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3-Methoxybenzyl bromide, also known as 1-bromomethyl-3-methoxybenzene, is a benzyl bromide derivative characterized by the presence of a methoxy group attached to a benzene ring and a bromine atom attached to the benzyl group. This organic compound is known for its reactivity and is commonly used in various chemical reactions and synthesis processes.

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  • 874-98-6 Structure
  • Basic information

    1. Product Name: 3-METHOXYBENZYL BROMIDE
    2. Synonyms: 3-(BroMoMethyl)phenyl Methyl Ether;3-Methoxy-1-(broMoMethyl)benzene;3-Methoxylbenzyl BroMide;3-Methoxyphenyl)Methyl broMide;M-(BroMoMethyl)anisole;1-(BroMMethyl)-3-Methoxybenzol;3-(Bromomethyl)anisole, 1-(Bromomethyl)-3-methoxybenzene, 3-(Bromomethyl)phenyl methyl ether;3-Methoxybenzyl broMide, 98+%, 98+%
    3. CAS NO:874-98-6
    4. Molecular Formula: C8H9BrO
    5. Molecular Weight: 201.06
    6. EINECS: N/A
    7. Product Categories: Methyl Halides;Phenyls & Phenyl-Het;Methyl Halides;Phenyls & Phenyl-Het;Aromatics;Catalyst;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 874-98-6.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 152 °C(lit.)
    3. Flash Point: >230 °F
    4. Appearance: Clear colorless to light yellow/Liquid
    5. Density: 1.436 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0567mmHg at 25°C
    7. Refractive Index: n20/D 1.575(lit.)
    8. Storage Temp.: -20?C Freezer
    9. Solubility: N/A
    10. CAS DataBase Reference: 3-METHOXYBENZYL BROMIDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 3-METHOXYBENZYL BROMIDE(874-98-6)
    12. EPA Substance Registry System: 3-METHOXYBENZYL BROMIDE(874-98-6)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34
    3. Safety Statements: 26-27-36/37/39-45
    4. RIDADR: UN 3265 8/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 874-98-6(Hazardous Substances Data)

874-98-6 Usage

Uses

Used in Catalysts:
3-Methoxybenzyl bromide is used as a benzyl group rearrangement catalyst in chemical reactions. Its unique structure allows it to facilitate the rearrangement of benzyl groups, making it a valuable component in various organic synthesis processes.
Used in Pharmaceutical Industry:
3-Methoxybenzyl bromide is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to participate in diastereoselective alkylation reactions with vicinal dianions of chiral succinic acid derivatives makes it a versatile building block for the development of new drugs.
Used in Organic Synthesis:
3-Methoxybenzyl bromide is used in the synthesis of a range of organic compounds, including:
1. 6-(3-methoxyphenyl)-hexane-2,4-dione: A compound that can be used as a precursor in the synthesis of various organic molecules.
2. N-(3-methoxybenzyl)-N-(1-methyl-1-phenylethyl)-amine: A compound with potential applications in the development of pharmaceuticals and other organic compounds.
3. 2-(3-methoxybenzyl)-3-[(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]-(3S)-2-thionia-bicyclo[2.2.1]heptane tetrafluoroborate: A complex organic molecule with potential applications in various fields.
4. 1-(3-methoxybenzyl)-5-(1-methyl-1H-imidazol-5-yl)-1H-1,2,3-triazole: A compound that can be used as a building block in the synthesis of various organic molecules and pharmaceuticals.

Check Digit Verification of cas no

The CAS Registry Mumber 874-98-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 4 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 874-98:
(5*8)+(4*7)+(3*4)+(2*9)+(1*8)=106
106 % 10 = 6
So 874-98-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H9BrO/c1-10-8-4-2-3-7(5-8)6-9/h2-5H,6H2,1H3

874-98-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-METHOXYBENZYL BROMIDE

1.2 Other means of identification

Product number -
Other names 3-METHOXY BENZYL BROMIDE

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 -
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More Details:874-98-6 SDS

