4-(oxiran-2-ylmethoxy)-9H-carbazole

Base Information

• Chemical Name: 4-(oxiran-2-ylmethoxy)-9H-carbazole
• CAS No.: 51997-51-4
• Molecular Formula: C15H13NO2
• Molecular Weight: 239.274
• Hs Code.: 29339900
• European Community (EC) Number: 610-764-2
• UNII: VX4N43V2E1
• ChEMBL ID: CHEMBL3580714
• DSSTox Substance ID: DTXSID401306928
• Nikkaji Number: J2.649.748E
• Wikidata: Q27292066
• Mol file: 51997-51-4.mol

Synonyms:51997-51-4;4-(2,3-Epoxypropoxy)carbazole;4-Glycidyloxycarbazole;4-(oxiran-2-ylmethoxy)-9H-carbazole;4-Epoxypropanoxycarbazole;4-Oxiranylmethoxy-9H-carbazole;4-(2,3-Epoxypropoxy)-carbazole;4-(2-oxiranylmethoxy)-9H-carbazole;9H-Carbazole, 4-(oxiranylmethoxy)-;VX4N43V2E1;MFCD03411884;4-Oxiranylmethoxy-carbazole;UNII-VX4N43V2E1;EC 610-764-2;SCHEMBL619267;CHEMBL3580714;4-(2,3-epoxy propoxy)carbazole;4-(2,3-epoxypropoxy) carbazole;4-(2,3-Epoxypropoxy)carbazole?;4-(oxiranylmethoxy)-9h-carbazole;SVWKIGRDISDRLO-UHFFFAOYSA-N;DTXSID401306928;AMY40799;BCP32066;4-(2-Oxiranylmethoxy)-9H-carbazol;AC8014;MFCD04973598;AKOS008901363;4-(oxirane-2-ylmethoxy)-9h-carbazole;AC-1994;CS-W014145;KS-1021;SB37482;9H-Carbazole, 4-(2-oxiranylmethoxy)-;SY038288;SY284588;FT-0616497;FT-0616498;FT-0642294;FT-0642295;G0296;NS00002385;(+/-)-4-OXIRANYLMETHOXY-9H-CARBAZOLE;A828878;A845180;J-513258;Q27292066;4-(2-Oxiranylmethoxy)-9H-carbazole, pharmaceutical impurity standard;USP Carvedilol Related Compound D;4-Carbazolylglycidic ether;SKF-106024;Carvedilol Related Compound D

Chemical Property of 4-(oxiran-2-ylmethoxy)-9H-carbazole

Chemical Property:

• Appearance/Colour: pale yellow to almost white powder
• Vapor Pressure: 2.23E-08mmHg at 25°C
• Melting Point: 130-132 °C
• Refractive Index: 1.729
• Boiling Point: 464.9 °C at 760 mmHg
• PKA: 16.59±0.30(Predicted)
• Flash Point: 166.4 °C
• PSA: 37.55000
• Density: 1.327 g/cm³
• LogP: 3.09870
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 239.094628657
• Heavy Atom Count: 18
• Complexity: 309

Purity/Quality:

98%min ^*data from raw suppliers

4-(2,3-Epoxypropoxy)carbazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 43-68
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)COC2=CC=CC3=C2C4=CC=CC=C4N3
• Uses: 4-(2,3-Epoxypropoxy)carbazole (Carvedilol EP Impurity D; Carvedilol USP-D) is an intermediate in the synthesis of Carvedilol (C184625).

Technology Process of 4-(oxiran-2-ylmethoxy)-9H-carbazole

There total 12 articles about 4-(oxiran-2-ylmethoxy)-9H-carbazole 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: 93.0%

C22H19NO4S → 4-(2,3-epoxypropoxy)carbazole (51997-51-4,95093-96-2)

Guidance literature:

With potassium hydroxide;

DOI:10.1007/s11426-021-1202-9

Reference yield: 80.5%

9H-carbazol-4-ol (52602-39-8) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 4-(2,3-epoxypropoxy)carbazole (51997-51-4,95093-96-2)

Guidance literature:

9H-carbazol-4-ol; With sodium hydroxide; In water; isopropyl alcohol; at 23 - 28 ℃; for 1h;

epichlorohydrin; In water; isopropyl alcohol; at 20 - 40 ℃; for 15 - 20h;

Reference yield: 80.0%

9H-carbazol-4-ol (52602-39-8) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 1-(9H-carbazol-4-yloxy)-3-chloropropan-2-ol (1187921-93-2) + 4-(2,3-epoxypropoxy)carbazole (51997-51-4,95093-96-2)

Guidance literature:

With pyridine; In isopropyl alcohol; at 50 - 60 ℃; for 12h; Inert atmosphere;

upstream raw materials:

9H-carbazol-4-ol

1,2-Epoxy-3-bromopropane

epichlorohydrin

glycidyl nosylate

Downstream raw materials:

(+/-)-15-(4-azidobenzyl)carazolol

(+/-)-15-(4-azido-3-iodobenzyl)carazolol

15-(2-nitrobenzyl)carazolol

(+/-)-15-(4-nitrobenzyl)carazolol

Refernces

• 1、 Zhang, Xiao,Wang, Ying,Wang, Sheng-nan,Chen, Qiu-he,Tu, Ya-lin,Yang, Xiao-hong,Chen, Jing-kao,Yan, Jin-wu,Pi, Rong-biao,Wang, Yan. "Discovery of a novel multifunctional carbazole–aminoquinoline dimer for Alzheimer's disease: copper selective chelation, anti-amyloid aggregation, and neuroprotection". . p. 777 - 784. Retrieved 2018.
• 2、 Chang, Qi,Long, Jing,Hu, Liqing,Chen, Zhuo,Li, Qianbin,Hu, Gaoyun. "Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents". . . Retrieved 2020/04/09.
• 3、 Xu, Yao,Chen, Shujun,Cao, Ying,Zhou, Pingzheng,Chen, Zhipeng,Cheng, Kui. "Discovery of novel small molecule TLR4 inhibitors as potent anti-inflammatory agents". . p. 253 - 266. Retrieved 2018/05/29.