61568-53-4

Usage

Classification

Bromophenyl dioxane

Uses

Intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Environmental impact

Known environmental contaminant found in industrial wastewater and contaminated groundwater

Health effects

Can cause irritation to skin, eyes, and respiratory system; prolonged exposure may lead to liver and kidney damage

Regulatory considerations

Use and disposal should be carefully regulated and managed due to potential health and environmental risks

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 504-63-2 trimethyleneglycol 
• 627-30-5 1-chloro-3-hydroxypropane 

Downstream Products

• 152035-58-0 2-<2-(4-Bromobutyl)phenyl>-1,3-dioxane 
• 171086-99-0 2-<2-(2-Hydroxyethyl)phenyl>-1,3-dioxane 
• 785828-52-6 2-(ortho-diisopropylphosphinophenyl)-1,3-dioxane 
• 785828-51-5 2-(ortho-diphenylphosphinophenyl)-1,3-dioxane 
• 208196-15-0 ethyl 2-(1,3-dioxan-2-yl)phenylglyoxylate 
• 139086-86-5 2-(1,3-dioxan-2-yl)benzaldehyde 
• 1346004-33-8 ethyl 3-(2-(1,3-dioxan-2-yl)phenyl)propanoate 
• 1346004-12-3 (S,E)-ethyl 3-(2-((1-(4-methoxyphenyl)ethylimino)methyl)phenyl)propanoate 
• 1346004-44-1 (2aR,7bR)-1-((S)-1-(4-methoxyphenyl)ethyl)-2a,3-dihydro-1H-indeno[1,2-b]azet-2(7bH)-one 
• 1346004-45-2 (2aS,7bS)-1-((S)-1-(4-methoxyphenyl)ethyl)-2a,3-dihydro-1H-indeno[1,2-b]azet-2(7bH)-one 
• 1346004-46-3 (1S,2R)-ethyl 1-((S)-1-(4-ethoxyphenyl)ethylamino)-2,3-dihydro-1H-indene-2-carboxylate 
• 1346004-58-7 (1S,2S)-ethyl-1-(((S)-1-(4-methoxyphenyl)ethyl)amino)-2,3-dihydro-1H-indene-2-carboxylate hydrochloride 
• 63969-80-2 ethyl 3-(2-formylphenyl)propanoate 
• 1610421-16-3 6-benzylbenzo[b]phenanthridine-5,7,12(6H)-trione 

Relevant academic research and scientific papers

Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes

γ-Aryl-β-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)2/t-Bu3P and stoichiometric amounts of Bu3SnF. The wide range of γ-(hetero)aryl-β-ketoesters that can be obtained illustrate the scope and limitations of this novel Hauser-Heck combination. γ-Aryl-β-ketoesters with a 1,3-dioxane acetal in the ortho position can easily be transformed into the hydroxy naphthoate in very good yield. Aqueous formic acid at 65 °C provides optimal conditions for this deprotective aromatization.

Simple Aza -conjugate addition methodology for the synthesis of isoindole nitrones and 3,4-dihydroisoquinoline nitrones

Aryl-aldehydes containing ortho-substituted α,β-unsaturated carboxylic acid derivatives react with hydroxylamine to afford reactive N-hydroxy-carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford isoindole nitrones and 3,4-dihydroisoquinoline nitrones in good yield. Conditions have been developed to reduce these isoindole nitrones to their corresponding hydroxylamine, enamine, and amine derivatives. Isoindole nitrones react with dimethyl acetylenedicarboxylate (DMAD) via a [4 + 2]-cycloaddition/deamination pathway to afford substituted naphthalene derivatives, while 3,4-dihydroisoquinoline nitrones react with DMAD via a [1,3]-dipolar cycloaddition pathway to afford tricyclic heteroarenes.

A synthetic route to highly substituted 1,2,3,4-tetrahydroisoquinolines via Yb(OTf)3-catalyzed diastereoselective ring opening of bridged oxazolidines: Asymmetric synthesis of 2-azapodophyllotoxin

We herein report a robust and efficient synthetic route to highly functionalized enantiopure 1,2,3,4-tetrahydroisoquinolines (THIQs) from Garner aldehyde. We utilized the inherent chirality of Garner aldehyde through 1,2- and 1,3-/1,4-asymmetric inductions iteratively to obtain 1,2,3,4-tetrasubstitued THIQs using rigid and isolable bridged oxazolidines without any external chiral sources. All possible stereoisomers of bridged oxazoliodines were efficiently synthesized from L- and D-Garner aldehydes and transformed into fully functionalized THIQs via diastereoselective ring opening with various nucleophiles in the presence of Yb(OTf)3. This methodology furnished four out of eight possible diastereomers of 1,2,3,4-tetrasubstituted THIQs despite the electronic nature of substituents on the aryl rings. Finally, the enantioselective synthesis of 2-azapodophyllotoxin was achieved with an overall yield of 35.4 % (eight steps) from D-Garner aldehyde using this synthetic route. A concise and efficient synthetic route to highly functionalized enantiopure 1,2,3,4-tetrahydroisoquinolines (THIQs) from the Garner aldehyde via Yb(OTf)3-catalyzed diastereoselective ring opening of bridged oxazolidines is reported. This methodology was successfully applied to the synthesis of four stereoisomers of THIQ and the enantioselective total synthesis of 2-azapodophyllotoxin (1) in eight steps from D-Garner aldehyde in an overall yield of 35.4 %. Copyright

