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Ethyl 2-(4-bromophenyl)-2-diazoacetate, also known as ethyl 2-(4-bromophenyl)-2-diazoacetoacetate, is a chemical compound belonging to the diazoacetate family. It is characterized by its 4-bromophenyl group and diazoacetate moiety, which contribute to its reactivity and versatility in organic synthesis. Ethyl 2-(4-bromophenyl)-2-diazoacetate is commonly used as a reagent in diazo transfer reactions to generate carbenes, highly reactive intermediates crucial for forming new carbon-carbon and carbon-heteroatom bonds. Due to its potential hazards and reactivity, it should be handled with caution under appropriate safety protocols.

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  • 758692-47-6 Structure
  • Basic information

    1. Product Name: Ethyl 2-(4-bromophenyl)-2-diazoacetate
    2. Synonyms: ETHYL 2-(4-BROMOPHENYL)-2-DIAZOACETATE;4-Bromo-alpha-diazobenzeneacetic acid ethyl ester
    3. CAS NO:758692-47-6
    4. Molecular Formula: C10H9BrN2O2
    5. Molecular Weight: 269.09
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 758692-47-6.mol
  • Chemical Properties

    1. Melting Point: 54 °C
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: Ethyl 2-(4-bromophenyl)-2-diazoacetate(CAS DataBase Reference)
    10. NIST Chemistry Reference: Ethyl 2-(4-bromophenyl)-2-diazoacetate(758692-47-6)
    11. EPA Substance Registry System: Ethyl 2-(4-bromophenyl)-2-diazoacetate(758692-47-6)
  • 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: 758692-47-6(Hazardous Substances Data)

758692-47-6 Usage

Uses

Used in Organic Synthesis:
Ethyl 2-(4-bromophenyl)-2-diazoacetate is used as a reagent for diazo transfer reactions in organic synthesis. It generates carbenes, which are highly reactive intermediates essential for forming new carbon-carbon and carbon-heteroatom bonds, enabling the creation of a wide range of chemical compounds.
Used in Aromatic Ring Functionalization:
The 4-bromophenyl group in Ethyl 2-(4-bromophenyl)-2-diazoacetate makes it useful for the functionalization of aromatic rings. This property allows for the modification and introduction of various functional groups onto aromatic compounds, expanding the scope of chemical transformations and applications in different industries.
Used in Chemical Research:
Ethyl 2-(4-bromophenyl)-2-diazoacetate is employed in chemical research for studying the reactivity and properties of diazo compounds and carbenes. Its unique structure and reactivity provide valuable insights into the development of new synthetic methods and understanding the underlying mechanisms of various chemical reactions.
Used in Pharmaceutical Industry:
Ethyl 2-(4-bromophenyl)-2-diazoacetate is used as a building block or intermediate in the synthesis of pharmaceutical compounds. Its ability to generate carbenes and functionalize aromatic rings makes it a valuable tool in the development of novel drug molecules with potential therapeutic applications.
Used in Material Science:
In the field of material science, Ethyl 2-(4-bromophenyl)-2-diazoacetate is utilized for the synthesis of advanced materials with specific properties. Its reactivity and versatility in forming carbon-carbon and carbon-heteroatom bonds contribute to the development of new polymers, coatings, and other materials with unique characteristics for various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 758692-47-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 7,5,8,6,9 and 2 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 758692-47:
(8*7)+(7*5)+(6*8)+(5*6)+(4*9)+(3*2)+(2*4)+(1*7)=226
226 % 10 = 6
So 758692-47-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H9BrN2O2/c1-2-15-10(14)9(13-12)7-3-5-8(11)6-4-7/h3-6H,2H2,1H3

758692-47-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(4-bromophenyl)-2-diazonio-1-ethoxyethenolate

