatization products or allylated heteroarenes with satisfactory yields.

A convenient synthesis by microwave heating and pharmacological evaluation of novel benzoyltriazole and saccharine derivatives as 5-HT1A receptor ligands

A series of novel 1,2,3-4-benzoyltriazole and saccharine derivatives were designed and synthesized by microwave heating. They were evaluated on a battery of receptors, including serotonin 5-HT1A, 5-HT2A and 5-HT2C, and the most interesting compounds were further evaluated on dopaminergic D1, D2 and adrenergic α1, α2 receptors. Conventional and microwave heating of the reactions were compared. Synthesis by microwave heating gave the desired compounds in better yields than those obtained by conventional heating. The overall times for the syntheses were considerably reduced. All compounds displayed moderate affinity for 5-HT1A receptor. The most interesting compound 33 showed a high affinity (Ki=93 nM) which was combined with no affinity on the other receptors considered.

Triazolylated teritiary amine compound or salt thereof

A triazolylated tertiary amine compound represented by general formula (I) or a salt thereof, having an aromatase inhibitory activity and being useful for preventing and treating breast cancer, mastopathy, endometriosis, prostatomergaly, etc., wherein A represents a single bond, lower alkylene or carbonyl; B represents lower alkyl, aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; D represents aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; and E represents 4H-1,2,4-triazolyl, 1H-1,2,4-triazolyl or 1H-1,2,3-triazolyl.

Herbicidal thiadiazole ureas

Herbicidal thiadiazole ureas are provided wherein the 5-position of the thiadiazole ring is hetero substituted and which exhibit enhanced selective herbicidal activity.