| Identification | Back Directory | [Name]
2-CHLOROPYRIMIDINE-5-BORONIC ACID | [CAS]
1003845-06-4 | [Synonyms]
ALKYL HYDROXIMIC ACID
2-Chloropyrimidine-5-boro...
2-Chloro-pyridineyl-5-boronic
2-Chloropyrimidine-5-BoronicAci
2-CHLORO-5-PYRIMIDINEBORONIC ACID
2-CHLOROPYRIMIDINE-5-BORONIC ACID
2-chloropyrimidin-5-ylboronic acid
2-Chloro-pyridineyl-5-boronic acid
4-Chloro-2-pyrimidine boronic acid
BORONIC ACID,B-(2-CHLORO-5-PYRIMIDINYL)-
2-CHLOROPYRIMIDINE-5-BORONIC ACID###1003845-06-4
2-ChloropyriMidine-5-boronic acid (contains varying aMounts of anhydride) | [Molecular Formula]
C4H4BClN2O2 | [MDL Number]
MFCD08063113 | [MOL File]
1003845-06-4.mol | [Molecular Weight]
158.35 |
| Chemical Properties | Back Directory | [Boiling point ]
425.4±37.0 °C(Predicted) | [density ]
1.52±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
Powder | [pka]
5.03±0.11(Predicted) | [color ]
White | [InChI]
InChI=1S/C4H4BClN2O2/c6-4-7-1-3(2-8-4)5(9)10/h1-2,9-10H | [InChIKey]
YTCIHPTZKKWKKC-UHFFFAOYSA-N | [SMILES]
B(C1=CN=C(Cl)N=C1)(O)O | [CAS DataBase Reference]
1003845-06-4 |
| Hazard Information | Back Directory | [Uses]
2-Chloropyrimidine-5-boronic acid is a pyrimidine-boronic acid compound, mainly used as a raw material for organic synthesis or a reagent for chemical reactions. | [Synthesis]
Step 1: Synthesis of 2-chloropyrimidin-5-ylboronic acid
Under argon protection, 5-bromo-2-chloropyrimidine (1.0 g, 5.170 mmol) was dissolved in a solvent mixture of THF and toluene (25 mL, 4:1 v/v), and cooled to -78 °C. n-Butyllithium (1.6 M hexane solution, 3.87 mL, 5.61 mmol) was slowly added dropwise at -78 °C, and the reaction was kept at -78 °C for 4 hours after completion of the dropwise addition. After completion of the reaction, the reaction mixture was diluted with ice water, returned to room temperature and stirred for 1 hour. Subsequently, the aqueous phase was extracted with ether and the organic phase was combined. The aqueous phase was acidified to pH 2-3 with 1N hydrochloric acid and extracted with ethyl acetate. All organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 2-chloropyrimidin-5-ylboronic acid (0.6 g, 73.3% yield) as a white solid. Mass spectrum (MS): 159.3 [M+H]+. | [References]
[1] Patent: US2017/291910, 2017, A1. Location in patent: Paragraph 0508-0510
[2] Patent: WO2008/9435, 2008, A1. Location in patent: Page/Page column 189-190
[3] Patent: WO2011/84402, 2011, A1. Location in patent: Page/Page column 153 |
|
|