3,4-Dimethoxyphenylacetonitrile

Base Information

• Chemical Name: 3,4-Dimethoxyphenylacetonitrile
• CAS No.: 93-17-4
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Hs Code.: 29269090
• European Community (EC) Number: 202-225-1
• NSC Number: 6324
• UNII: 62C8S706SP
• DSSTox Substance ID: DTXSID30239220
• Nikkaji Number: J31.172C
• Wikidata: Q27263471
• Mol file: 93-17-4.mol

Synonyms:3,4-dimethoxyphenylacetonitrile

Chemical Property of 3,4-Dimethoxyphenylacetonitrile

Chemical Property:

• Appearance/Colour: white to almost white crystals or cryst. needles
• Vapor Pressure: 0.000333mmHg at 25°C
• Melting Point: 54-57 °C(lit.)
• Refractive Index: 1.511
• Boiling Point: 319.7 °C at 760 mmHg
• Flash Point: 116.6 °C
• PSA: 42.25000
• Density: 1.082 g/cm³
• LogP: 1.76988
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: insoluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 196

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dimethoxybenzyl Cyanide >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 22-23/24/25-36/37/38-20/21/22
• Safety Statements: 36/37-45-22-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: COC1=C(C=C(C=C1)CC#N)OC
• Uses: An Impurity of Verapamil (V125000). An intermediate in the preparation of the muscle relaxant Papverine (P190500). (3,4-Dimethoxyphenyl)acetonitrile has been used in the synthesis of (Z)-3-(benzo[b]thiophen-2-yl)-2-(3,4-dimethoxyphenyl)acrylonitrile. It has also been used in the preparation of modified diterpene (±) nimbidiol which relies on a sulfenium ion promoted polyene cyclization.

Technology Process of 3,4-Dimethoxyphenylacetonitrile

There total 48 articles about 3,4-Dimethoxyphenylacetonitrile 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: 92.2%

2-(3,4-dimethoxyphenyl)acetamide (5663-56-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Guidance literature:

With ethyl phosphodichloridite; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/b614061k

Reference yield: 91.0%

4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Guidance literature:

With sodium cyanide;

DOI:10.1007/BF00605201

Reference yield: 90.0%

α-(3,4-dimethoxyphenyl)-α-(methylthio)acetonitrile (84784-38-3) → 3,4-dimethoxyphenylacetonitrile (93-17-4)

Guidance literature:

With acetic acid; zinc; at 100 ℃; for 1h;

upstream raw materials:

3,4-dimethoxyphenylpyruvic acid

2-(3,4-dimethoxyphenyl)acetaldehyde oxime

acetic anhydride

potassium cyanide

Downstream raw materials:

2-(3,4-dimethoxy-phenyl)-3c-[2]furyl-acrylonitrile

3,4-dimethoxyphenyl-(2-pyridyl)acetonitrile

3,4-dihydropapaverine

bis-[(3,4-dimethoxy-phenyl)-acetyl]-amine

Refernces

• 1、 -. "Method for synthesizing α - isopropyl -3 and 4 -methoxyacetonitrile". Paragraph 0005-0006; 0020; 0023-0024; 0027; 0030-0031.... . Retrieved 2021/09/29.
• 2、 Ramirez, Nieves P.,K?nig, Burkhard,Gonzalez-Gomez, Jose C.. "Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis". supporting information. . Retrieved 2019/03/08.