Cas no 850349-72-3 (1-Boc-5-bromo-3-iodo-indole)

1-Boc-5-bromo-3-iodo-indole is a versatile intermediate in organic synthesis, particularly in the preparation of complex indole derivatives. The presence of both bromo and iodo substituents at the 5- and 3-positions, respectively, allows for selective functionalization via cross-coupling reactions, such as Suzuki or Sonogashira couplings. The Boc (tert-butoxycarbonyl) protecting group enhances stability and facilitates further modifications under controlled conditions. This compound is valuable in pharmaceutical and agrochemical research, where indole scaffolds are frequently employed. Its well-defined reactivity profile makes it a reliable building block for constructing structurally diverse compounds with potential biological activity. Proper handling under inert conditions is recommended due to its sensitivity.
1-Boc-5-bromo-3-iodo-indole structure
1-Boc-5-bromo-3-iodo-indole structure
Product Name:1-Boc-5-bromo-3-iodo-indole
CAS No:850349-72-3
MF:C13H13BrINO2
MW:422.056295156479
MDL:MFCD05864761
CID:68957
PubChem ID:17749978
Update Time:2025-06-07

1-Boc-5-bromo-3-iodo-indole Chemical and Physical Properties

Names and Identifiers

    • tert-Butyl 5-bromo-3-iodo-1H-indole-1-carboxylate
    • 5-Bromo-3-iodoindole-1-carboxylic acid tert-butyl ester
    • tert-butyl 5-bromo-3-iodoindole-1-carboxylate
    • 1-Boc-5-bromo-3-iodo-indole
    • 1,1-Dimethylethyl 5-bromo-3-iodo-1H-indole-1-carboxylate (ACI)
    • AKOS015898532
    • 5-BROMO-3-IODOINDOLE, N-BOC PROTECTED
    • SS-6022
    • MFCD05864761
    • 850349-72-3
    • SCHEMBL12615032
    • MCFJOLCLHJYCDS-UHFFFAOYSA-N
    • CS-0045064
    • SY288527
    • 1-Boc-5-bromo-3-iodoindole
    • 1-Boc-5-bromo-3-iodo-1H-indole
    • 5-Bromo-3-iodo-indole-1-carboxylic acid tert-butyl ester
    • DB-015403
    • BCP07601
    • 1H-Indole-1-carboxylic acid, 5-bromo-3-iodo-, 1,1-dimethylethyl ester
    • DTXSID20590135
    • MDL： MFCD05864761
    • Inchi： 1S/C13H13BrINO2/c1-13(2,3)18-12(17)16-7-10(15)9-6-8(14)4-5-11(9)16/h4-7H,1-3H3
    • InChI Key： MCFJOLCLHJYCDS-UHFFFAOYSA-N
    • SMILES： O=C(N1C2C(=CC(=CC=2)Br)C(I)=C1)OC(C)(C)C

Computed Properties

  • Exact Mass: 420.91700
  • Monoisotopic Mass: 420.917
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 3
  • Complexity: 331
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 4.6
  • Topological Polar Surface Area: 31.2A^2

Experimental Properties

  • Density: 1.816
  • Boiling Point: 433.976°C at 760 mmHg
  • Flash Point: 216.261°C
  • Refractive Index: 1.64
  • PSA: 31.23000
  • LogP: 4.79160

1-Boc-5-bromo-3-iodo-indole Security Information

  • Hazard Statement： Irritant
  • Hazardous Material Identification： Xi

1-Boc-5-bromo-3-iodo-indole Customs Data

  • HS CODE：2933990090
  • Customs Data：

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

1-Boc-5-bromo-3-iodo-indole Pricemore >>

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1-Boc-5-bromo-3-iodo-indole Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Dichloromethane
Reference
Multicomponent Reactions Based on Sonogashira Coupling
Karpov, Alexei S., 2005, , ,

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium hydroxide ,  Iodine Solvents: Dimethylformamide
2.1 Reagents: Triethylamine Solvents: Dichloromethane
Reference
Multicomponent Reactions Based on Sonogashira Coupling
Karpov, Alexei S., 2005, , ,

Production Method 3

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  3 h, rt
Reference
Mono-selective β-C-H arylation of N-methylated amino acids and peptides promoted by the 2-(methylthio)aniline directing group
Kinsinger, Thorsten; et al, Organic & Biomolecular Chemistry, 2019, 17(22), 5595-5600

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium hydroxide ,  Iodine ,  Potassium iodide Solvents: Methanol ,  Water ;  3 h, rt
2.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  3 h, rt
Reference
Mono-selective β-C-H arylation of N-methylated amino acids and peptides promoted by the 2-(methylthio)aniline directing group
Kinsinger, Thorsten; et al, Organic & Biomolecular Chemistry, 2019, 17(22), 5595-5600

Production Method 5

Reaction Conditions
1.1 Reagents: N-Iodosuccinimide ,  2-Iodoxybenzoic acid Solvents: Dimethyl sulfoxide ;  3 h, 25 °C
Reference
Facile synthesis of isatins by direct oxidation of indoles and 3-iodoindoles using NIS/IBX
Chandra, Ajeet; et al, Tetrahedron, 2019, 75(14), 2169-2174

1-Boc-5-bromo-3-iodo-indole Raw materials

1-Boc-5-bromo-3-iodo-indole Preparation Products

1-Boc-5-bromo-3-iodo-indole Related Literature

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