4542-77-2

Basic information

• Product Name: 2 6-BIS(BROMOMETHYL)NAPHTHALENE 97
• Synonyms: 2 6-BIS(BROMOMETHYL)NAPHTHALENE 97;2,6-Bis(bromomethyl)naphthalene;2,6-Bis(bromomethyl)naphthalene 95%
• CAS NO: 4542-77-2
• Molecular Formula: C₁₂H₁₀Br₂
• Molecular Weight: 314.019
• Product Categories: Aryl;C9 to C12;Halogenated Hydrocarbons
• Mol File: 4542-77-2.mol

Chemical Properties

• Melting Point: 183-187 °C(lit.)
• Boiling Point: 386.3 °C at 760 mmHg
• Flash Point: 219.2 °C
• Appearance: /
• Density: 1.72 g/cm³
• Vapor Pressure: 7.95E-06mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2 6-BIS(BROMOMETHYL)NAPHTHALENE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 2 6-BIS(BROMOMETHYL)NAPHTHALENE 97(4542-77-2)
• EPA Substance Registry System: 2 6-BIS(BROMOMETHYL)NAPHTHALENE 97(4542-77-2)

Safety Data

• Hazard Codes: C,N
• Statements: 34-50/53
• Safety Statements: 26-36/37/39-45-60-61
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 4542-77-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Bis(bromomethyl)naphthalene 97 is used as a synthetic intermediate for the production of pharmaceuticals. Its reactivity in nucleophilic substitution reactions allows for the creation of complex organic molecules that can be further utilized in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2,6-Bis(bromomethyl)naphthalene 97 serves as a key component in the synthesis of various agrochemicals. Its ability to undergo nucleophilic substitution reactions is essential for the development of compounds that can be used in crop protection and other agricultural applications.
Used in Advanced Materials:
2,6-Bis(bromomethyl)naphthalene 97 is also used as a building block in the synthesis of advanced materials. Its unique chemical properties contribute to the development of new materials with specific properties for use in various industries, including electronics, plastics, and coatings.
However, due to its brominated nature, 2,6-Bis(bromomethyl)naphthalene 97 should be handled with caution, as it may pose potential hazards to human health and the environment. Proper safety measures and disposal methods must be adhered to during its use in any application.

InChI:InChI=1/C12H10Br2/c13-7-9-1-3-11-6-10(8-14)2-4-12(11)5-9/h1-6H,7-8H2

Upstream product

• 5859-93-8 naphthalene-2,6-dimethanol 
• 840-65-3 dimethyl 2,6-naphthalenedicarboxylate 
• 581-42-0 2.6-dimethylnaphthalene 

Downstream Products

• 6251-01-0 9,9,10,10-tetracyano-2,6-naphthoquinodimethane 
• 59919-41-4 2,6 diethyl naphthalene 
• 147025-66-9 2,6-bis<4',8',11'-tris(p-toluenesulfonyl)-1',4',8',11'-tetraazacyclotetradecan-1'-ylmethyl>naphthalene 
• 29041-32-5 <2.2> (2,6)naphthalenophane (achiral) 
• 43012-13-1 1,2-bis(6-methylnaphthalen-2-yl)ethane 
• 92827-62-8 2,6-naphthalenetetrathiodicarboxylic acid 
• 581-42-0 2.6-dimethylnaphthalene 
• 1187784-79-7 C₃₀H₂₈N₂O₄ 
• 1187784-85-5 2,6-bis(2-formylphenoxymethyl)naphthalene 
• 1187784-88-8 2,6-bis(4-amino-5-phenyl-1,2,4-triazol-3-ylsulfanylmethyl)naphthalene 
• 130800-10-1 C₂₄H₂₈O₂ 
• 42049-83-2 trans,trans-2.6-Bis(p-methylstyryl)naphthalen 
• 42049-82-1 cis,trans-2.6-Bis(p-methylstyryl)naphthalen 
• 42049-81-0 cis,cis-2.6-Bis(p-methylstyryl)naphthalen 

Relevant articles and documents

Molecular recognition in ternary complexes of γ-cyclodextrin with naphthalenedicarboxylate ions and a space-regulator ion

