INDOLE-3-GLYOXYLYL CHLORIDE

Base Information

• Chemical Name: INDOLE-3-GLYOXYLYL CHLORIDE
• CAS No.: 22980-09-2
• Molecular Formula: C10H6ClNO2
• Molecular Weight: 207.616
• Hs Code.: 2918300090
• European Community (EC) Number: 245-362-2
• NSC Number: 128332
• UNII: 34QT24PE76
• DSSTox Substance ID: DTXSID20177526
• Nikkaji Number: J318.378E
• Wikidata: Q27256381
• Mol file: 22980-09-2.mol

Synonyms:Indole-3-glyoxyloylchloride (6CI,7CI,8CI);(1H-Indol-3-yl)oxoacetyl chloride;2-(3-Indolyl)-2-oxoacetyl chloride;3-Indoleglyoxylyl chloride;NSC 128332;a-Oxo-1H-indole-3-acetyl chloride;

Chemical Property of INDOLE-3-GLYOXYLYL CHLORIDE

Chemical Property:

• Appearance/Colour: YELLOW TO ORANGE POWDER OR CRYSTALS
• Vapor Pressure: 4.63E-07mmHg at 25°C
• Melting Point: 138 °C (dec.)(lit.)
• Refractive Index: 1.676
• Boiling Point: 413.9 °C at 760 mmHg
• PKA: 14.29±0.30(Predicted)
• Flash Point: 204.1 °C
• PSA: 49.93000
• Density: 1.463 g/cm³
• LogP: 2.11600
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 207.0087061
• Heavy Atom Count: 14
• Complexity: 267

Purity/Quality:

98%,99%, ^*data from raw suppliers

Indole-3-glyoxyloylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C(=O)C(=O)Cl
• Uses: INDOLE-3-GLYOXYLYL CHLORIDE is an indole derivative used in the preparation of reagents for chemiluminescent enzyme immunoassay. It is an impurity in the manufacture of tryptamines and related compounds. ? ;Reactant for preparation of dual IGF-1R/SRC inhibitors1? ;Reactant for preparation of indolylglyoxylamides as a new class of antileishmanial agents2? ;Reactant for preparation of glyoxyl analogs of indole phytoalexins as anticancer agents3? ;Reactant for diastereoselective synthesis of heptacyclic core of dragmacidin E4? ;Reactant for preparation of benzoylmethylpyrrolopyridinylethanedione as HIV-1 inhibitor5? ;Reactant for preparation of fascaplysin-inspired diindolyls as selective inhibitors of CDK4/cyclin D16 Reactant for preparation of dual IGF-1R/SRC inhibitorsReactant for preparation of indolylglyoxylamides as a new class of antileishmanial agentsReactant for preparation of glyoxyl analogs of indole phytoalexins as anticancer agentsReactant for diastereoselective synthesis of heptacyclic core of dragmacidin EReactant for preparation of benzoylmethylpyrrolopyridinylethanedione as HIV-1 inhibitorReactant for preparation of fascaplysin-inspired diindolyls as selective inhibitors of CDK4/cyclin D1

Technology Process of INDOLE-3-GLYOXYLYL CHLORIDE

There total 6 articles about INDOLE-3-GLYOXYLYL CHLORIDE 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%

indole (120-72-9) + oxalyl dichloride (79-37-8) → indolyl-3-glyoxylyl chloride (22980-09-2)

Guidance literature:

In diethyl ether; for 0.416667h;

DOI:10.1016/j.bioorg.2018.07.029

Reference yield:

indole (120-72-9) → indolyl-3-glyoxylyl chloride (22980-09-2)

Guidance literature:

With oxalyl dichloride; In diethyl ether; at 0 ℃; for 3h; Heating / reflux;

Reference yield:

indole (120-72-9) + phosgene (75-44-5) → indolyl-3-glyoxylyl chloride (22980-09-2)

Guidance literature:

With diethyl ether; at 0 ℃; for 1.5h;

DOI:10.1021/acs.jafc.9b04093

upstream raw materials:

indole

oxalyl dichloride

3-indolylglyoxylic acid

4-methoxy-1H-indole

Downstream raw materials:

1-(1H-indol-3-yl)-2-morpholinoethane-1,2-dione

2-(3-indolyl)oxoacetic acid methyl ester

ethyl 2-(1H-indol-3-yl)-2-oxoacetate

2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

Refernces

• 1、 Sears, R. Bryan,Carpenter, Russell A.,Whitlock, Christine R.. "A general synthesis of tris-indole derivatives as potential iron chelators". . p. 488 - 491. Retrieved 2005.
• 2、 Singh, Palwinder,Pooja. "N-1, C-3 substituted indoles as 5-LOX inhibitors - In vitro enzyme immunoaasay, mass spectral and molecular docking investigations". . p. 1433 - 1437. Retrieved 2013.
• 3、 Zhang, Puyong,Sun, Xiaofei,Xu, Bin,Bijian, Krikor,Wan, Shengbiao,Li, Guigen,Alaoui-Jamali, Moulay,Jiang, Tao. "Total synthesis and bioactivity of the marine alkaloid pityriacitrin and some of its derivatives". . p. 6089 - 6097. Retrieved 2011.
• 4、 Collins, Ian,Davey, William B.,Rowley, Michael,Quirk, Kathleen,Bromidge, Frances A.,McKernan, Ruth M.,Thompson, Sally-Anne,Wafford, Keith A.. "N-(indol-3-ylglyoxylyl)piperidines: High affinity agonists of human GABA-A receptors containing the α1 subunit". . p. 1381 - 1384. Retrieved 2000.
• 5、 Wang, Yu-Yun,Chen, Chinpiao. "Synthesis of deuterium labeled tryptamine derivatives". . p. 1363 - 1368. Retrieved 2007.
• 6、 Jain, Palak,Utreja, Divya,Sharma, Poonam. "An efficacious synthesis of N-1–, C-3–substituted indole derivatives and their antimicrobial studies". . p. 428 - 435. Retrieved 2020.
• 7、 H?felinger, Günter,Nimtz, Manfred,Horstmann, Volker,Benz, Thomas. "Trifluoroacetylation of Methylated -Derivatives of Tryptamine and Serotonine by Different Reagents: Synthesis, Spectroscopic Characterizations, and Separations by Capillary-Gas-Chromatography". . p. 397 - 414. Retrieved 1999.
• 8、 Naaz, Fatima,Ahmad, Faiz,Lone, Bilal Ahmad,Pokharel, Yuba Raj,Fuloria, Neeraj Kumar,Fuloria, Shivkanya,Ravichandran, Manickam,Pattabhiraman, Lalitha,Shafi, Syed,Shahar Yar. "Design and synthesis of newer 1,3,4-oxadiazole and 1,2,4-triazole based Topsentin analogues as anti-proliferative agent targeting tubulin". . . Retrieved 2020.
• 9、 Barresi, Elisabetta,Giacomelli, Chiara,Marchetti, Laura,Baglini, Emma,Salerno, Silvia,Greco, Giovanni,Da Settimo, Federico,Martini, Claudia,Trincavelli, Maria Letizia,Taliani, Sabrina. "Novel positive allosteric modulators of A2B adenosine receptor acting as bone mineralisation promoters". . p. 286 - 294. Retrieved 2020/12/22.
• 10、 -. "Compound containing 2,4 - thiazole ring and preparation method and application thereof". Paragraph 0189-0191. . Retrieved 2021/08/25.