22502-03-0

Basic information

• Product Name: 2-Methoxyethyl acetoacetate
• Synonyms: Methoxyethyl acetoacetat;2-METHOXYETHYL ACETOACETATE;ACETOACETIC ACID 2-METHOXYETHYL ESTER;ACMOE;2-METHOXYETHYL ACETOACETATE, WACKER QUAL ITY;Methoxyethylacetoacetate;ACETOACETIC ACID 2-(METACRYLOXY)ETHYL ESTER;2-Methyoxyethyl Acetoacetate
• CAS NO: 22502-03-0
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• EINECS: 245-043-8
• Product Categories: API intermediates;Diketene esters;Diketene Derivatives;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 22502-03-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 120 °C20 mm Hg(lit.)
• Flash Point: 218 °F
• Appearance: clear/
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0721mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: 2-8°C
• PKA: 10.37±0.46(Predicted)
• Water Solubility: 100g/L at 20℃
• BRN: 2079850
• CAS DataBase Reference: 2-Methoxyethyl acetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxyethyl acetoacetate(22502-03-0)
• EPA Substance Registry System: 2-Methoxyethyl acetoacetate(22502-03-0)

Safety Data

• Hazard Codes: T,Xi
• Statements: 60-61-36/37/38
• Safety Statements: 53-26-45-24/25-37/39
• WGK Germany: 3
• Hazardous Substances Data: 22502-03-0(Hazardous Substances Data)

Usage

Description

2-Methoxyethyl acetoacetate is an organic compound that serves as an intermediate in the synthesis of various organic chemicals and pharmaceuticals, such as Nimodipine. It is characterized by its clear light yellowish liquid appearance.

Uses

Used in Pharmaceutical Industry:
2-Methoxyethyl acetoacetate is used as an intermediate for the synthesis of pharmaceuticals, specifically in the production of Nimodipine, a medication used to prevent and treat certain conditions related to blood vessels in the brain.
Used in Organic Chemical Synthesis:
2-Methoxyethyl acetoacetate is also utilized as an intermediate in the synthesis of various organic chemicals, contributing to the development of a wide range of chemical products and applications.

InChI:InChI=1/C7H12O4/c1-6(8)5-7(9)11-4-3-10-2/h3-5H2,1-2H3

Upstream product

• 109-86-4 2-methoxy-ethanol 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 85920-63-4 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 145695-56-3 4-(3-Benzoyl-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-(2-methoxy-ethyl) ester 
• 21835-72-3 3,5-diisopropyl 1,4-dihydro-2,6-dimethyl-4-(4-dimethylaminophenyl)-3,5-pyridinedicarboxylate 
• 1572180-89-2 2-methoxyethyl 2-methyl-1,5-diphenyl-1H-pyrrole-3-carboxylate 
• 299452-61-2 2-methyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (2-methoxyethyl) ester 
• 66085-59-4 nimodipin 
• 75130-29-9 J-6-163 
• 100287-10-3 2-methoxyethyl-2-(2-nitrobenzyliden)acetoacetate 
• 39562-22-6 (E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate 
• 50899-10-0 methoxyethyl 3-amino-2-butenoate 
• 145695-57-4 4-(3-Benzoyl-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid bis-(2-methoxy-ethyl) ester 

Relevant articles and documents

Revisiting ageless antiques; synthesis, biological evaluation, docking simulation and mechanistic insights of 1,4-Dihydropyridines as anticancer agents

The historic DHP nucleus was serendipitously discovered by Arthur Hantzsch about 130 years ago and is still considered a hidden treasure for various pharmacological activities. Twenty-one DHP analogues were synthesized using the expedient one pot Hantzsch synthesis for screening as anticancer agents. Initially, the in vitro anti-proliferative single dose against a panel of 18 cancer cell lines showed that compounds 11b and 8f were the superlative candidates regarding their antitumor effect (GI% mean = 66.40% and 50.42%, correspondingly) compared to cisplatin (GI% mean = 65.58%) and doxorubicin (GI% mean = 74.56%). Remarkably, compound 11b showed a remarkable MDA-MB-468 anticancer activity (GI%=80.81%), higher than cisplatin (64.44%) and doxorubicin (76.72%), as well as strong antitumor activity against lung cancer A549 (GI%= 83.02%), more powerful than both cisplatin and doxorubicin. Compound 11b exhibited an exceptional anticancer activity against lung cancer cell line (A549) as its GI50 in nanomolar was (540 nM) with a 9-fold increase greater than cisplatin (GI50 = 4.93 μM) and with a selectivity index = 131 to cancer cells over normal cells. Further mechanistic investigations proved that DHPs anticipate simultaneously TOPI and RTKs (VEGFR-2, HER-2 and BTK) which can stimulate BAX/BAK and the executioner caspases via rtPCR studies.

Nimodipine impurity IV reference substance as well as preparation method and application thereof

The invention discloses a nimodipine impurity IV reference substance and a preparation method thereof. The method includes the steps that diketene, ethyl alcohol and triethylamine are taken and addedinto a container to be heated and cooled, reaction liquid is washed with water, washing liquid is discarded, anhydrous sodium sulfate is added and placed overnight, filtrate is obtained after filtration, ammonia gas is introduced into the filtrate until the filtrate is saturated, and the nimodipine impurity IV reference substance is obtained; and after the reaction is finished, m-nitrobenzaldehyde, methoxyethyl acetoacetate and ethanol are added, heating refulx is performed, the mixture is cooled and filtered, the solvent is removed through volatilization in a water bath to obtain a yellow viscous liquid, and recrystallization is carried out to obtain a yellow acicular crystal, namely the nimodipine impurity IV reference substance. The invention also discloses an application of the nimodipine impurity IV reference substance in nimodipine tablet consistency evaluation. According to the preparation method, the impurity IV can be prepared in a general analysis laboratory, special preparation equipment is not needed, the operation is simple, the purity of the obtained impurity reference substance can reach 98.4%, the purity requirement of the reference substance is met, and the preparation method can be used for consistency evaluation of the variety.

NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS

The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.