| Identification | More | [Name]
Benzothiophene-3-boronic acid | [CAS]
113893-08-6 | [Synonyms]
1-BENZOTHIOPHEN-3-YLBORONIC ACID
AKOS BRN-0283
ASDI-INTER 500027787
BENZO[B]THIOPHENE-3-BORONIC ACID
BENZOTHIOPHENE-3-BORONIC ACID
THIANAPHTHENE-3-BORONIC ACID
Benzo[b]thiophen-3-yl-boronic acid
| [Molecular Formula]
C8H7BO2S | [MDL Number]
MFCD01114669 | [Molecular Weight]
178.02 | [MOL File]
113893-08-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
225-230 °C(lit.) | [Boiling point ]
390.2±34.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [form ]
powder to crystal | [pka]
8.29±0.30(Predicted) | [color ]
White to Light yellow to Light orange | [InChI]
InChI=1S/C8H7BO2S/c10-9(11)7-5-12-8-4-2-1-3-6(7)8/h1-5,10-11H | [InChIKey]
QVANIYYVZZLQJP-UHFFFAOYSA-N | [SMILES]
B(C1=CSC2=CC=CC=C21)(O)O | [CAS DataBase Reference]
113893-08-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Uses]
Benzo[b]thien-3-ylboronic acid can be used:
- To prepare thienyl substituted?pyrimidine derivatives as potent antimycobacterial?compounds.
- To prepare 3-O-protected 17-heteroaryl-3-hydroxyestra-1,3,5,16-tetraene-16-carbaldehyde, which in turn is used for the synthesis of heteroarenes-annelated estranes.
- As a substrate in the study of metal-free coupling reactions of allylic alcohols with heteroaryl boronic acids.
- As a starting material for the preparation of thienyl based quinoline and pyridine ligands, which are further used to synthesize platinum complexes.
| [Synthesis]
Under nitrogen protection, 10 g (47 mmol) of 3-bromobenzothiophene was dissolved in 100 ml of tetrahydrofuran (THF) and cooled to -60 °C. 36 ml of hexane solution of n-butyllithium (concentration 1.57 mol/L) was slowly added dropwise, and after the dropwise addition, the reaction mixture was continued to be stirred for 1 hour. Subsequently, 13.3 g (71 mmol) of triisopropyl borate was added and stirring was continued for 1 hour. The reaction system was slowly brought back to room temperature and the reaction was quenched by the addition of 50 ml of saturated aqueous ammonium chloride solution. The reaction mixture was extracted with 100 ml of toluene, the organic phase was washed three times (100 ml each) with distilled water and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was removed by concentration under reduced pressure to afford intermediate B-1. 6.9 g (39 mmol, 83% yield) of the target product, benzothiophene-3-boronic acid, was finally obtained. | [References]
[1] Patent: EP2617724, 2013, A1. Location in patent: Paragraph 0162; 0163
[2] Patent: EP2628743, 2013, A1. Location in patent: Paragraph 0175 |
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