Intramolecular ester enolate-imine cyclization reactions for the asymmetric synthesis of polycyclic β-lactams and cyclic β-amino acid derivatives

Enolates of chiral N-(α-methyl-p-methoxybenzyl)-ω-imino-esters undergo intramolecular cyclization reactions to afford (syn)-aza-anions of β-amino esters in high dr that cyclize to afford N-(α-methyl-p- methoxybenzyl)-β-lactams that can be readily deprotec

Bismuth compounds in organic synthesis: Synthesis of dioxanes, dioxepines, and dioxolanes catalyzed by bismuth(III) triflate

A simple method for the synthesis of 1,3-dioxolanes from carbonyl compounds has been developed using 1,2-bis(trimethylsilyloxy)ethane in the presence of bismuth(III) triflate as a catalyst. The bismuth(III) triflate catalyzed synthesis of a range of dioxanes and dioxepines has also been developed. In these latter cases, the carbonyl compound is treated with a diol, and triethyl orthoformate is used as a water scavenger. All these methods avoid the use of a Dean-Stark trap. Georg Thieme Verlag Stuttgart.

TRANS-FUSED CHROMENOISOQUINOLINES SYNTHESIS AND METHODS FOR USE

Optionally substituted chromenoisoquinolines and analogs and derivatives thereof are described herein. In addition, syntheses of these compounds are described herein. In addition, uses of these compounds as dopamine receptor binding compounds are described herein.

First asymmetric synthesis of (Un)saturated 1-Alkylbenzo[c]azepin-3-ones: Extension to the corresponding benzazeplnes

A flexible route for the stereoselective synthesis of a variety of structurally diverse (1R)-1-alkyldihydro and tetrahydro-benzazepin(ones) has been developed. The key step is a highly diastereoselective 1,2-addition process applied to a stereopure aromatic hydrazone combined with a ring-closing metathesis reaction to secure the formation of the seven-membered azaheterocycle ring system.

Intermolecular reactions of chlorohydrine anions: Acetalization of carbonyl compounds under basic conditions

Nonenolizable aldehydes and ketones react with 2-chloroethanol and 3-chloropropanol under basic conditions (t-BuOK, DMF/THF) with formation of 2-substituted 1,3-dioxolanes and 1,3-dioxanes, respectively. Conversion of the two-step addition-alkylation process depends on the electrophilicity of the carbonyl group that governs the equilibrium of addition of chloroalkoxides. This method of protection of carbonyl groups in the form of cyclic acetals under kinetically controlled conditions is complementary to the acid-catalyzed reaction with diols.

Synthesis of diastereoisomeric pairs of novel analogues of d4T having an isochroman glycon moiety; their enzymatic kinetic resolution, their enantiopure synthesis, molecular modeling and NMR structural study

An efficient route, starting from 2-bromobenzaldehyde, is described to synthesize racemic diastereoisomeric thymine derivatives of isochroman, which are aromatic analogues of Stavudine, an approved anti-HIV drug. The relative configurations were determined by NOE proton NMR experiments in connection with molecular modeling. Following the separation of the latter diastereoisomers, kinetic resolution was achieved via a transesterification reaction catalyzed by lipases. Using this method, moderate ee's were obtained (0.74-0.98). Thus, an alternative strategy starting from d-mannitol was proposed to provide pure enantiomers. The attribution of absolute configurations was made by chemical filiation on the basis of the configurations obtained from d-mannitol. The structural attributions were confirmed by studying the behavior of proton NMR shifts of the corresponding isochroman Mosher's esters.

A convenient and highly efficient method for the protection of aldehydes using very low loading hydrous ruthenium(III) trichloride as catalyst

A convenient method for the chemoselective protections of both aliphatic and aromatic aldehydes has been developed. Ruthenium(III) trichloride (0.1 mol %) has found to be an highly efficient catalyst in the acetalizations of aldehydes with various simple alcohols such as methanol, ethanol, or diols such as 1,2-ethylanediol and 1,3-propanediol under mild reaction conditions.