23754-53-2

Basic information

• Product Name: 3754-53-2
• Synonyms: 3-(2-broMoacetyl)-4-hydroxy-6-Methyl-2H-pyran-2-one
• CAS NO: 23754-53-2
• Molecular Formula: C₈H₇BrO₄
• Molecular Weight: 247.04278
• Mol File: 23754-53-2.mol

Chemical Properties

• Melting Point: 118-119 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• Boiling Point: 343.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.816±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 5.06±0.50(Predicted)
• CAS DataBase Reference: 3754-53-2(CAS DataBase Reference)
• NIST Chemistry Reference: 3754-53-2(23754-53-2)
• EPA Substance Registry System: 3754-53-2(23754-53-2)

Safety Data

• Hazardous Substances Data: 23754-53-2(Hazardous Substances Data)

Upstream product

• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 16807-48-0 3‐acetyl‐2‐hydroxy‐6‐methyl‐4H‐pyran‐4‐one 

Downstream Products

• 1190853-63-4 4-hydroxy-3-(1-oxo-2-(phenylamino)ethyl)-6-methyl-2H-pyran-2-one 
• 1190853-64-5 C₁₉H₂₁NO₄ 
• 1295500-85-4 4-hydroxy-6-methyl-3-(2-(phenyldiazenyl)thiazol-4-yl)-2H-pyran-2-one 
• 1295505-07-5 4-hydroxy-3-[1-hydroxy-2-(2-phenylhydrazinyl)vinyl]-6-methyl-2H-pyran-2-one 
• 1295505-11-1 1-(2,4-dinitrophenyl)-7-methyl-2,3-dihydro-1H-pyrano[4,3-c]pyridazine-4,5-dione 
• 1334544-70-5 3-[2-(N'-cyclohexylidenehydrazino)-6H-[1,3,4]thiadiazin-5-yl]-4-hydroxy-6-methylpyran-2-one 
• 1334544-60-3 4-hydroxy-6-methyl-3-{2-[N'-(4-methylbenzylidene)hydrazino]-6H-[1,3,4]thiadiazin-5-yl}pyran-2-one 
• 1334544-68-1 3-(2-{N'-[1-(4-chlorophenyl)ethylidene]hydrazino}-6H-[1,3,4]thiadiazin-5-yl)-4-hydroxy-6-methylpyran-2-one 
• 1334544-63-6 3-[2-((N'-benzylidene)hydrazino)-6H-[1,3,4]thiadiazin-5-yl]-4-hydroxy-6-methylpyran-2-one 
• 1334544-61-4 4-hydroxy-3-{2-[N'-(4-methoxybenzylidene)hydrazino]-6H-[1,3,4]thiadiazin-5-yl}-6-methylpyran-2-one 
• 1334544-62-5 4-hydroxy-3-{2-[N'-(2-hydroxybenzylidene)hydrazino]-6H-[1,3,4]thiadiazin-5-yl}-6-methylpyran-2-one 
• 1334544-65-8 4-hydroxy-6-methyl-3-[2-[N'-(1-phenylethylidene)hydrazino]-6H-[1,3,4]thiadiazin-5-yl]pyran-2-one 
• 1334544-66-9 4-hydroxy-6-methyl-3-{2-[N'-(1-(p-tolyl)ethylidene)hydrazino]-6H-[1,3,4]thiadiazin-5-yl}pyran-2-one 
• 1334544-67-0 4-hydroxy-3-[2-{N'-[1-(4-methoxyphenyl)ethylidene]hydrazino}-6H-[1,3,4]thiadiazin-5-yl]-6-methylpyran-2-one 

Relevant articles and documents

Synthetic Approach Toward Heterocyclic Hybrids of [1,2,4]Triazolo[3,4- b ][1,3,4]thiadiazines

The synthesis of novel heterocyclic [1,2,4]triazolo[3,4- b ][1,3,4]thiadiazine hybrids by a bimolecular reaction of 2-(4-amino-5-mercapto-4 H -[1,2,4]triazol-3-yl)phenol with an aromatic or heterocyclic α-bromoacetyl derivatives is described. This synthetic procedure starts from an unprotected phenol.

An Efficient Synthetic Access to Substituted Thiazolyl-pyrazolyl-chromene-2-ones from Dehydroacetic Acid and Coumarin Derivatives by a Multicomponent Approach

Two new series of pyran- or coumarin-substituted thiazolyl-pyrazole-chromen-2-one derivatives 10a-10d and 11a-11d were efficiently synthesized under environmentally friendly reaction conditions through a convenient one-pot multicomponent reaction of a heterocyclic bromoacetyl derivative 3 or 4 with thiosemicarbazide and a substituted 3-(acetoacetyl)coumarin derivative 5a-5d in anhydrous ethanol. The reaction proceeds through Hantzsch thiazole and Knorr pyrazole syntheses in refluxing ethanol. The key features of this approach are its operational simplicity, the quick access to the desired products, and the good to excellent yields. The structures of the newly synthesized compounds were established by IR spectroscopy, 1H, 13C, and 2D NMR spectroscopy, and mass spectrometry. Two new series of pyran- or coumarin-substituted (thiazolyl-pyrazole-chromen-2-ones) may be efficiently accessed from bromoacetyl derivatives of dehydroacetic acid or coumarin, thiosemicarbazide, and substituted 3-(acetoacetyl)coumarins by green multicomponent reactions. The newly synthesized structures were established by IR spectroscopy, 1H, 13C, and 2D NMR spectroscopy, and mass spectrometry.

