Phthalide

Base Information

• Chemical Name: Phthalide
• CAS No.: 87-41-2
• Deprecated CAS: 1135443-46-7
• Molecular Formula: C8H6O2
• Molecular Weight: 134.134
• Hs Code.: 29322980
• European Community (EC) Number: 201-744-0
• NSC Number: 1469
• UNII: 8VV922U86J
• DSSTox Substance ID: DTXSID0052594
• Nikkaji Number: J95.650C
• Wikipedia: Phthalide
• Wikidata: Q7188203
• Metabolomics Workbench ID: 45552
• ChEMBL ID: CHEMBL2391738
• Mol file: 87-41-2.mol

Synonyms:phthalide

Chemical Property of Phthalide

Chemical Property:

• Appearance/Colour: White to light beige crystalline powder
• Vapor Pressure: 0.00213mmHg at 25°C
• Melting Point: 71-74 °C(lit.)
• Refractive Index: 1.585
• Boiling Point: 289.999 °C at 760 mmHg
• Flash Point: 124.844 °C
• PSA: 26.30000
• Density: 1.265 g/cm³
• LogP: 1.35700
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: sparingly soluble
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 134.036779430
• Heavy Atom Count: 10
• Complexity: 153

Purity/Quality:

99.5%min ^*data from raw suppliers

Phthalide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 26-36-24/25-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: C1C2=CC=CC=C2C(=O)O1
• Description: White powder; sweet tonka, coumarin, powdery, coconut, phenolic, lactonic aroma.
• Uses: Phthalide may be used in scaffolds for the design of high potency monoamine oxidase (MAO) inhibitors.

Technology Process of Phthalide

There total 443 articles about Phthalide 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: 91.0%

Diethyl phthalate (84-66-2) → 2-benzofuran-1(3H)-one (87-41-2) + phthalyl alcohol (612-14-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; tert-butyl alcohol; Heating;

DOI:10.1246/bcsj.57.1948

Reference yield: 42.0%

2-Methyl-4-oxo-3,4-dihydro-1H-2-benzoselenopyranium Tetrafluoroborate → 2-benzofuran-1(3H)-one (87-41-2) + 2-(hydroxymethyl)benzoic acid (612-20-4)

Guidance literature:

With sodium hydroxide; In water; a) RT, 1 h, b) reflux, 10 h;

DOI:10.1021/jo00384a002

Reference yield: 36.0%

Phthaloyl dichloride (88-95-9) → 2-benzofuran-1(3H)-one (87-41-2) + phthalyl alcohol (612-14-6)

Guidance literature:

With zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at 40 ℃; for 4.5h;

DOI:10.1246/bcsj.61.2684

upstream raw materials:

ortho-methylbenzoic acid

methyl 2-bromomethylbenzoate

3H-isobenzofuran-1-ylideneamine

acetic anhydride

Downstream raw materials:

2-(1H-pyridin-2-ylidene)-indan-1,3-dione

2-p-tolyloxymethyl-benzoic acid benzyl ester

2-benzo[1,3]dioxol-5-yl-indan-1,3-dione

2-(Naphthalene-2-yl)methylbenzoic acid

Refernces

• 1、 Shaabani, Ahmad,Borjian Boroujeni, Mahmoud,Laeini, Mohmmad Sadegh. "Porous chitosan-MnO2 nanohybrid: A green and biodegradable heterogeneous catalyst for aerobic oxidation of alkylarenes and alcohols". . p. 154 - 159. Retrieved 2016.
• 2、 Grigg, Ronald,Khalil, Hashim,Levett, Philip,Virica, Julia,Sridharan, Visuvanathar. "Carbon monoxide as a One Carbon Component in Palladium Catalysed Cycloaddition Reactions". . p. 3197 - 3200. Retrieved 1994.
• 3、 Fu, Jun,Ren, Dezhang,Li, Lu,Liu, Yunjie,Jin, Fangming,Huo, Zhibao. "Efficient conversion of dimethyl phthalate to phthalide over CuO in aqueous media". . p. 123 - 127. Retrieved 2016.
• 4、 Sakurai. "-". . p. 127,130. Retrieved 1932.
• 5、 Liu, Ying Xin,Xing, Tie Feng,Luo, Yi Ming,Li, Xiao Nian,Yan, Wei. "Au/FeOx-TiO2 as an efficient catalyst for the selective hydrogenation of phthalic anhydride to phthalide". . p. 1322 - 1325. Retrieved 2010.
• 6、 Fife,Benjamin. "-". . p. 2059. Retrieved 1973.
• 7、 Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua. "Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source". . p. 68 - 74. Retrieved 2021/11/16.
• 8、 Feng, Xuanyu,Pi, Yunhong,Song, Yang,Xu, Ziwan,Li, Zhong,Lin, Wenbin. "Integration of Earth-Abundant Photosensitizers and Catalysts in Metal-Organic Frameworks Enhances Photocatalytic Aerobic Oxidation". . p. 1024 - 1032. Retrieved 2021/01/26.