3-(1,3-Benzodioxol-5-yl)-3-oxopropanenitrile

Base Information

• Chemical Name: 3-(1,3-Benzodioxol-5-yl)-3-oxopropanenitrile
• CAS No.: 96220-14-3
• Molecular Formula: C10H7 N O3
• Molecular Weight: 189.17
• Hs Code.: 2932999099
• European Community (EC) Number: 821-712-5
• DSSTox Substance ID: DTXSID90599099
• Wikidata: Q82494950
• Mol file: 96220-14-3.mol

Synonyms:96220-14-3;Piperonyloylacetonitrile;3-(1,3-benzodioxol-5-yl)-3-oxopropanenitrile;3-(2H-1,3-benzodioxol-5-yl)-3-oxopropanenitrile;3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanenitrile;5-(Cyanoacetyl)-1,3-benzodioxole;SCHEMBL170340;DTXSID90599099;WSZFLWZOMWQGPD-UHFFFAOYSA-N;WDA22014;MFCD08558157;STK350867;AKOS000168185;HC-0214;NCGC00339583-01;1,3-Benzodioxole-5-propanenitrile,b-oxo-;DB-080415;CS-0180973;EN300-43908;3-(1,3-dioxaindan-5-yl)-3-oxopropanenitrile;3-benzo[1,3]dioxol-5-yl-3-oxo-propionitrile;G31012;AB01175156-03;J-510800;2-(1,3-BENZODIOXOL-5-YL)-2-OXOETHYL CYANIDE;Z317042088

Chemical Property of 3-(1,3-Benzodioxol-5-yl)-3-oxopropanenitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 133-135°
• Refractive Index: 1.576
• Boiling Point: 409.7°Cat760mmHg
• Flash Point: 179.2°C
• PSA: 59.32000
• Density: 1.331g/cm³
• LogP: 1.51168
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 189.042593085
• Heavy Atom Count: 14
• Complexity: 280

Purity/Quality:

97% ^*data from raw suppliers

3-(1,3-benzodioxol-5-yl)-3-oxopropanenitrile ^*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(=O)CC#N

Technology Process of 3-(1,3-Benzodioxol-5-yl)-3-oxopropanenitrile

There total 4 articles about 3-(1,3-Benzodioxol-5-yl)-3-oxopropanenitrile 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%

methyl 3,4-methylenedioxybenzoate (326-56-7) + acetonitrile (75-05-8,26809-02-9) → 3-benzo[1,3]dioxol-5-yl-3-oxo-propionitrile (96220-14-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 70 ℃; for 5.5h; Cooling with ice;

Reference yield:

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → 3-benzo[1,3]dioxol-5-yl-3-oxo-propionitrile (96220-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(ll) bromide / ethyl acetate / Reflux

2: ethanol; water / 16 h / Cooling with ice

With copper(ll) bromide; In ethanol; water; ethyl acetate;

DOI:10.1021/acs.jmedchem.0c01152

Reference yield:

ethyl 1,3-benzodioxole-5-carboxylate (6951-08-2) + acetonitrile (75-05-8,26809-02-9) → 3-benzo[1,3]dioxol-5-yl-3-oxo-propionitrile (96220-14-3)

Guidance literature:

With sodium amide; benzene;

upstream raw materials:

ethyl 1,3-benzodioxole-5-carboxylate

acetonitrile

methyl 3,4-methylenedioxybenzoate

sodium cyanide