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| | 4,5-Dimethoxy-1-cyanobenzocyclobutane Basic information |
| Product Name: | 4,5-Dimethoxy-1-cyanobenzocyclobutane | | Synonyms: | 4,5-Dimethoxy-1-benzocyclobutenecarbonitrile;4,5-Dimethoxy-1-cyanobenzocyclobutane;Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile,3,4-diMethoxy-;4,5-DiMethxoy-1,2-dihydrocyclobutabenzene-1-carbonitrile;2-cyclobutyl-2-(3,4-diMethoxyphenyl)acetonitrile;3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-8-carbonitrile;1,2-Dihydro-4,5-diMethoxybenzocyclobutene-1-carbonitrile;NSC 154410 | | CAS: | 35202-54-1 | | MF: | C11H11NO2 | | MW: | 189.21 | | EINECS: | 609-091-7 | | Product Categories: | | | Mol File: | 35202-54-1.mol |  |
| | 4,5-Dimethoxy-1-cyanobenzocyclobutane Chemical Properties |
| Melting point | 83-84 °C | | Boiling point | 345.9±42.0 °C(Predicted) | | density | 1.18 | | vapor pressure | 0.004Pa at 25℃ | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMSO, Methanol | | form | Solid | | color | Light Brown | | InChI | InChI=1S/C11H11NO2/c1-13-10-4-7-3-8(6-12)9(7)5-11(10)14-2/h4-5,8H,3H2,1-2H3 | | InChIKey | HJTHVTHXHHFXMJ-UHFFFAOYSA-N | | SMILES | C12C(C(C#N)C1)=CC(OC)=C(OC)C=2 | | LogP | 1.22 at 30℃ and pH7 | | CAS DataBase Reference | 35202-54-1(CAS DataBase Reference) |
| | 4,5-Dimethoxy-1-cyanobenzocyclobutane Usage And Synthesis |
| Uses | 4,5-Dimethoxy-1-cyanobenzocyclobutane is used in the preparation of selective bradycardic agents. | | Uses | 4,5-Dimethoxy-1-benzocyclobutenecarbonitrile is used in the preparation of selective bradycardic agents. | | Synthesis | NaNH2 (39.0 g,
1.0 mol) was added in portions to a solution of hydrocinnamonitrile
8 (224.0 g, 0.83 mol) in liquid ammonia at -45°C, and the reaction
mixture was stirred at -45 °C for 2 h. After evaporation of the excess
NH3, NH4Cl (20.0 g) and water (1000 mL) were added in portions.
After standing at room temperature, greyish crystals separated
and were collected and recrystallised with ethanol to give 4,5-Dimethoxy-1-cyanobenzocyclobutane as a colourless powder. Yield 116.5 g (74%). | | References | [1] Patent: WO2011/138625, 2011, A1. Location in patent: Page/Page column 31-32
[2] Journal of Chemical Research, 2009, # 7, p. 420 - 422
[3] Patent: US2014/107334, 2014, A1. Location in patent: Paragraph 0048-0051
[4] Patent: US2014/128598, 2014, A1. Location in patent: Paragraph 0040-0043
[5] Patent: US2014/163220, 2014, A1. Location in patent: Paragraph 0034-0037 |
| | 4,5-Dimethoxy-1-cyanobenzocyclobutane Preparation Products And Raw materials |
| Raw materials | (E)-3-(3,4-dimethoxyphenyl)acrylonitrile-->3-(3,4-Dimethoxyphenyl)propanenitrile
-->3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one-->3-(2-BROMO-4,5-DIMETHOXYPHENYL)PROPANENITRILE-->4,5-dimethoxy-2-methylbenzaldehyde-->4,5-DIBROMOVERATROLE-->2-Bromo-4,5-Dimethoxybenzyl Bromide-->4-Bromoveratrole-->3,4-Dimethoxybenzyl alcohol-->Veratraldehyde-->1,2-Dimethoxybenzene | | Preparation Products | (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride-->(3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine hydrochloride-->C-(3,4-DIMETHOXY-BICYCLO[4.2.0]OCTA-1(6),2,4-TRIEN-7-YL)-METHYLAMINE |
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