Production Method 1

59453-47-3

88377-29-1

Reaction Conditions

1.1 Reagents: Lithium hydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor

Granchi, Carlotta; et al, Journal of Medicinal Chemistry, 2019, 62(4), 1932-1958

Production Method 2

3177-80-8

88377-29-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrogen bromide Solvents: Water
1.2 Reagents: Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water

Reference

Synthesis of novel fluorescent acridono- and thioacridono-18-crown-6 ligands

Huszthy, P.; et al, Tetrahedron, 2001, 57(23), 4967-4975

Production Method 3

3177-80-8

88377-29-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrogen bromide Solvents: Water ;  < 5 °C; 2 h, 0 °C
1.2 Reagents: Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water ;  15 h, 24 °C

Reference

Design of living ring-opening alkyne metathesis

Fischer, Felix R.; et al, Angewandte Chemie, 2010, 49(40), 7257-7260

Production Method 4

10401-18-0

88377-29-1

Reaction Conditions

1.1 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Acetone ,  Water ;  2 d, 55 °C

Reference

Chiral oxazoline route to enantiomerically pure biphenyls: magnesio and copper mediated asymmetric hetero- and homo-coupling reactions

Meyers, A. I.; et al, Tetrahedron, 2004, 60(20), 4459-4473

Production Method 5

591-31-1

88377-29-1

Reaction Conditions

1.1 Reagents: Butyllithium ,  N,N,N′-Trimethylethylenediamine Solvents: Toluene ,  Hexane ;  0 °C; 15 min, rt
1.2 15 min, rt
1.3 Reagents: Phenyllithium Solvents: Diethyl ether ,  Cyclohexane ;  8 h, rt
1.4 Solvents: Tetrahydrofuran ;  -78 °C
1.5 Reagents: 1,2-Dibromo-1,1,2,2-tetrafluoroethane ;  -78 °C; -78 °C → rt
1.6 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Acetone ,  Water ;  2 d, 55 °C

Reference

Chiral oxazoline route to enantiomerically pure biphenyls: magnesio and copper mediated asymmetric hetero- and homo-coupling reactions

Meyers, A. I.; et al, Tetrahedron, 2004, 60(20), 4459-4473

Production Method 6

3177-80-8

88377-29-1

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 3 - 24 h, 80 °C; 80 °C → rt
1.2 Solvents: Ethyl acetate ,  Water ;  rt
2.1 Reagents: Hydrogen bromide Solvents: 1,4-Dioxane ,  Water ;  rt; 30 min, rt; 0 °C → -5 °C
2.2 Reagents: Sodium nitrite Solvents: Water ;  -5 °C; 30 min, -5 °C
2.3 Reagents: Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water ;  -5 °C → rt; 5 h, 110 °C; cooled
2.4 Solvents: Water ;  rt
3.1 Reagents: Lithium hydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  overnight, rt
3.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor

Granchi, Carlotta; et al, Journal of Medicinal Chemistry, 2019, 62(4), 1932-1958

Production Method 7

630-25-1

586-38-9

88377-29-1

Reaction Conditions

1.1 Reagents: Butyllithium ,  2,2,6,6-Tetramethylpiperidine Solvents: Tetrahydrofuran ,  Hexane
1.2 Solvents: Water

Reference

Reactions of regioselective metalation of unprotected alkoxybenzoic acids. Scopes, limitations and mechanism

Nguyen, Thi Huu, 2006, , ,

Production Method 8

586-38-9

88377-29-1

Reaction Conditions

1.1 Reagents: Piperidine, 2,2,6,6-tetramethyl-, lithium salt (1:1) Solvents: Tetrahydrofuran ;  0 °C; 2 h, 0 °C
1.2 Reagents: Ethane, 1,2-dibromo-1,1,2,2-tetrachloro-, radical ion(1-) ;  30 min, 0 °C; 2 h, 65 °C

Reference

First General, Direct, and Regioselective Synthesis of Substituted Methoxybenzoic Acids by Ortho Metalation

Nguyen, Thi-Huu; et al, Journal of Organic Chemistry, 2007, 72(9), 3419-3429

Production Method 9

586-38-9

88377-29-1

Reaction Conditions

1.1 Reagents: Piperidine, 2,2,6,6-tetramethyl-, lithium salt (1:1) Solvents: Tetrahydrofuran ;  0 °C; 2 h, 0 °C
1.2 Reagents: 1,2-Dibromo-1,1,2,2-tetrachloroethane ;  30 min, 0 °C; 0 °C → 65 °C; 2 h, 65 °C
1.3 Reagents: Water
1.4 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt

Reference

Toward a Better Understanding on the Mechanism of Ortholithiation. Tuning of Selectivities in the Metalation of meta-Anisic Acid by an Appropriate Choice of Base

Nguyen, Thi-Huu; et al, Organic Letters, 2005, 7(12), 2445-2448

Production Method 10

1026003-01-9

88377-29-1

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water
2.1 Reagents: Sodium nitrite ,  Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water

Reference

Palladium-Catalyzed Dominocyclizations in the Efficient Total Synthesis of Tatracycline Antibiotics

Bell, Hubertus Peter, 2004, , ,

Production Method 11

5121-34-6

88377-29-1

Reaction Conditions

1.1 Reagents: Hydrogen bromide Solvents: 1,4-Dioxane ,  Water ;  rt; 30 min, rt; 0 °C → -5 °C
1.2 Reagents: Sodium nitrite Solvents: Water ;  -5 °C; 30 min, -5 °C
1.3 Reagents: Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water ;  -5 °C → rt; 5 h, 110 °C; cooled
1.4 Solvents: Water ;  rt
2.1 Reagents: Lithium hydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  overnight, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor

