884504-22-7

Basic information

• Product Name: 4-ISOPROPOXYBENZOYLACETONITRILE
• Synonyms: 4-ISOPROPOXYBENZOYLACETONITRILE;BENZENEPROPANENITRILE, 4-(1-METHYLETHOXY)-B-OXO-;(4-ISOPROPYLBENZOYL)ACETONITRILE
• CAS NO: 884504-22-7
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.24
• Mol File: 884504-22-7.mol

Chemical Properties

• Boiling Point: 375.7°C at 760 mmHg
• Flash Point: 164.3°C
• Appearance: /
• Density: 1.079g/cm³
• Vapor Pressure: 7.65E-06mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: 4-ISOPROPOXYBENZOYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ISOPROPOXYBENZOYLACETONITRILE(884504-22-7)
• EPA Substance Registry System: 4-ISOPROPOXYBENZOYLACETONITRILE(884504-22-7)

Safety Data

• Hazardous Substances Data: 884504-22-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-ISOPROPOXYBENZOYLACETONITRILE is used as a reagent and intermediate for the synthesis of various pharmaceutical compounds. Its role in the industry is crucial for the development of new drugs and the improvement of existing ones.
Used in Organic Synthesis:
In the field of organic synthesis, 4-ISOPROPOXYBENZOYLACETONITRILE serves as a key intermediate in the production of a wide range of organic compounds. Its unique chemical properties make it a valuable component in the synthesis of various organic molecules.
Used in Research and Development:
4-ISOPROPOXYBENZOYLACETONITRILE is also employed in research and development settings, where it is used to explore new chemical reactions and investigate the properties of novel compounds. Its versatility in organic synthesis makes it an essential tool for scientists and researchers in the field.

InChI:InChI=1/C12H13NO2/c1-9(2)15-11-5-3-10(4-6-11)12(14)7-8-13/h3-6,9H,7H2,1-2H3

Upstream product

• 99-76-3 methyl 4-hydroxylbenzoate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 122488-52-2 ethyl 4-isopropoxybenzoate 
• 75-05-8 acetonitrile 
• 35826-59-6 methyl 4-isopropoxybenzoate 

Downstream Products

• 868072-17-7 2-[2-(4'-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide 
• 1254174-27-0 2-[5,7-dimethyl-2-(4-(prop-2-yn-1-yloxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide 
• 1384517-66-1 2-[2-(4-isopropoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide 
• 1384517-64-9 3-cyano-N,N-diethyl-4-(4-isopropoxyphenyl)-4-oxobutanamide 
• 208519-13-5 3-amino-5-(4-isopropoxyphenyl)-1H-pyrazole 
• 1384517-65-0 2-[3-amino-5-(4-isopropoxyphenyl)-1H-pyrazol-4-yl]-N,N-diethylacetamide 
• 1262278-66-9 2-(2-(4-cyclobutoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide 

Relevant articles and documents

Synthesis and evaluation of novel potent TSPO PET ligands with 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamide

Translocator protein (TSPO) expression is closely related with neuroinflammation and neuronal damage which might cause several central nervous system diseases. Herein, a series of TSPO ligands (11a–c and 13a–d) with a 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamide structure were prepared and evaluated via an in vitro binding assay. Most of the novel ligands exhibited a nano-molar affinity for TSPO, which was better than that of DPA-714. Particularly, 11a exhibited a subnano-molar TSPO binding affinity with suitable lipophilicity for in vivo brain studies. After radiolabeling with fluorine-18, [18F]11a was used for a dynamic positron emission tomography (PET) study in a rat LPS-induced neuroinflammation model; the inflammatory lesion was clearly visualized with a superior target-to-background ratio compared to [18F]DPA-714. An immunohistochemical examination of the dissected brains confirmed that the uptake location of [18F]11a in the PET study was consistent with a positively activated microglia region. This study proved that [18F]11a could be employed as a potential PET tracer for detecting neuroinflammation and could give possibility for diagnosis of other diseases, such as cancers related with TSPO expression.

[18F] DPA-714 (N, N-diethyl-2-(2-(4-(2-[18]F-fluoroethyoxy)phenyl)-5, 7-dimethylpyrazolo[1, 5-a]pyrimidin-3-yl)aceamide) derivative and preparation and application methods thereof

The invention discloses a [18F] DPA-174 derivative. The [18F] DPA-174 derivative is prepared by modifying the benzene ring structure of or prolonging the carbon chain structure of a [18]F DPA-174 imaging agent. The invention also discloses preparation and application methods of the [18F] DPA-174 derivative. The [18F] DPA-174 derivative is simple in preparation, easy to implement, high in labellingyield and good in repeatability and can help in real time observe and in vivo monitor the status of intracerebral neuroinflammation of an animal model as well as the changes of the major organs and tissues of the animal model; the prepared imaging agents can achieve imaging effects on neuroinflammation; the [18F] DPAF imaging agent can achieve a high signal-to-noise ratio on neuroinflammation lesions to provide possibility for further monitoring and assessing the diagnosis and treatment effects on neuroinflammation..

Novel potential pyrazolopyrimidine based translocator protein ligands for the evaluation of neuroinflammation with PET

Translocator protein (TSPO) is an interesting biological target because TSPO overexpression is associated with microglial activation caused by neuronal damage or neuroinflammation, and these activated microglia are involved in several central nervous syst

Ether analogues of DPA-714 with subnanomolar affinity for the translocator protein (TSPO)

Sixteen new phenyl alkyl ether derivatives (12, 14-28) of the 5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylacetamide (DPA) class were synthesized and evaluated in a competition binding assay against [3H]PK11195 using 18 kDa translocator protein (TSPO) derived from rat kidney mitochondrial fractions. All analogues showed superior binding affinities for TSPO compared to DPA-713 (5) and DPA-714 (6). Picomolar affinities were observed for this class of TSPO ligands in this assay for the first time, with phenethyl ether 28 showing the greatest affinity (Ki Combining double low line 0.13 nM). Additionally, all analogues increased pregnenolone biosynthesis (134-331% above baseline) in a rat C6 glioma cell steroidogenesis assay.

A practical, multigram synthesis of the 2-(2-(4-alkoxyphenyl)-5,7- dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (DPA) class of high affinity translocator protein (TSPO) ligands

A practical, multigram approach to the 2-(2-(4-alkoxyphenyl)-5,7- dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (DPA) class of ligands targeting the translocator protein (TSPO) is described. This synthetic route offers several improvements over all previously described sequences, including the isolation of intermediates without resort to chromatography. The common precursor to the DPA class of high affinity TSPO ligands, N,N-diethyl-2-(2-(4- hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide, was produced in 40% yield over six steps, and was cleanly alkylated to give multigram quantities of several DPA analogues in 90-96% yield after recrystallization.

NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS

The present invention provides compounds of formula (I) and compositions thereof, methods of making them, and methods of using them to modulate alpha7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory system.