3-(Bromoacetyl)coumarin

Base Information

• Chemical Name: 3-(Bromoacetyl)coumarin
• CAS No.: 29310-88-1
• Molecular Formula: C11H7BrO3
• Molecular Weight: 267.079
• Hs Code.: 2932209090
• European Community (EC) Number: 628-499-6
• DSSTox Substance ID: DTXSID80366272
• Nikkaji Number: J522.602C
• Wikidata: Q72451254
• ChEMBL ID: CHEMBL2260553
• Mol file: 29310-88-1.mol

Synonyms:3-(Bromoacetyl)coumarin;29310-88-1;3-(2-bromoacetyl)-2H-chromen-2-one;3-(2-bromoacetyl)chromen-2-one;3-(bromoacetyl)-2H-chromen-2-one;3-Bromoacetylcoumarin;(3-Bromoacetyl)coumarin;2H-1-Benzopyran-2-one, 3-(bromoacetyl)-;2H-1-Benzopyran-2-one, 3-(2-bromoacetyl)-;bromoacetyl coumarin;3-(2-bromoacetyl)coumarin;SCHEMBL3022073;3-(Bromoacetyl)coumarin, 97%;CHEMBL2260553;DTXSID80366272;NTYOLVNSXVYRTJ-UHFFFAOYSA-N;3-(2-BROMOACETYL)-COUMARIN;BBL018887;MFCD00488331;STL195412;AKOS000117759;3-(2-bromo-acetyl)-2H-chromen-2-one;AS-64981;B4679;CS-0186703;FT-0656407;D78403;A819869;J-017471;Z56347196;F0110-0010

Chemical Property of 3-(Bromoacetyl)coumarin

Chemical Property:

• Vapor Pressure: 2.04E-07mmHg at 25°C
• Melting Point: 164-168 °C(lit.)
• Refractive Index: 1.629
• Boiling Point: 424.6 °C at 760 mmHg
• Flash Point: 210.6 °C
• PSA: 47.28000
• Density: 1.674 g/cm³
• LogP: 2.37060
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 265.95786
• Heavy Atom Count: 15
• Complexity: 322

Purity/Quality:

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

3-(Bromoacetyl)-2H-chromen-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=O)O2)C(=O)CBr
• Uses: 3-(bromoacetyl)coumarin may be used in the synthesis of the following:3-(bromoacetyl)coumarin oxime via reaction with hydroxylamine hydrochloride in methanol3-(bromoacetyl)coumarin-O-methyloxime via reaction with O-benzylhydroxylammonium chloride/diluted HCl in methanol3-(bromoacetyl)coumarin-O-benzyloxime via reaction with O-benzyl hydroxylamine hydrochloride in methanol3-[2′-(2′′-arylidenehydrazinyl)thiazolyl]coumarins via reaction with benzaldehyde thiosemicarbazones

Technology Process of 3-(Bromoacetyl)coumarin

There total 5 articles about 3-(Bromoacetyl)coumarin 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%

Phosphoric acid dimethyl ester 1-(2-oxo-2H-chromen-3-yl)-vinyl ester (219506-41-9) → 3-bromoacetylcoumarin (29310-88-1)

Guidance literature:

With N-Bromosuccinimide; toluene-4-sulfonic acid; In toluene; Heating;

DOI:10.1016/j.tet.2004.08.069

Reference yield: 98.0%

3-acetylcoumarin (3949-36-8) → 3-bromoacetylcoumarin (29310-88-1)

Guidance literature:

With bromine; In chloroform; for 0.25h; Reflux;

DOI:10.3109/14756366.2015.1077823

Reference yield:

salicylaldehyde (90-02-8) → 3-bromoacetylcoumarin (29310-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine / 0 - 5 °C

2: bromine / chloroform / 0 - 5 °C

With piperidine; bromine; In chloroform;

DOI:10.1016/j.ejmech.2011.05.044

upstream raw materials:

