5-Methoxy-1H-indole-3-carbaldehyde

Base Information

• Chemical Name: 5-Methoxy-1H-indole-3-carbaldehyde
• CAS No.: 10601-19-1
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339900
• European Community (EC) Number: 234-220-5
• NSC Number: 521754
• UNII: 63C50ZW2D0
• DSSTox Substance ID: DTXSID70147471
• Nikkaji Number: J227.022F
• Wikipedia: 5-methoxyindole-3-carboxaldehyde
• Wikidata: Q27263605
• ChEMBL ID: CHEMBL1417263
• Mol file: 10601-19-1.mol

Synonyms:10601-19-1;5-Methoxyindole-3-carboxaldehyde;5-Methoxy-1H-indole-3-carbaldehyde;3-Formyl-5-methoxyindole;5-METHOXYINDOLE-3-CARBOXYALDEHYDE;5-Methoxy-indol-3-aldehyde;5-methoxy-3-formylindole;1H-Indole-3-carboxaldehyde, 5-methoxy-;5-Methoxyindole-3-carbaldehyde;MFCD00005623;5-Methoxyindole-3-aldehyde;UNII-63C50ZW2D0;63C50ZW2D0;EINECS 234-220-5;NSC-521754;NSC521754;5-Methoxy-3-indolealdehyde;Cambridge id 5190808;Oprea1_121493;MLS000575461;SCHEMBL1093746;5-methoxy-indole-3-carbaldehyde;CHEMBL1417263;DTXSID70147471;CHEBI:177034;5-Methoxy-3-indole carboxaldehyde;HMS2352K13;BCP26978;Indole-3-carboxaldehyde, 5-methoxy-;STK500559;5-methoxy-1h-indole-3-carboxaldehyde;5-METHOXYINDOLE-3-FORMALDEHYDE;AKOS000265020;5-Methoxy-1H-indole-3-carbaldehyde #;AB00456;AC-8769;CS-W007560;NSC 521754;1H-Indole-3-carboxaldehyde, 5-methoxy;NCGC00245572-01;SMR000184711;SY001986;5-Methoxyindole-3-carboxaldehyde, >=99%;AM20061194;FT-0620572;M1268;EN300-62417;VU0208691-3;M-3490;AB00519716-07;11Z-0705;Tert-butyl3-(4-aminophenyl)piperidine-1-carboxylate;Q27263605;F3385-4658;Z385369982

Chemical Property of 5-Methoxy-1H-indole-3-carbaldehyde

Chemical Property:

• Appearance/Colour: yellowish to beige crystalline powder or needles
• Vapor Pressure: 7.89E-06mmHg at 25°C
• Melting Point: 179-183 °C(lit.)
• Refractive Index: 1.679
• Boiling Point: 375.2 °C at 760 mmHg
• PKA: 15.21±0.30(Predicted)
• Flash Point: 180.7 °C
• PSA: 42.09000
• Density: 1.273 g/cm³
• LogP: 1.98900
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: insoluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

98% ^*data from raw suppliers

5-Methoxy-3-formylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2C=O
• Uses: reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators 1 reactant in preparation of inhibitor of the C-terminal domain of RNA polymerase II reactant in preparation of imidazopyridines and imidazobenzothiazoles 2 reactant in preparation of fluorescent neuroactive probes for brain imaging 3 reactant in preparation of antibacterial agents 4 reactant in synthesis of antiandrogens. reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulatorsreactant in preparation of inhibitor of the C-terminal domain of RNA polymerase IIreactant in preparation of imidazopyridines and imidazobenzothiazolesreactant in preparation of fluorescent neuroactive probes for brain imagingreactant in preparation of antibacterial agentsreactant in synthesis of antiandrogens

Technology Process of 5-Methoxy-1H-indole-3-carbaldehyde

There total 24 articles about 5-Methoxy-1H-indole-3-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5-methoxylindole (1006-94-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-methoxyindole-3-carboxaldehyde (10601-19-1)

Guidance literature:

With trichlorophosphate; at 0 - 20 ℃;

DOI:10.1021/ol400884v

Reference yield: 92.0%

5-methoxylindole (1006-94-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → 5-methoxyindole-3-carboxaldehyde (10601-19-1)

Guidance literature:

