4-Morpholinecarboxaldehyde

Base Information

• Chemical Name: 4-Morpholinecarboxaldehyde
• CAS No.: 4394-85-8
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Hs Code.: 29349990
• European Community (EC) Number: 224-518-3
• NSC Number: 14833
• UNII: D1E63XO4RH
• DSSTox Substance ID: DTXSID7044427
• Nikkaji Number: J149.689A
• Wikipedia: N-Formylmorpholine
• Wikidata: Q27275975
• Mol file: 4394-85-8.mol

Synonyms:4-morpholinecarboxaldehyde

Chemical Property of 4-Morpholinecarboxaldehyde

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.0472mmHg at 25°C
• Melting Point: 23 °C(lit.)
• Refractive Index: n20/D 1.485(lit.)
• Boiling Point: 236.5 °C at 760 mmHg
• PKA: -0.75±0.20(Predicted)
• Flash Point: 107 °C
• PSA: 29.54000
• Density: 1.21 g/cm³
• LogP: 0.04880
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: SOLUBLE
• Water Solubility.: SOLUBLE
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 78.5

Purity/Quality:

99%, ^*data from raw suppliers

4-Morpholinecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 23-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Morpholines
• Canonical SMILES: C1COCCN1C=O
• Uses: 4-Formylmorpholine is widely used as a solvent and extracting agent for aromatics. It is used as a scrubbing agent for acidic gases. It is employed in the preparation of adenine hydrochloride labeled with 14C, 4-(trifluoromethyl)morpholine, 3-alkyl-2-chloro-5,6-dihydrobenzaldehyde and terphenyl dialdehyde. It plays an important role in the desulfurization of natural gas, synthetic gas, flue gas and gasoline. 4-Formylmorpholine has been used in the preparation of:adenine hydrochloride labelled with 14Cterphenyl dialdehyde

Technology Process of 4-Morpholinecarboxaldehyde

There total 89 articles about 4-Morpholinecarboxaldehyde 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%

morpholine (110-91-8,99108-56-2) + formamide (77287-34-4,77287-35-5,60100-09-6) → 4-morpholinecarboxaldehyde (4394-85-8)

Guidance literature:

With Iron(III) nitrate nonahydrate; In toluene; for 7h; Reflux;

DOI:10.1021/jo500562w

Reference yield: 100.0%

morpholine (110-91-8,99108-56-2) + carbon dioxide (124-38-9,18923-20-1) → 4-morpholinecarboxaldehyde (4394-85-8)

Guidance literature:

With phenylsilane; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In tetrahydrofuran-d8; at 100 ℃; for 6h; under 750.075 Torr; Inert atmosphere;

DOI:10.1002/anie.201105516

Reference yield: 100.0%

morpholine (110-91-8,99108-56-2) + formic acid (64-18-6) → 4-morpholinecarboxaldehyde (4394-85-8)

Guidance literature:

With cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; at 20 ℃; for 3h; Reagent/catalyst; Solvent;

DOI:10.1016/j.tetlet.2013.02.013

upstream raw materials:

morpholine

formic acid

hydrogen cyanide

chloral

Downstream raw materials:

7H-purin-2-amine

4-methyl-morpholine

4-[N-(5-nitro-[1,3,4]thiadiazol-2-yl)-formimidoyl]-morpholine

2-chloro-3-morpholin-4-ylmethylene-4-phenyl-3,4-dihydro-quinoline

Refernces

Reactions of 2-Cyclohexen-1-ones and Cyclohexane-1,3-diones with Chloro Methylene Iminium Salts

10.1021/jo00389a016

The research focuses on the reactions of cyclohexane-1,3-diones and 2-cyclohexen-1-ones with Vilsmeier reagents, which are formamides and phosphorus oxychloride (POCl3). The purpose of the study was to extend the understanding of formylation reactions and to provide mechanistic rationales for the variety of products formed under Vilsmeier conditions. The researchers identified two distinct reactivity patterns: Type A, where mono-, di-, or triformylated olefins or benzenes are formed, and Type B, where formylation occurs at the carbon atom of a 3-substituent in a 3-methyl-2-cyclohexen-1-one. The study concluded that the mechanistic pathways proposed are consistent with all observed products and with results reported by other workers, suggesting that many products formed by reacting acyclic α,β-unsaturated ketones with Vilsmeier reagents can be rationalized by extending the proposed pathways. Key chemicals used in the process include various 2-cyclohexen-1-ones, Vilsmeier reagents such as N-formylmorpholine and POCl3, as well as other formamides like DMF (dimethylformamide) and N-formylpyrrolidine.

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