Complexation of γ-cyclodextrin (γ-CD) with the 2,6- naphthalenedicarboxylate ion (2,6-NDC) in alkaline D2O was greatly enhanced by the addition of 2,6-bis(1-pyridiniomethyl)naphthalene dibromide (2,6-PMN) as a space-regulator. Formation of a ternary 1:1:1 complex between γ-CD, 2,6-NDC, and 2,6-PMN was confirmed by means of 1H NMR spectroscopy, together with the measurements of induced circular dichroism spectra and UV absorption spectra. Changes in chemical shifts (δ) of the γ-CD protons in the presence of an excess amount of 2,6-PMN with the addition of NDC regioisomers were analyzed by a curve-fitting procedure to give binding constants (K6) for complexation of NDC's with a γ-CD-2,6-PMN binary complex. The K6 values increased in the order of 1,5-NDC 1,4-NDC 1,8-NDC 1,3-NDC 1,6-NDC 2,3-NDC 2,7-NDC 2,6-NDC, indicating that a binary complex of γ-CD with 2,6-PMN is able to recognize the molecular structures of NDC's. The open space between the γ-CD cavity and 2,6-PMN will be favorable for the accommodation of a slender molecule such as 2,6-NDC, but unfavorable for the accommodation of a bulky molecule such as 1,5-NDC.

Preparation and conformational properties of 1,8-bridged fluorenophanes

Novel 1,8-bridged fluorenophanes consisting of benzene, benzoquinone, or naphthalene ring have been prepared. Their conformational properties are clarified by the NMR spectra and the X-ray analysis, especially in terms of a shielding effect on 9-protons of the fluorene unit. The dynamic structure was also examined by the variable-temperature NMR spectroscopy.

Design, synthesis and biological evaluation of low molecular weight CXCR4 ligands

The chemokine receptor CXCR4/stromal cell-derived factor-1 (SDF-1: CXCL12) signaling axis represents a crucial drug target due to its relevance to several diseases such as HIV-1 infection, cancer, leukemia, and rheumatoid arthritis. With the aim of enhancing the binding affinity and anti-HIV activity of a potent CXCR4 ligand as a lead, 23 low molecular weight compounds containing dipicolylamine (Dpa) and cyclam cationic moieties with varying spacers and spatial positioning were designed, synthesized and biologically evaluated. All of the synthesized compounds screened at 1.0 μM in the NanoBRET assay system exhibited >70% inhibition of the binding of a competitive probe TAMRA-Ac-TZ14011 (10 nM) to CXCR4 in the presence of zinc (II) ion. Furthermore, selected compounds 3, 8, 9, 19 and 21 with spatial distances between the next carbon to Dpa and the next carbon to cyclam within the range of 6.5–7.5 ? showed potent binding affinity selective for CXCR4 with IC50 values of 1.6, 7.9, 5.7, 3.5 and 4.5 nM, respectively, with corresponding high anti-HIV activity with EC50s of 28, 13, 21, 28 and 61 nM, respectively, in the presence of zinc (II) ion. Some compounds with remarkably more potent CXCR4-binding affinity than that of an initial lead were obtained. These compounds interact with different but overlapping amino acid residues of CXCR4. The present studies have developed new low molecular weight CXCR4 ligands with high CXCR4-binding and anti-HIV activities, which open avenue into the development of more potent CXCR4 ligands.

Facile synthesis of fluorescent distyrylnaphthalene derivatives for bioapplications

A series of novel 2,6-bis(4-aminostyryl)naphthalene based derivatives were synthesized and their spectroscopic properties investigated. Due to their low cytotoxicity, suitable optical properties and potential affinity towards biological structures these d

Electronic Coupling between Two Covalently Bonded Dimolybdenum Units Bridged by a Naphthalene Group

Using 2,6-naphthalenedicarboxylate and its thiolated derivatives as bridging ligands, three Mo2 dimers of the type [Mo2(DAniF)3](E2CC10H6CE2)[Mo2(DAniF)3] (DAniF = N,N′-di-p-anisylformamidinate; E = O, S) have been synthesized and characterized by X-ray diffraction. These compounds can be generally formulated as [Mo2]-naph-[Mo2], where the complex unit [Mo2] ([Mo2(DAniF)3(μ-E2C)]) functions as an electron donor (acceptor) and the naphthalene (naph) group is the bridge. The mixed-valence (MV) complexes, generated by one-electron oxidation of the neutral precursors, display weak, very broad intervalence charge-transfer absorption bands in the near-to-mid-IR regions. The electronic coupling matrix elements for the MV complexes, Hab = 390-570 cm-1, are calculated from the Mulliken-Hush equation, which fall between those for the phenyl (ph) and biphenyl (biph) analogues reported previously. The three series consisting of three complexes with the same [Mo2] units exhibit exponential decay of Hab as the bridge changes from ph to biph via naph, with decay factors of 0.21-0.17 ?-1. Therefore, it is evidenced that while the extent of the bridge conjugacy varies, the electronic coupling between the two [Mo2] units is dominated by the Mo2···Mo2 separation. The absorption band energies for metal-to-ligand charge transfer are in the middle of those for the ph and biph analogues, which is consistent with variation of the HOMO-LUMO energy gaps for the complex series. These results indicate that the interplay of the bridge length and conjugacy is to affect the enegy for charge transfer crossing the intervening moiety, in accordance with a superechange mechanism.

