Identification | Back Directory | [Name]
4-(4-broMo-3-(hydroxyMethyl)phenoxy)benzonitrile | [CAS]
906673-45-8 | [Synonyms]
Crisaborole Intermediate 1 2-bromo-5-(4-cyanophenoxy)benzyl alcohol 2-Bromo-5-(4-cyanophenoxyl)benzyl alcohol 4-(4-broMo-3-(hydroxyMethyl)phenoxy)benzonitrile Benzonitrile, 4-[4-bromo-3-(hydroxymethyl)phenoxy]- | [Molecular Formula]
C14H10BrNO2 | [MDL Number]
MFCD12165918 | [MOL File]
906673-45-8.mol | [Molecular Weight]
304.14 |
Chemical Properties | Back Directory | [Boiling point ]
447.6±45.0 °C(Predicted) | [density ]
1.57±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
13.96±0.10(Predicted) | [Appearance]
Light yellow to yellow Solid | [InChI]
InChI=1S/C14H10BrNO2/c15-14-6-5-13(7-11(14)9-17)18-12-3-1-10(8-16)2-4-12/h1-7,17H,9H2 | [InChIKey]
DAMOSKSUIVLOJT-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC=C(OC2=CC=C(Br)C(CO)=C2)C=C1 |
Hazard Information | Back Directory | [Chemical Properties]
Class white powder | [Synthesis]
The general procedure for the synthesis of 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile from 4-(4-bromo-3-formylphenoxy)benzonitrile was as follows: 100 g of 4-(4-bromo-3-formylphenoxy)benzonitrile (VI) was dissolved in 500 mL of methanol at 25-30 °C, and subsequently cooled to 10-15 °C. While maintaining 10-15 °C, 6.2 g of sodium borohydride was slowly added for 60-90 min. After the addition was completed, the temperature of the reaction system was slowly increased to 15-20°C. Upon completion of the reaction, 1000 mL of water was added to the reaction mixture and stirred at 25-30 °C for 1 hour. The resulting solid product was collected by vacuum filtration, washed with water and dried under vacuum at not more than 55 °C to obtain 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile (V). Yield: 99.0%; purity: 99.02%. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 8, p. 2129 - 2132 [2] Patent: WO2018/207216, 2018, A1. Location in patent: Page/Page column 10 [3] Patent: CN108659024, 2018, A. Location in patent: Paragraph 0038-0039 [4] Patent: WO2018/115362, 2018, A1. Location in patent: Paragraph 0121 [5] Patent: US2007/293457, 2007, A1. Location in patent: Page/Page column 39-40 |
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