3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chloride

Base Information

• Chemical Name: 3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chloride
• CAS No.: 26930-49-4
• Molecular Formula: C₁₀H₇ClO₃
• Molecular Weight: 210.617
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID00696447
• Mol file: 26930-49-4.mol

Synonyms:DTXSID00696447;WBJQTHIVYWAEDD-UHFFFAOYSA-N;AKOS030230269;3-Benzo[1,3]dioxol-5-yl-acryloyl chloride;3-(1,3-benzodioxol-5-yl)prop-2-enoyl chloride;3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chloride

Chemical Property of 3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chloride

Chemical Property:

• Boiling Point: 332.6±11.0 °C(Predicted)
• PSA: 35.53000
• Density: 1.403±0.06 g/cm3(Predicted)
• LogP: 2.19390
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 210.0083718
• Heavy Atom Count: 14
• Complexity: 252

Purity/Quality:

98%Min ^*data from raw suppliers

(2E)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enoylchloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C=CC(=O)Cl

Technology Process of 3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chloride

There total 5 articles about 3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chloride 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: 42.0%

3,4-(methylenedioxy)cinnamic acid (2373-80-0,38489-76-8) → 3-benzo[1,3]dioxol-5-yl-acryloyl chloride (96249-87-5,26930-49-4) + 3-chloro-5,6-methylenedioxybenzothiophene-2-carbonyl chloride (137278-46-7)

Guidance literature:

With pyridine; thionyl chloride; In N,N-dimethyl-formamide; Yields of byproduct given; 1.) reflux, 4 h, 2.) 140-150 deg C, 1 h;

DOI:10.1007/BF00824304

Reference yield:

3,4-(methylenedioxy)cinnamic acid (2373-80-0,38489-76-8) → 3-benzo[1,3]dioxol-5-yl-acryloyl chloride (96249-87-5,26930-49-4)

Guidance literature:

With oxalyl dichloride; In dichloromethane; at 25 ℃;

DOI:10.3390/molecules14104166

Reference yield:

→ 3-benzo[1,3]dioxol-5-yl-acryloyl chloride (96249-87-5,26930-49-4)

Guidance literature:

With thionyl chloride;

upstream raw materials:

3,4-methylenedioxy-trans-cinnamic acid

3,4-(methylenedioxy)cinnamic acid

Downstream raw materials:

trans-fagaramide

(E)-3-benzo[1,3]dioxol-5-yl-N-[4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]acrylamide

2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one

5363077

Refernces

• 1、 Feng, Feng,Jiang, Pan,Li, Qi,Liao, Qinghong,Liu, Wenyuan,Qu, Wei,Sun, Haopeng,Yan, Yuhui,Zhao, Yifan. "Design, synthesis and biological evaluation of novel carboline-cinnamic acid hybrids as multifunctional agents for treatment of Alzheimer's disease". . . Retrieved 2020/04/22.
• 2、 Shen, Yue,Chai, Jun,Yang, Gaosheng,Chen, Wenlong,Chai, Zhuo. "Stereocontrolled Synthesis of trans/ cis-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans". supporting information. p. 12549 - 12558. Retrieved 2018/10/09.