Granchi, Carlotta; et al, Journal of Medicinal Chemistry, 2019, 62(4), 1932-1958

Production Method 12

154150-18-2

88377-29-1

Reaction Conditions

1.1 Reagents: tert-Butyllithium Solvents: Diethyl ether ,  Pentane
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water
3.1 Reagents: Sodium nitrite ,  Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water

Reference

Palladium-Catalyzed Dominocyclizations in the Efficient Total Synthesis of Tatracycline Antibiotics

Bell, Hubertus Peter, 2004, , ,

Production Method 13

24424-99-5

88377-29-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran
2.1 Reagents: tert-Butyllithium Solvents: Diethyl ether ,  Pentane
3.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water
4.1 Reagents: Sodium nitrite ,  Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water

Reference

Palladium-Catalyzed Dominocyclizations in the Efficient Total Synthesis of Tatracycline Antibiotics

Bell, Hubertus Peter, 2004, , ,

Production Method 14

95970-22-2

88377-29-1

31786-45-5

Reaction Conditions

1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  rt → -40 °C; 2 h, -40 °C
1.2 1 h, -40 °C

Reference

Regioselective halogen-metal exchange reaction of 3-substituted 1,2-dibromo arenes: the synthesis of 2-substituted 5-bromobenzoic acids

Menzel, Karsten; et al, Synlett, 2006, (12), 1948-1952

2-Bromo-3-methoxybenzoic acid Raw materials

• Di-tert-butyl dicarbonate
• Boc-2-amino-3-methoxybenzoic Acid
• Methyl 2-amino-3-methoxybenzoate
• 2-Bromo-3-methoxybenzaldehyde
• 1,2-Dibromotetrachloroethane
• 1,2-dibromo-3-methoxybenzene
• 3-Methoxybenzoic acid
• 3-Methoxybenzaldehyde
• 2-Amino-3-methoxybenzoic acid
• tert-Butyl N-(2-Methoxyphenyl)carbamate
• methyl 2-bromo-3-methoxybenzoate

2-Bromo-3-methoxybenzoic acid Preparation Products

• 2-Bromo-3-methoxybenzoic acid (88377-29-1)
• 2-Bromo-6-methoxybenzoic acid (31786-45-5)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Methoxybenzoic acids and derivatives

2-Bromo-3-Methoxybenzoic Acid: A Comprehensive Overview

2-Bromo-3-methoxybenzoic acid (CAS No. 88377-29-1) is a versatile organic compound with significant applications in various fields, including pharmaceuticals, agrochemicals, and materials science. This compound is characterized by its unique structure, which combines a bromine atom at the 2-position and a methoxy group at the 3-position on the benzoic acid backbone. The combination of these substituents imparts distinctive chemical and physical properties to the molecule, making it a valuable building block in organic synthesis.

The synthesis of 2-bromo-3-methoxybenzoic acid has been extensively studied, with researchers exploring various methodologies to optimize its production. Recent advancements in catalytic systems and green chemistry have enabled more efficient and environmentally friendly routes for its synthesis. For instance, the use of microwave-assisted synthesis has been reported to significantly reduce reaction times while maintaining high yields. These developments underscore the importance of sustainable practices in modern chemical manufacturing.

One of the most notable applications of 2-bromo-3-methoxybenzoic acid is in drug discovery. The compound serves as an intermediate in the synthesis of bioactive molecules with potential therapeutic effects. For example, derivatives of this compound have been investigated for their anti-inflammatory, antioxidant, and anticancer properties. A study published in 2023 highlighted the ability of certain analogs to inhibit key enzymes involved in inflammation pathways, suggesting promising avenues for future drug development.

In addition to its role in pharmaceuticals, 2-bromo-3-methoxybenzoic acid has found applications in agrochemicals. Researchers have explored its potential as a precursor for herbicides and fungicides. The compound's reactivity and stability make it an ideal candidate for designing molecules with targeted pest control properties. Recent studies have focused on improving the bioavailability and selectivity of these derivatives to minimize environmental impact while maintaining efficacy.

The electronic properties of 2-bromo-3-methoxybenzoic acid also make it a valuable material in the field of electronics. Its ability to act as a semiconductor has led to its investigation in organic electronics applications such as field-effect transistors (FETs) and light-emitting diodes (LEDs). A 2023 study demonstrated that incorporating this compound into polymer blends could enhance charge transport properties, paving the way for next-generation electronic devices.

From a structural perspective, 2-bromo-3-methoxybenzoic acid exhibits interesting spectroscopic characteristics that are useful for analytical purposes. Its UV-vis spectrum shows strong absorption bands due to conjugation within the aromatic ring, while its NMR spectra provide insights into the spatial arrangement of substituents. These spectroscopic features are invaluable for identifying and characterizing derivatives of this compound.

Recent research has also focused on understanding the environmental fate and toxicity of 2-bromo-3-methoxybenzoic acid. Studies indicate that the compound undergoes biodegradation under specific environmental conditions, with microbial activity playing a significant role in its transformation. However, further investigations are needed to assess its long-term impact on ecosystems and human health.

In conclusion, 2-bromo-3-methoxybenzoic acid (CAS No. 88377-29-1) is a multifaceted compound with diverse applications across various industries. Its unique structure enables it to serve as a versatile building block in organic synthesis, contributing to advancements in pharmaceuticals, agrochemicals, and electronics. As research continues to uncover new properties and applications of this compound, its significance in both academic and industrial settings is expected to grow further.

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