5-Bromoindole

Base Information

• Chemical Name: 5-Bromoindole
• CAS No.: 10075-50-0
• Molecular Formula: C8H6BrN
• Molecular Weight: 264.33
• Hs Code.: 2905.49
• European Community (EC) Number: 233-208-7
• NSC Number: 75581
• UNII: R8FGF42R4A
• DSSTox Substance ID: DTXSID6073996
• Nikkaji Number: J255K
• Wikipedia: 5-bromoindole
• Wikidata: Q72457312
• Metabolomics Workbench ID: 130887
• ChEMBL ID: CHEMBL325917
• Mol file: 10075-50-0.mol

Synonyms:5-BROMOINDOLE;10075-50-0;5-Bromo-1H-indole;1H-Indole, 5-bromo-;5-bromo indole;MFCD00005670;5-bromo-indole;5-bromanyl-1~{H}-indole;R8FGF42R4A;CHEMBL325917;EINECS 233-208-7;NSC 75581;NSC-75581;220310-64-5;5bromoindole;H4N;NSC75581;5-bromo 1H indole;5-Bromoindole, 99%;5-Bromo-1H-indole #;Maybridge1_006195;UNII-R8FGF42R4A;NCIOpen2_000472;SCHEMBL74304;BIDD:GT0232;DTXSID6073996;HMS559B13;BCP26677;CS-D0617;BBL013012;BDBM50358747;CCG-42502;GEO-00480;s5439;STK249656;AKOS000120596;AB00482;AC-1348;FS-1805;SB40564;HY-30236;SY005268;AM20060209;B1738;FT-0620159;FT-0620160;EN300-21081;B-8420;B-8424;SR-01000632498-1;F8881-6102;Z104489174

Chemical Property of 5-Bromoindole

Chemical Property:

• Appearance/Colour: white to light brown powder or chunks
• Vapor Pressure: 0.000738mmHg at 25°C
• Melting Point: 89-92 °C
• Refractive Index: 1.711
• Boiling Point: 316.9 °C at 760 mmHg
• PKA: 16.04±0.30(Predicted)
• Flash Point: 145.5 °C
• PSA: 15.79000
• Density: 1.66 g/cm³
• LogP: 2.93040
• Storage Temp.: -20°C
• Solubility.: 126mg/l (calculated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 194.96836
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

5-Bromoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)C=C1Br
• Description: 5-Bromoindole, known for its pungent odor reminiscent of indole, presents itself as a white or off-white solid, resistant to dissolution in water yet readily soluble in common organic solvents. As a versatile aryl halide frequently employed in organic synthesis, it engages in Suzuki coupling reactions and serves as a pivotal intermediate, albeit prone to decomposition at elevated temperatures and in the presence of air or water.
• Uses: Its utility extends to various domains, acting as a precursor for organic light-emitting materials, indole bioactive molecules, and amorphous silicon materials. In the pharmaceutical sector, it emerges as a crucial chemical intermediate, exhibiting potential as a glycogen synthase kinase 3 (GSK-3) inhibitor and finding applications in veterinary drugs, particularly as a feed additive for livestock and poultry with antibacterial, anti-diarrheal, and growth-promoting properties. Moreover, its role as a heterocyclic building block underscores its significance in chemical synthesis, including its involvement in cancer gene therapy studies when combined with 3-acetic acid and horseradish peroxidase for in vivo characterization.; Studies on the luminescence properties of 5-Bromoindole in PVA films emphasize its weak fluorescence but relatively strong phosphorescence, which can be effectively excited at longer wavelengths, making it a potential candidate for various applications involving luminescent materials.^[1]; 5-Bromoindole is noted for their potential applications in various fields, including the electrochemical industry and pharmacology. It is considered for use as electrocatalysts, anode materials in batteries, and in the development of antifungal and antibacterial agents.^[2]
• References: [1] Luminescence properties of 5-Bromoindole in PVA films at room temperature: Direct triplet state excitation (DOI 10.1016/j.jlumin.2020.117724); [2] Experimental thermochemical study of 5-bromoindole and 5-bromoindoline (DOI 10.1016/j.jct.2008.07.016)

Technology Process of 5-Bromoindole

There total 63 articles about 5-Bromoindole 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: 99.0%

