Production Method 1

59276-28-7

874-98-6

Reaction Conditions

1.1 Reagents: Acetyl bromide ,  Triethylsilane ,  Tin dibromide Solvents: Dichloromethane

Reference

Ionic and organometallic-catalyzed organosilane reductions

Larson, Gerald L.; et al, Organic Reactions (Hoboken, 2008, 71, 1-737

Production Method 2

6971-51-3

874-98-6

Reaction Conditions

1.1 Reagents: Chlorotrimethylsilane ,  Lithium bromide Solvents: Acetonitrile ;  22 h, reflux

Reference

Intramolecular cyclizations via arylnitrenium ions. Formation of a six-membered ring rather than a macrocycle

Abramovitch, Rudolph A.; et al, Journal of Organic Chemistry, 1999, 64(16), 5904-5912

Production Method 3

100-84-5

874-98-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Carbon tetrachloride

Reference

Nuclear versus Side-Chain Bromination of Methyl-Substituted Anisoles by N-Bromosuccinimide

Gruter, Gert-Jan M.; et al, Journal of Organic Chemistry, 1994, 59(16), 4473-81

Production Method 4

100-84-5

874-98-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Benzene ;  2.5 h, reflux

Reference

Design, synthesis, and peroxisome proliferator-activated receptor γ agonistic activity of novel indenone derivatives

Qu, Li-li; et al, Yaoxue Xuebao, 2013, 48(4), 508-513

Production Method 5

1058648-97-7

874-98-6

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide Catalysts: 12-Tungstophosphoric acid Solvents: 1-Butyl-3-methylimidazolium tetrachloroferrate ;  1.5 min, 130 - 142 °C

Reference

H3PW12O40-[bmim][FeCl4]: A novel and green catalyst-medium system for microwave-promoted selective interconversion of alkoxymethyl ethers into their corresponding nitriles, bromides and iodides

Mohammadpoor-Baltork, Iraj; et al, Comptes Rendus Chimie, 2010, 13(12), 1468-1473

Production Method 6

161358-52-7

874-98-6

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide Catalysts: 1H-Imidazolium, 1-butyl-3-methyl-, (T-4)-tetrachloroindate(1-) (1:1) ;  2 - 5.5 min, 135 - 140 °C

Reference

Microwave-promoted, one-pot conversion of alkoxymethylated protected alcohols into their corresponding nitriles, bromides, and iodides using [bmim][InCl4] as a green catalyst

Mirjafari, Arsalan; et al, Tetrahedron Letters, 2010, 51(25), 3274-3276

Production Method 7

591-31-1

874-98-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  3 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  cooled

Reference

Synthesis of Atropisomeric Hydrazides by One-Pot Sequential Enantio- and Diastereoselective Catalysis

Portolani, Chiara ; et al, Angewandte Chemie, 2022, 61(42),

Production Method 8

874-98-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone
2.1 Reagents: N-Bromosuccinimide

Reference

Studies on the synthesis of a natural product-piceatannol and its analogs

Piao, Zhi Song; et al, Chinese Chemical Letters, 2002, 13(6), 521-524

Production Method 9

59276-28-7

874-98-6

Reaction Conditions

1.1 Reagents: Acetyl bromide ,  Triethylsilane Catalysts: Tin dibromide Solvents: Dichloromethane

Reference

Halogenative allylation and reduction of aromatic acetals by double substitution of alkoxyl groups in acetal

Oriyama, Takeshi; et al, Bulletin of the Chemical Society of Japan, 1991, 64(4), 1410-12

Production Method 10

6971-51-3

874-98-6

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  15 min, 0 °C

Reference

Synthesis of Stilbene Derivatives: A Comparative Study of their Antioxidant Activities

Romero, Miguel A.; et al, Natural Product Communications, 2015, 10(7),

Production Method 11

6971-51-3

874-98-6

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Benzene ;  0 °C; 2 h, rt
1.2 Reagents: Water ;  0 °C

