4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE

Base Information

• Chemical Name: 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE
• CAS No.: 50329-91-4
• Molecular Formula: C10H5ClO3
• Molecular Weight: 208.601
• Hs Code.: 2932209090
• European Community (EC) Number: 626-816-2
• DSSTox Substance ID: DTXSID20353262
• Nikkaji Number: J996.056B
• Wikidata: Q82130740
• Mol file: 50329-91-4.mol

Synonyms:4-Chloro-3-formylcoumarin;4-Chlorocoumarin-3-carboxaldehyde;AKOS BB-9945;4-Chloro-2-oxo-2h-chromene-3-carbaldehyde;

Chemical Property of 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE

Chemical Property:

• Vapor Pressure: 8.34E-06mmHg at 25°C
• Melting Point: 126-130 °C(lit.)
• Refractive Index: 1.618
• Boiling Point: 374.5 °C at 760 mmHg
• Flash Point: 173.7 °C
• PSA: 47.28000
• Density: 1.47 g/cm³
• LogP: 2.25890
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 207.9927217
• Heavy Atom Count: 14
• Complexity: 309

Purity/Quality:

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

4-Chloro-2-oxo-2H-chromene-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(C(=O)O2)C=O)Cl
• Uses: 4-Chloro-3-formylcoumarin may be used as a reactant in the preparation of:2-aryl[1]benzopyrano[4,3-c]pyrazol-4(2H)-onesbiaryl lactones (benzo[c]chromen-6-ones)N-monosubstituted 4-amino-3-formylcoumarinschromeno[4,3-b]quinolin-6-one

Technology Process of 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE

There total 13 articles about 4-CHLORO-2-OXO-2H-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: 90.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4-chloro-3-formylcoumarin (50329-91-4)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 - 50 ℃; for 0.5h;

4-hydroxy[1]benzopyran-2-one; In N,N-dimethyl-formamide; at 60 ℃; for 12h;

DOI:10.1021/ol203229z

Reference yield: 84.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → 4-chloro-3-formylcoumarin (50329-91-4)

Guidance literature:

With trichlorophosphate; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1007/s00044-017-1902-1

Reference yield: 84.0%

4-methyl-2H-chromen-2-one (607-71-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4-chloro-3-formylcoumarin (50329-91-4)

Guidance literature:

With trichlorophosphate; Reflux;

DOI:10.1007/s00044-016-1661-4

upstream raw materials:

4-hydroxy[1]benzopyran-2-one

N,N-dimethyl-formamide

N-methyl-N-phenylformamide

3-bromo-4-hydroxycoumarin

Downstream raw materials:

4-chloro-3-[(α-dimethoxyphosphoryl-α-hydroxy)methyl]coumarin

Refernces

• 1、 Chen, Long-Wang,Wang, Ze-Feng,Zhu, Bo,Man, Ruo-Jun,Liu, Yan-Dong,Zhang, Yuan-Heng,Wang, Bao-Zhong,Wang, Zhong-Chang,Zhu, Hai-Liang. "Design, synthesis and biological evaluation of novel benzo-α-pyrone containing piperazine derivatives as potential BRAFV600Einhibitors". . p. 4983 - 4991. Retrieved 2016.
• 2、 Angelova, Violina T.,Voynikov, Yulian,Andreeva-Gateva, Pavlina,Surcheva, Slavina,Vassilev, Nikolay,Pencheva, Tania,Tchekalarova, Jana. "In vitro and in silico evaluation of chromene based aroyl hydrazones as anticonvulsant agents". . p. 1884 - 1896. Retrieved 2017.
• 3、 Borah, Pallabi,Bhuyan, Pulak J.. "Synthesis of some novel spiro substituted pyrido[2,3-c]coumarins by exploring ‘tertiary amino effect’ reaction strategy". . p. 6949 - 6951. Retrieved 2013.
• 4、 Angelova, Violina T.,Valcheva, Violeta,Vassilev, Nikolay G.,Buyukliev, Rosen,Momekov, Georgi,Dimitrov, Ivan,Saso, Luciano,Djukic, Mirjana,Shivachev, Boris. "Antimycobacterial activity of novel hydrazide-hydrazone derivatives with 2H-chromene and coumarin scaffold". . p. 223 - 227. Retrieved 2017.
• 5、 Milevskii,Chibisova,Solov'Eva,Anisimova,Lebedev,Ivanov,Traven. "Synthesis and structure of Schiff bases derived from 3-formyl-4- hydroxycoumarin and diamines". . p. 1781 - 1792. Retrieved 2013.
• 6、 Heber,Ivanov,Karagiosov. "The Vilsmeier reaction in the synthesis of 3-substituted [1]Benzopyrano[4,3-b]pyridin-5-ones. An unusual pyridine ring closure". . p. 505 - 509. Retrieved 1995.
• 7、 Yin, Yong,Hu, Jia-Qin,Wu, Xu,Sha, Shao,Wang, She-Feng,Qiao, Fang,Song, Zhong-Cheng,Zhu, Hai-Liang. "Design, synthesis and biological evaluation of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates containing sulfonamido as potential PI3Kα inhibitors". . p. 2261 - 2267. Retrieved 2019.
• 8、 Wittine, Karlo,Ratkaj, Ivana,Benci, Kre?imir,Suhina, Tomislav,Mandi?, Leo,Ili?, Nata?a,Paveli?, Sandra Kraljevi?,Paveli?, Kre?imir,Mintas, Mladen. "The novel coumarin[3,2-c]thiophene and its hydroxamic acid and ureido derivatives: Synthesis and cytostatic activity evaluations". . p. 728 - 737. Retrieved 2016.
• 9、 Ibrahim, Nabila M.,Yosef, Hisham Abdallah A.,Yakout, El-Sayed M. A.,Mahran, Mohamed Refat H.. "The behavior of 4-azidocoumarin-3-carboxaldehyde towards certain sulfur reagents and primary amines". . p. 1124 - 1138. Retrieved 2009.
• 10、 L. N. Rao, Maddali,Nand, Sachchida. "Pd-Catalyzed cross-coupling synthesis of 4-aryl-3-formylcoumarins". supporting information. p. 1053 - 1057. Retrieved 2022/02/11.