Synthesis and preclinical pharmacokinetic study of DHA-10, a novel potential antifungal pogostone analogue

Objectives: The emergence of fungal disease calls for the urgency of development of novel drug. In this study, we developed a novel pogostone analogue, DHA-10 and investigated its preclinical pharmacokinetics, tissue distribution, excretion and protein binding rate in rats. Methods: DHA-10 was synthesized with dehydroacetic acid (DHA) as the starting material and the structure confirmed by NMR and HRMS. The LC-MS/MS was applied to quantitative analysis of DHA-10 concentrations in the biological samples. Key finding: DHA-10 was eliminated rapidly in rat plasma with half-lives of 3.39 ± 0.5, 3.24 ± 0.32 and 3.80 ± 0.40 h after single oral doses of 70, 140 and 280 mg/kg, respectively, and showed linear pharmacokinetic within the examined dosage range. The oral bioavailability of DHA-10 was 69.09 ± 3.9%. DHA-10 distributed widely in tissues with highest tissue concentration was found in small intestine at 2.5 h postdose, followed by the stomach, liver and uterus. Approximately, 1.50 ± 0.26% and 9.12 ± 2.53% of parent drug was excreted via the urine and faeces within 48 h, respectively; 1.45 ± 0.12% was excreted into the bile up to 36 h after a single oral administration of 140 mg/kg. Binding rate of DHA-10 with plasma protein was about 78.80 ± 1.75% in a concentration-independent manner. Conclusions: DHA-10 was successfully synthesized and characterized. The preclinical pharmacokinetics study in rats supported the further development of this new antifungal candidate compound.

A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2 H -furo[3,2- c ]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure

Novel furopyran-3,4-dione-fused heterocycles have been obtained by a one-pot reaction of α-brominated dehydroacetic acid and benzaldehydes under organobase conditions. The prepared 2-[aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones were fully

The Dianion of Dehydroacetic Acid: A Direct Synthesis of Pogopyrone A

Dehydroacetic acid was converted into a silyl enol ether and titanium enolate. These reacted effectively with aldehydes and N -bromosuccinimide. Oxidation of the adduct with benzaldehyde afforded pogopyrone A in excellent overall yield.

Selective bromination of dehydroacetic acid with N-bromosuccinimide

(Chemical Equation Presented) Bromination of dehydroacetic acid has been carried out with N-bromosuccinimide under various conditions. The reactions led to selective bromination, thereby offering efficient synthesis of 3β-bromodehydroacetic acid (3), 3β,5

New synthesis and reactivity of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran- 2-one with binucleophilic amines

3-(Bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one was synthesized by the reaction of dehydroacetic acid (DHAA) with bromine in glacial acetic acid. Novel heterocyclic products were synthesized from the reaction of bromo-DHAA with alkanediamines, phenylhydrazines, ortho-phenylenediamines, and ortho-aminobenzenethiol. The obtained new products 3-(2-N-substituted-acetyl)-4- hydroxy-6-methyl-2H-pyran-2-ones, 4-hydroxy-3-[1-hydroxy-2-(2-phenylhydrazinyl) vinyl]-6-methyl-2H-pyran-2-one, 1-(2,4-dinitrophenyl)-7-methyl-2,3-dihydro-1H- pyrano[4,3-c]pyridazine-4,5-dione, 3-(3,4-dihydroquinoxalin-2-yl)-4-hydroxy-6- methyl-2H-pyran-2-one/3-(3,4-dihydroquinoxalin-2-yl)-6-methyl-2H-pyran-2,4(3H) -dione, 6-methyl-3-(3,4-dihydroquinoxalin-2-yl)-2H-pyran-2,4(3H)-dione, and (E)-3-(2H-benzo[b][1,4]thiazin-3(4H)-ylidene)-6-methyl-2H-pyran-2,4(3H)-dione were fully characterized by IR, 1H and 13C NMR, and mass spectra.

Synthesis and reactivity of 6-methyl-4H-furo[3,2c]pyran-3,4-dione

An efficient synthesis of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran-2-one by bromination of dehydroacetic acid in glacial acetic acid is described. Novel 4-hydroxy-6-methyl-3-(2-substituted-thiazol-4-yl)-2H-pyran-2-ones have been prepared from the reactio

A convenient synthesis of furans using bromacetylpyran-2-one

Conversions of 3-bromacetyl-4-hydroxy-6-methyl-2Hpyran-2-ones (3β-brom-dehydroacetic acids) with amines are highly influenced by the type of amine. In contrast to aniline, where a dehydroacetic acid derivative was obtained, utilization of phenylethylamine