3384-04-1

Basic information

• Product Name: (3-chloropropoxy)benzene
• Synonyms: 1-Phenoxy-3-chloropropane;3-Phenoxy-1-chloropropane;NSC 404105;(3-Chloropropoxy)
• CAS NO: 3384-04-1
• Molecular Formula: C₉H₁₁ClO
• Molecular Weight: 170.64
• EINECS: 222-192-7
• Mol File: 3384-04-1.mol

Chemical Properties

• Melting Point: 12°C
• Boiling Point: 241.51°C (rough estimate)
• Flash Point: 175.2°C
• Appearance: /
• Density: 1.1167
• Vapor Pressure: 0.0338mmHg at 25°C
• Refractive Index: 1.5235 (estimate)
• CAS DataBase Reference: (3-chloropropoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (3-chloropropoxy)benzene(3384-04-1)
• EPA Substance Registry System: (3-chloropropoxy)benzene(3384-04-1)

Safety Data

• Hazardous Substances Data: 3384-04-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(3-chloropropoxy)benzene is used as a chemical intermediate for the synthesis of various compounds, including dyes, fragrances, and flavors. Its unique structure allows it to serve as a versatile building block in the creation of a wide range of products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (3-chloropropoxy)benzene is utilized as a key component in the production of certain drugs. Its reactivity and functional groups make it suitable for the development of new medicinal compounds.
Used in Agrochemicals:
(3-chloropropoxy)benzene also finds application in the agrochemical sector, where it is employed in the synthesis of pesticides and other agricultural chemicals. Its properties contribute to the effectiveness of these products in protecting crops and enhancing agricultural yields.
Used as a Solvent:
Due to its solubility properties, (3-chloropropoxy)benzene is used as a solvent in various industrial processes. It can dissolve a range of substances, making it a valuable component in the manufacturing of different products.
Used in Organic Synthesis Research:
(3-chloropropoxy)benzene is employed as a reagent in organic synthesis research, where its unique properties are explored and harnessed to develop new synthetic pathways and methodologies.
Safety Considerations:
It is crucial to handle (3-chloropropoxy)benzene with care, as it is a flammable liquid and may pose health risks if not properly managed. Adequate safety measures should be taken during its use to minimize potential hazards.

InChI:InChI=1/C9H11ClO/c10-7-4-8-11-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 109-70-6 1.3-chlorobromopropane 
• 108-95-2 phenol 
• 142-28-9 1,3-Dichloropropane 
• 78-99-9 1,1-dichloropropane 
• 627-30-5 1-chloro-3-hydroxypropane 
• 71-43-2 benzene 
• 100-67-4 potassium phenolate 
• 6180-61-6 3-phenoxypropanol 

Downstream Products

• 32599-03-4 1-(3-phenoxypropyl)piperidine 
• 865086-04-0 N-(3-phenoxypropyl)-isoindoline 
• 20549-68-2 1-(3-iodopropoxy)benzene 
• 69781-95-9 1-phenoxy-3-hydrazinopropane 
• 859201-71-1 (3-phenoxy-propyl)-propyl-malonic acid diethyl ester 
• 854658-80-3 2-cyano-5-phenoxy-valeric acid ethyl ester 
• 6345-89-7 (3-phenoxypropyl)diethyl propanedioate 
• 117023-22-0 (1-(3-phenoxypropyl)piperidin-4-yl)diphenylmethanol 
• 64010-38-4 1-bromo-4-(3-chloropropoxy)benzene 
• 187737-37-7 propene 
• 10125-18-5 1,6-diphenoxyhexane 
• 139-02-6 sodium phenoxide 
• 2430-76-4 6-phenyl-1,4-hexanediol 

Relevant articles and documents

3,4-Diaza-bicyclo[4.1.0]hept-4-en-2-one phenoxypropylamine analogs of irdabisant (CEP-26401) as potent histamine-3 receptor inverse agonists with robust wake-promoting activity

A novel series of 3,4-diaza-bicyclo[4.1.0]hept-4-en-2-ones were designed and synthesized as H3R analogs of irdabisant 6. Separation of the isomers, assignment of the stereochemistry by crystallography, and detailed profiling of diastereomers 25 and 26 led to the identification of (1R,6S)-5-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)propoxy]phenyl}-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one 25 as a potential second generation H3R candidate. Diastereomer 25 had high H3R binding affinity, excellent selectivity, displayed potent H3R functional antagonism and robust wake-promoting activity in vivo, and showed acceptable pharmacokinetic and pharmaceutical profiles for potential further development.

