Pindone

Base Information

• Chemical Name: Pindone
• CAS No.: 83-26-1
• Molecular Formula: C14H14 O3
• Molecular Weight: 230.263
• Hs Code.: 29143990
• European Community (EC) Number: 201-462-8
• ICSC Number: 1515
• NSC Number: 31211,6281
• UN Number: 2810,2588
• UNII: 2KFI1XBH7G
• DSSTox Substance ID: DTXSID1025930
• Nikkaji Number: J4.628K
• Wikipedia: Pindone
• Wikidata: Q2276931
• Metabolomics Workbench ID: 143643
• ChEMBL ID: CHEMBL1369243
• Mol file: 83-26-1.mol

Synonyms:pindone;pindone, sodium salt;pivaloylindan-1,3-dione

Chemical Property of Pindone

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 76.833mmHg at 25°C
• Melting Point: 155 - 156 C
• Refractive Index: 1.5557 (estimate)
• Boiling Point: 82.987°C at 760 mmHg
• PKA: 3.47±0.10(Predicted)
• Flash Point: -13.169°C
• PSA: 51.21000
• Density: 1.1914 (rough estimate)
• LogP: 2.29700
• Storage Temp.: APPROX 20°C
• Solubility.: Soluble in most organic solvents (Worthing and Hance, 1991)
• Water Solubility.: 18 ppm at 25 °C (Gunther et al., 1968)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 351
• Transport DOT Label: Poison

Purity/Quality:

98%min ^*data from raw suppliers

2-Pivaloyl-1,3-indandione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by inhalation and ingestion; inhibits blood clotting. TLV: 0.1 mg/m³.
• Hazard Codes: T,N
• Statements: 25-48/25-50/53
• Safety Statements: 37-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Rodenticides, Anticoagulant
• Canonical SMILES: CC(C)(C)C(=O)C1C(=O)C2=CC=CC=C2C1=O
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly , especially if powdered.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in haemorrhage. The effects may be delayed. Medical observation is indicated.
• Uses: Insecticide; rodenticide Pindone may be used as an analytical reference standard for the quantification of the analyte in biological samples using different chromatography techniques.

Technology Process of Pindone

There total 6 articles about Pindone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

C13H15IO2 (1396604-89-9) + phenyl formate (1864-94-4) → pindone (83-26-1)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In dimethyl sulfoxide; at 95 ℃; for 24h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.5b01758

Reference yield:

2-Iodobenzoic acid (88-67-5) → pindone (83-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride / 4 h / 80 °C

2.1: lithium hexamethyldisilazane / toluene / 3 h / 0 °C / Inert atmosphere

2.2: 5 h / Inert atmosphere

3.1: dichloro bis(acetonitrile) palladium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium phosphate / dimethyl sulfoxide / 24 h / 95 °C / Sealed tube; Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); potassium phosphate; thionyl chloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; In dimethyl sulfoxide; toluene;

DOI:10.1021/acs.joc.5b01758

Reference yield:

2-Iodobenzoyl chloride (609-67-6) → pindone (83-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / toluene / 3 h / 0 °C / Inert atmosphere

1.2: 5 h / Inert atmosphere

2.1: dichloro bis(acetonitrile) palladium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium phosphate / dimethyl sulfoxide / 24 h / 95 °C / Sealed tube; Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; In dimethyl sulfoxide; toluene;

DOI:10.1021/acs.joc.5b01758

upstream raw materials:

3,3-dimethyl-butan-2-one

phthalic acid dimethyl ester

C₂₈H₃₂O₈

C₁₃H₁₅IO₂

Downstream raw materials:

3-(1,1-dimethylethyl)indeno<1,2-c>pyrazol-4(1H)-one

1-carbamoyl-3-tert-butyl-3a,8b-dihydro-8b-hydroxyindeno<1,2-c>pyrazol-4-one

3-t-Butylindeno<1,2-c>isoxazol-4-one

2-methyl-3-t-butylindeno<1,2-c>pyrazol-4(1H)-one

Refernces

Vinyl imidates in cycloaddition reactions: Synthesis of (±)-alloyohimbane

10.1016/S0040-4039(00)01093-5

The study focuses on the synthesis of (+)-alloyohimbane, a yohimbine alkaloid, using the intramolecular Diels-Alder reaction of N-acylvinyl imidates as a key methodology. This approach provides a rapid entry into cis-fused hexahydroisoquinolones, which are essential for constructing the DE rings of yohimbine alkaloids. The chemicals used in the study include sorbic acid, LDA (lithium diisopropylamide), acid chloride, 2-ethoxy-1-aza-1,3-butadiene, benzene, NaBH3CNBH3 (sodium cyanoborohydride), TFA (trifluoroacetic acid), and various other reagents for the synthesis and transformation of intermediates. These chemicals serve to deconjugate sorbic acid, form the Diels-Alder precursor, effect the cycloaddition to form the cycloaddduct, and subsequently reduce and modify the product to afford the target lactam and ultimately (+)-alloyohimbane. The study also developed a radical-based strategy for synthesizing indoline electrophiles from o-bromoaniline derivatives, which are crucial for the synthesis of substituted indolines and the completion of the alkaloid structure.