36316-83-3

Basic information

• Product Name: 1,4-Diiodonaphthalene
• Synonyms: 1,4-Diiodonaphthalene
• CAS NO: 36316-83-3
• Molecular Formula: C₁₀H₆I₂
• Molecular Weight: 379.96358
• Mol File: 36316-83-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-Diiodonaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Diiodonaphthalene(36316-83-3)
• EPA Substance Registry System: 1,4-Diiodonaphthalene(36316-83-3)

Safety Data

• Hazardous Substances Data: 36316-83-3(Hazardous Substances Data)

Usage

Derivative of

Naphthalene

Primary use

Organic synthesis and chemical research

Physical state

Crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Common use

Reagent in the preparation of organometallic compounds and other organic chemicals

Application

Building block for the synthesis of pharmaceuticals and agrochemicals

Potential applications

Materials science, specifically in the development of organic semiconductors for electronic devices

Upstream product

• 90-14-2 1-Iodonaphthalene 
• 83-53-4 1,4-dibromonaphthalene 
• 91-20-3 naphthalene 
• 134-32-7 1-amino-naphthalene 
• 776-34-1 1-amino-4-nitronaphthalene 
• 637340-74-0 naphthalene-1,4-disulfinic acid 
• 58258-66-5 1-iodo-4-nitronaphthalene 

Downstream Products

• 1207956-93-1 1,4-bis((Z)-5-phenyl-5-((2,4,6-tri-tert-butylphenyl)phosphinylidene)penta-1,3-diynyl)naphthalene 
• 1032744-88-9 C₁₂₂H₁₇₂O₆ 
• 73888-66-1 1,4-bis(phenylglyoxaloyl)naphthalene 
• 285571-20-2 2,2'-(naphthalene-1,4-diyl)dibenzaldehyde 
• 73888-61-6 1,4-bis(phenylethynyl)naphthalene 
• 73888-65-0 1-phenylethynyl-4-iodonaphthalene 
• 80236-28-8 1,4-distyrylnaphthalene 

Relevant articles and documents

Pre-inverse-crowns: Synthetic, structural and reactivity studies of alkali metal magnesiates primed for inverse crown formation

Two new alkali metal monoalkyl-bisamido magnesiates, the potassium compound [KMg(TMP)2nBu] and its sodium congener [NaMg(TMP) 2nBu] have been synthesised in crystalline form (TMP = 2,2,6,6-tetramethylpiperidide). Devoid of solvating ligands and possessing excellent solubility in hydrocarbon solvents, these compounds open up a new gateway for the synthesis of inverse crowns. X-ray crystallography established that [KMg(TMP)2nBu] exists in three polymorphic forms, namely a helical polymer with an infinite KNMgN chain, a hexamer with a 24-atom (KNMgN)6 ring having endo-disposed alkyl substituents, and a tetramer with a 16-atom (KNMgN)4 ring also having endo-disposed alkyl substituents. Proving their validity as pre-inverse-crowns, both magnesiates react with benzene and toluene to generate known inverse crowns in syntheses much improved from the original, supporting the idea that the metallations take place via a template effect. [KMg(TMP)2nBu] reacts with naphthalene to generate the new inverse crown [KMg(TMP)2(2-C 10H7)]6, the molecular structure of which shows a 24-atom (KNMgN)6 host ring with six naphthalene guest anions regioselectively magnesiated at the 2-position. An alternative unprecedented 1,4-dimagnesiation of naphthalene was accomplished via [NaMg(TMP) 2nBu] and its NaTMP co-complex [NaMg(TMP) 2nBu]·NaTMP , manifested in [{Na 4Mg2(TMP)4(2,2,6-trimethyl-1,2,3,4- tetrahydropyridide)2}(1,4-C10H6)]. Adding to its novelty, this 12-atom (NaNNaNMgN)2 inverse crown structure contains two demethylated TMP ligands as well as four intact ones. Reactivity studies show that the naphthalen-ide and -di-ide inverse crowns can be regioselectively iodinated to 2-iodo and 1,4-diiodonaphthalene respectively.

Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene

Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.

Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4: Synthesis of benzocyclic ketones

(Chemical Equation Presented) Iodine helps: Aldehydes acylate arenes upon treatment at low temperature with IPy2BF4 and HBF 4. This reaction is exploited in a novel intramolecular approach to the preparation of benzocyclic ketones (see scheme). A plausible mechanistic rational is also given.

Synthesis, characterisation and optical spectroscopy of platinum(II) di-ynes and poly-ynes incorporating condensed aromatic spacers in the backbone

A series of protected and terminal dialkynes with extended π-conjugation through a condensed aromatic linker unit in the backbone, 1,4- bis(trimethylsilylethynyl)naphthalene, 2a, 1,4-bis(ethynyl)naphthalene, 2b, 9, 10-bis(trimethylsilyl-ethynyl)anthracene

Synthesis of bis(phenylethynyl)arylene-linked diporphyrins designed for studies of intramolecular energy transfer

A series of donor-bridge-acceptor systems has been designed to give information on how the medium between the donor and the acceptor influences the excitation energy transfer process. The donor and the acceptor are zinc and free base porphyrins, respectiv

Synthetic use of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one: Iodination of aromatic rings

Treatment of various aromatic compounds with 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 1A and iodine gave the corresponding iodinated compounds in good yields. Similarly, chlorination and bromination proceeded effectively. As compared with other trivalent iodine compounds, the iodinane 1A showed the best reactivity as a halogenation reagent.