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4-(N-Morpholino)-benzene methylcarboxylate is a versatile chemical compound derived from benzene, featuring a morpholine group and a methyl ester functional group. It is known for its unique reactivity and synthetic utility, making it a valuable building block in organic chemistry.

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  • 23676-05-3 Structure
  • Basic information

    1. Product Name: 4-(N-MORPHOLINO)-BENZENE METHYLCARBOXYLATE
    2. Synonyms: RARECHEM AL BF 1130;METHYL 4-MORPHOLINOBENZENECARBOXYLATE;4-(N-MORPHOLINO)-BENZENE METHYLCARBOXYLATE;Methyl 4-morpholin-4-yl-benzoate;methyl 4-morpholinobenzoate;4-morpholinobenzoic acid methyl ester;4-(4-morpholinyl)Benzoic acid Methyl ester
    3. CAS NO:23676-05-3
    4. Molecular Formula: C12H15NO3
    5. Molecular Weight: 221.25
    6. EINECS: N/A
    7. Product Categories: pharmacetical
    8. Mol File: 23676-05-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 371.9°Cat760mmHg
    3. Flash Point: 178.7°C
    4. Appearance: /
    5. Density: 1.16g/cm3
    6. Vapor Pressure: 9.98E-06mmHg at 25°C
    7. Refractive Index: 1.54
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: 4-(N-MORPHOLINO)-BENZENE METHYLCARBOXYLATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-(N-MORPHOLINO)-BENZENE METHYLCARBOXYLATE(23676-05-3)
    12. EPA Substance Registry System: 4-(N-MORPHOLINO)-BENZENE METHYLCARBOXYLATE(23676-05-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 23676-05-3(Hazardous Substances Data)

23676-05-3 Usage

Uses

Used in Pharmaceutical Industry:
4-(N-Morpholino)-benzene methylcarboxylate is used as a reagent for the synthesis of various drugs and pharmaceutical intermediates, contributing to the development of new medications and improving existing ones.
Used in Research Laboratories:
In academic settings, 4-(N-Morpholino)-benzene methylcarboxylate is utilized for the preparation of diverse organic compounds, facilitating scientific research and the discovery of novel chemical entities.
Used in Organic Synthesis:
4-(N-Morpholino)-benzene methylcarboxylate is employed as a key component in organic synthesis, leveraging its morpholine group to enable unique reactions and the formation of a wide range of chemical products.
Overall, 4-(N-Morpholino)-benzene methylcarboxylate's applications span across various industries, including pharmaceuticals and research, due to its flexibility and synthetic potential.

Check Digit Verification of cas no

The CAS Registry Mumber 23676-05-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,6,7 and 6 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 23676-05:
(7*2)+(6*3)+(5*6)+(4*7)+(3*6)+(2*0)+(1*5)=113
113 % 10 = 3
So 23676-05-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H15NO3/c1-15-12(14)10-2-4-11(5-3-10)13-6-8-16-9-7-13/h2-5H,6-9H2,1H3

23676-05-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 4-morpholin-4-ylbenzoate

1.2 Other means of identification

Product number -
Other names Methyl 4-morpholin-4-yl-benzoate

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:23676-05-3 SDS

23676-05-3Relevant articles and documents

Electrochemical Cross-Dehydrogenative Aromatization Protocol for the Synthesis of Aromatic Amines

Tao, Shao-Kun,Chen, Shan-Yong,Feng, Mei-Lin,Xu, Jia-Qi,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua,Zheng, Xue-Li,Yu, Xiao-Qi

supporting information, p. 1011 - 1016 (2022/02/05)

The introduction of amines onto aromatics without metal catalysts and chemical oxidants is synthetically challenging. Herein, we report the first example of an electrochemical cross-dehydrogenative aromatization (ECDA) reaction of saturated cyclohexanones and amines to construct anilines without additional metal catalysts and chemical oxidants. This reaction exhibits a broad scope of cyclohexanones including heterocyclic ketones, affording a variety of aromatic amines with various functionalities, and shows great potential in the synthesis of biologically active compounds.

Enabling Metallophotoredox Catalysis in Parallel Solution-Phase Synthesis Using Disintegrating Reagent Tablets

Borlinghaus, Niginia,Sch?nfeld, Barbara,Heitz, Stephanie,Klee, Johanna,Vukeli?, Stella,Braje, Wilfried M.,Jolit, Anais

, p. 16535 - 16547 (2021/12/02)

Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and user-friendly chemical delivery system for two different metallophotoredox-catalyzed reactions. This delivery method simplifies the preparation of compound libraries using photoredox chemistry in a parallel setting. The reagent tablets were successfully applied to late-stage functionalization of drug-like intermediates. These tablets can be prepared with various reagents and catalysts in different sizes and be stored on the bench thanks to blister packaging.

Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling

Bortnikov, Evgeniy O.,Semenov, Sergey N.

supporting information, p. 782 - 793 (2020/12/01)

The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to al

Discovery of a Potent FLT3 Inhibitor (LT-850-166) with the Capacity of Overcoming a Variety of FLT3 Mutations

Cai, Jiongheng,Chen, Yadong,Chen, Yun,Cheng, Jie,Cheng, Zitian,Heng, Hao,Huang, Fei,Jia, Kun,Li, Hongmei,Lu, Shuai,Lu, Tao,Ren, Jiwei,Sheng, Tiancheng,Song, Shiyu,Tang, Weifang,Wang, Zhijie,Wu, Yingli,Zhu, Yifan

, p. 14664 - 14701 (2021/10/12)

Secondary mutations of FLT3 have become the main mechanism of FLT3 inhibitor resistance that presents a significant clinical challenge. Herein, a series of pyrazole-3-amine derivatives were synthesized and optimized to overcome the common secondary resistance mutations of FLT3. The structure-activity relationship and molecular dynamics simulation studies illustrated that the ribose region of FLT3 could be occupied to help address the obstacle of secondary mutations. Among those derivatives, compound 67 exhibited potent and selective inhibitory activities against FLT3-ITD-positive acute myeloid leukemia (AML) cells and possessed equivalent potency against transformed BaF3 cells with a variety of secondary mutations. Besides, cellular mechanism assays demonstrated that 67 strongly inhibited phosphorylation of FLT3 and its downstream signaling factors, as well as induced cell cycle arrest and apoptosis in MV4-11 cells. In the MV4-11 xenograft models, 67 exhibited potent antitumor potency without obvious toxicity. Taken together, these results demonstrated that 67 might be a drug candidate for the treatment of FLT3-ITD-positive AML.

Reagent and Catalyst Capsules: A Chemical Delivery System for Reaction Screening and Parallel Synthesis

Borlinghaus, Niginia,Kaschel, Johannes,Klee, Johanna,Haller, Vanessa,Schetterl, Jasmin,Heitz, Stephanie,Lindner, Tanja,Dietrich, Justin D.,Braje, Wilfried M.,Jolit, Anais

, p. 1357 - 1370 (2020/12/21)

Commercially available hydroxypropyl methylcellulose capsules are employed as a fast, safe, and user-friendly chemical delivery system containing all reagents (catalyst, ligand, and base) for three important transition-metal-catalyzed reactions: Buchwald-Hartwig, Suzuki-Miyaura, and metallophotoredox C-N cross-coupling reactions. This encapsulation methodology simplifies the screening of reaction conditions and the preparation of compound libraries using parallel synthesis in organic solvents or aqueous media. These reagents-containing HPMC capsules are easy to prepare, come in different sizes, and can be stored on the bench under noninert conditions.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven

supporting information, p. 17887 - 17896 (2020/08/19)

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes

Ghosh, Indrajit,Khamrai, Jagadish,Savateev, Aleksandr,Shlapakov, Nikita,Antonietti, Markus,K?nig, Burkhard

, p. 360 - 366 (2019/08/15)

Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.

Combining structure- and property-based optimization to identify selective FLT3-ITD inhibitors with good antitumor efficacy in AML cell inoculated mouse xenograft model

Heng, Hao,Wang, Zhijie,Li, Hongmei,Huang, Yatian,Lan, Qingyuan,Guo, Xiaoxing,Zhang, Liang,Zhi, Yanle,Cai, Jiongheng,Qin, Tianren,Xiang, Li,Wang, Shuxian,Chen, Yadong,Lu, Tao,Lu, Shuai

, p. 248 - 267 (2019/05/21)

FLT3 mutation is among the most common genetic mutations in acute myeloid leukemia (AML), which is also related with poor overall survival and refractory in AML patients. Recently, FLT3 inhibitors have been approved for AML therapy. Herein, a series of new compounds with pyrazole amine scaffold was discovered, which showed potent inhibitory activity against FLT3-ITD and significant selectivity against both FLT3-ITD and AML cells expressing FLT3-ITD. Compound 46, possessing the most promising cellular activity, blocked the autophosphorylation of FLT3 pathway in MV4-11 cell line. Furthermore, the apoptosis and downregulation of P-STAT5 were also observed in tumor cells extracted from the MV4-11 cell xenografts model upon compound 46 treatment. Compound 46 was also metabolically stable in vitro and suppressed tumor growth significantly in MV4-11 xenografts model in vivo. Compound 46 showed no toxicity to the viscera of mice and caused no decrease in body weight of mice. In conclusion, the results of this study could provide valuable insights into discovery of new FLT3 inhibitors, and compound 46 was worthy of further development as potential drug candidate to treat AML.

Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines

Nishizawa, Akihiro,Takahira, Tsuyoshi,Yasui, Kosuke,Fujimoto, Hayato,Iwai, Tomohiro,Sawamura, Masaya,Chatani, Naoto,Tobisu, Mamoru

supporting information, p. 7261 - 7265 (2019/05/16)

Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants.

Nickel-Catalyzed Amide Bond Formation from Methyl Esters

Ben Halima, Taoufik,Masson-Makdissi, Jeanne,Newman, Stephen G.

supporting information, p. 12925 - 12929 (2018/09/14)

Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel-catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid- and base-mediated amidations, the reaction is proposed to proceed by a neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.

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