204915-71-9

Basic information

• Product Name: 4-(2-CHLOROETHOXY)-3-METHOXYBENZALDEHYDE
• Synonyms: 4-(2-CHLOROETHOXY)-3-METHOXYBENZALDEHYDE
• CAS NO: 204915-71-9
• Molecular Formula: C₁₀H₁₁ClO₃
• Molecular Weight: 214.65
• Mol File: 204915-71-9.mol

Chemical Properties

• Melting Point: 60-61℃
• Boiling Point: 338.495 °C at 760 mmHg
• Flash Point: 145.977 °C
• Appearance: /
• Density: 1.212
• CAS DataBase Reference: 4-(2-CHLOROETHOXY)-3-METHOXYBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-CHLOROETHOXY)-3-METHOXYBENZALDEHYDE(204915-71-9)
• EPA Substance Registry System: 4-(2-CHLOROETHOXY)-3-METHOXYBENZALDEHYDE(204915-71-9)

Safety Data

• Hazardous Substances Data: 204915-71-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-Chloroethoxy)-3-methoxybenzaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 4-(2-Chloroethoxy)-3-methoxybenzaldehyde is utilized in the production of various agrochemicals. Its properties make it suitable for the development of new pesticides, herbicides, and other agricultural chemicals that can improve crop yield and protect plants from pests and diseases.
Used in Organic Synthesis:
4-(2-Chloroethoxy)-3-methoxybenzaldehyde serves as an important intermediate in organic synthesis. Its reactive functional groups enable it to participate in various chemical reactions, leading to the formation of a wide range of organic compounds with diverse applications.
Used as a Building Block for Chemical Production:
Due to its unique structure and properties, 4-(2-Chloroethoxy)-3-methoxybenzaldehyde is used as a building block for the production of other chemicals. It can be further modified and transformed into different chemical entities, contributing to the advancement of the chemical industry.

Upstream product

• 121-33-5 vanillin 
• 107-06-2 1,2-dichloro-ethane 
• 107-04-0 1-Bromo-2-chloroethane 

Downstream Products

• 221642-63-3 methyl α-azido-4-(2-chloroethoxy)-3-methoxycinnamate 
• 1204415-64-4 4-(ethenyloxy)-3-methoxybenzaldehyde 
• 1321907-17-8 6-amino-5-{[4-(2-chloroethoxy)-3-methoxybenzylidene]amino}-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 1321907-24-7 8-[4-(2-chloroethoxy)-3-methoxyphenyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione 
• 1321907-28-1 3,7-dihydro-8-{4-[2-(1H-imidazol-1-yl)ethoxy]-3-methoxyphenyl}-1,3-dimethyl-1H-purine-2,6-dione 
• 1446339-61-2 (S)-3-{1-[2-(2-methoxy-4-formylphenoxy)ethyl]piperidin-2-yl}pyridine oxalate 

Relevant articles and documents

First Discovery of Novel Pyrido[1,2- a]pyrimidinone Mesoionic Compounds as Antibacterial Agents

Plant bacterial diseases cause tremendous decreases in crop yield and quality, and there is a lack of highly effective and low-risk antibacterial agents. A series of novel pyrido[1,2-a]pyrimidinone mesoionic compounds containing vanillin moieties were synthesized, and the application of these mesoionic compounds as plant antibacterial agents was reported here for the first time. The bioassay results revealed that the mesoionic compounds had good antibacterial activity. Of these compounds, compound 11 showed excellent in vitro activity against Xanthomonas oryzae pv. oryzae, with an EC50 value of 1.1 μg/mL, which was substantially better than that of bismerthiazol (92.7 μg/mL) and thiodiazole copper (105.4 μg/mL). Moreover, greenhouse condition trials indicated that the protective and curative activities of compound 11 against rice bacterial leaf blight were 75.12 and 72.04%, respectively, which were better than those of bismerthiazol (62.24 and 50.83%, respectively) and thiodiazole copper (53.35 and 65.04%, respectively). These results provide a basis for the application of mesoionic vanillin moieties as new antibacterial agents.

