Production Method 1

117390-06-4

88738-86-7

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  Bromine Solvents: Acetonitrile

Reference

New aldose reductase inhibitors. Part I. Syntheses of (rac)3-substituted 4-methoxycarbonyl-1,3-thiazolidine-2-thiones via rearrangement of a substituted group from exo-S to N in (rac)2-substituted thio-4-methoxycarbonyl-Δ2-1,3-thiazolines

Nagao, Yoshimitsu; Inoue, Keiko; Yamaki, Masae; Takagi, Shuzo; Fujita, Eiichi, Chemical & Pharmaceutical Bulletin, 1988, 36(2), 495-508

Production Method 2

117390-06-4

88738-86-7

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  cooled; 90 min, cooled; rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

The Binding of Synthetic Retinoids to Lipocalin β-Lactoglobulins

Riihimaki-Lampen, Laura H.; Vainio, Mikko J.; Vahermo, Mikko; Pohjala, Leena L.; Heikura, Jonna M. S.; et al, Journal of Medicinal Chemistry, 2010, 53(1), 514-518

Production Method 3

20754-20-5

88738-86-7

Reaction Conditions

1.1 Reagents: Benzoyl peroxide ,  N-Bromosuccinimide Solvents: Carbon tetrachloride ;  6 h, reflux

Reference

Process for synthesizing ozagrel

Xue, Xuming; Lu, Chunxu, Huagong Jinzhan, 2009, 28(11), 2024-2027

Production Method 4

20754-20-5

88738-86-7

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Carbon tetrachloride ;  rt

Reference

Cyclophanes, LXII. Paracyclophanes: extending the bridges. Synthesis

Pechlivanidis, Zissis; Hopf, Henning; Ernst, Ludger, European Journal of Organic Chemistry, 2009, (2), 223-237

methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate Raw materials

• methyl (2E)-3-(4-methylphenyl)prop-2-enoate
• 2-Propenoic acid, 3-[4-(hydroxymethyl)phenyl]-, methyl ester, (E)-

methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate Preparation Products

• methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate (88738-86-7)

• 1. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 2. An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes?
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• 3. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
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• 4. An antioxidant self-healing hydrogel for 3D cell cultures?
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• 5. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812

• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Cinnamic acid esters

Methyl 3-[4-(Bromomethyl)phenyl]prop-2-enoate (CAS No. 88738-86-7): An Overview of Its Properties, Applications, and Recent Research

Methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate (CAS No. 88738-86-7) is a versatile organic compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This compound, also known as methyl cinnamate derivative, is characterized by its unique structural features and chemical reactivity, making it a valuable intermediate in various synthetic pathways.

The molecular structure of methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate consists of a cinnamate moiety linked to a bromomethyl-substituted phenyl group. The presence of the bromomethyl group provides a reactive site for various chemical transformations, such as nucleophilic substitution and cross-coupling reactions. This versatility has led to its widespread use in the synthesis of complex organic molecules, including pharmaceuticals and functional materials.

In the realm of medicinal chemistry, methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate has been explored as a key intermediate in the development of novel therapeutic agents. Recent studies have highlighted its potential in the synthesis of compounds with anti-inflammatory, anti-cancer, and neuroprotective properties. For instance, a study published in the Journal of Medicinal Chemistry reported the use of this compound in the synthesis of a series of cinnamate derivatives that exhibited potent anti-inflammatory activity in vitro and in vivo.

Moreover, the bromomethyl group in methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate can be readily functionalized through palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura coupling and Stille coupling. These reactions allow for the introduction of a wide range of substituents at the phenyl ring, thereby expanding the scope of its applications. A recent publication in Organic Letters described the efficient synthesis of substituted phenyl derivatives using this compound as a starting material, demonstrating its utility in the preparation of complex organic frameworks.

In addition to its role in organic synthesis, methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate has also found applications in materials science. Its ability to undergo polymerization reactions makes it a promising candidate for the development of functional polymers with tailored properties. Research conducted at the University of California, Berkeley, explored the use of this compound in the synthesis of conjugated polymers with enhanced electronic and optical properties. The resulting polymers exhibited high conductivity and excellent photoluminescence, making them suitable for applications in organic electronics and optoelectronics.

The physical properties of methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate are also noteworthy. It is typically obtained as a colorless liquid with a characteristic odor. The compound is soluble in common organic solvents such as ethanol, acetone, and dichloromethane, which facilitates its handling and processing in laboratory settings. Its melting point is reported to be around -10°C, while its boiling point is approximately 150°C at reduced pressure.

Safety considerations are an important aspect when working with any chemical compound. While methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate is not classified as a hazardous substance under current regulations, it is advisable to handle it with appropriate precautions to ensure laboratory safety. This includes wearing personal protective equipment (PPE) such as gloves and goggles, working under a fume hood to minimize exposure to vapors, and following standard laboratory practices for waste disposal.

In conclusion, methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate (CAS No. 88738-86-7) is a multifaceted compound with significant potential in various scientific disciplines. Its unique structural features and chemical reactivity make it an invaluable tool for researchers engaged in organic synthesis, medicinal chemistry, and materials science. As ongoing research continues to uncover new applications and properties, this compound is likely to remain an important player in the development of innovative solutions across multiple fields.

• 86761-30-0(2-Propenoic acid, 3-(3,5-dimethylphenyl)-, methyl ester)
• 7560-43-2(Methyl (2E)-3-(4-methylphenyl)propenoate)
• 103-26-4(Methyl cinnamate)
• 188991-25-5(2-Propenoic acid,3-(4-methylphenyl)-,methyl ester,radical ion(1+) (9CI))
• 60633-90-1(2-Propenoic acid, 3-[2-(bromomethyl)phenyl]-, ethyl ester, (E)-)
• 60682-98-6(Ethyl 4-bromomethylcinnamate)
• 946-99-6(Methyl 4-Bromomethylcinnamate)
• 70625-38-6(2-Propenoic acid, 3-[2-(bromomethyl)phenyl]-, methyl ester)
• 19713-73-6(2-Propenoic acid, 3-phenyl-, methyl ester, (2Z)-)
• 832734-32-4(2-Propenoic acid, 3-bromo-3-(4-methylphenyl)-, methyl ester, (2Z)-)