Production Method 1

50672-84-9

92616-49-4

Reaction Conditions

1.1 Reagents: Triethylamine ,  Hydroxyamine hydrochloride Solvents: Acetonitrile ;  rt; 3 h, 79 °C
1.2 Catalysts: Cupric acetate Solvents: Acetonitrile ;  overnight, 79 °C

Reference

Preparation of 4-bromo-1-naphthonitrile with 1-methylnaphthalene as starting material

, China, , ,

Production Method 2

2298-07-9

92616-49-4

Reaction Conditions

1.1 Reagents: Boron trifluoride etherate ,  tert-Butyl nitrite Solvents: 1,2-Dimethoxyethane ;  15 min, -15 °C; 1 h, -15 °C; 20 min, -15 °C → 5 °C
1.2 Solvents: Pentane ;  rt
1.3 Reagents: Cuprous cyanide Solvents: Acetonitrile ,  Water ;  rt; 2 h, reflux; reflux → rt

Reference

Oligo(naphthylene-ethynylene) molecular rods

Cramer, Jacob R.; Ning, Yanxiao; Shen, Cai; Nuermaimaiti, Ajiguli; Besenbacher, Flemming; et al, European Journal of Organic Chemistry, 2013, 2013(14), 2813-2822

Production Method 3

83-53-4

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide
1.2 Solvents: Benzene ,  Water

Reference

Bromination of tetralin. Short and efficient synthesis of 1,4-dibromonaphthalene

Cakmak, Osman; Kahveci, Ismail; Demirtas, Ibrahim; Hokelek, Tuncer; Smith, Keith, Collection of Czechoslovak Chemical Communications, 2000, 65(11), 1791-1804

Production Method 4

83-53-4

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  17 h, reflux

Reference

Enhancement of fluorescence quenching and exciplex formation in DNA major groove by double incorporation of modified fluorescent deoxyuridines

Tanaka, Makiko; Oguma, Kazuhiro; Saito, Yoshio; Saito, Isao, Bioorganic & Medicinal Chemistry Letters, 2012, 22(12), 4103-4105

Production Method 5

58728-64-6

92616-49-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  5 min, rt; rt → 0 °C
1.2 Reagents: Sodium nitrite Solvents: Water ;  < 5 °C; 45 min, 0 °C
1.3 Reagents: Copper bromide (CuBr) Solvents: Water ;  0 °C; 1 d, rt
1.4 Reagents: Water ;  rt

Reference

Preparation of heterocyclyl-piperidinyl/piperazinyl-isochromans as CNS agents

, World Intellectual Property Organization, , ,

Production Method 6

14874-70-5

13715-19-0

92616-49-4

Reaction Conditions

Reference

SRN1 syntheses of bis(phenylthio)- and dicyanonaphthalenes via diazo sulfides

Novi, M.; Garbarino, G.; Petrillo, G.; Dell'Erba, C., Tetrahedron, 1990, 46(6), 2205-12

Production Method 7

92616-49-4

Reaction Conditions

Reference

Preparation of naphthylisothiazoline derivatives for use as pesticides

, World Intellectual Property Organization, , ,

Production Method 8

2298-07-9

92616-49-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  10 min, rt; rt → 0 °C
1.2 Reagents: Sodium nitrite Solvents: Water ;  < 5 °C; 30 min, < 5 °C
1.3 Reagents: Sodium bicarbonate ;  neutralized
1.4 Reagents: Cuprous cyanide Solvents: Water ;  rt; rt → 70 °C; 30 min, 70 °C

Reference

Preparation of indole sulfonamides as modulators of progesterone receptors

, World Intellectual Property Organization, , ,

Production Method 9

6627-78-7

92616-49-4

Reaction Conditions

1.1 Reagents: Hydrogen peroxide ,  Hydrogen bromide Solvents: Carbon tetrachloride ,  Water ;  rt; 2 h, 20 °C
1.2 Reagents: Iodine ,  Ammonia Solvents: Acetonitrile ,  Water ;  rt; 4 h, 60 °C; 60 °C → rt
1.3 Reagents: Sodium sulfite Solvents: Water ;  rt

