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Methyl α-bromophenylacetate is an ester with a light yellow to yellow liquid appearance. It is known for its involvement in various chemical reactions, such as the palladium-catalyzed homocoupling reaction with 3,5-dimethyl phenyl boronic acid.

3042-81-7

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3042-81-7 Usage

Uses

Used in Polymer Science:
Methyl α-bromophenylacetate is used as an initiator for the atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA) and ethylene glycol dimethacrylate (EGDMA). This application is significant in the study of ESR (Electron Spin Resonance) techniques, which are crucial for understanding the polymerization process and the properties of the resulting polymers.
Used in Supercritical Fluid Polymerization:
Methyl α-bromophenylacetate is also used as a reagent in the homopolymerization of MMA in supercritical carbon dioxide. This process allows for the production of polymers with unique properties and characteristics, making it an important application in the field of materials science and engineering.

Synthesis Reference(s)

Tetrahedron, 42, p. 2275, 1986 DOI: 10.1016/S0040-4020(01)90607-6

Check Digit Verification of cas no

The CAS Registry Mumber 3042-81-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,4 and 2 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3042-81:
(6*3)+(5*0)+(4*4)+(3*2)+(2*8)+(1*1)=57
57 % 10 = 7
So 3042-81-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H9BrO2/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8H,1H3/t8-/m1/s1

3042-81-7 Well-known Company Product Price

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  • Alfa Aesar

  • (L09043)  Methyl alpha-bromophenylacetate, 97%   

  • 3042-81-7

  • 5g

  • 721.0CNY

  • Detail
  • Alfa Aesar

  • (L09043)  Methyl alpha-bromophenylacetate, 97%   

  • 3042-81-7

  • 25g

  • 2914.0CNY

  • Detail

3042-81-7SDS

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 methyl 2-bromo-2-phenylacetate

1.2 Other means of identification

Product number -
Other names Methyl alpha-bromophenylacetate

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:3042-81-7 SDS

3042-81-7Relevant academic research and scientific papers

Dynamic kinetic resolution in the hydrolysis of an α-bromo ester

Jones, Matthew M.,Williams, Jonathan M. J.

, p. 2519 - 2520 (1998)

Bromide can be employed to racemise an α-bromo ester more rapidly than the corresponding acid (carboxylate), and this rate difference has been employed as the basis of a dynamic kinetic resolution reaction.

NEGATIVE ALLOSTERIC MODULATION OF GLUN3-CONTAINING N-METHYL-D-ASPARTATE RECEPTORS

-

Page/Page column 65, (2021/08/06)

Disclosed are negative allosteric modulators of GluN3-containing NMDA receptors. In general, these compounds are highly selective for GluN3 (such as GluN3A and/or GluN3B) over GluN1 and/or GluN2. They can function as non-competitive antagonists with activity that is independent of membrane potential, glycine concentration, and extracellular pH. Also disclosed are pharmaceutical formulations of the negative allosteric modulators. These compounds can be used to enhance synaptic function and/or treating a neurological condition or disorder. Exemplary neurological conditions or disorders include, but are not limited to, major mental disorders, conditions that involve basal ganglia or altered dopamine, substance abuse/addiction or predisposition to substance abuse/addiction, pain disorders, developmental delay or situations with impaired learning, memory, and/or cognition, acute neuronal or glial injuries, and circuit disorders.

Manganese/bipyridine-catalyzed non-directed C(sp3)–H bromination using NBS and TMSN3

Sneh, Kumar,Torigoe, Takeru,Kuninobu, Yoichiro

supporting information, p. 885 - 890 (2021/05/05)

A Mn(II)/bipyridine-catalyzed bromination reaction of unactivated aliphatic C(sp3)?H bonds has been developed using N-bromosuccinimide (NBS) as the brominating reagent. The reaction proceeded in moderate-to-good yield, even on a gram scale. The introduced bromine atom can be converted into fluorine and allyl groups.

MALIC ENZYME INHIBITORS

-

, (2021/04/23)

The present invention relates to novel compounds useful as malic enzyme (ME) inhibitors, processes for their preparation and use of these compounds for the therapeutic treatment of disorders mediated by ME such as cancers (e.g. pancreatic ductal adenocarcinoma (PDAC)) in humans.

Bromination of α-Diazo Phenylacetate Derivatives Using Cobalt(II) Bromide

Wang, Haifeng,Sun, Xiangli,Hu, Manman,Zhang, Xiaoyi,Xie, Lele,Gu, Shuangxi

supporting information, p. 3347 - 3351 (2020/07/04)

A method for the bromination of α-diazo phenylacetate derivatives using cobalt(II) bromide is described. This bromination reaction features a short reaction time, broad substrate scope, operational simplicity, acid-free conditions, and gram-scalability. (Figure presented.).