1.2 Other means of identification

Product number -
Other names -

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:758692-47-6 SDS

758692-47-6Relevant articles and documents

Efficient and regioselective chromium(0)-catalyzed reaction of 2-substituted furans with diazo compounds: Stereoselective synthesis of (2E,4Z)-2-aryl-hexadienedioic acid diesters

Hahn, Norbert D.,Nieger, Martin,D?tz, Karl Heinz

, p. 2662 - 2673 (2004)

Pentacarbonyl (η2-cis-cyclooctene)chromium(0) (1) catalyzes efficiently reactions of diazo compounds with electron-rich furans. The reaction of 2-methoxyfuran (2) with alkyl α-diazoarylacetate (3a-g) furnishes the (2E,4Z -2-aryl-hexadienedioic

Synthesis of functionalized trans-A2B2-porphyrins using donor-acceptor cyclopropane-derived dipyrromethanes

Beyzavi, M. Hassan,Nietzold, Carolin,Reissig, Hans-Ulrich,Wiehe, Arno

, p. 1409 - 1422 (2013)

meso-Substituted trans-A2B2-porphyrins bearing specific patterns of substituents are crucial building blocks in porphyrin-based biomimetic systems and molecular materials and can be used for the construction of well-defined porphyrin-based architectures. A new stepwise and rational synthesis of functionalized trans-A2B2-porphyrins is reported in which for the first time donor-acceptor-substituted cyclopropane precursors (d-a cyclopropanes) are exploited. The three presented d-a cyclopropanes are readily accessible in a multi-gram scale and serve as aldehyde equivalents in the reaction with an excess of pyrrole to afford the corresponding dipyrromethanes (DPMs). The three DPMs were synthesized in yields of 60-74%. They are stable in purified form in the absence of light and air and were subsequently condensed with a wide range of aliphatic and aromatic aldehydes bearing electron-donating or electron-withdrawing substituents followed by oxidation to form the corresponding trans-A2B 2-porphyrins. Fourteen functionalized porphyrins were synthesized in yields of 14-31%, indicating the broad scope of the synthetic procedure. The possibility to introduce key functional groups is emphasized, which enables subsequent modification of these porphyrins with moieties inducing biological activity. Modification of the tetrapyrroles may occur by addition to one of the porphyrin peripheral double bonds, the use of substituents of the aryl groups or via the methoxycarbonyl group at two of the meso-substituents. Three examples of porphyrins were converted into the corresponding 7,8-dihydroxychlorins by osmium-mediated dihydroxylation and one of the resulting chlorins was subjected to saponification to give a highly polar chlorin dicarboxylic acid. A 4-bromophenyl-substituted d-a cyclopropane was prepared by rhodium-catalyzed cyclopropanation and then transformed into a DPM which was subsequently condensed to a porphyrin. Its Zn complex allowed a Heck reaction to afford the functionalized bis(alkenyl)-substituted trans-A2B2-Zn- porphyrin. Copyright

An immunomodulator

-

Paragraph 0130-0133, (2022/01/20)

The present invention discloses an immunomodulator, specifically relates to a class of compounds inhibiting IL-17A and its use as an immunomodulator in the preparation of drugs. The present invention discloses a compound shown in formula I, or a stereoisomer thereof in the preparation of inhibiting IL-17A class of drugs, for clinical screening and / or preparation of drugs associated with IL-17A activity related to the drug provides a new option.

Synthesis of Rhodium Complexes with Chiral Diene Ligands via Diastereoselective Coordination and Their Application in the Asymmetric Insertion of Diazo Compounds into E?H Bonds

Ankudinov, Nikita M.,Chusov, Denis A.,Nelyubina, Yulia V.,Perekalin, Dmitry S.

supporting information, p. 18712 - 18720 (2021/07/20)

A new method for the synthesis of chiral diene rhodium catalysts is introduced. The readily available racemic tetrafluorobenzobarrelene complexes [(R2-TFB)RhCl]2 were separated into two enantiomers via selective coordination of one of them with the auxiliary S-salicyl-oxazoline ligand. One of the resulting chiral complexes with an exceptionally bulky diene ligand [(R,R-iPr2-TFB)RhCl]2 was an efficient catalyst for the asymmetric insertion of diazoesters into B?H and Si?H bonds giving the functionalized organoboranes and silanes with high yields (79–97 %) and enantiomeric purity (87–98 % ee). The stereoselectivity of separation via auxiliary ligand and that of the catalytic reaction was predicted by DFT calculations.

Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant

Liu, Wenbin,Twilton, Jack,Wei, Bo,Lee, Maizie,Hopkins, Melissa N.,Bacsa, John,Stahl, Shannon S.,Davies, Huw M. L.

, p. 2676 - 2683 (2021/03/03)

A mild method for accessing diazo compounds via aerobic oxidation of hydrazones is described. This catalytic transformation employs a Cu(OAc)2/pyridine catalyst and molecular oxygen from ambient air as the terminal oxidant, generating water as the sole byproduct and affording the desired diazo compounds within minutes at room temperature. A broad array of electronically diverse aryldiazo esters, ketones, and amides can be accessed. Pyridine dramatically enhances the rate of the reaction by solubilizing the copper catalyst and serving as the Br?nsted base in the turnover-limiting proton-coupled oxidation of hydrazone by copper(II). Insights gained from mechanistic studies led to expansion of the scope of this method to include diaryl hydrazones, delivering diaryl diazomethane derivatives, which cannot be accessed via established diazo transfer methods. The products of this method may be employed in rhodium carbene catalysis without isolation of the diazo intermediate to afford cyclopropane products in good yield with high enantioselectivity.

B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Guo, Jing,Mandal, Dipendu,Stephan, Douglas W.,Wu, Yile,Zhao, Yunbo

, p. 7758 - 7761 (2021/08/13)

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.

Azide Radical Initiated Ring Opening of Cyclopropenes Leading to Alkenyl Nitriles and Polycyclic Aromatic Compounds

Muriel, Bastian,Waser, Jerome

supporting information, p. 4075 - 4079 (2021/01/18)

We report herein a radical-mediated amination of cyclopropenes. The transformation proceeds through a cleavage of the three-membered ring after the addition of an azide radical on the strained double bond and leads to tetrasubstituted alkenyl nitrile derivatives upon loss of N2. With 1,2-diaryl substituted cyclopropenes, this methodology could be extended to a one-pot synthesis of highly functionalized polycyclic aromatic compounds (PACs). This transformation allows the synthesis of nitrile-substituted alkenes and aromatic compounds from rapidly accessed cyclopropenes using only commercially available reagents.

Immunomodulator

-

Paragraph 0254; 0427-0430, (2021/05/22)

The invention discloses an immunomodulator, and particularly relates to a compound for inhibiting IL-17A and application of the compound serving as the immunomodulator in preparation of drugs. The invention discloses application of a compound shown in a formula I or a stereoisomer thereof in preparation of medicines for inhibiting IL-17A, and provides a new choice for clinically screening and/or preparing medicines for treating diseases related to IL-17A activity.

Tropylium-Catalyzed O-H Insertion Reactions of Diazoalkanes with Carboxylic Acids

Empel, Claire,Nguyen, Thanh Vinh,Koenigs, Rene M.

supporting information, p. 548 - 553 (2021/01/26)

Herein, we describe the application of a nonbenzenoid aromatic carbocation, namely tropylium, as an organic Lewis acid catalyst in O-H functionalization reactions of diazoalkanes with benzoic acids. The newly developed protocol is applicable to a wide range of diazoalkane and carboxylic acid substrates with excellent efficiency (43 examples, up to 99% yield).

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters

Chu, Changhu,Dong, Wenwen,Lin, Jia,Teng, Jiangge,Wang, Zhiwei,Zhao, Rong

, p. 6120 - 6126 (2021/07/21)

By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.

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