(Z)-Butylidenephthalide

Base Information

• Chemical Name: (Z)-Butylidenephthalide
• CAS No.: 72917-31-8
• Molecular Formula: C12H14O2
• Molecular Weight: 188.226
• Mol file: 72917-31-8.mol

Synonyms:(Z)-Butylidenephthalide;

Chemical Property of (Z)-Butylidenephthalide

Chemical Property:

• Vapor Pressure: 0.000191mmHg at 25°C
• Boiling Point: 328.3°Cat760mmHg
• Flash Point: 135.7°C
• PSA: 26.30000
• Density: 1.17g/cm³
• LogP: 2.07030

Purity/Quality:

99%+, ^*data from raw suppliers

Z-Butylidenephthalide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-Butylidenephthalide

There total 4 articles about (Z)-Butylidenephthalide 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: 70.0%

phthalic anhydride (85-44-9) + pentanoic anhydride (2082-59-9) → (Z)-3-(1-butylidene)phthalide (72917-31-8)

Guidance literature:

With sodium valerate; at 170 - 190 ℃; for 4h;

Reference yield: 34.0%

phthalic anhydride (85-44-9) + n-butyllithium (109-72-8,29786-93-4) → (Z)-3-(1-butylidene)phthalide (72917-31-8)

Guidance literature:

phthalic anhydride; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 12h; Inert atmosphere;

With toluene-4-sulfonic acid; In toluene; Reflux;

Reference yield:

dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate (61260-15-9) + butyraldehyde (123-72-8) → (E)-3-butylidene-3H-isobenzofuran-1-one (76681-73-7) + (Z)-3-(1-butylidene)phthalide (72917-31-8)

Guidance literature:

With potassium tert-butylate; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 30 min, 2.) room temp., 30 min;

DOI:10.1055/s-1985-31097

upstream raw materials:

dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate

butyraldehyde

phthalic anhydride

n-butyllithium

Downstream raw materials:

(±)-2-(1-hydroxypentyl)benzoic acid

butylphthalide

2-pentanoylbenzoic acid

senkyunolide E

Refernces

• 1、 Li, Yong,Luo, Zhongfu,Luo, Bilan,Lan, Qing,Fan, Judi,Xue, Wei,Miao, Jing,Li, Yi,Tang, Lei,Fan, Lingling. "Design, Synthesis and Antifungal Activities of 6-Substituted 3-Butylphthalide Derivatives against Phytopathogenic Fungi". . . Retrieved 2020/09/23.
• 2、 -. "Ligustrazine-butyphthalide combination compound, preparation method of ligustrazine-butyphthalide combination compound, and application of ligustrazine-butyphthalide combination compound to pharmaceuticals". Paragraph 0028; 0033. . Retrieved 2017/08/30.