6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
- Product Name
- 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
- CAS No.
- 16732-73-3
- Chemical Name
- 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
- Synonyms
- 6-METHOXYINDOLE-2-CARBOXYLIC ACID;NSC 27988;AKOS JY2082559;6-Methoxindole-2-Carboxylic Acid;6-Methoxy-1H-indole-2-carboxylic aci;6-Methoxy-1H-indol-2-carboxylic acid;6-Methoxyindole-2-carboxylicacid,95%;Indole-2-carboxylic acid, 6-methoxy-;6-Methoxyindole-2-carboxylic acid 95%;6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
- CBNumber
- CB2341464
- Molecular Formula
- C10H9NO3
- Formula Weight
- 191.18
- MOL File
- 16732-73-3.mol
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID Property
- Melting point:
- 198-203℃
- Boiling point:
- 447.6±25.0 °C(Predicted)
- Density
- 1.381±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly)
- pka
- 4.54±0.30(Predicted)
- form
- Solid
- color
- Light Pink
- InChIKey
- XNBGANWAZJWOHS-UHFFFAOYSA-N
- CAS DataBase Reference
- 16732-73-3(CAS DataBase Reference)
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
- 722014
- Product name
- 6-Methoxyindole-2-carboxylic acid
- Purity
- 95%
- Packaging
- 1g
- Price
- $46.5
- Updated
- 2023/06/20
- Product number
- M262800
- Product name
- 6-Methoxyindole-2-carboxylic acid
- Packaging
- 2.5g
- Price
- $110
- Updated
- 2021/12/16
- Product number
- 012222
- Product name
- 6-Methoxy-1H-indole-2-carboxylic acid
- Packaging
- 500mg
- Price
- $10
- Updated
- 2021/12/16
- Product number
- 012222
- Product name
- 6-Methoxy-1H-indole-2-carboxylic acid
- Packaging
- 1g
- Price
- $15
- Updated
- 2021/12/16
- Product number
- J52566
- Product name
- 6-Methoxyindole-2-carboxylic acid
- Packaging
- 5g
- Price
- $49
- Updated
- 2021/12/16
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID Chemical Properties,Usage,Production
Uses
• ;Reactant for demethylation reactions using ionic liquids under microwave irradiation1• ;Reactant for preparation of pyrazinoindoledione via Ugi reaction and microwave-assisted cyclization2• ;Reactant for preparation of isoquinolinecarboxamides and their derivatives as opioid receptor antagonists3• ;Synthetic intermediate for preparation of indole fatty alcohol derivatives4• ;Reactant for preparation of acylaminoalkylindoles as MT2-selective melatonin antagonists5
Uses
- Reactant for demethylation reactions using ionic liquids under microwave irradiation
- Reactant for preparation of pyrazinoindoledione via Ugi reaction and microwave-assisted cyclization
- Reactant for preparation of isoquinolinecarboxamides and their derivatives as opioid receptor antagonists
- Synthetic intermediate for preparation of indole fatty alcohol derivatives
- Reactant for preparation of acylaminoalkylindoles as MT2-selective melatonin antagonists
Synthesis
15050-04-1
16732-73-3
Ethyl 6-methoxy-1H-indole-2-carboxylate (5.0 g) was dissolved in tetrahydrofuran (90 mL), lithium hydroxide (2.33 g) and water (30 mL) were added and the reaction was stirred for 16 hours at room temperature. After completion of the reaction, the reaction mixture was acidified with 10% hydrochloric acid solution, diluted with water and subsequently extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 6-methoxy-1H-indole-2-carboxylic acid (4.60 g). The resulting carboxylic acid (4.64 g) was dissolved with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.60 g) in dichloromethane (200 mL), N-methylpiperazine (3.23 mL) was added, and the reaction was stirred for 16 hours at room temperature. The reaction mixture was diluted with dichloromethane (200 mL), washed sequentially with water, saturated sodium bicarbonate solution and brine, the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0-10% 2M ammonia in methanol solution/dichloromethane) to give (6-methoxy-1H-indol-2-yl)-(4-methylpiperazin-1-yl)-methanone (6.60 g). The product (0.16 g) was dissolved in dichloromethane (10 mL) and 1M boron tribromide solution (1.5 mL) was added slowly and dropwise at room temperature, followed by heating the reaction mixture to reflux overnight. After cooling, the reaction was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0-10% 2M ammonia in methanol solution/dichloromethane) to give 6-methoxyindole-2-carboxylic acid as final product.
References
[1] Patent: US2003/207893, 2003, A1
[2] Patent: WO2004/22061, 2004, A1. Location in patent: Page/Page column 71
[3] Patent: EP1373204, 2016, B1. Location in patent: Paragraph 0216
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1943 - 1948
[5] Patent: CN106478606, 2017, A. Location in patent: Paragraph 0122; 0123; 0128; 0129
6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID manufacturers
- Product
- 6-Methoxyindole-2-carboxylic acid 16732-73-3
- Price
- US $0.01-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 tons
- Release date
- 2020-04-22
- Product
- 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID 16732-73-3
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 95%-99%
- Supply Ability
- as request
- Release date
- 2018-12-24