Reference

One-pot transformation of methylarenes into aromatic nitriles with inorganic metal-free reagents

Kawagoe, Yuhsuke; Moriyama, Katsuhiko; Togo, Hideo, European Journal of Organic Chemistry, 2014, 2014(19), 4115-4122

Production Method 10

79996-99-9

92616-49-4

Reaction Conditions

1.1 Reagents: Ammonium hydroxide ,  Iodine Solvents: 1,4-Dioxane ;  3.5 h, 30 °C

Reference

Process for preparation of halogenated arylcarbonitrile

, China, , ,

Production Method 11

16650-55-8

92616-49-4

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Dimethylformamide Solvents: Toluene ;  1 h, 60 °C
1.2 Reagents: Sulfolane ,  Sulfamide Solvents: Toluene ;  60 °C → 120 °C
1.3 Solvents: Toluene ;  90 min, 120 °C

Reference

Process Development, Manufacture, and Understanding of the Atropisomerism and Polymorphism of Verinurad

Ring, Oliver T. ; Hayter, Barry R.; Ronson, Thomas O. ; Agnew, Lauren R.; Ashworth, Ian W. ; et al, Organic Process Research & Development, 2022, 26(3), 936-948

Production Method 12

83-53-4

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  16 h, 125 °C
1.2 Reagents: Ammonia Solvents: Ethyl acetate ;  1 h, rt

Reference

Preparation of condensed ring derivatives for treating hyperuricemia and related diseases

, World Intellectual Property Organization, , ,

Production Method 13

83-53-4

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  12 h, 130 °C

Reference

Method for preparing urate-anion exchanger 1 inhibitor

, China, , ,

Production Method 14

83-53-4

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  12 h, 130 °C

Reference

Discovery of Flexible Naphthyltriazolylmethane-based Thioacetic Acids as Highly Active Uric Acid Transporter 1 (URAT1) Inhibitors for the Treatment of Hyperuricemia of Gout

Zhang, Xiansheng; Wu, Jingwei; Liu, Wei; Liu, Yuqiang; Xie, Yafei; et al, Medicinal Chemistry (Sharjah, 2017, 13(3), 260-281

Production Method 15

83-53-4

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  overnight, rt → 125 °C

Reference

Thioacetate compounds as URAT-1 agonists and their preparation, compositions and methods of use

, World Intellectual Property Organization, , ,

Production Method 16

83-53-4

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  rt → 130 °C; 12 h, 130 °C
1.2 Solvents: Dichloromethane ;  3 h, 130 °C

Reference

Design, synthesis and bioactivity of highly sterically congested flexible uric acid transporter 1 (URAT1) inhibitors

Cai, Wenqing; Liu, Wei; Zhang, Shuo; Wang, Jianwu; Zhao, Guilong, Youji Huaxue, 2017, 37(9), 2303-2314

Production Method 17

16650-55-8

92616-49-4

Reaction Conditions

1.1 Reagents: Dimethylformamide ,  Thionyl chloride Solvents: Toluene ;  60 °C
1.2 Reagents: Sulfolane ,  Hydrazine sulfate ;  120 °C

Reference

Significant rate enhancement via potassium pivalate in a Miyaura borylation approach to verinurad

Ring, Oliver T.; Campbell, Andrew D.; Hayter, Barry R.; Powell, Lyn, Tetrahedron Letters, 2020, 61(10),

Production Method 18

83-53-4

92616-49-4

3029-30-9

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  12 h, 130 °C

Reference

Study on synthesis process of RDEA3170

Zhang, Xian-sheng; Liu, Yu-qiang; Xie, Ya-fei; Li, Chuan; Xin, Xiao; et al, Xiandai Yaowu Yu Linchuang, 2015, 30(10), 1179-1184

4-Bromonaphthalene-1-carbonitrile Raw materials

• 4-bromonaphthalene-1-carboxylic acid
• Borate(1-),tetrafluoro-
• Cuprate(1-), bis(cyano-kC)-, sodium (1:1)
• 1,4-Dibromonaphthalene
• 1-Bromo-4-methylnaphthalene
• 1-Amino-4-bromonaphthalene
• 4-aminonaphthalene-1-carbonitrile
• 4-Bromo-1-napthaldehyde
• 1-Bromo-4-(bromomethyl)naphthalene

