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ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE, also known as 2,3-Dihydro-1,4-benzodioxin-2-carboxylic Acid Ethyl Ester, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical agents. It is characterized by its benzodioxane ring structure and carboxylate ester functional group, which contribute to its reactivity and potential applications in the medical field.

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  • 4739-94-0 Structure
  • Basic information

    1. Product Name: ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE
    2. Synonyms: TIMTEC-BB SBB008613;ETHYL 2,3-DIHYDRO-1,4-BENZODIOXIN-2-CARBOXYLATE;ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE;2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBOXYLIC ACID ETHYL ESTER;1,4-BENZODIOXAN-2-CARBOXYLIC ACID ETHYL ESTER;2,3-Dihydro-2-Carboethoxy-1,4-;2,3-Dihydro-2-carboethoxy-1, 4-benzodioxane;ETHYL 1,4-BENZODIOXANE-2-CARBOXYLATE
    3. CAS NO:4739-94-0
    4. Molecular Formula: C11H12O4
    5. Molecular Weight: 208.21
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 4739-94-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 88-95 °C0.3 mm Hg(lit.)
    3. Flash Point: >230 °F
    4. Appearance: /
    5. Density: 1.208 g/mL at 25 °C
    6. Vapor Pressure: 0.00252mmHg at 25°C
    7. Refractive Index: n20/D 1.523
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE(4739-94-0)
    12. EPA Substance Registry System: ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE(4739-94-0)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22
    3. Safety Statements: N/A
    4. WGK Germany: 2
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 4739-94-0(Hazardous Substances Data)

4739-94-0 Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE is used as an intermediate for the synthesis of presynaptic α2-adrenoreceptor antagonists. These antagonists are essential in the development of potential antidepressant medications, as they help modulate the neurotransmitter levels in the brain, leading to improved mood and reduced symptoms of depression.
Additionally, ETHYL 1,4-BENZODIOXAN-2-CARBOXYLATE is used as an intermediate for the preparation of aminoalkylbenzodioxins. These compounds act as calcium antagonists, which are vital in the treatment of various cardiovascular diseases. Calcium antagonists work by blocking the influx of calcium ions into cardiac and smooth muscle cells, thereby reducing the contraction of these muscles and helping to regulate blood pressure and heart rate.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 5373, 1955 DOI: 10.1021/ja01625a050

Check Digit Verification of cas no

The CAS Registry Mumber 4739-94-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,3 and 9 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 4739-94:
(6*4)+(5*7)+(4*3)+(3*9)+(2*9)+(1*4)=120
120 % 10 = 0
So 4739-94-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H12O4/c1-2-13-11(12)10-7-14-8-5-3-4-6-9(8)15-10/h3-6,10H,2,7H2,1H3/t10-/m0/s1

4739-94-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 1,4-Benzodioxane-2-carboxylate

1.2 Other means of identification

Product number -
Other names 1,4-Benzodioxane-2-carboxylic Acid Ethyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4739-94-0 SDS

4739-94-0Relevant articles and documents

Imaging the static dielectric constant in vitro and in living cells by a bioconjugable GFP chromophore analog

Signore, Giovanni,Abbandonato, Gerardo,Storti, Barbara,Stoeckl, Martin,Subramaniam, Vinod,Bizzarri, Ranieri

, p. 1723 - 1725 (2013)

A fluorescent probe structurally similar to the GFP chromophore is demonstrated to report the local static dielectric constant. This probe can be chemically functionalized for selective targeting at the intracellular level. The Royal Society of Chemistry

Investigation of the effect of different linker chemotypes on the inhibition of histone deacetylases (HDACs)

Linciano, Pasquale,Benedetti, Rosaria,Pinzi, Luca,Russo, Fabiana,Chianese, Ugo,Sorbi, Claudia,Altucci, Lucia,Rastelli, Giulio,Brasili, Livio,Franchini, Silvia

, (2020/11/24)

