6-methoxy-4-oxo-4H-chromene-3-carbaldehyde

Base Information

• Chemical Name: 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde
• CAS No.: 42059-79-0
• Molecular Formula: C11H8 O4
• Molecular Weight: 204.182
• Hs Code.: 2914509090
• European Community (EC) Number: 663-598-8
• DSSTox Substance ID: DTXSID30350989
• Nikkaji Number: J1.214.756B
• Wikidata: Q82127069
• Metabolomics Workbench ID: 73932
• Mol file: 42059-79-0.mol

Synonyms:6-methoxy-4-oxo-4H-chromene-3-carbaldehyde;42059-79-0;6-methoxy-4-oxochromene-3-carbaldehyde;3-Formyl-6-methoxychromone;6-Methoxychromone-3-carboxaldehyde;6-methoxy-3-formylchromone;6-methoxy-4-oxo-chromene-3-carbaldehyde;3-Formyl-6-methoxy chromone;4H-1-Benzopyran-3-carboxaldehyde, 6-methoxy-4-oxo-;SCHEMBL1572774;DTXSID30350989;ILFXSWVYDSZVBC-UHFFFAOYSA-N;3-Formyl-6-methoxychromone, 98%;BBL022596;MFCD02683011;STK505092;AKOS000267432;VS-07237;CS-0307668;F1115;FT-0679366;EN300-04582;6-Methoxy-4-oxo-4H-chromene-3-carboxaldehyde;T72449;A825741;SR-01000039462;A1-00150;SR-01000039462-1;Z56886303;3-Formyl-6-methoxychromone, 6-Methoxy-4-oxo-4H-chromene-3-carboxaldehyde

Chemical Property of 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 1.6E-05mmHg at 25°C
• Melting Point: 162-166°C
• Boiling Point: 365.2°Cat760mmHg
• Flash Point: 165.2°C
• PSA: 56.51000
• Density: 1.401g/cm³
• LogP: 1.61410
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 204.04225873
• Heavy Atom Count: 15
• Complexity: 308

Purity/Quality:

98%min ^*data from raw suppliers

6-Methoxy-4-oxo-4H-chromene-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 36/37-45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)OC=C(C2=O)C=O

Technology Process of 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde

There total 6 articles about 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde 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: 95.0%

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one (705-15-7) + oxalyl dichloride (79-37-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde (42059-79-0)

Guidance literature:

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one; N,N-dimethyl-formamide; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

oxalyl dichloride; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.2174/1573406412666160314151900

Reference yield: 76.0%

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one (705-15-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde (42059-79-0)

Guidance literature:

With trichlorophosphate;

DOI:10.1016/S0960-894X(99)00115-8

Reference yield:

2,5-Dihydroxyacetophenone (490-78-8) → 6-methoxy-4-oxo-4H-chromene-3-carbaldehyde (42059-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaI; K₂CO₃ / dimethylformamide / 24 h / 60 °C

2: POCl₃ / 20 °C

With potassium carbonate; sodium iodide; trichlorophosphate; In N,N-dimethyl-formamide; 2: Vilsmeier-Haack reaction;

DOI:10.1021/jm010382z

upstream raw materials:

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one

N,N-dimethyl-formamide

2,5-Dihydroxyacetophenone

oxalyl dichloride

Downstream raw materials:

6-methoxy-3-[(1E)-2-phenylethenyl]-4H-1-benzopyran-4-one

(2-hydroxy-5-methoxyphenyl)(p-tolyl)methanone

Refernces

• 1、 Takao, Koichi,Takemura, Yuri,Nagai, Junko,Kamauchi, Hitoshi,Hoshi, Kaori,Mabashi, Ryo,Uesawa, Yoshihiro,Sugita, Yoshiaki. "Synthesis and biological evaluation of 3-styrylchromone derivatives as selective monoamine oxidase B inhibitors". . . Retrieved 2021/06/15.
• 2、 Gordon, Allen T.,Ramaite, Isaiah D.I.,Mnyakeni-Moleele, Simon S.. "Synthesis and biological evaluation of chromone-3-carboxamides". . p. 148 - 160. Retrieved 2021/01/20.