Synthesis and Evaluation of a New Series of 8-(2-Nitroaryl)Xanthines as Adenosine Receptor Ligands

(Table presented.). A new series of 1,3-dimethylxanthine derivatives bearing 8-(2-nitroaryl) residue was synthesized and evaluated for affinity for recombinant human adenosine receptors subtypes. Nitrate esters of 7-substituted-1,3-dimethyl-8-phenylxanthines were also synthesized and tested. Introducing a nitro substituent at the 2-position of the 8-substituted phenyl ring resulted in generally low affinity for adenosine receptors (ARs), selectivity toward the A2A subtype was enhanced in some of the compounds. 8-(4-Cyclopentyloxy-5-methoxy-2-nitrophenyl)-1,3-dimethylxanthine (9e) proved to be a potent compound among the 2-nitrophenyl substituted xanthines exhibiting a Ki = 1 μM at human A2A ARs with at least 30 fold selectivity versus human A1 and A2B ARs. Replacement of 8-chloropropoxy phenyl with 8-nitrooxypropoxy phenyl resulted in a negligible change in binding affinity of the 8-substituted xanthines for various AR subtypes. Drug Dev Res 77 : 241–250, 2016.

Synthesis of N-aryloxyalkylanabasine derivatives

N-Aryloxyalkylanabasine derivatives were prepared via the reaction of anabasine hydrochloride with various aryloxyhaloalkanes in the presence of potash in DMF. The reaction occurred with retention of the chiral center C-(2) of the piperidine group. Side products of bis(aryloxy)ethanes were characterized.

Synthesis of a new series of 1H-imidazol-1-yl substituted 8-phenylxanthines as adenosine receptor ligands

A new series of 1H-imidazol-1-yl substituted 8-phenylxanthine analogs has been synthesized to study the effects of the imidazole group on the binding affinity of compounds for adenosine receptors. Competition binding studies of these compounds were carrie

Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates

Tranilast is an anti-inflammatory drug in use for asthma and atopic dermatitis. In studies over the last decade it has been revealed that tranilast can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. We report a structure-activity study aimed at optimizing the antifibrotic activity of tranilast. A series of cinnamoyl anthranilates were prepared and assessed for their ability to prevent TGF-β-stimulated production of collagen in cultured renal mesangial cells. We reveal derivatives with improved potency and reduced cellular toxicity relative to tranilast. 3-Methoxy-4-propargyloxycinnamoyl anthranilate reduces albuminuria in a rat model of progressive diabetes, and thus has potential as an innovative treatment for diabetic nephropathy.

3-PHENYL-N- ((1, 3, 4) THIADIAZOL-2-YL) -ACRYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS OF ESTROGEN-RELATED RECEPTORS FOR THE TREATMENT OF E.G. CANCER, RHEUMATOID ARTHRITIS OR NEUROLOGICAL DISORDERS

Compounds of formula (I) are provided as well as compositions and methods of using compounds of formula (I) for modulating the activity of the estrogen-related receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder related to the activity of the estrogen-related receptor. Considering the wide range of activity of the nuclear hormone receptor ERRα, the compounds described herein which are capable of modulating ERRα activity, are useful for treating a range of disease states including cancer, diabetes, obesity, hyperlipidermia, arthritis, atherosclerosis, osteoporosis, anxiety, depression, Parkinson’s disease and Alzheimer’s disease. Formula (I). The substituents are defined in the claims.

Condensed N-aclyindoles as antitumor agents

The invention provides compounds of general formula (I), wherein: X is halogen or OSO2R, where R represents H or is unsubstituted or hydroxy-or amino-substituted lower alkyl; Y is a nitro or amine group or a substituted derivative thereof; W is selected from the structures of formulae (Ia, Ib or Ic), where E is -N= or -CH=, G is O, S, or NH, and Q is either up to three of R, OR, NRR, NO2, CONHR, NHCOR or NHCONHR, or is an additional group of formulae (Ia, Ib or Ic) and HET represents a 5- or 6-membered carbocycle or heterocycle; and A and B collectively represent a fused benzene or 2-CO2R pyrrole ring. In one embodiment, the group Y is an amine derivative substituted by a group which is a substrate for a nitroreductase or carboxypeptidase enzyme such that one of said enzymes is able to bring about removal of that group.

Synthesis of 1-substituted 3-(chloromethyl)-6-aminoindoline (6-amino- seco-CI) DNA minor groove alkylating agents and structure-activity relationships for their cytotoxicity

A series of racemic 6-amino-seco-cyclopropylindole (seco-CI)-compounds was prepared by coupling 1-(tert-butyloxycarbonyl)-3-(chloromethyl)-6- nitroindoline with appropriate acids, followed by nitro group reduction, and evaluated for cytotoxicity in AA8, U