Histone Deacetylases (HDACs) are among the most attractive and interesting targets in anticancer drug discovery. The clinical relevance of HDAC inhibitors (HDACIs) is testified by four FDA-approved drugs for cancer treatment. However, one of the main drawbacks of these drugs resides in the lack of selectivity against the different HDAC isoforms, resulting in severe side effects. Thus, the identification of selective HDACIs represents an exciting challenge for medicinal chemists. HDACIs are composed of a cap group, a linker region, and a metal-binding group interacting with the catalytic zinc ion. While the cap group has been extensively investigated, less information is available about the effect of the linker on isoform selectivity. To this aim, in this work, we explored novel linker chemotypes to direct isoform selectivity. A small library of 25 hydroxamic acids with hitherto unexplored linker chemotypes was prepared. In vitro tests demonstrated that, depending on the linker type, some candidates selectively inhibit HDAC1 over HDAC6 isoform or vice versa. Docking calculations were performed to rationalize the effect of the novel linker chemotypes on biologic activity. Moreover, four compounds were able to increase the levels of acetylation of histone H3 or tubulin. These compounds were also assayed in breast cancer MCF7 cells to test their antiproliferative effect. Three compounds showed a significant reduction of cancer proliferation, representing valuable starting points for further optimization.

Enantioselective Access to Chiral 2-Substituted 2,3-Dihydrobenzo[1,4]dioxane Derivatives through Rh-Catalyzed Asymmetric Hydrogenation

Yin, Xuguang,Huang, Yi,Chen, Ziyi,Hu, Yang,Tao, Lin,Zhao, Qingyang,Dong, Xiu-Qin,Zhang, Xumu

supporting information, p. 4173 - 4177 (2018/07/29)

Rh-catalyzed asymmetric hydrogenation of various benzo[b][1,4]dioxine derivatives was successfully developed to prepare chiral 2-substituted 2,3-dihydrobenzo[1,4]dioxane derivatives using ZhaoPhos and N-methylation of ZhaoPhos ligands with high yields and excellent enantioselectivities (up to 99% yield, >99% enantiomeric excess (ee), turnover number (TON) = 24 000). Moreover, this asymmetric hydrogenation methodology, as the key step with up to 10 000 TON, was successfully applied to develop highly efficient synthetic routes for the construction of some important biologically active molecules, such as MKC-242, WB4101, BSF-190555, and (R)-doxazosin·HCl.

Halogen bonding enhances activity in a series of dual 5-HT6/D2 ligands designed in a hybrid bioisostere generation/virtual screening protocol

Staroń, Jakub,Warszycki, Dawid,Kurczab, Rafa?,Sata?a, Grzegorz,Bugno, Ryszard,Hogendorf, Adam,Bojarski, Andrzej J.

, p. 54918 - 54925 (2016/07/06)

A novel hybrid bioisostere generation/virtual screening method combined with narrowing of chemical space through similarity to compounds that are active at the second target was successfully applied for the development of structurally new dual 5-HT6/D2 receptor ligands. Consequently, a series of derivatives of the found hit 1d (N-[2-(dimethylamino)ethyl]-N-(2-phenylethyl)aniline) was synthesized. The most active 5-HT6/D2 ligands also showed affinity for 5-HT7R and 5-HT2AR. The para-chloroaniline derivative was identified as a potent dual 5-HT6/5-HT7 receptor antagonist (Ki = 24 nM and Kb = 30 nM, Ki = 4 nM and Kb = 1.4 nM, respectively). In the case of halogen-containing compounds, interesting structure-activity relationships were observed at 5-HT6, D2 and 5-HT7 receptors, and the ligand-receptor complexes were subsequently examined using a molecular modelling approach that combined quantum-polarized ligand docking (QPLD) and Molecular-Mechanics-Generalized-Born/Surface Area (MM/GBSA) free-energy calculation, which permitted the identification of putative halogen binding pockets.

