Methyl indolyl-3-glyoxylate
- CAS No.
- 18372-22-0
- Chemical Name:
- Methyl indolyl-3-glyoxylate
- Synonyms
- Methyl 2-(1H-indol-3-yl)-2-oxoacetate;IGA-OMe;METHYL 3-INDOLEGLYOXYLATE;Methyl Indol-3-Glyoxylate;Methylindole-3-glyoxylate;METHYL INDOLYL-3-GLYOXYLATE;Methyl 3-indoleglyoxylate 98%;METHYL (INDOL-3-YL)OXOACETATE;INDOLE-3-GLYOXYLIC METHYL ESTER;Methyl α-oxo-1H-indole-3-acetate
- CBNumber:
- CB8174842
- Molecular Formula:
- C11H9NO3
- Molecular Weight:
- 203.19
- MDL Number:
- MFCD00047173
- MOL File:
- 18372-22-0.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 227-230 °C (lit.) |
|---|---|
| Boiling point | 383.2±15.0 °C(Predicted) |
| Density | 1.324±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Acetone, Methanol |
| form | Solid |
| pka | 14.54±0.30(Predicted) |
| color | Pale Yellow |
| Stability | Temperature Sensitive |
| InChI | InChI=1S/C11H9NO3/c1-15-11(14)10(13)8-6-12-9-5-3-2-4-7(8)9/h2-6,12H,1H3 |
| InChIKey | VFIJGAWYVXDYLK-UHFFFAOYSA-N |
| SMILES | C12C=CC=CC=1NC=C2C(=O)C(=O)OC |
| CAS DataBase Reference | 18372-22-0(CAS DataBase Reference) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319-H335 |
| Precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| target organs | Respiratory system |
| PPE | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| HS Code | 2933.99.8290 |
| HazardClass | IRRITANT |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
Methyl indolyl-3-glyoxylate price More Price(67)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 515213 | Methyl 3-indoleglyoxylate 98% | 18372-22-0 | 5g | $154 | 2026-04-30 | Buy |
| TCI Chemical | M3254 | Methyl 3-Indoleglyoxylate | 18372-22-0 | 1G | $49 | 2026-04-30 | Buy |
| TCI Chemical | M3254 | Methyl 3-Indoleglyoxylate | 18372-22-0 | 5G | $196 | 2026-04-30 | Buy |
| TRC | TRC-M313500-2G | Methyl Indolyl-3-glyoxylate | 18372-22-0 | 2g | $117 | 2026-06-03 | Buy |
| TRC | TRC-M313500-200MG | Methyl Indolyl-3-glyoxylate | 18372-22-0 | 200mg | $70 | 2026-06-03 | Buy |
Methyl indolyl-3-glyoxylate Chemical Properties, Uses, Production
Chemical Properties
Pale Yellow Fine Powder
Uses
Reactant for preparation of sotrastaurin analogs as protein kinase inhibitors 1 Reactant for synthesis of GSK-3 inhibitors 2 Reactant for Diels-Alder cycloaddition 3 Reactant for preparation of a Janus kinase 3 inhibitor 4 Reactant for synthesis of cephalandole alkaloids 5 Reactant for stereoselective preparation of COX-2 inhibitor as anticancer agent 6 Reactant for synthesis of cycloalkene indole carbazole alkaloids via ring-closing metathesis.
Uses
Methyl Indolyl-3-glyoxylate (cas# 18372-22-0) is a compound useful in organic synthesis.
Synthesis
120-72-9
79-37-8
124-41-4
18372-22-0
To a three-necked flask equipped with a magnetic stirrer and two addition funnels were added indole (10.1 g, 0.086 mol) and 100 mL of diethyl ether. Oxalyl chloride (7.3 mL, 0.086 mol) was added slowly and dropwise over 0.5 h at 0 °C under nitrogen protection. A yellow precipitate appeared in the reaction mixture and stirring was continued for 0.5 hr. Subsequently, the reaction mixture was cooled to -70 °C via a dry ice bath and sodium methanolate (25% methanol solution, 37.3 g, 0.173 mol) was added dropwise over 1 hour. After the dropwise addition, the reaction mixture was slowly warmed to 0 °C and 50 mL of water was added. The precipitate was collected by filtration, washed with water several times, and dried under vacuum at 60 ℃ to obtain methyl indole-3-glyoxylate as a yellow powder with 90% yield, which could be used in the next reaction without further purification. In another three-necked flask equipped with a magnetic stirrer and a dosing funnel, 3-indoleacetamide (8.0 g, 0.046 mol), indole-3-glyoxalic acid methyl ester (10.0 g, 0.049 mol) and 80 mL of tetrahydrofuran were added. A solution of potassium tert-butanolate (15.2 g, 0.135 mol) in 130 mL of tetrahydrofuran was slowly added dropwise over a period of 1.5 h at 0 °C under nitrogen protection. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirring was continued for 3 hours. Subsequently, a 35% aqueous hydrochloric acid solution (64 mL) was added slowly and dropwise over 1 hour. Upon completion of the reaction, 200 mL of ethyl acetate and 100 mL of water were added and stirred until completely dissolved. The organic phase was separated, washed sequentially with water to neutral, brine once, and dried with anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated. Add 1:1 (v/v) mixed solvent of ethyl acetate and n-hexane dropwise to the concentrated solution, and crystallize at 50~60°C to obtain 3,4-bisindolylmaleimide pure as red crystals.
References
[1] Chinese Chemical Letters, 2018, vol. 29, # 3, p. 513 - 516
[2] Journal of Materials Chemistry A, 2018, vol. 6, # 39, p. 18794 - 18798
[3] Archiv der Pharmazie, 2013, vol. 346, # 5, p. 349 - 358
[4] Patent: CN104693198, 2017, B. Location in patent: Paragraph 0035; 0036
[5] Patent: WO2018/132636, 2018, A1. Location in patent: Page/Page column 41
Methyl indolyl-3-glyoxylate Preparation Products And Raw materials
Raw materials
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Jiangxi Yuanxing Biomedical Technology Co., Ltd. | 13642377995 | 258676831@qq.com | China | 305 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Chembest Research Laboratories Limited | 021-20908456 | sales@BioChemBest.com | China | 5996 | 61 |
| Carbott PharmTech Inc. | 0535-6385396 | info@carbottpharm.com | China | 996 | 56 |
| Capot Chemical Co., Ltd | +86 (0) 571 85 58 67 18 | China | 18187 | 66 | |
| Adamas Reagent, Ltd. | 400-6009262 15618770481 | yhx@titansci.com | China | 14098 | 59 |
| Shanghai Hanhong Scientific Co.,Ltd. | 021-54306202 13764082696 | info@hanhongsci.com | China | 42917 | 64 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| Wuhan Luohua Medical Technology Co.,Ltd. | 13477084141; 13477084141 | sales@luohuapharm.com | China | 468 | 60 |
View Latest Price from Methyl indolyl-3-glyoxylate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2019-07-06 | Methyl indolyl-3-glyoxylate
18372-22-0
|
$1.00 | 1KG | 95% | 500kg | Career Henan Chemical Co |
-
- Methyl indolyl-3-glyoxylate
18372-22-0
- $1.00
- 95%
- Career Henan Chemical Co
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