4-Bromonaphthalene-1-carbonitrile Preparation Products

• 4-Bromonaphthalene-1-carbonitrile (92616-49-4)
• 1,4-Dicyanonaphthalene (3029-30-9)

• 1. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 2. An investigation of the electrochemical delithiation process of carbon coated α-Fe2O3nanoparticles
  Adrian Brandt,Florian Winter,Sebastian Klamor,Frank Berkemeier,Jatinkumar Rana,Rainer P?ttgen,Andrea Balducci J. Mater. Chem. A, 2013,1, 11229-11236
• 3. An anti-leakage liquid metal thermal interface material
  Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng Chu RSC Adv., 2020,10, 18824-18829
• 4. An alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage?
  Xiang Liu,Qian Sun,A. B. Djuri?i?,Maohai Xie,Baohu Dai,Jinyao Tang,Charles Surya,Changzhong Liao,Kaimin Shih RSC Adv., 2015,5, 100783-100789
• 5. An amphipathic trans-acting phosphorothioate RNA element delivers an uncharged phosphorodiamidate morpholino sequence in mdx mouse myotubes?
  H. V. Jain,D. Verthelyi,S. L. Beaucage RSC Adv., 2017,7, 42519-42528

4-Bromonaphthalene-1-carbonitrile: A Comprehensive Overview

The compound with CAS No 92616-49-4, commonly referred to as 4-Bromonaphthalene-1-carbonitrile, is a highly specialized organic molecule that has garnered significant attention in the fields of organic chemistry, materials science, and pharmacology. This compound is characterized by its unique structure, which combines a naphthalene ring system with a bromine substituent and a cyano group. The naphthalene core provides a rigid aromatic framework, while the bromine and cyano groups introduce functional diversity, making this compound versatile for various applications.

Recent advancements in synthetic methodologies have enabled the efficient synthesis of 4-Bromonaphthalene-1-carbonitrile. Researchers have explored diverse strategies, including nucleophilic aromatic substitution and transition-metal-catalyzed coupling reactions, to construct this compound with high precision. These methods not only enhance the yield but also ensure the purity required for downstream applications. The ability to synthesize this compound in large quantities has paved the way for its exploration in advanced materials and drug discovery.

One of the most promising applications of 4-Bromonaphthalene-1-carbonitrile lies in its potential as a building block for constructing complex heterocyclic frameworks. Its aromaticity and functional groups make it an ideal candidate for forming conjugated systems, which are crucial in optoelectronic materials. Recent studies have demonstrated that derivatives of this compound exhibit remarkable photovoltaic properties, making them strong contenders for next-generation solar cells.

In the realm of pharmacology, 4-Bromonaphthalene-1-carbonitrile has shown potential as a lead compound for drug development. Its ability to interact with biological targets, such as enzymes and receptors, has been extensively studied using computational modeling and in vitro assays. Preliminary results suggest that this compound may possess anti-inflammatory and anticancer properties, warranting further investigation in preclinical models.

The structural versatility of 4-Bromonaphthalene-1-carbonitrile also extends to its use in polymer chemistry. Researchers have successfully incorporated this compound into polymer networks, leveraging its electronic properties to develop advanced materials with tailored functionalities. These materials exhibit enhanced mechanical strength and thermal stability, making them suitable for high-performance applications in aerospace and automotive industries.

Moreover, the environmental impact of 4-Bromonaphthalene-1-carbonitrile has been a focal point of recent studies. Scientists have evaluated its biodegradability and toxicity profiles under various conditions, aiming to ensure its safe utilization in industrial processes. These findings underscore the importance of sustainable practices in the synthesis and application of such compounds.

In conclusion, 4-Bromonaphthalene-1-carbonitrile (CAS No 92616-49-4) stands as a testament to the ingenuity of modern chemical synthesis and its wide-ranging applications across multiple disciplines. As research continues to unravel its potential, this compound is poised to play a pivotal role in shaping future innovations in materials science and pharmacology.

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