Containing 1,4-benzodioxane structure of the pyrazoline derivatives and the preparation and use thereof

-

Paragraph 0036-0038, (2016/12/01)

The invention relates to pyrazoline derivatives comprising a 1,4-benzodioxan structure. The derivatives are characterized in that the derivatives have a general formula as the following. R1, R3, and R3 in the formula are as the following. The pyrazoline d

Ultrasound-assisted synthesis and biological evaluation of 1,4-benzodioxane-2-carboxyl-amino acids and Peptides

Malipeddi, Himaja,Gowda, Visruth,Das, Moonjit

, p. 113 - 118 (2019/01/16)

A series of peptides containing 1,4-benzodioxane nucleus were attempted to synthesize by conventional as well as green techniques like microwave-assisted and sonication, using dicyclohexylcarbodiimide (DCC) as a coupling reagent and triethylamine as a bas

Synthesis and antibacterial activity of cinnamaldehyde acylhydrazone with a 1,4-benzodioxan fragment as a novel class of potent ss-Ketoacyl-acyl carrier protein synthase III (FabH) inhibitor

Song, Xiaoda,Yang, Yushun,Zhao, Jing,Chen, Yangjian

, p. 1110 - 1118 (2014/12/11)

Fatty acid biosynthesis is essential for bacterial survival. ss-Ketoacyl-acyl carrier protein (ACP) synthase III (FabH), is a particularly attractive antibacterial target, since it is central to the initiation of fatty acid biosynthesis. Three series of 2

Chemoenzymatic synthesis of piperoxan, prosympal, dibozane, and doxazosin

Rouf, Abdul,Gupta, Pankaj,Aga, Mushtaq A.,Kumar, Brijesh,Chaubey, Asha,Parshad, Rajinder,Taneja, Subhash C.

supporting information, p. 1615 - 1623 (2013/02/22)

The synthesis of both enantiomers of 1,4-benzodioxan-2-carboxylic acid 1, a key synthetic intermediate for the therapeutic agents piperoxan, prosympal, dibozane, and doxazosin was achieved with good yields and high enantioselectivities via the Arthrobacter sp. lipase catalyzed kinetic resolution of ester (±)-17a. The influence of the co-solvents and the immobilization of the lipase upon kinetic resolution demonstrated that immobilized whole cells, in the presence of n-butanol as a co-solvent, resulted in the optimal resolution of the substrate (ee ~99%, E = 535) at 258 mmol (50 g/L) substrate concentration.

Discovery of novel 1,4-benzodioxane containing thiazolidinone derivatives as potential antihepatotoxic agent

Khalilullah, Habibullah,Khan, Shamshir,Ahsan, Mohamed Jawed,Ahmed, Bahar

experimental part, p. 575 - 582 (2012/05/19)

In continuance of our search for newer antihepatotoxic agents some novel thiazolidinone derivatives containing 1,4-benzodioxane ring system were synthesized starting from 2,3-dihydro-1,4-benzodioxane-2-carbohydrazide. The synthesized compounds were evalua

Design, modification and 3D QSAR studies of novel 2,3-dihydrobenzo[b][1,4] dioxin-containing 4,5-dihydro-1H-pyrazole derivatives as inhibitors of B-Raf kinase

Yang, Yu-Shun,Li, Qing-Shan,Sun, Shuai,Zhang, Yan-Bin,Wang, Xiao-Liang,Zhang, Fei,Tang, Jian-Feng,Zhu, Hai-Liang

, p. 6048 - 6058 (2012/11/07)

Two series of novel 2,3-dihydrobenzo[b][1,4]dioxin-containing 4,5-dihydro-1H-pyrazole derivatives C1-C15 and D1-D15 have been synthesized and evaluated for their B-Raf inhibitory and anti-proliferation activities. Compound C14 ((3-(4-bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3- dihydrobenzo[b][1,4]dioxin-6-yl)methanone) showed the most potent biological activity against B-RafV600E (IC50 = 0.11 μM) and WM266.4 human melanoma cell line (GI50 = 0.58 μM), being comparable with the positive control Erlotinib and more potent than our previous best compound, while D10 ((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(5-(3- fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone) performed the best in the D series (IC50 = 1.70 μM; GI50 = 1.45 μM). The docking simulation was performed to analyze the probable binding models and poses and the QSAR model was built for reasonable design of B-Raf inhibitors in future. The introduction of 2,3-dihydrobenzo[b][1,4]dioxin structure reinforced the combination of our compounds and the receptor, resulting in progress of bioactivity.

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