Reference

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

Nagasawa, Shota ; et al, Journal of Organic Chemistry, 2021, 86(9), 6952-6968

Production Method 12

100-84-5

874-98-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride

Reference

Preparation of aromatic sulfides. Carbon-13 NMR study

Mieloszynski, J. L.; et al, Sulfur Letters, 1988, 8(1), 31-5

Production Method 13

1058648-97-7

874-98-6

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide Catalysts: 1H-Imidazolium, 1-butyl-3-methyl-, (T-4)-tetrachloroindate(1-) (1:1) ;  2 - 5.5 min, 135 - 140 °C

Reference

Microwave-promoted, one-pot conversion of alkoxymethylated protected alcohols into their corresponding nitriles, bromides, and iodides using [bmim][InCl4] as a green catalyst

Mirjafari, Arsalan; et al, Tetrahedron Letters, 2010, 51(25), 3274-3276

Production Method 14

161358-52-7

874-98-6

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide Catalysts: 12-Tungstophosphoric acid Solvents: 1-Butyl-3-methylimidazolium tetrachloroferrate ;  1.5 min, 130 - 142 °C

Reference

H3PW12O40-[bmim][FeCl4]: A novel and green catalyst-medium system for microwave-promoted selective interconversion of alkoxymethyl ethers into their corresponding nitriles, bromides and iodides

Mohammadpoor-Baltork, Iraj; et al, Comptes Rendus Chimie, 2010, 13(12), 1468-1473

Production Method 15

514829-71-1

874-98-6

Reaction Conditions

1.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  5 h, -76 °C

Reference

New results on the stereoselective alkylations of malic acid derivatives supported by molecular modeling

Sefkow, Michael; et al, Helvetica Chimica Acta, 2002, 85(12), 4216-4229

Production Method 16

75-62-7

100-84-5

874-98-6

Reaction Conditions

Reference

Benzylic bromination with bromotrichloromethane

Baldwin, S. W.; et al, Synthetic Communications, 1976, 6(2), 109-12

Production Method 17

128-08-5

100-84-5

874-98-6

Reaction Conditions

1.1 Solvents: Chloroform

Reference

The Asymmetric Synthesis of (-)-Quinocarcin

Ho, Wen-Bin, 1992, , ,

Production Method 18

591-31-1

874-98-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  4 h, rt
1.2 Reagents: Water ;  rt
2.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  0 °C; 12 h, 0 °C
2.2 Reagents: Water

Reference

Photocatalytic defluorocarboxylation using formate salts as both a reductant and a carbon dioxide source

Min, Shi-Yun; et al, Green Chemistry, 2023, 25(16), 6194-6199

Production Method 19

874-98-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide ;  5 h, 50 °C
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  5 h, reflux

Reference

A practical synthesis of sarpogrelate hydrochloride and in vitro platelet aggregation inhibitory activities of its analogues

Chen, Guo Hua; et al, Chinese Chemical Letters, 2010, 21(3), 287-289

3-Methoxybenzyl bromide Raw materials

• Bromotrichloromethan\u200be
• (4S)-2-(1,1-Dimethylethyl)-α-[(3-methoxyphenyl)methyl]-5-oxo-1,3-dioxolane-4-acetic acid
• 3-Methoxy-1-[(ethoxymethoxy)methyl]benzene
• Benzene, 1-methoxy-3-[(methoxymethoxy)methyl]-
• 1-(Dimethoxymethyl)-3-methoxybenzene
• 3-Methoxybenzenemethanol
• 3-Methoxybenzaldehyde
• N-Bromosuccinimide
• Meta-Methylanisole

3-Methoxybenzyl bromide Preparation Products

• 3-Methoxybenzyl bromide (874-98-6)

