Production Method 1

1003-29-8

931-33-9

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt → 0 °C
1.2 Reagents: N-Bromosuccinimide ;  15 min, 0 °C; 0 °C → rt

Reference

Refined syntheses of hydrodipyrrin precursors to chlorin and bacteriochlorin building blocks

Krayer, Michael; Balasubramanian, Thiagarajan; Ruzie, Christian; Ptaszek, Marcin; Cramer, David L.; et al, Journal of Porphyrins and Phthalocyanines, 2009, 13(10), 1098-1110

Production Method 2

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran

Reference

Pyrido five-element aromatic ring compound, preparation method therefor and use thereof

, World Intellectual Property Organization, , ,

Production Method 3

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  15 min, 0 °C

Reference

One-Pot Synthesis of Highly Substituted N-Fused Heteroaromatic Bicycles from Azole Aldehydes

Outlaw, Victor K.; d'Andrea, Felipe B.; Townsend, Craig A., Organic Letters, 2015, 17(8), 1822-1825

Production Method 4

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: Hydrogen bromide Solvents: Dimethyl sulfoxide ,  Water ;  2 h, 50 °C; 50 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 7 - 8, rt

Reference

Selective bromination of pyrrole derivatives, carbazole and aromatic amines with DMSO/HBr under mild conditions

Liu, Cong; Dai, Rongji; Yao, Guowei; Deng, Yulin, Journal of Chemical Research, 2014, 38(10), 593-596

Production Method 5

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  15 min, 0 °C

Reference

Access to 6-hydroxy indolizines and related imidazo[1,5-a]pyridines through the SN2 substitution/condensation/tautomerization cascade process

Duan, Guiyun; Liu, Hao; Zhang, Liqing; Yuan, Chunhao; Li, Yongchao; et al, RSC Advances, 2021, 11(41), 25624-25627

Production Method 6

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  15 min, 0 °C

Reference

Fused pyrimidinone and triazinone derivative as antifungal and/or antiparasitic agent, and method for the preparation thereof

, World Intellectual Property Organization, , ,

Production Method 7

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  1 h, -78 °C; 6.5 h, -78 °C; -78 °C → 0 °C

Reference

Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of sulphone-based CRTh2 antagonists

Buil, Maria Antonia; Calbet, Marta; Castillo, Marcos; Castro, Jordi; Esteve, Cristina; et al, European Journal of Medicinal Chemistry, 2016, 113, 102-133

Production Method 8

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  rt → -70 °C; -70 °C; 1 h, -78 °C
1.2 Reagents: Hexane ,  Water ;  -78 °C → rt
1.3 Solvents: Tetrahydrofuran ,  Hexane ;  1 h, rt

Reference

Preparation of quinazoline derivatives as protein kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 9

1003-29-8

128-08-5

931-33-9

931-34-0

932-82-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran

Reference

Chemical Investigations of Great Barrier Reef Ascidians: Natural Product and Synthetic Studies

Davis, Rohan Andrew, 2000, , ,

Production Method 10

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: 1,3-Dibromo-5,5-dimethylhydantoin Solvents: Tetrahydrofuran ;  10 min, -78 °C; 5 h, -78 °C → rt
1.2 Reagents: Potassium bisulfate Solvents: Water ;  rt

Reference

Preparation of tambjamines and B-ring functionalized prodiginines as potent antimalarials

, World Intellectual Property Organization, , ,

Production Method 11

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: 1,3-Dibromo-5,5-dimethylhydantoin Solvents: Tetrahydrofuran ;  10 min, -78 °C; 5 h, -78 °C → rt
1.2 Reagents: Potassium bisulfate Solvents: Water

Reference

Synthesis and Structure-Activity Relationships of Tambjamines and B-Ring Functionalized Prodiginines as Potent Antimalarials

Kancharla, Papireddy; Kelly, Jane Xu; Reynolds, Kevin A., Journal of Medicinal Chemistry, 2015, 58(18), 7286-7309

Production Method 12

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  30 min, 0 °C

Reference

Polycyclic amide derivatives as CDK9 inhibitors, its preparation method, and its application in treating of cancer

