5-bromo-2,3-dimethyl-1H-indole

Base Information

• Chemical Name: 5-bromo-2,3-dimethyl-1H-indole
• CAS No.: 4583-55-5
• Molecular Formula: C10H10BrN
• Molecular Weight: 224.1
• Hs Code.: 2933990090
• ChEMBL ID: CHEMBL5194440
• DSSTox Substance ID: DTXSID30510046
• Nikkaji Number: J2.453.103A
• Wikidata: Q72454976
• Mol file: 4583-55-5.mol

Synonyms:5-bromo-2,3-dimethyl-1H-indole;4583-55-5;5-Bromo-2,3-dimethylindole;MFCD00850844;1H-Indole, 5-bromo-2,3-dimethyl-;SCHEMBL410289;CHEMBL5194440;DTXSID30510046;IOGAIEWEHFPGNO-UHFFFAOYSA-N;AKOS000283161;CCG-340069;AC-26894;AS-19043;SY104933;B5272;BB 0304429;CS-0153594;C75233;AF-963/00523045

Chemical Property of 5-bromo-2,3-dimethyl-1H-indole

Chemical Property:

• Melting Point: 136-137 °C
• Refractive Index: 1.5923
• Boiling Point: 340.35 °C at 760 mmHg
• PKA: 16.91±0.30(Predicted)
• Flash Point: 159.638 °C
• PSA: 15.79000
• Density: 1.488 g/cm³
• LogP: 3.54720
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 222.99966
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

99%, ^*data from raw suppliers

5-Bromo-2,3-dimethylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(NC2=C1C=C(C=C2)Br)C
• Uses: 5-Bromo-2,3-dimethylindole is used to prepare 1-[(arylsulfonyl)amino]alkylindole derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists. It is also used to prepare modulators of secreted frizzled related protein-1 (SFRP-1).

Technology Process of 5-bromo-2,3-dimethyl-1H-indole

There total 16 articles about 5-bromo-2,3-dimethyl-1H-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: 94.0%

5-bromo-2-methyl-1H-indole (1075-34-9) + C17H19NO2 → 5-bromo-2,3-dimethyl-1H-indole (4583-55-5)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; In 1,2-dichloro-ethane; at 110 ℃; for 16h;

DOI:10.1021/acscatal.0c01141

Reference yield: 81.0%

1-azido-4-bromo-2-(1-ethoxy-2-methylpropan-2-yl)benzene (1417407-56-7) → 5-bromo-2,3-dimethyl-1H-indole (4583-55-5)

Guidance literature:

With iron(II) bromide; In toluene; at 140 ℃; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1021/ja3113565

Reference yield: 80.0%

4-bromophenylhydrazine hydrochloride (622-88-8,41931-18-4) + butanone (78-93-3) → 5-bromo-2,3-dimethyl-1H-indole (4583-55-5)

Guidance literature:

In acetic acid; for 2h; Heating;

DOI:10.3987/COM-06-S(K)22

upstream raw materials:

4-bromophenylhydrazine hydrochloride

butanone

sec.-butyllithium

4-bromobenzenediazonium tetrafluoroborate

Downstream raw materials:

N-(2-acetyl-4-bromophenyl)acetamide

5-bromo-2,3-dimethyl-1-(phenylmethyl)-1H-indole

Refernces

• 1、 Hughes-Whiffing, Christopher A.,Perry, Alexis. "One-pot, three-component Fischer indolisation-N-alkylation for rapid synthesis of 1,2,3-trisubstituted indoles". supporting information. p. 627 - 634. Retrieved 2021/02/06.
• 2、 -. "Heterocyclic com pounds and organic light-emitting diode including the same". Paragraph 0444; 0463-0468; 0624-0630. . Retrieved 2021/01/29.