Synthesis and evaluation of aryl substituted propyl piperazines for potential atypical antipsychotic activity

Background: Schizophrenia is a disorder with complex etiology with hyperdopaminer-gia as the leading underlying cause. Atypical antipsychotics are the agents which do not give rise to significant extrapyramidal side effects and are more effective against negative symptoms of schizophrenia. Introduction: A new series of chloro-substituted substituted aryloxypiperazine derivatives and their indole based derivatives was designed and evaluated for atypical antipsychotic activity based on established models for combined dopaminergic and serotonergic antagonism. Method: The present series of compounds were designed based on 3D similarity studies, synthesized and evaluated for atypical antipsychotic activity in animal models for combined dopaminer-gic and serotonergic antagonism. The blood-brain barrier penetration potential was assessed from theoretical log BB values computed through an online software program. Results: Theoretical ADME profiling of the designed compounds based on selected physicochem-ical parameters suggested excellent compliance with Lipinski’s rules. The log BB values obtained for the compounds suggested a good potential for brain permeation. Indole substitution contributed towards an improved efficacy over aryloxy analogs. Lead compounds showed a potential for combined dopaminergic and serotonergic antagonism. Conclusion: The 5-methoxy indole based compounds 16 and 17 were identified as the lead compounds displaying a potential atypical antipsychotic profile.

Halogenation through Deoxygenation of Alcohols and Aldehydes

An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.

Benzene C-H Etherification via Photocatalytic Hydrogen-Evolution Cross-Coupling Reaction

Aryl ethers can be constructed from the direct coupling between the benzene C-H bond and the alcohol O-H bond with the evolution of hydrogen via the synergistic merger of photocatalysis and cobalt catalysis. Utilizing the dual catalyst system consisting of 3-cyano-1-methylquinolinum photocatalyst and cobaloxime, intermolecular etherification of arenes with various alcohols and intramolecular alkoxylation of 3-phenylpropanols with formation of chromanes are accomplished. These reactions proceed at remarkably mild conditions, and the sole byproduct is equivalent hydrogen gas.

Process for the preparation of 3-aroyl-5-aminobenzofuran derivatives

The present invention relates to a process for the preparation of 3-aroyl-5-aminobenzofuran derivatives useful as antiarrhythmic drugs which avoids the use of nitro intermediates.

PROCESS FOR THE PREPARATION OF 3-AROYL-5-AMINOBENZOFURAN DERIVATIVES

The present invention relates to a process for the preparation of 3-aroyl -5- aminobenzofuran derivatives useful as antiarrhythmic drugs which avoids the use of nitro intermediates.

Arylsulfonamido-substituted hydroxamic acid derivatives

α-Amino hydroxamic acid derivative of formula (I), in which R is C2–C7-alkyl, which is mono-, di- or trisubstituted by halogen, nitro, lower acyloxy, trifluoromethoxy, cyano, C3–C5-cycloalkyl or unsubstituted or substituted C3–C4-heteroaryl comprising one or two heteroatoms selected from the group consisting of O, S and N; or C3–C7-alkenyl or C3–C7-alkynyl, which in each case is unsubstituted or mono-, di- or trisubstituted by halogen, nitro, lower acyloxy, trifluoromethoxy, cyano, C3–C5-cycloalkyl or unsubstituted or substituted C3–C6-heteroaryl comprising one or two heteroatoms selected from the group consisting of O, S and N; and the other symbols are as defined in claim 1, are described. These compounds are MMP and in particular MMP2 inhibitors and can be used for treatment of MMP dependent diseases, in particular inflammation conditions, rheumatoid arthritis, osteoarthritis, tumors (tumor growth, metastasis, progression or invasi n) and pulmonary disorders (e.g. emphysema, COPD).

Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists

It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-methoxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl] benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects. Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N- (piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor. Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2.

Copper(II)-catalyzed ether synthesis from aliphatic alcohols and potassium organotrifluoroborate salts

(Matrix presented) A protocol for the copper(II)-catalyzed etherification of aliphatic alcohols under mild and essentially neutral conditions is described. Air- and moisture-stable potassium alkenyl- and aryltrifluoroborate salts undergo cross-coupling with a variety of aliphatic primary and secondary alcohols and phenols, and are tolerant of a range of functional groups. The optimized conditions utilize catalytic copper(II) acetate with 4-(dimethylamino)pyridine as ligand in the presence of 4 A molecular sieves under an atmosphere of oxygen.

Acetylcholinesterase inhibitors: SAR and kinetic studies on ω-[N-methyl-N-(3-alkylcarbamoyloxyphenyl]methyl] aminoalkoxyaryl derivatives

In this work, we further investigated a class of carbamic cholinesterase inhibitors introduced in a previous paper (Rampa et al. J. Med. Chem. 1998, 41, 3976). Some new ω-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl analogues were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The structure of the lead compound (xanthostigmine) was systematically varied with the aim to optimize the different parts of the molecule. Moreover, such a structure-activity relationships (SAR) study was integrated with a kinetic analysis of the mechanism of AChE inhibition for two representative compounds. The structural modifications lead to a compound (12b) showing an IC50 value for the AChE inhibition of 0.32 ± 0.09 nM and to a group of BuChE inhibitors also active at the nanomolar level, the most potent of which (15d) was characterized by an IC50 value of 3.3 ± 0.4 nM. The kinetic analysis allowed for clarification of the role played by different molecular moieties with regard to the rate of AChE carbamoylation and the duration of inhibition. On the basis of the results presented here, it was concluded that the cholinesterase inhibitors of this class possess promising characteristics in view of a potential development as drugs for the treatment of Alzheimer's disease.