4,5-Dimethoxy-1-cyanobenzocyclobutane

Base Information

• Chemical Name: 4,5-Dimethoxy-1-cyanobenzocyclobutane
• CAS No.: 35202-54-1
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 2926909090
• European Community (EC) Number: 609-091-7
• NSC Number: 154410
• DSSTox Substance ID: DTXSID301020939
• Mol file: 35202-54-1.mol

Synonyms:4,5-Dimethoxy-1-cyanobenzocyclobutane;35202-54-1;3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile;1-Cyano-4,5-dimethoxybenzocyclobutene;4,5-Dimethoxy-1-benzocyclobutenecarbonitrile;BICYCLO[4.2.0]OCTA-1,3,5-TRIENE-7-CARBONITRILE, 3,4-DIMETHOXY-;NSC154410;3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-triene-7-carbonitrile;MFCD01846132;NSC 154410;SCHEMBL333286;DTXSID301020939;BCP10456;BBL029490;STL250406;1-cyano-4,5-dimethoxybenzocyclobutane;AKOS004907934;DS-1889;NSC-154410;4,5-dimethoxy-1-cyano-benzocyclobutane;AC-22607;SY053303;AM20090736;CS-0097967;D4485;FT-0659839;J-514095;4,5-DIMETHOXY-1,2-DIHYDROCYCLOBUTABENZENE-1-CARBONITRILE;3,4-DIMETHOXYBICYCLO[4.2.0]OCTA-1(6),2,4-TRIENE-7-CARBONITRILE

Chemical Property of 4,5-Dimethoxy-1-cyanobenzocyclobutane

Chemical Property:

• Vapor Pressure: 5.98E-05mmHg at 25°C
• Melting Point: 83-84 °C
• Refractive Index: 1.557
• Boiling Point: 345.9 °C at 760 mmHg
• Flash Point: 140.5 °C
• PSA: 42.25000
• Density: 1.18 g/cm³
• LogP: 1.86708
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO, Methanol
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 257

Purity/Quality:

99%, ^*data from raw suppliers

4,5-Dimethoxy-1-benzocyclobutenecarbonitrile >98.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(CC2=C1)C#N)OC
• Uses: 4,5-Dimethoxy-1-cyanobenzocyclobutane is used in the preparation of selective bradycardic agents. 4,5-Dimethoxy-1-benzocyclobutenecarbonitrile is used in the preparation of selective bradycardic agents.

Technology Process of 4,5-Dimethoxy-1-cyanobenzocyclobutane

There total 17 articles about 4,5-Dimethoxy-1-cyanobenzocyclobutane 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: 80.0%

3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile (35249-62-8) → 3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile (35202-54-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -10 ℃; Inert atmosphere;

Reference yield: 54.0%

3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one (55171-76-1) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) → 3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile (35202-54-1)

Guidance literature:

[(p-methylphenyl)sulfonylmethyl]isonitrile; With methanol; potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.833333h; Inert atmosphere;

3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one; With lithium bromide; In tetrahydrofuran; at 0 - 40 ℃; Inert atmosphere;

Reference yield: 50.0%

2-(2-cyanoethyl)-4,5-dimethoxyphenyl dimethylsulphamate (1232191-48-8) → 3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile (35202-54-1)

Guidance literature:

2-(2-cyanoethyl)-4,5-dimethoxyphenyl dimethylsulphamate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -60 - -5 ℃; Inert atmosphere;

With water; In tetrahydrofuran; hexane;

upstream raw materials:

7-Chloro-3,4-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-triene

4,5-dimethoxy-2-methylbenzaldehyde

1-Dichloromethyl-4,5-dimethoxy-2-methyl-benzene

3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile

Downstream raw materials:

1-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine hydrochloride

({3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl)(methyl)amine

ivabradine

(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF 3-(2-BROMO-4,5-DIMETHOXYPHENYL)PROPANENITRILE, AND APPLICATION IN THE SYNTHESIS OF IVABRADINE AND ADDITION SALTS THEREOF WITH A PHARMACEUTICALLY ACCEPTABLE ACID". Paragraph 0048-0051. . Retrieved 2014/05/07.
• 2、 -. "PROCESS FOR THE SYNTHESIS OF 3-(2-BROMO-4,5-DIMETHOXYPHENYL)PROPANENITRILE, AND APPLICATION IN THE SYNTHESIS OF IVABRADINE AND ADDITION SALTS THEREOF WITH A PHARMACEUTICALLY ACCEPTABLE ACID". Paragraph 0034-0037. . Retrieved 2014/06/24.