6-bromo-1H-indole-2-carbaldehyde

Base Information

• Chemical Name: 6-bromo-1H-indole-2-carbaldehyde
• CAS No.: 105191-12-6
• Molecular Formula: C9H6BrNO
• Molecular Weight: 224.057
• Hs Code.: 29349990
• European Community (EC) Number: 831-173-8
• DSSTox Substance ID: DTXSID90544009
• Wikidata: Q82420982
• Mol file: 105191-12-6.mol

Synonyms:6-bromo-1H-indole-2-carbaldehyde;105191-12-6;6-Bromo-1H-indole-2-carboxaldehyde;1H-Indole-2-carboxaldehyde, 6-bromo-;MFCD06738308;6-bromoindole carboxaldehyde;SCHEMBL2550820;DTXSID90544009;IGZHNWFLHSANSN-UHFFFAOYSA-N;AKOS005072387;AB26861;ED-0747;NCGC00338898-01;SY066232;CS-0050314;EN300-28288;6-Bromo-1H-indole-2-carbaldehyde, AldrichCPR;P10395;AB01148719-03;A801159;W-204548;Z228589116

Chemical Property of 6-bromo-1H-indole-2-carbaldehyde

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 181-183 °C
• Refractive Index: 1.752
• Boiling Point: 395.55 °C at 760 mmHg
• PKA: 14.12±0.30(Predicted)
• Flash Point: 193.022 °C
• PSA: 32.86000
• Density: 1.727 g/cm³
• LogP: 2.74290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 222.96328
• Heavy Atom Count: 12
• Complexity: 185

Purity/Quality:

98%min ^*data from raw suppliers

6-Bromo-1H-indole-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)NC(=C2)C=O
• Uses: 6-Bromo-1H-indole-2-carbaldehyde is used as a reactant in the optimization of bis-indole pyruvate kinase inhibitors as potential therapeutics for the methicillin-resistant Staphylococcus aureus infection treatment.

Technology Process of 6-bromo-1H-indole-2-carbaldehyde

There total 4 articles about 6-bromo-1H-indole-2-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%

(6-bromo-1H-indol-2-yl)methanol (923197-75-5) → 6-bromo-1H-indole-2-carbaldehyde (105191-12-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;

Reference yield:

6-bromo-indole-2-carboxylic acid(Ref.7.) (16732-65-3) → 6-bromo-1H-indole-2-carbaldehyde (105191-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: 70 percent / Mangandioxid / diethyl ether / 2 h / Ambient temperature

With lithium aluminium tetrahydride; Mangandioxid; In diethyl ether;

Reference yield:

6-bromoindole 2-carboxylic acid methyl ester (372089-59-3) → 6-bromo-1H-indole-2-carbaldehyde (105191-12-6)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 5.5 h / 0 - 20 °C

2: manganese(IV) oxide / acetonitrile / 20 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; In tetrahydrofuran; acetonitrile;

upstream raw materials:

(6-bromo-1H-indol-2-yl)methanol

6-bromo-indole-2-carboxylic acid(Ref_.7.)

6-bromoindole 2-carboxylic acid methyl ester

ethyl 6-bromo-1H-indole-2-carboxylate

Refernces

• 1、 Hao, Yanke,Zhou, Pan,Niu, Kaikai,Song, Hongjian,Liu, Yuxiu,Zhang, Jingjing,Wang, Qingmin. "Synthesis of Indole- and Pyrrole-Fused Seven-Membered Nitrogen Heterocycles via Acid-Base Switchable Cyclization Involving Cleavage of Amide C?N Bonds". supporting information. p. 281 - 285. Retrieved 2021/11/09.
• 2、 Liu, Yonggui,Luo, Guoyong,Yang, Xing,Jiang, Shichun,Xue, Wei,Chi, Yonggui Robin,Jin, Zhichao. "Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones". supporting information. p. 442 - 448. Retrieved 2019/11/25.