3-acetylcoumarin

Phosphoric acid dimethyl ester 1-(2-oxo-2H-chromen-3-yl)-vinyl ester

salicylaldehyde

Downstream raw materials:

3-(2-amino-1,3-thiazol-4-yl)coumarin

3-[2-(phenylamino)acetyl]-2H-chromen-2-one

3?(2?(4?tolylamino)thiazol?4?yl)?2H?chromen?2?one

3-[2-(4-ethoxy-anilino)-thiazol-4-yl]-chromen-2-one

Refernces

• 1、 Alizadeh, Abdolali,Ghanbaripour, Rashid. "An efficient synthesis of pyrrolo[2,1-a]isoquinoline derivatives containing coumarin skeletons via a one-pot, three-component reaction". . p. 8785 - 8796. Retrieved 2015.
• 2、 Boukhari, Abbes,Cheraiet, Zinelaabidine,Djahoudi, Abdelghani,Litim, Bilal,Meliani, Saida. "Synthesis and potent antimicrobial activity of novel coumarylthiazole α-aminophosphonates derivatives". . . Retrieved 2021.
• 3、 Brindha,Reji, T.F. Abbs Fen. "Synthesis and molecular docking studies of coumarinyl thiazole as cell division protein kinase 2 inhibitor". . p. 2453 - 2456. Retrieved 2019.
• 4、 Saeed, Aamer,Ejaz, Syeda Abida,Shehzad, Muddasar,Hassan, Sidra,Al-Rashida, Mariya,Lecka, Joanna,Sévigny, Jean,Iqbal, Jamshed. "3-(5-(Benzylideneamino)thiazol-3-yl)-2H-chromen-2-ones: A new class of alkaline phosphatase and ecto-5′-nucleotidase inhibitors". . p. 21026 - 21036. Retrieved 2016.
• 5、 Kurt, Belma Z.,Sonmez, Fatih,Gokce, Basak,Ergun, Adem,Gencer, Nahit,Demir, Taki,Arslan, Oktay,Kucukislamoglu, Mustafa. "In vitro inhibition effects on erythrocyte carbonic anhydrase I and II and structure-activity relationships of cumarylthiazole derivatives". . p. 506 - 511. Retrieved 2016.
• 6、 Dwivedi, Sushil K.,Razi, Syed S.,Misra, Arvind. "Sensitive colorimetric detection of CN? and AcO? anions in a semi-aqueous environment through a coumarin-naphthalene conjugate azo dye". . p. 5126 - 5132. Retrieved 2019.
• 7、 Sonmez, Fatih,Zengin Kurt, Belma,Gazioglu, Isil,Basile, Livia,Dag, Aydan,Cappello, Valentina,Ginex, Tiziana,Kucukislamoglu, Mustafa,Guccione, Salvatore. "Design, synthesis and docking study of novel coumarin ligands as potential selective acetylcholinesterase inhibitors". . p. 285 - 297. Retrieved 2017.
• 8、 Hosny, Mohamed,Salem, Mostafa E.,Darweesh, Ahmed F.,Elwahy, Ahmed H. M.. "Synthesis of Novel Bis(thiazolylchromen-2-one) Derivatives Linked to Alkyl Spacer via Phenoxy Group". . p. 2342 - 2348. Retrieved 2018.
• 9、 Kavitha, Kotthireddy,Srikrishna, Devulapally,Dubey, Pramod Kumar,Aparna, Pasula. "An efficient one-pot four-component Gewald reaction: Synthesis of substituted 2-aminothiophenes with coumarin–thiazole scaffolds under environmentally benign conditions". . p. 195 - 208. Retrieved 2019.
• 10、 Mishra, Rakesh K.,Upadhyay. "Coumarin-based chromogenic receptor for Ni2+ in aqueous medium exhibiting a reconfigurable logic gate pattern". . p. 4799 - 4805. Retrieved 2011.