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Methyl 4-(2-bromoethynyl)benzoate, a chemical compound with the molecular formula C11H9BrO2, is a pale yellow liquid characterized by a distinct odor. It is recognized for its high stability and low reactivity, which makes it a valuable building block in organic synthesis. methyl 4-(2-bromoethynyl)benzoate is primarily used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, and also finds application in the manufacturing of dyes and perfumes.

225928-10-9

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225928-10-9 Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Methyl 4-(2-bromoethynyl)benzoate is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals for its ability to contribute to the formation of complex organic molecules that are otherwise challenging to produce directly.
Used in Dye and Perfume Manufacturing:
In the dye and perfume industry, methyl 4-(2-bromoethynyl)benzoate is utilized for its capacity to enhance the color and fragrance properties of products, leveraging its chemical structure to create unique and desirable characteristics in these consumer goods.
Safety and Handling:
It is important to handle methyl 4-(2-bromoethynyl)benzoate with care due to its potential to cause skin and eye irritation upon contact. To ensure safety, it should be stored in a cool, dry place away from direct sunlight and heat sources to maintain its stability and prevent any adverse reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 225928-10-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,5,9,2 and 8 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 225928-10:
(8*2)+(7*2)+(6*5)+(5*9)+(4*2)+(3*8)+(2*1)+(1*0)=139
139 % 10 = 9
So 225928-10-9 is a valid CAS Registry Number.

225928-10-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 4-(2-bromoethynyl)benzoate

1.2 Other means of identification

Product number -
Other names S01-0612

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:225928-10-9 SDS

225928-10-9Relevant articles and documents

Copper-Catalyzed Perfluoroalkylation of Alkynyl Bromides and Terminal Alkynes

Fan, Shilu,Zheng, Chenggong,Zheng, Kaiting,Li, Junlan,Liu, Yaomei,Yan, Fangpei,Xiao, Hua,Feng, Yi-Si,Zhu, Yuan-Yuan

supporting information, p. 3190 - 3194 (2021/05/05)

A copper-catalyzed one-pot perfluoroalkylation of alkynyl bromides and terminal alkynes has been disclosed, and the corresponding perfluoroalkylated alkynes could be attained in good to excellent yields. The new straightforward transformation shows high efficiency (0.01-0.5 mol % catalyst loading), broad substrate scope, and remarkable functional group tolerance and provides a facile approach for useful application in life and material sciences.

COMPOUND ACTING AS ANTIBIOTICS

-

, (2020/12/22)

The present invention provides a novel antibiotic compound represented by the following formula (I), a pharmaceutically acceptable salt thereof, an ester thereof, a prodrug thereof, a solvate thereof, or a deuterated analog thereof, or a stereoisomer thereof. The compound of the present invention exhibits excellent antibacterial activity, especially against Gram bacteria. wherein each group is defined as in the description.

Multicolor Cocktail for Breast Cancer Multiplex Phenotype Targeting and Diagnosis Using Bioorthogonal Surface-Enhanced Raman Scattering Nanoprobes

Wang, Jing,Liang, Duanwei,Feng, Jie,Tang, Xinjing

, p. 11045 - 11054 (2019/09/09)

Early precise diagnosis of cancers is crucial to realize more effective therapeutic interventions with minimal toxic effects. Cancer phenotypes may also alter greatly among patients and within individuals over the therapeutic process. The identification and characterization of specific biomarkers expressed on tumor cells are in high demand for diagnosis and treatment, but they are still a challenge. Herein, we designed three new bioorthogonal surface-enhanced Raman scattering (SERS) nanoprobes and successfully applied the cocktail of them for MDA-MB-231 and MCF-7 breast cancer multiplex phenotype detection. The SERS nanoprobes containing Raman reporters with diynl, azide, or cyano moieties demonstrated apparent Raman shift peaks in 2205, 2120, and 2230 cm-1, respectively, in the biologically Raman-silent region. Three target ligands, including oligonucleotide aptamer (AS1411), arginine-glycine-aspatic acid (RGD) peptide, and homing cell adhesion molecule antibody (anti-CD44), were separately conjugated to the nanoprobes for active recognition capability. The cocktail of the nanoprobes manifested minimal cytotoxicity and simultaneously multiplex phenotype imaging of MDA-MB-231 and MCF-7 cells. Quantitative measurement of cellular uptake by inductively coupled plasma mass spectrometry (ICPMS) verified that MDA-MB-231 cells harbored a much higher expression level of CD44 receptor than MCF-7 cells. For in vivo SERS detection, Raman shift peaks of 2120, 2205, and 2230 cm-1 in the micro-tumor were clearly observed, representing the existence of three specific biomarkers of nucleolin, integrin αvβ3, and CD44 reporter, which could be used for early cancer phenotype identification. The biodistribution results indicated that target ligand modified nanoprobes exhibited much more accumulation in tumors than those nanoprobes without target ligands. The multicolor cocktail of bioorthogonal SERS nanoprobes offers an attractive and insightful strategy for early cancer multiplex phenotype targeting and diagnosis in vivo that is noninvasive and has low cross-talk, unique spectral-molecular signature, high sensitivity, and negligible background interference.

