41014-20-4

Basic information

• Product Name: 4-(BROMOMETHYL)NAPHTHALENE-1-CARBONITRILE
• Synonyms: 4-(BROMOMETHYL)NAPHTHALENE-1-CARBONITRILE;4-(bromomethyl)-1-naphthonitrile
• CAS NO: 41014-20-4
• Molecular Formula: C₁₂H₈BrN
• Molecular Weight: 246.1
• Mol File: 41014-20-4.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(BROMOMETHYL)NAPHTHALENE-1-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(BROMOMETHYL)NAPHTHALENE-1-CARBONITRILE(41014-20-4)
• EPA Substance Registry System: 4-(BROMOMETHYL)NAPHTHALENE-1-CARBONITRILE(41014-20-4)

Safety Data

• Hazardous Substances Data: 41014-20-4(Hazardous Substances Data)

Usage

Description

4-(Bromomethyl)naphthalene-1-carbonitrile, with the molecular formula C13H8BrN, is a naphthalene derivative featuring a cyanide functional group and a bromomethyl substituent. It is a valuable chemical building block in medicinal and organic chemistry, known for its reactivity with nucleophiles and its role as an intermediate in the synthesis of other organic compounds and pharmaceuticals.

Uses

Used in Organic Synthesis:
4-(Bromomethyl)naphthalene-1-carbonitrile is used as an intermediate for the synthesis of various organic compounds. Its reactivity with nucleophiles makes it a versatile building block in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Bromomethyl)naphthalene-1-carbonitrile is used as a key intermediate in the development of new drugs. Its unique structure and reactivity contribute to the design and synthesis of novel pharmaceutical agents.
Used as a Reagent in Organic Chemical Reactions:
4-(Bromomethyl)naphthalene-1-carbonitrile serves as a reagent in various organic chemical reactions, facilitating the formation of desired products and aiding in the advancement of organic chemistry research.
It is crucial to handle 4-(Bromomethyl)naphthalene-1-carbonitrile with care due to its toxic nature, ensuring proper safety measures are in place to prevent harm during its use in research and industrial applications.

Upstream product

• 90-12-0 1-Methylnaphthalene 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 91-57-6 2-Methylnaphthalene 
• 36062-93-8 1-cyano-4-methylnaphthalene 
• 46258-62-2 1-(4-bromonaphthalen-1-yl)ethanone 
• 56052-26-7 (4-bromonaphthalen-1-yl)methanol 
• 90-11-9 1-Bromonaphthalene 
• 6627-78-7 1-bromo-4-methylnaphthalene 
• 79996-90-0 4-(Hydroxymethyl)-1-naphthalenecarbonitrile 
• 16650-55-8 4-bromonaphthalene-1-carboxylic acid 

Downstream Products

• 1416978-65-8 (E)-3,3,3-Trifluoro-N-((4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)naphthalen-1-yl)methyl)propanamide 
• 1416980-55-6 (E)-2-((4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)naphthalen-1-yl)methyl)isoindoline-1,3-dione 
• 1416980-56-7 (E)-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)naphthalen-1-yl)methanamine 
• 3839-19-8 4-cyano-1-naphthoic acid 
• 154913-01-6 1-(4-Methoxyphenyl)-4-<(4-cyano-1-naphthyl)methylene>piperidine 
• 154913-02-7 1-(4-Methylphenyl)-4-<(4-cyano-1-naphthyl)methylene>piperidine 
• 91759-52-3 4-<(1-Phenyl-4-piperidinylidene)methyl>-1-naphthalenecarbonitrile 

Relevant articles and documents

Intermolecular hydrogen bonding controlled stereoselective photocycloaddition of vinyl ethers to 1-cyanonaphthalenes

With the aim of developing photoreactions that use intermolecular hydrogen bonding interactions to control the efficiency and stereochemistry, the 1,2-[2 + 2] photocycloaddition reactions of 1-cyanonaphthalene derivatives with vinyl ethers possessing hydroxy groups were examined. The photoreaction of 1-cyano-4-(hydroxymethyl)naphthalene (1a) with 2-hydroxyethyl vinyl ether (2a) at room temperature was found to produce cycloadducts, endo-3aa and exo-3aa, in a non-stereoselective manner (56?:?44). However, this photoreaction at ?40 °C displays a high endo-selectivity (81?:?19). In the reaction of 1a with ethyl vinyl ether (2b), high endo selectivity was observed both at room temperature and at ?40 °C. The endo selectivity in the [2 + 2] photocycloaddition process is attributed to the intermolecular hydrogen bonding interactions between the reacting partners in the ground and excited states. Evidence to support this conclusion comes from the results of VT NMR and fluorescence quenching experiments, as well as the photoreactions of deuterated substrates.

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor

In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.

SUBSTITUTED 4-ARYL-1,4-DIHYDRO-1,6-NAPHTHYRIDINAMIDES AND USE THEREOF

1,6-Naphthyridine or 8-azaquinazoline derivatives (I) are new. 1,6-Naphthyridine or 8-azaquinazoline derivatives of formula (I) are new. D : N or CR 4>; R 4> : H, F, CF 3 or 1-4C alkyl; Ar : 5-R 5>-6-R 6>-2-methyl-4-oxo-4H-1-benzopyran-8-yl; 3-R 6>-4-R 8>-1-naphthyl optionally substituted with 1-3 of R 7>; 7-R 6>-8-R 8>-5-quinolinyl optionally substituted with 1-2 of R 7>; or 2-R 9>-3-R 10>-4-R 8>-5-R 6>-phenyl; R 5> : H, F, Cl, CN, NO 2, CF 3 or 1-4C alkyl; R 6> : H or F; R 7> : halo, 1-4C alkyl, CF 3, 1-4C alkoxy or OCF 3; R 8> : CN or NO 2; R 9> : H or halo; optionally fluorinated 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio of di(1-4C alkyl)amino; or phenyl optionally substituted with halo, 1-4C alkyl or CF 3; R 10> : H, halo or 1-4C alkyl; R 1> : optionally fluorinated 1-4C alkyl; R 2> : 1-6C alkyl optionally substituted with 3-7C cycloalkyl or F; or SO 2R 11>; R 11> : 1-6C alkyl, CF 3 or 3-7C cycloalkyl; or phenyl or heteroaryl optionally substituted with 1-2 of halo, CN, 1-4C alkyl, CF 3, 1-4C alkoxy and/or OCF 3; R 3> : H, F, CF 3 or 1-4C alkyl. An independent claim is also included for a process for preparing (I). [Image] ACTIVITY : Hypotensive; Cardiant; Hepatotropic; Nephrotropic; Cerebroprotective. MECHANISM OF ACTION : Mineralocorticoid receptor (MR) antagonist. 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide had an IC 50 of 35 nM when tested on cells expressing a GAL4-MR chimera.