5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde
- Product Name
- 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde
- CAS No.
- 881674-56-2
- Chemical Name
- 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde
- Synonyms
- 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde;5-(2-Fluorophenyl)-1H-pyrrole-3-carboxaldehyde;5-(2-Fluorophenyl)pyrrole-3-carboxaldehyde;Vonorazan;VONOPRAZAN IST-1;5-(2-FL;e-3-carbaL;)-1H-pyrroL;Vonoprazan-1;Vonoprazan-023
- CBNumber
- CB52638918
- Molecular Formula
- C11H8FNO
- Formula Weight
- 189.19
- MOL File
- 881674-56-2.mol
5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde Property
- Melting point:
- 133 °C
- Boiling point:
- 370.6±32.0 °C(Predicted)
- Density
- 1.270±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 14.77±0.50(Predicted)
- color
- Light Brown to Brown
- Stability:
- Hygroscopic
- InChI
- InChI=1S/C11H8FNO/c12-10-4-2-1-3-9(10)11-5-8(7-14)6-13-11/h1-7,13H
- InChIKey
- MQULPEUCGKEHEG-UHFFFAOYSA-N
- SMILES
- N1C(C2=CC=CC=C2F)=CC(C=O)=C1
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
N-Bromosuccinimide Price
- Product number
- F1074
- Product name
- 5-(2-Fluorophenyl)pyrrole-3-carboxaldehyde
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $98
- Updated
- 2025/07/31
- Product number
- F1074
- Product name
- 5-(2-Fluorophenyl)pyrrole-3-carboxaldehyde
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $295
- Updated
- 2025/07/31
- Product number
- F489655
- Product name
- 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde
- Packaging
- 1g
- Price
- $105
- Updated
- 2021/12/16
- Product number
- F489655
- Product name
- 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde
- Packaging
- 250mg
- Price
- $50
- Updated
- 2021/12/16
- Product number
- CS-W004473
- Product name
- 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde
- Purity
- 99.96%
- Packaging
- 10g
- Price
- $67
- Updated
- 2021/12/16
5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde Chemical Properties,Usage,Production
Description
5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde is an ether. It can be used to prepare vonoprazan fumarate, which is a potent orally active potassium-competitive acid blocker (P-CAB) with antisecretory activity. It is used in the study of acid-related diseases.
Chemical Properties
Light orange to Yellow to Green powder to crystal.
Uses
5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde acts as a reagent in the synthetic preparation of novel pyrrole derivatives as potassium-competitive acid blocker (P-CAB).
Application
5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde is a potassium ion-competitive acid blocker used in therapy Acid-related diseases, gastric ulcer, duodenal ulcer, reflux esophagitis, etc.
Preparation
Synthesis of 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde: Using pyrrole as raw material, after being protected by N-alkylation of triisopropylsilyl chloride, it is then reacted with Vilsmeier reagent to obtain 1H-Pyrrole-3-carbaldehyde, which is then purified by N-bromosuccinimide (NBS) bromination and 2-fluorophenylboronic acid for Suzuki coupling reaction to obtain crude 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde, which was purified with toluene. The total yield was 35.5%.
Definition
The 5-(2-fluorophenyl) -1H-pyrrole-3-formaldehyde is an important intermediate of Voranolan fumarate, a competitive potassium ion acid blocker. Voranolan fumarate treats gastric ulcers, duodenal ulcers, reflux esophagitis, etc. 5-(2-fluorophenyl) -1H-pyrrole-3-formaldehyde can be synthesized in one pot using 2-(2-fluorobenzoyl)malononitrile as raw material.
Hazard
5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde has acute toxin effects and is a skin and eye irritant.
Synthesis
1240948-77-9
881674-56-2
5-(2-Fluorophenyl)-1H-pyrrole-3-carbonitrile (5.0 g, 26.9 mmol) was added to a four-necked flask with THF (33 mL) and stirred at 15-25 °C until completely dissolved. Subsequently, acetic acid (55 mL) and water (11 mL) were added sequentially. Under nitrogen protection, Raney nickel catalyst (Kawaken Fine Chemicals Co., Ltd., NDHT-90, 2.5 mL, wet weight 4 g) was added. The reaction mixture was stirred vigorously at 15-25 °C for about 3 h under hydrogen atmosphere. Upon completion of the reaction, the hydrogen was replaced with nitrogen, the Raney nickel was removed by filtration, and the catalyst was washed with ethyl acetate (50 mL). The filtrate was adjusted to pH 7 with 5N aqueous sodium hydroxide (~180 mL) at 10-35 °C. The organic layer was washed sequentially with 5% aqueous sodium bicarbonate (25 mL) and 5% brine (25 mL). Water (25 mL) was added to the organic layer and washed again with water. Subsequently, the pH was adjusted to 3.0-3.5 with 6N hydrochloric acid at 15-25 °C. After stirring overnight, the organic layer was separated and washed with 5% brine (25 mL). The organic layer was concentrated under reduced pressure, warmed to 65-70 °C and then cooled to 45-55 °C with continued stirring for 1 hour. Further cooled to 15 °C, n-heptane (25 mL) was added dropwise and stirred at the same temperature for 1 hour. Finally, the mixture was stirred at 0-10 °C for 1 h. The precipitated crystals were collected by filtration, washed with ethyl acetate:n-heptane (1:2, 15 mL), and dried under reduced pressure at 50 °C to constant weight to afford the target product 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (23.9 g, 78% yield). The product was confirmed by 1H-NMR (300 MHz, DMSO-d6) and elemental analysis with melting point 123.0-126.0 °C.
References
[1] Patent: US2018/186736, 2018, A1. Location in patent: Paragraph 0139; 0140; 0141
[2] Patent: US2011/306769, 2011, A1. Location in patent: Page/Page column 28
[3] Patent: CN106432191, 2017, A. Location in patent: Paragraph 0019; 0022; 0023
[4] Patent: CN108558831, 2018, A. Location in patent: Paragraph 0161-0164
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View Lastest Price from 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde manufacturers
- Product
- 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde 881674-56-2
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%min
- Supply Ability
- 20tons
- Release date
- 2025-08-28
- Product
- 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde 881674-56-2
- Price
- US $0.00/Kg/Bag
- Min. Order
- 10g
- Purity
- 99%min
- Supply Ability
- 10kg
- Release date
- 2022-01-10
- Product
- 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde 881674-56-2
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 800kg
- Release date
- 2025-03-18