Indole-4-carboxaldehyde CAS 1074-86-8
Introduction：Basic information about Indole-4-carboxaldehyde CAS 1074-86-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Indole-4-carboxaldehyde Basic information
| Product Name: | Indole-4-carboxaldehyde |
| Synonyms: | 1H-indol-4-carbaldehyde;1H-indole-4-carbaldehyde(SALTDATA: FREE);INDOLE-4-CARBALDEHYDE;INDOLE-4-CARBOXALDEHYDE;INDOLE-4-ALDEHYDE;4-FORMYLINDOLE;4-INDOLECARBALDEHYDE;4-INDOLE-CARBOXALDEHYDE |
| CAS: | 1074-86-8 |
| MF: | C9H7NO |
| MW: | 145.16 |
| EINECS: | 625-162-5 |
| Product Categories: | Simple Indoles;Building Blocks;IndolesOxindoles;Indoles and derivatives;Indole;Indoles;ALDEHYDE;Aldehydes;blocks;pharmacetical;Heterocycle-Indole series |
| Mol File: | 1074-86-8.mol |
Indole-4-carboxaldehyde Chemical Properties
| Melting point | 139-143 °C(lit.) |
| Boiling point | 339.1±15.0 °C(Predicted) |
| density | 1.278±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | DMF: 10 mg/ml; DMSO: 3 mg/ml; Ethanol: 10 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml |
| pka | 15.84±0.30(Predicted) |
| form | powder to crystal |
| color | Light yellow to Brown |
| Water Solubility | Soluble in ethanol and acetone. Insoluble in water. |
| Sensitive | Air Sensitive |
| InChI | InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H |
| InChIKey | JFDDFGLNZWNJTK-UHFFFAOYSA-N |
| SMILES | N1C2=C(C(C=O)=CC=C2)C=C1 |
| CAS DataBase Reference | 1074-86-8(CAS DataBase Reference) |
| NIST Chemistry Reference | 1H-indole-4-carboxaldehyde(1074-86-8) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-36-43 |
| Safety Statements | 26-36/37 |
| WGK Germany | 3 |
| Hazard Note | Irritant/Keep Cold |
| HazardClass | IRRITANT |
| HS Code | 29333990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Irrit. 2 Skin Sens. 1 |
| Chemical Properties | White to dark brown solid |
| Uses | Indole-4-carboxaldehyde is usually used as reactant in Biginelli reaction,preparation of antitumor agents,intramolecular Friedel-Crafts acylation,preparation of inhibitors of cell division in E. Coli,synthesis of Hantzsch pyridine-containing Schiff bases. |
| Uses | 4-Indolecarbaldehyde is a synthetic intermediate used for pharmaceutical synthesis. Also used as reactant in Biginelli reaction, synthesis of aurora kinase A inhibitors, preparation of antitumor agents, intermolecular Friedel-Crafts acylation, preparation of inhibitors of cell division in E. coli and synthesis of Hantzsch pyridine-containing Schiff bases. |
| Definition | ChEBI: Indole-4-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 4 has been replaced by a formyl group. It has a role as an algal metabolite. It is a member of indoles and a heteroarenecarbaldehyde. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 46, p. 1752, 1981 DOI: 10.1021/jo00321a053 Tetrahedron, 39, p. 3695, 1983 DOI: 10.1016/S0040-4020(01)88608-7 |
| General Description | Indole-4-carboxaldehyde participates in the synthesis of arcyriacyanin A. Synthesis of 4-indole-4-carboxaldehyde has been reported. Intramolecular Friedel-Crafts (FC) acylation of indole-4-carboxaldehyde has been reported. |
| Synthesis | Tetrapropylammonium perruthenate (0.3 g, 0.85 mmol) was added in portions to a mixture of alcohol product from 1H-Indole-4-Methanol (2.5 g, 17 mmol), N-methylmorpholine N-oxide (3.0 g, 25 mmol) and 4 A molecular sieves (3.0 g) in anhydrous methylene chloride (30 mL) at room temperature. The mixture was stirred at room temperature under nitrogen for 1 h and then filtered. The filtrate was concentrated in vacuo, and the residue was purified by chromatography (SiO2, CH2Cl2) to provide Indole-4-carboxaldehyde as a white powder (2.0 g, 80percent): 1H NMR (300 MHz, CDCl3) δ10.2 (s, 1H), 8.52 (br s, 1H), 7.64-7.69 (m, 2H), 7.31-7.44 (m, 3H), CI MS m/z=146 [C9H7NO+H]+. |
| References | [1] Journal of Organic Chemistry, 1980, vol. 45, # 16, p. 3350 - 3352 [2] Journal of Medicinal Chemistry, 2002, vol. 45, # 26, p. 5755 - 5775 [3] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 8, p. 983 - 988 [4] Patent: US2006/111385, 2006, A1. Location in patent: Page/Page column 20 [5] Chemistry Letters, 1980, p. 813 - 816 |
Indole-4-carboxaldehyde Preparation Products And Raw materials
| Raw materials | 1H-Indole-4-carboxaldehyde, 1-[(4-methylphenyl)sulfonyl]--->(E)-Methyl 2-(2-(diMethylaMino)vinyl)-3-nitrobenzoate-->INDOLE-4-METHANOL-->Methyl 2-methyl-3-nitrobenzoate-->3-Nitro-o-xylene-->4-Cyanoindole-->[(1H-Indol-4-yl)methyl](methyl)amine-->Methyl indole-4-carboxylate-->TETRAPROPYLAMMONIUM PERRUTHENATE-->N-ForMylsaccharin |
| Preparation Products | 4-(Azetidin-1-ylMethyl)-1H-indole-->1-(PHENYLMETHYL)-1H-INDOLE-4-CARBOXALDEHYDE-->(1-METHYL-1H-INDOL-4-YL)METHANOL |
