ChemicalBook > CAS DataBase List > 5-Indolylboronic acid

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
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
666467
Product name
5-Indolylboronic acid
Purity
≥95%
Packaging
1g
Price
$46.7
Updated
2025/07/31
TRC
Product number
I577753
Product name
Indole-5-boronicacid
Packaging
100mg
Price
$45
Updated
2021/12/16
TRC
Product number
I577753
Product name
Indole-5-boronicacid
Packaging
500mg
Price
$65
Updated
2021/12/16
ChemScene
Product number
CS-W020721
Product name
Boronicacid,B-1H-indol-5-yl-
Purity
99.62%
Packaging
5g
Price
$70
Updated
2021/12/16
Synthonix
Product number
I3820
Product name
Indole-5-boronicacid
Purity
97.0%
Packaging
5g
Price
$60
Updated
2021/12/16
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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

Trimethyl borate 5-Bromoindole Potassium hydride Tetrahydrofuran n-Butyllithium

Preparation Products

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View Lastest Price from 5-Indolylboronic acid manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
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
Career Henan Chemical Co
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

144104-59-6, 5-Indolylboronic acidRelated Search:

Indole-3-butyric acid Indole-3-acetic acid Indometacin Folic acid 5-INDANOL Boric acid Ethyl 2-(Chlorosulfonyl)acetate Indoline Citric acid Indole-5-carboxaldehyde Indole-3-carboxaldehyde Indole-4-carboxaldehyde Methyl indole-5-carboxylate Methyl indole-4-carboxylate Indole-3-carboxylic acid Methyl indole-6-carboxylate Ethyl indole-2-carboxylate Ascoric Acid

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