• 1. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 2. Enantiomeric two-fold interpenetrated 3D zinc(ii) coordination networks as a catalytic platform: significant difference between water within the cage and trace water in transesterification?
  Eunkyung Choi,Minjoo Ryu,Haeri Lee,Ok-Sang Jung Dalton Trans., 2017,46, 4595-4601
• 3. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 4. Exciton manipulation in rippled transition metal dichalcogenides?
  Chen Long,Ying Dai,Jianwei Li,Hao Jin Nanoscale, 2020,12, 21124-21130
• 5. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl halides Benzyl bromides
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

3-Methoxybenzyl bromide (CAS No. 874-98-6): A Versatile Intermediate in Modern Chemical Synthesis

3-Methoxybenzyl bromide, with the chemical formula C₇H₇BrO and CAS number 874-98-6, is a widely utilized intermediate in the field of organic synthesis. This compound, characterized by its brominated aromatic ring and a methoxy substituent, plays a pivotal role in the development of pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structural properties make it an invaluable tool for chemists and researchers seeking to construct complex molecular frameworks.

The utility of 3-Methoxybenzyl bromide stems from its reactivity as a brominated aromatic compound. The presence of the bromine atom allows for various nucleophilic substitution reactions, enabling the introduction of diverse functional groups. This characteristic is particularly valuable in the synthesis of biologically active molecules, where precise functionalization is often required. The methoxy group, on the other hand, provides stability and influences the electronic properties of the aromatic system, making it an excellent choice for further derivatization.

In recent years, 3-Methoxybenzyl bromide has garnered significant attention in the pharmaceutical industry. Its role as a protecting group for alcohols and amination reactions has been well-documented. The compound is frequently employed in the synthesis of peptidomimetics and other therapeutic agents, where its ability to form stable amides and esters is crucial. Furthermore, its use in cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, has expanded its applications in drug discovery and development.

The importance of 3-Methoxybenzyl bromide is further highlighted by its involvement in cutting-edge research. For instance, recent studies have demonstrated its utility in the synthesis of novel heterocyclic compounds, which are known for their potential pharmacological properties. These studies often leverage the compound's reactivity to construct complex scaffolds that mimic natural products and bioactive molecules. The ability to efficiently incorporate 3-Methoxybenzyl bromide into these syntheses underscores its significance as a synthetic building block.

Another area where 3-Methoxybenzyl bromide has made a notable impact is in the field of material science. Researchers have explored its use in the preparation of functional polymers and organic electronic materials. The compound's ability to undergo selective functionalization allows for the creation of polymers with tailored properties, such as conductivity or luminescence. These advancements highlight the compound's versatility beyond traditional organic synthesis applications.

The industrial production of 3-Methoxybenzyl bromide adheres to stringent quality control measures to ensure consistency and purity. Manufacturers employ advanced synthetic techniques to optimize yield and minimize byproducts. This commitment to quality ensures that researchers and industrial chemists can rely on this compound for their most demanding applications.

In conclusion, 3-Methoxybenzyl bromide (CAS No. 874-98-6) is a cornerstone in modern chemical synthesis. Its unique structural features and reactivity make it an indispensable tool for pharmaceutical researchers, synthetic chemists, and material scientists alike. As new methodologies and applications continue to emerge, the importance of this versatile intermediate will only grow, solidifying its place as a cornerstone of organic chemistry.

• 2746-25-0(4-Methoxybenzyl bromide)
• 877-88-3(3,5-Dimethoxybenzyl bromide)
• 51632-16-7(1-(Bromomethyl)-3-phenoxybenzene)
• 36132-96-4(1,2-bis(bromomethyl)-4-methoxybenzene)
• 3898-24-6(1-(bromomethyl)-3-ethoxy-benzene)
• 61000-22-4(Benzene, 2-(bromomethyl)-5-methoxy-1,3-dimethyl-)
• 4542-75-0(4,4'-Oxybis((bromomethyl)benzene))
• 36881-42-2(1-(Bromomethyl)-4-phenoxybenzene)
• 21852-32-4(4-(Bromomethyl)-1,2-dimethoxybenzene)
• 106116-42-1(1-(Bromomethyl)-3-methoxy-5-methylbenzene)