Activating ATRP Initiators to Incorporate End-Group Modularity into Photo-RAFT Polymerization

Hakobyan, Karen,McErlean, Christopher S. P.,Müllner, Markus

, p. 10357 - 10365 (2020/12/23)

Heterogeneous photocatalysis is increasingly used in reversible deactivation radical polymerization (RDRP). In this study, we found that alkyl bromide redox chemistry typically found in atom transfer radical polymerization (ATRP) can be incorporated in concert with dithiocarbonyl disulfide chemistry into the reversible addition-fragmentation chain transfer (RAFT) process via bismuth oxide photocatalysis. This amalgamation of mechanisms introduces end-group modularity - a new layer of control - into RAFT polymers uniquely enabled by photoredox catalysis. We found that a diversity of functionality can be installed at the α-end group via alkyl bromides, while the molecular weight distribution can be tuned seamlessly at the ω-end group through the simultaneous addition of multiple disulfides.

Visible Light-Mediated Conversion of Alcohols to Bromides by a Benzothiadiazole-Containing Organic Photocatalyst

Li, Run,Gehrig, Dominik W.,Ramanan, Charusheela,Blom, Paul W. M.,Kohl, Fabien F.,Wagner, Manfred,Landfester, Katharina,Zhang, Kai A. I.

, p. 3852 - 3859 (2019/07/15)

The search for metal-free, stable and high effective photocatalysts with sufficient photo-redox potentials remains a key challenge for organic chemists. Here, we present a benzothiadiazole-containing molecular organic photocatalyst with redox potentials of ?1.30 V and +1.64 V vs. SCE. The singlet state lifetime is 13 ns. Direct conversion from aliphatic alcohols to bromides has been conducted with the designed organic photocatalyst under visible light irradiation with high efficiency and selectivity. The catalytic efficiency of the novel benzothiadiazole-based photocatalyst is comparable with the state-of-art metal and non-metal catalysts. Furthermore, advanced photophysical studies including time-resolved photoluminescence and transient absorption spectroscopy offer a powerful support for photo-induced electron transfer from photocatalyst to the reactive substrates. Lastly, no photo-bleaching effect is observed, demonstrating the high stability and recyclable of the designed organic photocatalyst. (Figure presented.).

Synthesis and biological evaluation of 3-functionalized 2-phenyl- and 2-alkylbenzo[b]furans as antiproliferative agents against human melanoma cell line

Kwiecień, Halina,Peru?yńska, Magdalena,Stachowicz, Karolina,Piotrowska, Katarzyna,Bujak, Joanna,Kopytko, Patrycja,Dro?dzik, Marek

supporting information, (2019/04/29)

The key function of microtubules and mitotic spindle in cell division make them attractive targets in anticancer therapy. In the present study, functionalized in 3 position 2-phenyl- and 2-alkylbenzo[b]furans were synthesized and evaluated as antitumor ag

New 4-aryl-1,3,2-oxathiazolylium-5-olates: Chemical synthesis and photochemical stability of a novel series of S-nitrosothiols

Eilertsen, Monica,Allin, Steve M.,Pearson, Russell J.

supporting information, p. 1106 - 1110 (2018/02/28)

S-nitrosothiols (RSNOs) remain one of the most popular classes of NO-donating compounds due to their ability to release nitric oxide (NO) under non-enzymatic means whilst producing an inert disulphide by-product. However, alligning these compounds to the different biological fields of NO research has proved to be problematic due to the inherent instability of such compounds under a variety of conditions including heat, light and the presence of copper ions. 1,3,2-Oxathiazolylium-5-olates (OZOs) represent an interesting subclass of S-nitrosothiols that lock the –SNO moiety into a five membered heterocyclic ring in an attempt to improve the compound's overall stability. The synthesis of a novel series of halogen-containing OZOs was comprehensively studied resulting in a seven-step route and overall yields ranging between 21 and 37%. The photochemical stability of these compounds was assessed to determine if S-nitrosothiols locked within these mesoionic ring systems can offer greater stability and thereby release NO in a more controllable fashion than their non-cyclic counterparts.

Mandelic acid derived ionic liquids: synthesis, toxicity and biodegradability

Prydderch, Hannah,Haiβ, Annette,Spulak, Marcel,Quilty, Brid,Kümmerer, Klaus,Heise, Andreas,Gathergood, Nicholas

, p. 2115 - 2126 (2017/01/22)

A series of ten ionic liquids (ILs) was synthesised from the renewable resource mandelic acid. The ILs showed low antimicrobial activity towards the thirteen bacterial and twelve fungal strains they were screened against. A general trend of increasing bacterial toxicity in the order methyl ester 60% in 28 days), a series of biodegradation transformation products has been proposed based on the degradation of the ester/amide alkyl chain. This data has allowed for an assessment of the effect of IL structural features on toxicity and biodegradation, particularly allowing for a comparison to earlier work where additional oxygen atoms were present to facilitate biodegradation and attenuate toxicity. The mandelic acid derived ILs did not pass the Closed Bottle test (OECD 301D) and can be included in the rules of thumb for the design of biodegradable ILs.

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