13997-70-1

Basic information

• Product Name: 1-ALLYLOXY-4-CHLORO BENZENE
• Synonyms: ALLYL P-CHLOROPHENYL ETHER;ALLYL 4-CHLOROPHENYL ETHER;4-CHLORO-ALLYLOXYBENZENE;1-ALLYLOXY-4-CHLORO BENZENE;1-chloro-4-prop-2-enoxybenzene;1-chloro-4-prop-2-enoxy-benzene;1-Chloro-4-(2-propen-1-yloxy)-benzene
• CAS NO: 13997-70-1
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.62
• Product Categories: Aromatic Compounds;monomer
• Mol File: 13997-70-1.mol

Chemical Properties

• Boiling Point: 238.18°C (rough estimate)
• Flash Point: 98.8 °C
• Appearance: cream
• Density: 1.1310
• Vapor Pressure: 0.0937mmHg at 25°C
• Refractive Index: 1.5348 (estimate)
• CAS DataBase Reference: 1-ALLYLOXY-4-CHLORO BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ALLYLOXY-4-CHLORO BENZENE(13997-70-1)
• EPA Substance Registry System: 1-ALLYLOXY-4-CHLORO BENZENE(13997-70-1)

Safety Data

• Hazardous Substances Data: 13997-70-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Allyloxy-4-chloro benzene is used as a key intermediate in the synthesis of various pharmaceuticals. Its reactivity and versatility make it an essential component in the development of new drugs and medicinal compounds.
Used in Pesticide Industry:
In the pesticide industry, 1-Allyloxy-4-chloro benzene serves as an important intermediate for the production of various agrochemicals. Its chemical properties contribute to the effectiveness of these pesticides in controlling pests and protecting crops.
Used in Organic Synthesis:
1-Allyloxy-4-chloro benzene is used as a versatile building block in organic synthesis. Its reactivity allows for the formation of various allyl ether derivatives, which can be further utilized in the synthesis of a wide range of organic compounds.
Used in Industrial Applications:
Due to its chemical properties, 1-Allyloxy-4-chloro benzene is employed in various industrial applications, where it serves as a precursor for the production of different organic compounds and materials. Its versatility and reactivity make it a valuable component in the development of new products and processes.

InChI:InChI=1/C9H9ClO/c1-2-7-11-9-5-3-8(10)4-6-9/h2-6H,1,7H2

Upstream product

• 106-48-9 4-chloro-phenol 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 1193-00-6 sodium 4-chlorophenolate 
• 31456-94-7 methyl 2-allyloxy-5-chlorobenzoic acid 
• 4068-78-4 methyl 5-chloro-2-hydroxybenzoate 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 100-39-0 benzyl bromide 
• 35466-83-2 allyl methyl carbonate 
• 791590-30-2 2,3-dibromopropyl 4-chlorophenyl ether 
• 244056-17-5 2-bromo-3-(4-chlorophenoxy)propene 
• 2212-05-7 4-chlorophenyl 2,3-epoxypropyl ether 
• 51896-45-8 (Z)-1-chloro-4-(prop-1-en-1-yloxy)benzene 
• 132356-17-3 allyldiisobutyltelluronium bromide 

Downstream Products

• 36895-32-6 5-(4-chloro-phenoxymethyl)-3-phenyl-4,5-dihydro-isoxazole 
• 128234-67-3 C₁₈H₁₈Cl₄O₂S 
• 112652-61-6 (R)-3-(4-chlorophenoxy)propane-1,2-diol 
• 54912-31-1 4-chlorophenyl-(E)-1-propenyl ether 
• 18859-35-3 4-chlorophenoxyacetone 
• 875559-61-8 benzoic acid 4-(4-chloro-phenoxy)-1-cyano-3-ethoxythiocarbonylsulfanyl-butyl ester 
• 59227-79-1 4-(4-chlorophenoxy)butyric acid ethyl ester 
• 95-20-5 2-methyl-1H-indole 

