Homophthalic anhydride

Base Information

• Chemical Name: Homophthalic anhydride
• CAS No.: 703-59-3
• Molecular Formula: C9H6O3
• Molecular Weight: 162.145
• Hs Code.: 29173995
• European Community (EC) Number: 211-873-4
• NSC Number: 401693,2825
• UNII: DZ8M2RM8MF
• DSSTox Substance ID: DTXSID00220569
• Nikkaji Number: J193.071K
• Wikidata: Q72482621
• Mol file: 703-59-3.mol

Synonyms:homophthalic acid anhydride

Chemical Property of Homophthalic anhydride

Chemical Property:

• Appearance/Colour: slightly yellow to beige or light green powder
• Vapor Pressure: 0.000244mmHg at 25°C
• Melting Point: 140-142 °C(lit.)
• Refractive Index: 1.584
• Boiling Point: 324.5 °C at 760 mmHg
• Flash Point: 159 °C
• PSA: 43.37000
• Density: 1.347 g/cm³
• LogP: 0.92610
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Moisture Sensitive
• Water Solubility.: Decomposes in water.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 162.031694049
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

98%,99%, ^*data from raw suppliers

Homophthalic Anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=CC=CC=C2C(=O)OC1=O
• Uses: It is used as a chemical and organic intermediates.

Technology Process of Homophthalic anhydride

There total 14 articles about Homophthalic anhydride 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: 100.0%

Homophthalic acid (89-51-0) → homophthalic anhydride (703-59-3)

Guidance literature:

With trimethylsilylethoxyacetylene; In dichloromethane; at 20 ℃; for 7h;

DOI:10.1021/jo00372a010

Reference yield: 98.0%

2-Methoxymethylen-1-hydrindanon (17215-98-4) → homophthalic anhydride (703-59-3)

Guidance literature:

With ozone; In dichloromethane; at -70 ℃; for 0.0333333h;

DOI:10.1002/hlca.200490182

Reference yield: 90.0%

5,8-dimethoxy-1-hydroxy-3-methylisochroman (141058-88-0) → 1-Hydroxy-5,8-dioxo-3-methyl-5,8-dihydroisochroman (141058-89-1) + homophthalic anhydride (703-59-3)

Guidance literature:

With cerium (IV) ammonium nitrate;

upstream raw materials:

Homophthalic acid

phenylacetic acid

carbon monoxide

dimethyl homophthalate

Downstream raw materials:

2-(2-carboxy-phenyl)-5t-phenyl-penta-2ξ,4-dienoic acid-anhydride

2-(2-indol-3-yl-ethyl)-4H-isoquinoline-1,3-dione

2-(3',4'-dimethoxybenzoylmethyl)benzoic acid

2-[5-(4-nitro-phenoxy)-pentyl]-4H-isoquinoline-1,3-dione

Refernces

Stereoselective synthesis of (+)-isoindolo-β-carboline

10.1016/j.tetasy.2009.01.001

Prasad B. Wakchaure, Vedavati G. Puranik, and Narshinha P. Argade describe a stereoselective synthesis of enantiomerically pure (+)-isoindole-b-carbolines starting from homophthalic anhydride (a cyclic anhydride with a benzene ring and two carboxylic acid groups) and (S)-tryptophan. The synthesis involves several key steps: homophthalimide formation, oxidative ring contraction, intramolecular dehydration ring closure, and geometry-specific demethoxycarbonylation. The authors achieved an overall yield of 35% and an enantiomeric excess (ee) of 98% by optimizing conditions and combining air oxidation, acid-catalyzed cyclization, and demethoxycarbonylation. The study highlights the importance of chemoselective oxidation and the remarkable diastereoselectivity obtained during the intramolecular cyclization. The final product was confirmed by X-ray crystallography and chiral HPLC analysis, indicating that the target compound was successfully synthesized with high stereoselectivity.

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