1-Boc-indole

Base Information

• Chemical Name: 1-Boc-indole
• CAS No.: 75400-67-8
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.268
• Hs Code.: 2933990090
• European Community (EC) Number: 806-633-6
• DSSTox Substance ID: DTXSID10393394
• Nikkaji Number: J416.460A
• Mol file: 75400-67-8.mol

Synonyms:1-Boc-indole;75400-67-8;tert-butyl 1H-indole-1-carboxylate;tert-butyl indole-1-carboxylate;tert-Butyl 1-indolecarboxylate;N-BOC-INDOLE;1H-INDOLE-1-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER;1-(TERT-BUTOXYCARBONYL)INDOLE;N-Boc indole;1-tert-butoxycarbonylindole;SCHEMBL691666;1-tert-Butoxycarbonyl-1H-indole;DTXSID10393394;OWPIFQXNMLDXKW-UHFFFAOYSA-N;AB8727;MFCD02093939;tert-Butyl 1-indolecarboxylate, 97%;AKOS015837044;AB10863;AM87172;indole-1-carboxlic acid tert-butyl ester;1-indole carboxylic acid tert-butyl ester;AS-60099;CS-0008655;FT-0607416;1H-indole-1-carboxylic acid tert-butyl ester

Chemical Property of 1-Boc-indole

Chemical Property:

• Vapor Pressure: 0.000368mmHg at 25°C
• Melting Point: 24-26 °C
• Refractive Index: n20/D 1.543(lit.)
• Boiling Point: 318.2 °C at 760 mmHg
• Flash Point: 146.2 °C
• PSA: 31.23000
• Density: 1.07 g/cm³
• LogP: 3.42450
• Storage Temp.: Keep Cold
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 217.110278721
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

99% ^*data from raw suppliers

1-BOC-Indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC2=CC=CC=C21
• Uses: Reactant for preparation of:Potent plant-growth inhibitorsCannabinoid CB2 receptor ligandsAnalogues of isomeridianin G and evaluation as GSK-3β inhibitorsInhibitor of the Yersinia pestis salicylate adenylation domain YbtECholecystokinin-2 receptor antagonistsAntileishmanial agentsReactant for:Palladium-catalyzed Suzuki-Miyaura cross coupling reactionsFriedel-Crafts alkylation reactions

Technology Process of 1-Boc-indole

There total 11 articles about 1-Boc-indole 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: 58.0%

1,3-dioxoisoindolin-2-yl 3-((tert-butoxycarbonyl)(phenyl)amino)propanoate → tertbutylethyl(phenyl)carbamate (210285-26-0) + indole-1-carboxylic acid tert-butyl ester (75400-67-8) + 1-(tert-butoxycarbonyl)indoline (143262-10-6)

Guidance literature:

With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; trifluoroacetic acid; In dimethyl sulfoxide; at 20 ℃; for 0.583333h; Irradiation;

DOI:10.1021/acs.joc.9b00432

Reference yield: 53.0%

benzaldehyde (100-52-7) + tert-butyl 3-iodo-1H-indol-1-carboxylate (192189-07-4) → 3-(hydroxyphenylmethyl)indole-1-carboxylic acid tert-butyl ester (1239950-41-4) + indole-1-carboxylic acid tert-butyl ester (75400-67-8)

Guidance literature:

tert-butyl 3-iodo-1H-indol-1-carboxylate; With TurboGrignard; In tetrahydrofuran; at 0 ℃; for 0.2h;

benzaldehyde; In tetrahydrofuran; at 0 ℃; for 0.116667h;

DOI:10.1002/chem.200903284

Reference yield: 43.0%

1-iodo-1-(3,4,5-trimethoxyphenyl)ethylene + 2-((trimethylsilyl)ethynyl)phenylaminocarboxylic acid tert-butyl ester (187099-49-6) → C24H27NO5 (1334314-86-1) + indole-1-carboxylic acid tert-butyl ester (75400-67-8)

Guidance literature:

1-iodo-1-(3,4,5-trimethoxyphenyl)ethylene; With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; N,N-dimethyl-formamide; at 20 ℃; for 0.0333333h;

2-((trimethylsilyl)ethynyl)phenylaminocarboxylic acid tert-butyl ester; In water; N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201100540

upstream raw materials:

benzophenone

1-(tert-butoxycarbonyl)indoline

methyl-phenyl-thioether

benzenediazonium tetrafluoroborate

Downstream raw materials:

N-Boc-indole-2-boronic acid

phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate

N-boc-2-oxyindole

2-chlorosulfonyl-indole-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Hentz, Alexandre,Retailleau, Pascal,Gandon, Vincent,Cariou, Kevin,Dodd, Robert H.. "Transition-metal-free tunable chemoselective nfunctionalization of indoles with ynamides". supporting information. p. 8333 - 8337. Retrieved 2014/08/18.
• 2、 Tricotet, Thomas,O'Shea, Donal F.. "Automated generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors". experimental part. p. 6678 - 6686. Retrieved 2010/08/20.