4-Salicyloylmorpholine

Base Information

• Chemical Name: 4-Salicyloylmorpholine
• CAS No.: 3202-84-4
• Molecular Formula: C11H13 N O3
• Molecular Weight: 207.229
• Hs Code.: 2934999090
• European Community (EC) Number: 654-296-7
• NSC Number: 23201
• UNII: 71U6BE85KU
• DSSTox Substance ID: DTXSID20281834
• Nikkaji Number: J7.689I
• Wikidata: Q27265991
• ChEMBL ID: CHEMBL2135599
• Mol file: 3202-84-4.mol

Synonyms:3202-84-4;4-Salicyloylmorpholine;2-(morpholin-4-ylcarbonyl)phenol;2-(morpholine-4-carbonyl)phenol;(2-Hydroxyphenyl)(morpholino)methanone;2-(4-morpholinylcarbonyl)phenol;(2-hydroxyphenyl)-morpholin-4-ylmethanone;NSC-23201;4-Salicyloylmorpholine [MI];RVC-570;Methanone, (2-hydroxyphenyl)-4-morpholinyl-;71U6BE85KU;L-1102;Morpholine, 4-salicyloyl-;UNII-71U6BE85KU;NSC23201;Morpholine, 4-(2-hydroxybenzoyl)-;TimTec1_005962;Oprea1_471995;MLS000777427;SCHEMBL554704;CHEMBL2135599;4-(2'-hydroxybenzoyl)morpholine;DTXSID20281834;HMS1550O22;HMS2759P05;MFCD00038032;STK739541;AKOS000118208;SMR000413821;(2-hydroxyphenyl)(morpholin-4-yl)methanone;(2-Hydroxy-phenyl)-morpholin-4-yl-methanone;CS-0241958;EU-0008351;EN300-24222;SR-01000463855;A1-54482;SR-01000463855-1;Q27265991;Z56754369;F0914-6110

Chemical Property of 4-Salicyloylmorpholine

Chemical Property:

• Vapor Pressure: 7.99E-07mmHg at 25°C
• Melting Point: 175 °C
• Refractive Index: 1.4950 (estimate)
• Boiling Point: 395.6°C at 760 mmHg
• PKA: 9.03±0.30(Predicted)
• Flash Point: 193°C
• PSA: 49.77000
• Density: 1.263g/cm³
• LogP: 0.80250
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 226

Purity/Quality:

98%min ^*data from raw suppliers

2-(morpholine-4-carbonyl)phenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C(=O)C2=CC=CC=C2O

Technology Process of 4-Salicyloylmorpholine

There total 9 articles about 4-Salicyloylmorpholine 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%

morpholine (110-91-8,99108-56-2) + 2-(trifluoromethyl)phenol (444-30-4) → (2-hydroxyphenyl)morpholin-4-yl-methanone (3202-84-4)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; at 75 ℃; for 1.2h;

DOI:10.1021/ol100507n

Reference yield: 81.0%

4-(phenyloxycarbonyl)morpholine (69630-20-2) → (2-hydroxyphenyl)morpholin-4-yl-methanone (3202-84-4)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0029-1217991

Reference yield: 79.0%

4-benzoylmorpholine (1468-28-6) → (2-hydroxyphenyl)morpholin-4-yl-methanone (3202-84-4)

Guidance literature:

4-benzoylmorpholine; With dirhodium tetraacetate; triethylamine triflouroacetate; trifluoroacetic acid; trifluoroacetic anhydride; at 20 ℃; Electrolysis; Inert atmosphere; Schlenk technique;

With water; sodium hydrogencarbonate; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.202017359

upstream raw materials:

morpholine

phenyl Salicylate

salicylic acid

anionic phenyl salicylate

Downstream raw materials:

2-{2-hydroxy-3-[2-(morpholine-4-carbonyl)-phenoxy]-propoxy}-benzoic acid amide

2-(morpholinomethyl)phenol

C₁₃H₁₆BrNO₃

[2-(morpholine-4-carbonyl)-phenoxy]-propyl-malonic acid diethyl ester

Refernces

• 1、 Massignan, Leonardo,Tan, Xuefeng,Meyer, Tjark H.,Kuniyil, Rositha,Messinis, Antonis M.,Ackermann, Lutz. "C?H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes". supporting information. p. 3184 - 3189. Retrieved 2020/01/24.
• 2、 Thirunavukkarasu, Vedhagiri S.,Hubrich, Jonathan,Ackermann, Lutz. "Ruthenium-catalyzed oxidative C(sp2)-H bond hydroxylation: Site-selective C-O bond formation on benzamides". supporting information; experimental part. p. 4210 - 4213. Retrieved 2012/10/08.