, China, , ,

Production Method 13

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  30 min, 0 °C

Reference

Preparation of ((aryl)chloropyridyl)acetamides as CDK inhibitor

, China, , ,

Production Method 14

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  15 min, 0 °C

Reference

Preparation of novel fused pyrimidinone and triazinone derivatives as antifungal and/or antiparasitic agents

, World Intellectual Property Organization, , ,

Production Method 15

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  15 min, 0 °C

Reference

New azole antifungals with a fused triazinone scaffold

Montoir, David; Guillon, Remi; Gazzola, Sophie; Ourliac-Garnier, Isabelle; Soklou, Kossi Efouako; et al, European Journal of Medicinal Chemistry, 2020, 189,

Production Method 16

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  rt → -78 °C; 1 h, -78 °C
1.2 Reagents: Hexane ,  Water ;  -78 °C → 0 °C

Reference

Synthesis of chlorins and phorbines with enhanced red spectral features for use in photodynamic therapy or in solar cells

, World Intellectual Property Organization, , ,

Production Method 17

1003-29-8

931-33-9

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  rt → -78 °C
1.2 Reagents: N-Bromosuccinimide ;  1 h, -78 °C
1.3 Solvents: Hexane ,  Water ;  -78 °C; -78 °C → rt

Reference

Synthetic chlorins bearing auxochromes at the 3- and 13-positions

Laha, Joydev K.; Muthiah, Chinnasamy; Taniguchi, Masahiko; McDowell, Brian E.; Ptaszek, Marcin; et al, Journal of Organic Chemistry, 2006, 71(11), 4092-4102

Production Method 18

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  -78 °C; 1 h, -78 °C

Reference

Preparation of oxoindolylidene derivatives for use as AMPK activators

, World Intellectual Property Organization, , ,

Production Method 19

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  15 min, 0 °C

Reference

Fluorination of pyrrole derivatives by Selectfluor

Heeran, Darren; Sandford, Graham, Tetrahedron, 2016, 72(19), 2456-2463

Production Method 20

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  0 °C; 0 °C
1.2 Reagents: Sodium sulfite Solvents: Water

Reference

Design, Sustainable Synthesis, and Programmed Reactions of Templated N-Heteroaryl-Fused Vinyl Sultams

Laha, Joydev K. ; Sharma, Shubhra; Kirar, Seema; Banerjee, Uttam C., Journal of Organic Chemistry, 2017, 82(18), 9350-9359

Production Method 21

1003-29-8

931-33-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  1 h, -78 °C

Reference

Iterative Suzuki-Miyaura Cross-coupling/Bromo-desilylation Reaction Sequences for the Assembly of Chemically Well-defined, Acyclic Oligopyrrole/Benzenoid Hybrids Embodying Mixed Modes of Connectivity

Lee, BoRa; Willis, Anthony C.; Ward, Jas S.; Smith, Warren T.; Lan, Ping; et al, Chemistry - An Asian Journal, 2020, 15(19), 3059-3081

4-Bromo-1H-pyrrole-2-carbaldehyde Raw materials

• Pyrrole-2-carboxaldehyde
• N-Bromosuccinimide

4-Bromo-1H-pyrrole-2-carbaldehyde Preparation Products

• 4-Bromo-1H-pyrrole-2-carbaldehyde (931-33-9)
• 5-Bromo-1H-pyrrole-2-carbaldehyde (931-34-0)
• 4,5-Dibromo-1H-pyrrole-2-carboxaldehyde (932-82-1)

• 1. An insight into the role of side chains in the microstructure and carrier mobility of high-performance conjugated polymers?
  Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
• 2. An intermolecular C–C coupling reaction of iridium complexes?
  Kathrin Kutlescha,Rhett Kempe New J. Chem., 2010,34, 1954-1960
• 3. Achieving excellent anti-corrosion and tribological performance by tailoring the surface morphology and chemical composition of aluminum alloys
  Wenjie Zhao,Hua Hou,Yuchun Jin,Zhixiang Zeng,Xuedong Wu,Qunji Xue RSC Adv., 2014,4, 60307-60315
• 4. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
  Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378
• 5. An aquatic host–guest complex between a supramolecular G-quadruplex and the anticancer drug doxorubicin?
  José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565