Relevant articles and documents

Profiling of LINS01 compounds at human dopamine D2 and D3 receptors

Abstract: Histamine and dopamine neuronal pathways display interesting overlapping in the CNS, especially in the limbic areas, making them very attractive to designing drugs with synergistic and/or additive effects. The roles of these systems to treat schizophrenia, drug addiction, Parkinson’s and Alzheimer’s diseases, among others are widely known. The LINS01 compounds were previously reported as histamine H3 receptor (H3R) antagonists and some of them are under evaluation in rodent memory models. Considering their pharmacological potential and similarities to literature dopamine D2 receptor (D2R) and dopamine D3 receptor (D3R) ligands, this work aimed to evaluate these compounds as ligands these receptors by using [3H]spiperone displacement assays. A set of 11 compounds containing the dihydrobenzofuranyl-piperazine core with substituents at 5-position of dihydrobenzofuran ring and at the piperazine nitrogen was examined. The compounds showed low to moderate affinities at both, D2R and D3R. N-Phenyl compounds LINS01005 (1d), LINS01011 (1h), LINS01012 (1i) and LINS01016 (1k) showed the highest affinities in the set to D3R (Ki 0.3–1.5 μM), indicating that N-phenylpiperazine moiety increases the affinity to this receptor subtype with some selectivity, since they showed lower affinities to D2R (Ki 1.3–5.5 μM). With the LINS01 compounds showing moderate binding affinity, new lead structures for optimization with regards to combined H3R and D2R/D3R-ligands are provided. Graphic abstract: Histamine and dopamine neuronal pathways display interesting overlapping in the CNS, and thus LINS01 compounds previously reported as histamine H3 receptor antagonists were evaluated as dopamine D2R and D3R ligands. The compounds showed micromolar affinities to both receptors[Figure not available: see fulltext.].

Highly regioselective O-allylation of phenol derivatives using MMZCu(I)Y catalyst

A clean and effective method has been developed for the regioselective of O-allylation of phenol derivatives using a recyclable Cu(I)-exchanged multi-size porous material. Ease of preparation of catalyst through simple solid-state exchange and its compatibility in producing excellent amount of O-allylated products and a plausible mechanistic pathway for the regioselectivity are highlighted. This reported procedure is not requiring any external stabilizing ligand for Cu(I) species and further purification of products.

A new and facile synthesis of chroman-3-ols, 3,4-dihydro-2H-[1]-benzopyran-3-ols

o-Allyl phenols react with m-chloroperoxybenzoic acid (m-CPBA) in dry chloroform to give chroman-3-ols in a single step in good yields (93-96%).

Investigation on Claisen rearrangement of allyl phenyl ethers in near-critical water

Catalyst-free Clasien rearrangement of allyl phenyl ethers were investigated in near-critical water. The effects on the reaction in near-critical water and conventional conditions were compared. The results demonstrate that near-critical water could greatly accelerate the Claisen rearrangement of allyl phenyl ethers. This process is simple, fast, efficient and environmentally benign.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Preparation method 3 - phenoxybromopropane or analogue thereof

The invention discloses a preparation method of 3 -phenoxybromopropane or an analogue thereof, wherein 3 - phenoxybromopropane and an allyl compound thereof are obtained through substitution reaction and addition reaction so as to avoid the inconvenience of using gaseous hydrogen bromide, 2nd-step addition reaction is realized by using the brominated salt and the acid in situ, and the process is simple in operation. The condition is easy to control, the atom economy is good, the aspect of environmental impact is low pollution, zero emission accords with the current green chemical synthesis direction, and the cost is economic.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors

In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

Novel potent vasodilating agents: Evaluation of the activity and potency of LINS01005 and derivatives in rat aorta

Cardiovascular diseases (CVDs) present high prevalence rates in the current world. It is estimated that approximately one-third of the global deaths are related to CVDs, and thus there is still a need for novel drugs to treat these disorders. We serendipitously discovered that LINS01005 (5a) is a potent vasodilating agent in rat aorta, and therefore a set of analogues were evaluated for the vasodilating potency in Wistar and SHR rat thoracic aorta precontracted with norepinephrine, with endothelium intact (E+) or denuded (E–) aortic rings. Compounds 5a and 5b were the most potent, showing submicromolar potency for endothelium intact vessels (EC50 853 and 941 nM, respectively) and micromolar values for E– vessels (EC50 2.4 and 7.1 μM, respectively). These compounds were indeed significantly more potent vasodilating agents in SHR-derived aortic rings (p 50 2.4 nM (E+) 9.0 nM (E–)] and 5b [EC50 20 nM (E+) 2.1 μM (E–)]. SAR analysis though PCA and HCA were performed, suggesting that N-phenylpiperazine is essential to the activity, while increasing volume in the substituted aromatic moiety is detrimental to the potency. This is the first report of the vasodilating properties of such compounds, and studies regarding the mechanism of action are in progress in our group.