With iron(III) chloride; ammonia; In water; N,N-dimethyl-formamide; at 130 ℃; for 1h;

DOI:10.1055/s-0036-1589079

Reference yield: 91.0%

5-methoxylindole (1006-94-6) + hexamethylenetetramine (100-97-0) → 5-methoxyindole-3-carboxaldehyde (10601-19-1)

Guidance literature:

With iodine; oxygen; pyrographite; In N,N-dimethyl-formamide; at 120 ℃; for 0.8h;

DOI:10.1016/j.tetlet.2017.05.050

upstream raw materials:

5-methoxylindole

chloroform

N,N-dimethyl-formamide

1,3-diacetyl-2-(5-methoxyindol-3-yl)-4-imidazoline

Downstream raw materials:

2-(5-Methoxy-1H-indol-3-yl)-5,7-dimethyl-1,3-diaza-tricyclo[3.3.1.1^3,7]decan-6-one

5-methoxy-1-(p-methylphenylsulfonyl)-1H-indol-3-carbaldehyde

5-methoxy-1H-indole-3-carbonitrile

5-methoxy-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde

Refernces

• 1、 Chen, Chou-Hsiung,Genapathy, Sivaneswary,Fischer, Peter M.,Chan, Weng C.. "A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues". . p. 9764 - 9768. Retrieved 2014.
• 2、 Tsotinis, Andrew,Vlachou, Margarita,Papahatjis, Demetris P.,Calogeropoulou, Theodora,Nikas, Spyros P.,Garratt, Peter J.,Piccio, Vincent,Vonhoff, Stefan,Davidson, Kathryn,Teh, Muy-Teck,Sugden, David. "Mapping the melatonin receptor. 7. Subtype selective ligands based on β-substituted N-acyl-5-methoxytryptamines and β-Substituted N-acyl-5-methoxy-1-methyltryptamines". . p. 3509 - 3519. Retrieved 2006.
• 3、 Chen, Jie,Yan, Jun,Hu, Jinhui,Pang, Yanqing,Huang, Ling,Li, Xingshu. "Synthesis, biological evaluation and mechanism study of chalcone analogues as novel anti-cancer agents". . p. 68128 - 68135. Retrieved 2015.
• 4、 Xu, Shengtao,Yao, Hong,Pei, Lingling,Hu, Mei,Li, Dahong,Qiu, Yangyi,Wang, Guangyu,Wu, Liang,Yao, Hequan,Zhu, Zheying,Xu, Jinyi. "Design, synthesis, and biological evaluation of NAD(P)H: Quinone oxidoreductase (NQO1)-targeted oridonin prodrugs possessing indolequinone moiety for hypoxia-selective activation". . p. 310 - 321. Retrieved 2017.
• 5、 Selen Gurkan-Alp,Mumcuoglu, Mine,Andac, Cenk A.,Dayanc, Emre,Cetin-Atalay, Rengul,Buyukbingol, Erdem. "Synthesis, anticancer activities and molecular modeling studies of novel indole retinoid derivatives". . p. 346 - 354. Retrieved 2012.
• 6、 Ding, Yangyang,Kang, Congmin,Liu, Kai. "Synthesis and Antiproliferative Activity of New N-Acylhydrazone Derivatives Containing Benzothiazole and Indole Based Moiety". . p. 345 - 352. Retrieved 2020.
• 7、 Sung, Ha Kyoung,Kim, Dong Hyun,Kim, Joon Seok,Park, Chan Pil. "C3-Formylation of Indoles in Continuous Flow". . p. 388 - 392. Retrieved 2021.
• 8、 Zhang, Pu Yong,Wan, Sheng Biao,Ren, Su Mei,Jiang, Tao. "First total synthesis of marine alkaloid hyrtiosulawesine". . p. 1307 - 1309. Retrieved 2010.
• 9、 Itoh, Tomoki,Abe, Takumi,Nakamura, Shuhei,Ishikura, Minoru. "Cu-mediated oxidative dimerization of skatole to tryptanthrin, an indolo[2,1-b]quinazolone alkaloid". . p. 1423 - 1428. Retrieved 2015.
• 10、 Lin, Jin-Hong,Xiao, Ji-Chang,Zhu, Yu-Rong. "Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide". supporting information. . Retrieved 2021/11/22.