Recent Advances in the Application of 4-Bromo-1H-pyrrole-2-carbaldehyde (CAS: 931-33-9) in Chemical Biology and Pharmaceutical Research

4-Bromo-1H-pyrrole-2-carbaldehyde (CAS: 931-33-9) is a versatile heterocyclic compound that has garnered significant attention in chemical biology and pharmaceutical research due to its unique structural features and reactivity. This compound serves as a crucial building block in the synthesis of various biologically active molecules, including pharmaceuticals, agrochemicals, and materials. Recent studies have explored its potential in drug discovery, particularly in the development of kinase inhibitors, antimicrobial agents, and anti-inflammatory compounds. The bromine substitution at the 4-position and the aldehyde functionality at the 2-position make it a valuable intermediate for further chemical modifications, enabling the construction of diverse molecular architectures.

In a recent study published in the Journal of Medicinal Chemistry, researchers investigated the use of 4-Bromo-1H-pyrrole-2-carbaldehyde as a precursor for the synthesis of novel pyrrole-based kinase inhibitors. The study demonstrated that derivatives of this compound exhibited potent inhibitory activity against several cancer-related kinases, including EGFR and VEGFR2. The researchers employed a combination of computational docking and structure-activity relationship (SAR) studies to optimize the lead compounds, resulting in molecules with improved selectivity and pharmacokinetic properties. These findings highlight the potential of 4-Bromo-1H-pyrrole-2-carbaldehyde as a scaffold for developing targeted cancer therapies.

Another notable application of 4-Bromo-1H-pyrrole-2-carbaldehyde is in the field of antimicrobial research. A study in Bioorganic & Medicinal Chemistry Letters reported the synthesis of pyrrole-containing analogs with broad-spectrum antibacterial activity. The researchers utilized the aldehyde group of 4-Bromo-1H-pyrrole-2-carbaldehyde to introduce various hydrazone and Schiff base functionalities, which were found to enhance the compounds' ability to disrupt bacterial cell membranes. The most promising analogs showed potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli, suggesting their potential as novel antibiotics.

Beyond its applications in drug discovery, 4-Bromo-1H-pyrrole-2-carbaldehyde has also been employed in materials science. A recent publication in ACS Applied Materials & Interfaces described its use as a key intermediate in the synthesis of conductive polymers with tunable electronic properties. The bromine atom facilitated cross-coupling reactions, while the aldehyde group allowed for further functionalization, enabling the creation of polymers with high charge-carrier mobility. These materials hold promise for applications in organic electronics, including flexible displays and solar cells.

In conclusion, 4-Bromo-1H-pyrrole-2-carbaldehyde (CAS: 931-33-9) continues to be a valuable tool in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate, combined with its potential to yield biologically active compounds, makes it a focal point for ongoing investigations. Future research directions may include the development of more efficient synthetic routes, exploration of its role in targeted drug delivery systems, and further optimization of its derivatives for clinical applications. As the field advances, this compound is likely to remain at the forefront of innovation in drug discovery and materials science.

• 131747-63-2(4-Bromopyridine-2-carbaldehyde)
• 448906-71-6(4-bromo-6-methyl-pyridine-2-carbaldehyde)
• 408359-07-9(3-Bromo-1H-pyrrole-2-carbaldehyde)
• 1289031-61-3(4,5-dibromopicolinaldehyde)
• 405174-97-2(3-bromopyridine-2-carbaldehyde)
• 183997-68-4(3-bromo-1H-Pyrrole-2,5-dicarboxaldehyde)
• 128184-01-0(4-Bromo-2,6-diformylpyridine)
• 31181-90-5(5-Bromopyridine-2-carbaldehyde)
• 27746-02-7(4-Bromo-1H-pyrrole-2-carboxylic Acid)
• 137778-18-8(5-bromo-6-methylpyridine-2-carbaldehyde)