CHROMONE-3-CARBOXALDEHYDE

Base Information

• Chemical Name: CHROMONE-3-CARBOXALDEHYDE
• CAS No.: 17422-74-1
• Molecular Formula: C10H6O3
• Molecular Weight: 174.156
• Hs Code.: 29329900
• European Community (EC) Number: 241-451-5
• NSC Number: 291317
• UNII: BLA42VBH65
• DSSTox Substance ID: DTXSID30169795
• Nikkaji Number: J287.046K
• Wikidata: Q72498591
• Metabolomics Workbench ID: 73927
• ChEMBL ID: CHEMBL86905
• Mol file: 17422-74-1.mol

Synonyms:3-Formyl-4H-1-benzopyran-4-one;3-Formylchromone;4-Oxo-1-benzopyran-3-carboxaldehyde;4-Oxo-4H-1-benzopyran-3-carboxaldehyde;4-Oxo-4H-benzopyran-3-carboxaldehyde;4-Oxo-4H-chromene-3-carboxaldehyde;Chromon-3-carboxaldehyde;Chromone-3-aldehyde;Chromone-3-carboxaldehyde;NSC 291317;

Chemical Property of CHROMONE-3-CARBOXALDEHYDE

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 0.000951mmHg at 25°C
• Melting Point: 151-153 °C(lit.)
• Refractive Index: 1.687
• Boiling Point: 303.1 °C at 760 mmHg
• Flash Point: 134.7 °C
• PSA: 47.28000
• Density: 1.431 g/cm³
• LogP: 1.60550
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Air Sensitive
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 174.031694049
• Heavy Atom Count: 13
• Complexity: 267

Purity/Quality:

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

4-Oxo-4H-chromene-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C(=CO2)C=O
• Uses: 3-Formylchromone may be used in the following studies:Preparation of library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones, by three-component domino reactions with (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones and anilines under catalyst-free conditions.Facile and ecofriendly synthesis of new chromonyl chalcones.Synthesis of 3-(2-hydroxybenzoyl)quinolines and 7H-chromeno[3,2-c]quinolin-7-ones.

Technology Process of CHROMONE-3-CARBOXALDEHYDE

There total 19 articles about CHROMONE-3-CARBOXALDEHYDE 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: 96.0%

o-hydroxyacetophenone (118-93-4,104809-67-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 3-Formylchromone (17422-74-1)

Guidance literature:

o-hydroxyacetophenone; N,N-dimethyl-formamide; With trichlorophosphate; at 20 - 80 ℃; for 0.351667h; Inert atmosphere;

With sodium acetate; In water; for 0.5h;

DOI:10.1021/op300168z

Reference yield: 95.0%

bis(trichloromethyl) carbonate (32315-10-9) + o-hydroxyacetophenone (118-93-4,104809-67-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 3-Formylchromone (17422-74-1)

Guidance literature:

bis(trichloromethyl) carbonate; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.833333h; Inert atmosphere;

o-hydroxyacetophenone; In 1,2-dichloro-ethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.2174/1573406412666160314151900

Reference yield: 90.0%

3-[bis(acetyloxy)methyl]-4H-1-benzopyran-4-one (74990-95-7) → 3-Formylchromone (17422-74-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 70 ℃; for 3h;

upstream raw materials:

o-hydroxyacetophenone

N,N-dimethyl-formamide

2-(4-oxo-4H-1-benzopyran-3-yl)-1,3-dioxolane

3-[bis(acetyloxy)methyl]-4H-1-benzopyran-4-one

Downstream raw materials:

(E)-1-(2'-hydroxyphenyl)-3-(piperidin-1-yl)prop-2-en-1-one

1,3-Dimethyl-6-(2-hydroxybenzoyl)-1,2,3,4-tetrahydro-pyrido<2,3-d>pyrimidin-2,4-dion

3-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-4H-chromen-4-one

3-<(4-Oxo-4H-1-benzopyran-3-yl)-methylene>pentan-2,4-dione

Refernces

• 1、 Mayuri, Bheemarasetti,Kavitha,Basavoju, Srinivas,Bhargavi,Reddy, K. Laxma. "Synthesis, structural characterisation and biological evolution of chromanones". . p. 1 - 9. Retrieved 2017.
• 2、 Molefe, Duduzile M.,Kaye, Perry T.. "Catalytic effects in baylis-hillman reactions of chromone-3-carbaldehydes with acrylonitrile and methyl acrylate". . p. 3586 - 3600. Retrieved 2009.
• 3、 Yuan, Jiaqi,He, Qian,Song, Shanshan,Zhang, Xiaofei,Miao, Zehong,Yang, Chunhao. "One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones". . . Retrieved 2019.
• 4、 Adly, Omima M.I.,Taha, Ali,Fahmy, Shery A.. "Synthesis, characterization of binary and ternary copper(II)-semicarbazone complexes: Solvatochromic shift, dipole moments and TD-DFT calculations". . p. 362 - 376. Retrieved 2019.
• 5、 Rao, B. Kanakadurga,Rao, Y. Jayaprakash. "An efficient and facile synthesis of novel triazole C-N linked chromone hybrids". . p. 1806 - 1808. Retrieved 2020.
• 6、 Shebl, Magdy,Ibrahim,Khalil, Saied M.E.,Stefan,Habib. "Binary and ternary copper(II) complexes of a tridentate ONS ligand derived from 2-aminochromone-3 carboxaldehyde and thiosemicarbazide: Synthesis, spectral studies and antimicrobial activity". . p. 399 - 408. Retrieved 2013.
• 7、 Molefe, Duduzile M.,Ganto, Mlungiseleli M.,Lobb, Kevin A.,Kaye, Perry T.. "Chromone studies. Part 17. Tricyclic scaffolds from reactions of chromone- 3-carbaldehydes and methyl vinyl ketone under Baylis-Hillman conditions". . p. 452 - 456. Retrieved 2009.
• 8、 Zwergel, Clemens,Valente, Sergio,Salvato, Angela,Xu, Zhanjie,Talhi, Oualid,Mai, Antonello,Silva, Artur,Altucci, Lucia,Kirsch, Gilbert. "Novel benzofuran-chromone and -coumarin derivatives: Synthesis and biological activity in K562 human leukemia cells". . p. 1571 - 1579. Retrieved 2013.
• 9、 Wang, Guangcheng,Chen, Ming,Wang, Jing,Peng, Yaping,Li, Luyao,Xie, ZhenZhen,Deng, Bing,Chen, Shan,Li, Wenbiao. "Synthesis, biological evaluation and molecular docking studies of chromone hydrazone derivatives as α-glucosidase inhibitors". . p. 2957 - 2961. Retrieved 2017.
• 10、 Nazreen, Syed,Alam, Mohammad Sarwar,Hamid, Hinna,Yar, Mohammad Shahar,Dhulap, Abhijeet,Alam, Perwez,Pasha,Bano, Sameena,Alam, Mohammad Mahboob,Haider, Saqlain,Kharbanda, Chetna,Ali, Yakub,Pillai. "Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression". . p. 3034 - 3042. Retrieved 2014.