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| | 2-(1,3,2-Dioxaborolan-2-yl)benzonitrile Basic information |
| Product Name: | 2-(1,3,2-Dioxaborolan-2-yl)benzonitrile | | Synonyms: | AKOS BRN-0170;2-(1,3,2-DIOXABORINAN-2-YL)BENZONITRILE;(2-CYANOPHENYL)BORONIC ACID, 1,3-PROPANEDIOL CYCLIC ESTER;(2-CYANOPHENYL)BORONIC ACID PROPANE-1,3-DIOL CYCLIC ESTER;2-CYANOPHENYLBORONIC ACID PROPANEDIOL-1,3 CYCLIC ESTER;2-CYANOPHENYLBORONIC ACID PROPANEDIOL ESTER;2-Cyanobenzeneboronic acid propane-1,3-diol cyclic ester;2-Cyanophenylboronic acid 1,3-propanediol ester, 96% | | CAS: | 172732-52-4 | | MF: | C10H10BNO2 | | MW: | 187 | | EINECS: | | | Product Categories: | blocks;BoronicAcids | | Mol File: | 172732-52-4.mol |  |
| | 2-(1,3,2-Dioxaborolan-2-yl)benzonitrile Chemical Properties |
| Melting point | 46-56 °C(lit.) | | Boiling point | 372.4±25.0 °C(Predicted) | | density | 1.13±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | solid | | color | white | | Stability: | Hygroscopic | | InChI | 1S/C10H10BNO2/c12-8-9-4-1-2-5-10(9)11-13-6-3-7-14-11/h1-2,4-5H,3,6-7H2 | | InChIKey | REQZFVYFYAZUMG-UHFFFAOYSA-N | | SMILES | N#Cc1ccccc1B2OCCCO2 |
| Hazard Codes | Xi | | Risk Statements | 20/21/22-36/37/38 | | Safety Statements | 26-36/37/39 | | RIDADR | 3439 | | WGK Germany | 3 | | Hazard Note | Irritant | | TSCA | No | | HS Code | 2931900090 | | Storage Class | 13 - Non Combustible Solids |
| | 2-(1,3,2-Dioxaborolan-2-yl)benzonitrile Usage And Synthesis |
| Chemical Properties | White powder | | Uses | 2-(2-Cyanophenyl)-1,3,2-dioxaborinane is used in the synthesis of AMPA receptor antagonists in the treatment of neurological diseases causing dysfunction of glutamatergic neurotransmission. Also used in the small scale synthesis of Perampanel (P285520), an AMPA receptor antagonist. | | Synthesis | The general procedure for the synthesis of 2-cyanophenylboronic acid-1,3-propanediol cyclic ester from 2-cyanophenylboronic acid and 1,3-propanediol is as follows: 3.69 g (48.5 mmol) of 1,3-propanediol was added to the organic phase obtained from Example 1 and the reaction mixture was stirred for 1 hour at room temperature. Upon completion of the reaction, the aqueous phase was separated and removed, followed by distillation using a rotary evaporator to remove the organic solvent. To the residual oily substance, 2 ml of toluene and 120 ml of heptane were added to induce crystallization. The resulting crystals were washed with 30 mL of heptane and 7.44 g (yield: 82.4%) of the target product 1,3-propanediol ester (2-(1,3,2-dioxaborolan-2-yl)benzonitrile) was obtained after drying. The crystals were analyzed to contain 0.40% impurity of 1-phenyl-1-(2,2,6,6-tetramethylpiperidin-1-yl)methanimine. | | References | [1] Patent: JP2015/160823, 2015, A. Location in patent: Paragraph 0056
[2] Patent: EP2243785, 2010, A1
[3] Patent: US9281483, 2016, B2. Location in patent: Page/Page column 93
[4] Patent: KR2016/30582, 2016, A. Location in patent: Paragraph 0258; 0259; 0260; 0261; 0262
[5] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 3867 - 3876 |
| | 2-(1,3,2-Dioxaborolan-2-yl)benzonitrile Preparation Products And Raw materials |
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