| Identification | More | [Name]
Indole-4-carboxaldehyde | [CAS]
1074-86-8 | [Synonyms]
1H-INDOLE-4-CARBALDEHYDE
1H-INDOLE-4-CARBOXALDEHYDE
4-FORMYLINDOLE
4-INDOLECARBALDEHYDE
4-INDOLE-CARBOXALDEHYDE
INDOLE-4-ALDEHYDE
INDOLE-4-CARBALDEHYDE
INDOLE-4-CARBOXALDEHYDE
NSC 337264
RARECHEM AH BS 0110
4-Formyl-1H-indole
3-Indole Carboxyaldehyde
1H-Indole-4-carboxaldehyde (9CI)
1H-Indole-4-carboxaldehyde 98%
INDOLE-4-CARBOXALDEHYDE (4-FORMYLINDOLE)
4-FLUOROINDOLE
Indole-4-carboxaldehyde ,98% | [EINECS(EC#)]
625-162-5 | [Molecular Formula]
C9H7NO | [MDL Number]
MFCD01632221 | [Molecular Weight]
145.16 | [MOL File]
1074-86-8.mol |
| Chemical Properties | Back Directory | [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 Cold | [solubility ]
DMF: 10 mg/ml; DMSO: 3 mg/ml; Ethanol: 10 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml | [form ]
powder to crystal | [pka]
15.84±0.30(Predicted) | [color ]
Light yellow to Brown | [Water Solubility ]
Soluble in ethanol and acetone. Insoluble in water. | [Sensitive ]
Air Sensitive | [Detection Methods]
HPLC,NMR | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H317-H319 | [Precautionary statements ]
P280-P301+P312+P330-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to dark brown solid | [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. | [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.
| [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 |
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