Gold-Catalyzed C(sp2)?C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes

Yang, Yangyang,Schie?l, Jasmin,Zallouz, Sirine,G?ker, Verena,Gross, Jürgen,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.

supporting information, p. 9624 - 9628 (2019/07/05)

A gold(I)-catalyzed cascade cyclization–alkynylation of allenoates using alkynyl bromide to generate β-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of β-alkynyl-γ-butenolides in moderate to good yields without the need for any external oxidant.

Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids

Wang, Lu,Lu, Chengrong,Yue, Yanni,Feng, Chao

supporting information, p. 3514 - 3517 (2019/05/16)

A visible-light-promoted oxo-sulfonylation of ynamides with sulfonic acids is reported, giving rise to a collection of functionalized α-sulfonylated amides in a straightforward manner. The reaction proceeds sequentially through a cascade of electrophilic addition and photoinduced sulfonyl radical-sustained skeleton rearrangement. The high atom economy, mild reaction conditions, and wide substrate scope comprised the merits of this synthetic transformation.

Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group

Pan, Rui,Shi, Cong,Zhang, Dongquan,Tian, Yang,Guo, Songjin,Yao, Hequan,Lin, Aijun

supporting information, p. 8915 - 8920 (2019/11/14)

An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.

Visible Light-Induced Difunctionalization of Alkynes: The Synthesis of Thiazoles and 1,1-Dibromo-1-en-3-ynes

Huang, Xiaoying,Chen, Hui,Huang, Zhongzhi,Xu, Yanli,Li, Fangyao,Ma, Xianli,Chen, Yanyan

, p. 15283 - 15293 (2019/12/04)

A visible light-induced cascade cyclization of thioamides with alkynes was developed to synthesize 1,3-thiozoles. The sulfur radical generated from thioamide via the single-electron transfer (SET) pathway was promoted by photocatalysis as a key intermediate in this reaction. When bromoalkynes were used as the substrate, the self-coupling products 1,1-dibromo-1-en-3-ynes were obtained in moderate yields, and an energy transfer pathway for this transformation promoted by visible-light photocatalysis was proposed.

Palladium-Catalyzed Oxygenative Cross-Coupling of Ynamides and Benzyl Bromides by Carbene Migratory Insertion

Gao, Yunpeng,Wu, Guojiao,Zhou, Qi,Wang, Jianbo

supporting information, p. 2716 - 2720 (2018/02/13)

A palladium-catalyzed oxygenative cross-coupling of ynamides and benzyl bromides has been developed. After subsequent hydrogenation, α,α-disubstituted amide derivatives were obtained in good yields. Migratory insertion of α-oxo palladium carbene species, generated by intermolecular oxidation, is proposed as the key step in this reaction. The study demonstrates the potential of ynamides to serve as carbene precursors in palladium-catalyzed C?C bond-forming cross-coupling reactions.

Photochemical Dual-Catalytic Synthesis of Alkynyl Sulfides

Santandrea, Jeffrey,Minozzi, Clémentine,Cruché, Corentin,Collins, Shawn K.

, p. 12255 - 12259 (2017/09/06)

A photochemical dual-catalytic cross-coupling to form alkynyl sulfides via C(sp)?S bond formation is described. The cross-coupling of thiols and bromoalkynes is promoted by a soluble organic carbazole-based photocatalyst using continuous flow techniques. Synthesis of alkynyl sulfides bearing a wide range of electronically and sterically diverse aromatic alkynes and thiols can be achieved in good to excellent yields (50–96 %). The simple continuous flow setup also allows for short reaction times (30 min) and high reproducibility on gram scale. In addition, we report the first application of photoredox/nickel dual catalysis towards macrocyclization, as well as the first example of the incorporation of an alkynyl sulfide functional group into a macrocyclic scaffold.

Direct spirocyclization from keto-sulfonamides: An approach to azaspiro compounds

Beltran, Frédéric,Fabre, Indira,Ciofini, Ilaria,Miesch, Laurence

, p. 5042 - 5045 (2017/11/06)

Spontaneous spirocyclization of keto-sulfonamides via ynamides through a one-pot process is presented. Push-pull ynamides were obtained through Michael addition/elimination without Cu. The obtained azaspiro compounds are building blocks for indole alkaloids. Theoretical studies provide insights into the mechanism of the formal Conia-ene reaction.

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