5-Indolylboronic acid
- Product Name
- 5-Indolylboronic acid
- CAS No.
- 144104-59-6
- Chemical Name
- 5-Indolylboronic acid
- Synonyms
- INDOLE-5-BORONIC ACID;AKOS BRN-0120;5-Indolylboronic;5-Borono-1H-indole;RARECHEM AH PB 0158;5-Indole Boric Acid;5-INDOLBORONIC ACID;5-INDOYLBORONIC ACID;5-Indolyboronic acid;5-INDOLEBORONIC ACID
- CBNumber
- CB9294899
- Molecular Formula
- C8H8BNO2
- Formula Weight
- 160.97
- MOL File
- 144104-59-6.mol
5-Indolylboronic acid Property
- Melting point:
- 170-175 °C
- Boiling point:
- 433.2±37.0 °C(Predicted)
- Density
- 1.33±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 8.91±0.30(Predicted)
- form
- Crystalline Powder
- color
- White
- Sensitive
- Air Sensitive
- CAS DataBase Reference
- 144104-59-6(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36/37/38-21/22
- Safety Statements
- 26-36/37/39
- WGK Germany
- 3
- Hazard Note
- Irritant/Keep Cold
- HazardClass
- IRRITANT, KEEP COLD
- HS Code
- 29339900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 666467
- Product name
- 5-Indolylboronic acid
- Purity
- ≥95%
- Packaging
- 1g
- Price
- $46.7
- Updated
- 2025/07/31
- Product number
- I577753
- Product name
- Indole-5-boronicacid
- Packaging
- 100mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- I577753
- Product name
- Indole-5-boronicacid
- Packaging
- 500mg
- Price
- $65
- Updated
- 2021/12/16
- Product number
- CS-W020721
- Product name
- Boronicacid,B-1H-indol-5-yl-
- Purity
- 99.62%
- Packaging
- 5g
- Price
- $70
- Updated
- 2021/12/16
- Product number
- I3820
- Product name
- Indole-5-boronicacid
- Purity
- 97.0%
- Packaging
- 5g
- Price
- $60
- Updated
- 2021/12/16
5-Indolylboronic acid Chemical Properties,Usage,Production
Chemical Properties
White to light yellow crystal powde
Uses
Indole-5-boronic acid is a useful reagent for palladium and copper catalyzed oxidative cross-coupling of mercaptoacetylenes and arylboronic acids. A reagent used in the synthesis of other biologically active molecules.
Uses
Reactant involved in the synthesis of biologically active molecules including:
- Indole inhibitors of MMP-13 for arthritic disease treatment
- Substituted pyrimidines acting as tubulin polymerization inhibitors
Reactant involved in Suzuki coupling reactions for synthesis of
- Aryl- hetarylfurocoumarins
- Aryl-substituted oxabenzindoles and methanobenzindoles
Reactant involved in:
- Oxidative cross-coupling with mercaptoacetylenes
- Trifluoromethylation
General Description
May contain varying amounts of anhydride
Synthesis
10075-50-0
5419-55-6
144104-59-6
General procedure for the synthesis of 5-bromoindole and triisopropyl borate as raw materials for the synthesis of 5-bromoindoleboronic acid: In a dry and nitrogen-protected three-necked flask, anhydrous THF (80 mL) solution of NaH (1.02 g, 42.5 mmol) was added, equipped with a magnetic stirrer and a septum. The reaction system was cooled to 0 °C under N2 atmosphere and 5-bromoindole (5.0 g, 25.5 mmol) was added slowly dropwise, and stirring was continued for 15 min after completion of the dropwise addition. Subsequently, n-BuLi (2.5 M hexane solution, 15 mL, 37.5 mmol) was added slowly and stirred for 10 min. Then, triisopropyl borate (22 mL, 51 mmol) was added dropwise. After completion of the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirred overnight, and stirring was continued for 2 hours. After completion of the reaction, the reaction was quenched with saturated NH4Cl solution and stirred for 30 minutes. The organic layer was separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed sequentially with water and brine and dried over Na2SO4. After complete removal of the solvent, the residue was treated with EtOAc/petroleum ether and filtered to afford the target product 1H-indol-5-ylboronic acid (b1) as a colorless solid (1.02 g, 25% yield). The structure of the product was determined by 1H-NMR (DMSO-d6) δ 11.1 (s, 1H), 8.30 (s, 1H), 7.81 (d, 1H, J = 8.1 Hz), 7.47 (d, 1H, J = 8.1 Hz), 7.34 (s, 1H) and 13C-NMR (100 MHz, DMSO-d6) δ 138.0, 128.0, 127.5, 127.4, 127.3, 125.4, 111.0, 102.0 confirmed.
References
[1] Tetrahedron Letters, 2017, vol. 58, # 1, p. 35 - 42
5-Indolylboronic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-Indolylboronic acid manufacturers
- Product
- 1H-Indol-5-ylboronic acid 144104-59-6
- Price
- US $3.00-9.00/KG
- Min. Order
- 0.1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2025-07-05
- Product
- 5-Indolylboronic acid 144104-59-6
- Price
- US $8.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10MT
- Release date
- 2018-12-17