Gold(I) styrylbenzene, distyrylbenzene, and distyrylnaphthalene complexes: High emission quantum yields at room temperature

One gold(I)-substituted styrylbenzene, six digold(I) distyrylbenzenes, one tetragold distyrylbenzene, and four digold distyrylnaphthalene complexes were synthesized using base-promoted auration, alkynylation, triazolate formation, and Horner-Wadsworth-Emmons reactions. The gold(I) fragments are either σ-bonded to the aromatic system, or they are attached through an alkynyl or triazolate spacer. Product formation was monitored using 31P{ 1H} NMR spectroscopy. Systems in which gold(I) binds to the central benzene ring or the terminal phenyl rings were designed. All of these complexes have strong ultraviolet absorptions and emit blue light. The position of the gold(I) attachment influences the luminescence efficiency. Complexes with two gold(I) fragments attached to the ends of the conjugated system have fluorescence quantum yields up to 0.94, when using 7-diethylamino-4- methylcoumarin as the emission standard. Density-functional theory calculations on three high-yielding emitters suggest that luminescence originates from the distyrylbenzene or -naphthalene bridge. Copyright

Secondary interactions in crystals of all ten isomers of Di(bromomethyl)naphthalene

The packing of all ten isomers of di(bromomethyl)naphthalene is analysed; nine of the structures were determined here, one (the 1,8-isomer) was already known. The 1,5- and 2,6-isomers display crystallographic inversion symmetry and the 2,7-isomer mirror symmetry through the central bond. For the 1,2-, 1,7- and 2,7-isomers, the bromomethyl groups point to the same side of the ring system, and for all other isomers to opposite sides. As expected, the molecules are linked into aggregates by various types of interactions: weak hydrogen bonds CH...Br, Br...Br interactions, CH...π contacts, π ...π stacking and Br...π contacts. The weak hydrogen bonds tend to be numerous but relativelyi; long, and do not combine to form readily recognisable patterns; a more readily assimilated view of the packing is based on the Br...Br interactions, which are observed for all isomers except 1,7 and 2,3, and in some cases lead to aggregation to form quadrilaterals or chains. With decreasing frequency, the interactions π ...π, C-H...π and Br...π are observed, but the latter are rare (just two examples) and very asymmetric, with contacts to only one or two carbons.

Unique behavior of 2,6-bis(bromomethyl)naphthalene as a highly active organic DNA crosslinking molecule

Among 14 bis-halomethylated naphthalenes and quinolines, 2,6-bis(bromomethyl)naphthalene was found to have highly active crosslinking activity on DNA. The unique behavior of high microbial mutagenicity, even though it had a low propensity to form double-strands in linearized plasmid DNA, suggested that it would offer a new seed, capable of forming intrastrand crosslinks similar to cisplatin. The electron withdrawal extent of the halogen atoms, the substitution patterns of two halomethyl groups, and the introduction of a nitrogen atom into the aromatic nucleus had remarkable effects on the activity of the molecule.

Synthesis of novel amide-crownophanes and Schiff base-crownophanes based on p-phenylene, 2,6-naphthalene, and 9,10-anthracene

(Chemical Equation Presented) The novel macrocyclic diamides 11-13, 16-18 are obtained in 45-66% yields by the reaction of dipotassium salts 10a-c and 15 with each of 1,4-di(bromomethyl)benzene 4, 2,6-di(bromomethyl)naphthalene 6 and 9,10-di(bromomethyl)anthracene 8, repectively, in boiling DMF. On the other hand, the new macrocyclic Schiff bases 28 and 29 are obtained in 44% and 42% yields by heating the appropriate bis-amines 25b, 26b with the corresponding bis-aldehydes 21, 22, respectively, in refluxing acetic acid under high-dilution conditions.

Highly enantioselective and practical cinchona-derived phase-transfer catalysts for the synthesis of α-amino acids

A new class of naphthalene-based dimeric cinchona alkaloids 1 are very efficient and practical phase-transfer catalysts in the alkylation of a glycine derivative. The mild reaction conditions and the high catalytic efficiency (high yields and ee values) could make these alkaloids practical catalysts in the industrial synthetic process for natural and nonnatural chiral α-amino acids.