52190-28-0

Basic information

• Product Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one
• Synonyms: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one;2-Bromo-3',4'-(methylenedioxy)propiophenone;1-(1,3-Benzodioxol-5-yl)-2-broMo-1-propanone;3',4'-Methylenedioxy-α-broMopropiophenone;1-(1,3-benzodioxol-5-yl)-2-bromopropan-1-one
• CAS NO: 52190-28-0
• Molecular Formula: C₁₀H₉BrO₃
• Molecular Weight: 257.08066
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 52190-28-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 345.673 °C at 760 mmHg
• Flash Point: 162.857 °C
• Appearance: /
• Density: 1.585 g/cm³
• CAS DataBase Reference: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(52190-28-0)
• EPA Substance Registry System: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(52190-28-0)

Safety Data

• Hazardous Substances Data: 52190-28-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one can be used in the preparation of antifungal agents and MDMA analogs.

Upstream product

• 63740-97-6 1-(2H-benzo[3,4-d]1,3-dioxolen-5-yl)butan-1-one 
• 28281-49-4 3,4-methylenedioxypropiophenone 
• 7451-98-1 3',4'-dihydroxypropiophenone 

Downstream Products

• 161096-64-6 methyl 3-hydroxy-4-α-piperonyloylethoxy-5-methoxybenzoate 
• 528-64-3 5,5'-(3,4-dimethyltetrahydrofuran-2,5-diyl)bis(benzo[d][1,3]dioxole) 
• 1206768-27-5 (S)-1-(3,4-(methylenedioxy)phenyl)-2-phenylpropan-1-one 
• 857953-22-1 N-acetyl-sulfanilic acid-(4-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-2-ylamide) 
• 161096-65-7 methyl 3-hydroxy-4-α-methyl-β-hydroxy-β-(3,4-methylenedioxyphenyl)ethoxy-5-methoxybenzoate 
• 186028-79-5 1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one 
• 850852-86-7 4-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-2-ylamine 

Relevant articles and documents

α-PPP and its derivatives are selective partial releasers at the human norepinephrine transporter: A pharmacological characterization of interactions between pyrrolidinopropiophenones and uptake1 and uptake2 monoamine transporters

While classical cathinones, such as methcathinone, have been shown to be monoamine releasing agents at human monoamine transporters, the subgroup of α-pyrrolidinophenones has thus far solely been characterized as monoamine transporter reuptake inhibitors. Herein, we report data from previously undescribed α-pyrrolidinopropiophenone (α-PPP) derivatives and compare them with the pharmacologically well-researched α-PVP (α-pyrrolidinovalerophenone). Radiotracer-based in vitro uptake inhibition assays in HEK293 cells show that the investigated α-PPP derivatives inhibit the human high-affinity transporters of dopamine (hDAT) and norepinephrine (hNET) in the low micromolar range, with α-PVP being ten times more potent. Similar to α-PVP, no relevant pharmacological activity was found at the human serotonin transporter (hSERT). Unexpectedly, radiotracer-based in vitro release assays reveal α-PPP, MDPPP and 3Br-PPP, but not α-PVP, to be partial releasing agents at hNET (EC50 values in the low micromolar range). Furthermore, uptake inhibition assays at low-affinity monoamine transporters, i.e., the human organic cation transporters (hOCT) 1–3 and human plasma membrane monoamine transporter (hPMAT), bring to light that all compounds inhibit hOCT1 and 2 (IC50 values in the low micromolar range) while less potently interacting with hPMAT and hOCT3. In conclusion, this study describes (i) three new hybrid compounds that efficaciously block hDAT while being partial releasers at hNET, and (ii) highlights the interactions of α-PPP-derivatives with low-affinity monoamine transporters, giving impetus to further studies investigating the interaction of drugs of abuse with OCT1-3 and PMAT.

Structure-activity relationships of talaumidin derivatives: Their neurite-outgrowth promotion in vitro and optic nerve regeneration in vivo

(–)-Talaumidin (1), a 2,5-biaryl-3,4-dimethyltetrahydrofuran lignan, shows potent neurotrophic activities such as neurite-outgrowth promotion and neuroprotection. Previously, we found that (–)-(1S,2R,3S,4R)-stereoisomer 2 exhibited more significant activity than did the natural product talaumidin (1). However, the preparation of optically active (–)-2 requires a complicated synthetic route. To explore new neurotrophic compounds that can be obtained on a large scale, we established a short step synthetic route for talaumidin derivatives and synthesized fourteen analogues based on the structure of (–)-2. First, we synthesized a racemic compound of (–)-2 (2a) and assessed its neurotrophic activity. We found that the neurotrophic property of racemic 2a is similar in activity to that of (–)-2. Using the same synthetic methodology, several talaumidin derivatives were synthesized to optimize the oxy-functionality on aromatic rings. As a result, bis(methylenedioxybenzene) derivative 2b possessed the highest neurotrophic activity. Furthermore, examination of the structure-activity relationships of 2b revealed that the 2,5-diphenyl-tetrahydrofuran structure was an essential structure and that two methyl groups on THF ring could enhance neurotrophic activity. In addition, compounds 2a and 2b were found to induce mouse optic nerve regeneration in vivo.

Nickel/bis(oxazoline)-catalyzed asymmetric Kumada reactions of alkyl electrophiles: Cross-couplings of racemic α-bromoketones

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