874-98-6Relevant articles and documents

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

Nagasawa, Shota,Fujiki, Shogo,Sasano, Yusuke,Iwabuchi, Yoshiharu

, p. 6952 - 6968 (2021/05/29)

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors

Butts, Craig P.,Collingridge, Graham L.,Jane, David E.,Mallah, Shahida,Molnár, Elek,Re?nik, Lisa-Maria,Thatcher, Robert J.,Willis, Christine L.

supporting information, p. 9154 - 9162 (2021/11/16)

(-)-Arctigenin and a series of new analogues have been synthesised and then tested for their potential as AMPA and kainate receptor antagonists of human homomeric GluA1 and GluK2 receptors expressed in HEK293 cells using a Ca2+ influx assay. In general, these compounds showed antagonist activity at both receptors with greater activity evident at AMPARs. Schild analysis indicates that a spirocyclic analogue 6c acts as a non-competitive antagonist. Molecular docking studies in which 6c was docked into the X-ray crystal structure of the GluA2 tetramer suggest that (-)-arctigenin and its analogues bind in the transmembrane domain in a similar manner to the known AMPA receptor non-competitive antagonists GYKI53655 and the antiepileptic drug perampanel. The arctigenin derivatives described herein may serve as novel leads for the development of drugs for the treatment of epilepsy. This journal is

Design and synthesis of substituted (1-(benzyl)-1: H -1,2,3-triazol-4-yl)(piperazin-1-yl)methanone conjugates: Study on their apoptosis inducing ability and tubulin polymerization inhibition

Alvala, Mallika,Babu, Bathini Nagendra,Devi, Ganthala Parimala,Godugu, Chandraiah,Manasa, Kesari Lakshmi,Nagesh, Narayana,Sigalapalli, Dilep Kumar,Thatikonda, Sowjanya,Vuppaladadium, Sowmya

supporting information, p. 1295 - 1302 (2020/12/01)

A library of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone derivatives were designed, synthesized and screened for their in vitro cytotoxic activity against BT-474, HeLa, MCF-7, NCI-H460 and HaCaT cells by employing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized analogues, compound 10ec displayed the highest cytotoxicity with the IC50 value of 0.99 ± 0.01 μM towards BT-474 cancer cell line. The target compound (10ec) was also evaluated for its tubulin polymerization inhibition study. Detailed biological studies such as acridine orange/ethidium bromide (AO/EB), DAPI and annexin V-FITC/propidium iodide staining assay suggested that compound 10ec induced the apoptosis of BT-474 cells. The clonogenic assay revealed that the inhibition of colony formation in BT-474 cells by 10ec in concentration-dependent manner. Moreover, the flow cytometric analysis revealed that 10ec induced apoptosis via cell cycle arrest at the sub-G1 and G2/M phase. In silico studies of sulfonyl piperazine-integrated triazole conjugates unveil that they possess drug-like properties. According to the molecular modelling studies, compound 10ec binds to the colchicine binding site of the tubulin.

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

Houle, Camille,Savoie, Paul R.,Davies, Clotilde,Jardel, Damien,Champagne, Pier Alexandre,Bibal, Brigitte,Paquin, Jean-Fran?ois

supporting information, p. 10620 - 10625 (2020/07/24)

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

Synthesis and biological evaluation of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides as antimitotic agents

Prasad, Budaganaboyina,Lakshma Nayak,Srikanth,Baig, Mirza Feroz,Subba Reddy,Babu, Korrapati Suresh,Kamal, Ahmed

, p. 535 - 548 (2018/11/26)

A library of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides (7a–al) have been designed, synthesized and screened for their anti-proliferative activity against some selected human cancer cell lines namely DU-145, A-549, MCF-7 and HeLa. Most of them have shown promising cytotoxicity against lung cancer cell line (A549), amongst them 7f was found to be the most potent anti-proliferative congener. Furthermore, 7f exhibited comparable tubulin polymerization inhibition (IC50 value 2.04 μM) to the standard E7010 (IC50 value 2.15 μM). Moreover, flow cytometric analysis revealed that this compound induced apoptosis via cell cycle arrest at G2/M phase in A549 cells. Induction of apoptosis was further observed by examining the mitochondrial membrane potential and was also confirmed by Hoechst staining as well as Annexin V-FITC assays. Furthermore, molecular docking studies indicated that compound 7f binds to the colchicine binding site of the β-tubulin. Thus, 7f exhibits anti-proliferative properties by inhibiting the tubulin polymerization through the binding at the colchicine active site and by induction of apoptosis.

Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

Otake, Yuma,Williams, Jason D.,Rincón, Juan A.,De Frutos, Oscar,Mateos, Carlos,Kappe, C. Oliver

supporting information, p. 1384 - 1388 (2019/02/14)

BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space-time-yield of 1.27 kg L?1 h?1

Anti-influenza activity of monoterpene-containing substituted coumarins

Khomenko, Tatyana M.,Zarubaev, Vladimir V.,Orshanskaya, Iana R.,Kadyrova, Renata A.,Sannikova, Victoria A.,Korchagina, Dina V.,Volcho, Konstantin P.,Salakhutdinov, Nariman F.

supporting information, p. 2920 - 2925 (2017/06/01)

Compounds simultaneously carrying the monoterpene and coumarin moieties have been tested for cytotoxicity and inhibition of activity against influenza virus A/California/07/09 (H1N1)pdm09. The structure of substituents in the coumarin framework, as well as the structure and the absolute configuration of the monoterpenoid moiety, are shown to significantly influence the anti-influenza activity and cytotoxicity of the compounds under study. The compounds with a bicyclic pinane framework exhibit the highest selectivity indices (the ratios between the cytotoxicity and the active dose). The derivative of (?)-myrtenol 15c, which is characterized by promising activity, low cytotoxicity, and synthetic accessibility, has the greatest potential among this group of compounds. It exhibited the highest activity when added to the infected cell culture at early stages of viral reproduction.

New inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 7-hydroxycoumarin and monoterpenoid moieties

Khomenko, Tatyana,Zakharenko, Alexandra,Odarchenko, Tatyana,Arabshahi, Homayon John,Sannikova, Victoriya,Zakharova, Olga,Korchagina, Dina,Reynisson, Jóhannes,Volcho, Konstantin,Salakhutdinov, Nariman,Lavrik, Olga

, p. 5573 - 5581 (2016/10/24)

A number of derivatives of 7-hydroxycoumarins containing aromatic or monoterpene substituents at hydroxy-group were synthesized based on a hit compound from a virtual screen. The ability of these compounds to inhibit tyrosyl-DNA phosphodiesterase I (Tdp 1), important target for anti-cancer therapy, was studied for the first time. It was found that the 7-hydroxycoumarin derivatives with monoterpene pinene moiety are effective inhibitors of Tdp 1 with the most active derivative (+)-25c with IC50value of 0.675?μM. This compound has low cytotoxicity (CC50?>100?μM) when tested against human cancer cells which is crucial for presupposed application in combination with clinically established anticancer drugs. The ability of the new compounds to enhance the cytotoxicity of camptothecin, an established topoisomerase 1 poison, was demonstrated.

Preparation method of benzylamine compound

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Paragraph 0041-0043, (2017/01/23)

The invention discloses a preparation method of a benzylamine compound. The method adopting an aryl methane compound as a raw material comprises the following steps: carrying out an NBS bromination reaction to synthesize a bromobenzyl compound, carrying out an N-hydrocarbylation reaction to synthesize a 1-benzylpyrrolidyl-2,5-dione compound, and carrying out a hydrolyzing reaction to obtain the benzylamine compound. The preparation method of the benzylamine compound has the advantages of wide source of the raw material, no need of separation of intermediates generated in above reactions, realization of an all-in-a-pot technology, simple operation, mild reaction conditions, high reaction yield, few three wastes, and convenience for industrial production.

DIHYDROBENZOFURAN DERIVATIVES AS INSECTICIDAL COMPOUNDS

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Page/Page column 130, (2014/09/29)

Provided are compounds of formula (I) and methods of controlling insects, acarines, nematodes or molluscs, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I).

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