1-(5-bromo-1H-indol-1-yl)-2,2-dimethylpropan-1-one (1196980-99-0) → 5-bromo-1H-indole (10075-50-0)

Guidance literature:

With water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2011.10.098

Reference yield: 99.0%

5-bromo-1H-indole-3-carboxylic acid (10406-06-1) → 5-bromo-1H-indole (10075-50-0)

Guidance literature:

With potassium carbonate; In ethanol; at 140 ℃; Schlenk technique;

DOI:10.1080/00397911.2019.1703137

Reference yield: 98.0%

5-bromoindoline (22190-33-6) → 5-bromo-1H-indole (10075-50-0)

Guidance literature:

With potassium tert-butylate; In decane; at 150 ℃; for 36h; Inert atmosphere; Schlenk technique;

DOI:10.1002/cctc.201900367

upstream raw materials:

5-bromoindoline

5-bromo-2-indolecarboxylic acid

N-(4-bromophenyl)ethenesulfinamide

5-Bromo-1-(methylsulfonyl)indole

Downstream raw materials:

5-Bromo-indole-3-carbinol

2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride

5-methylthio-1H-indole

1-(1H-indol-5-yl)ethanone

Refernces

• 1、 An, Li-Tao,Cai, Jing-Jing,Pan, Xiang-Qiang,Chen, Tang-Ming,Zou, Jian-Ping,Zhang, Wei. "Ga(DS)3-catalysed double hydroarylation of acetylenic esters with indoles for the synthesis of bisindolyl propanoates". . p. 3996 - 3998. Retrieved 2015.
• 2、 Ismail, Mohamed A.H.,Abou El Ella, Dalal A.,Abouzid, Khaled A.M.,Mahmoud, Amr H.. "Erratum: Integrated structure-based activity prediction model of benzothiadiazines on various genotypes of HCV NS5b polymerase (1a, 1b and 4) and its application in the discovery of new derivatives (Bioorganic and Medicinal Chemistry (2012) 20:7 (2455-2478))". . p. 5647 - 5647. Retrieved 2013.
• 3、 Hong, Zonghan,Chong, Wee Kiang,Ng, Andrew Yun Ru,Li, Mingjie,Ganguly, Rakesh,Sum, Tze Chien,Soo, Han Sen. "Hydrophobic Metal Halide Perovskites for Visible-Light Photoredox C?C Bond Cleavage and Dehydrogenation Catalysis". . p. 3456 - 3460. Retrieved 2019.
• 4、 Bratulescu, George. "A new and efficient one-pot synthesis of indoles". . p. 984 - 986. Retrieved 2008.
• 5、 Sun, Hao,Ehlhardt, William J.,Kulanthaivel, Palaniappan,Lanza, Diane L.,Reilly, Christopher A.,Yost, Garold S.. "Dehydrogenation of indoline by cytochrome P450 enzymes: A novel "aromatase" process". . p. 843 - 851. Retrieved 2007.
• 6、 Suarez-Castillo, Oscar R.,Beiza-Granados, Lidia,Melendez-Rodriguez, Myriam,Alvarez-Hernandez, Alejandro,Morales-Rios, Martha S.,Joseph-Nathan, Pedro. "Synthesis of bromoindole alkaloids from Laurencia brongniartii". . p. 1596 - 1600. Retrieved 2006.
• 7、 Luo, Zaoli,Liu, Yungen,Tong, Ka-Chung,Chang, Xiao-Yong,To, Wai-Pong,Che, Chi-Ming. "Luminescent Platinum(II) Complexes with Bidentate Diacetylide Ligands: Structures, Photophysical Properties and Application Studies". . p. 2978 - 2992. Retrieved 2021.
• 8、 Li, Bo,Li, Zheyu,Ma, Wenbo,Tan, Yuqiang,Wang, Yang,Yu, Yao,Zhang, Chunran,Zhao, Huan. "Ruthenium-Catalyzed Vinylene Carbonate Annulation by C?H/N?H Functionalizations: Step-Economical Access to Indoles". . . Retrieved 2022/01/11.
• 9、 Abinaya, R.,Balasubramaniam, K. K.,Baskar, B.,Divya, P.,Mani Rahulan, K.,Rahman, Abdul,Sridhar, R.,Srinath, S.. "Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles". . p. 5990 - 6007. Retrieved 2021/08/24.