6-Acetyl-2(3H)-benzoxazolone

Base Information

• Chemical Name: 6-Acetyl-2(3H)-benzoxazolone
• CAS No.: 54903-09-2
• Molecular Formula: C9H7 N O3
• Molecular Weight: 177.159
• Hs Code.: 2934999090
• European Community (EC) Number: 681-017-6
• DSSTox Substance ID: DTXSID20203399
• Nikkaji Number: J400.430B
• Wikidata: Q83076769
• ChEMBL ID: CHEMBL4549960
• Mol file: 54903-09-2.mol

Synonyms:6-Acetyl-2(3H)-benzoxazolone;54903-09-2;2(3H)-Benzoxazolone, 6-acetyl-;6-Acetylbenzo[d]oxazol-2(3H)-one;6-acetyl-3H-1,3-benzoxazol-2-one;JPB 2;6-acetyl-3H-benzooxazol-2-one;6-acetyl-2,3-dihydro-1,3-benzoxazol-2-one;Acetyl-6 benzoxazolinone [French];Acetyl-6 benzoxazolinone;BRN 1073843;MFCD01664312;6-acetyl-1,3-benzoxazol-2(3H)-one;6-ACETYL-2-BENZOXAZOLINONE;6-Acetyl-2-benzoxazolone;6-Acetyl-2-hydroxybenzoxazole;6-acetyl-3H-benzoxazol-2-one;SCHEMBL2546849;6-Acetylbenzoxazol-2(3H)-one;6-acetyl-3H-benzoxazole-2-one;CHEMBL4549960;DTXSID20203399;6-acetyl-2-(3h)-benzoxazolinone;6-Acetyl-2-hydroxybenzo[d]oxazole;6-Acetyl-2(3H)-benzoxazolone,97%;AKOS009311656;BG-0216;6-acetyl-1,3-benzoxazole-2(3H)-one;LS-42326;CS-0181805;FT-0758603;EN300-74471;Z381350958

Chemical Property of 6-Acetyl-2(3H)-benzoxazolone

Chemical Property:

• Melting Point: 232-236°C
• PKA: 8.79±0.70(Predicted)
• PSA: 63.07000
• Density: 1.325g/cm3
• LogP: 1.32370
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 251

Purity/Quality:

98%, ^*data from raw suppliers

6-Acetyl-2-benzoxazolinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC2=C(C=C1)NC(=O)O2

Technology Process of 6-Acetyl-2(3H)-benzoxazolone

There total 9 articles about 6-Acetyl-2(3H)-benzoxazolone 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: 89.0%

3-acetylbenzo[d]oxazol-2(3H)-one (24963-28-8) → 6-acetyl-3H-benzooxazol-2-one (54903-09-2)

Guidance literature:

With PPA; at 110 ℃; for 1.5h; Product distribution; acyl migration in 3-acyl-2,3-dihydrobenzoxazol-2-one in the presence of polyphosphoric acid;

Reference yield: 77.0%

2-Benzoxazolinone (59-49-4) + acetyl chloride (75-36-5) → 6-acetyl-3H-benzooxazol-2-one (54903-09-2)

Guidance literature:

With aluminum (III) chloride; In N,N-dimethyl-formamide; at 80 ℃; for 3h; regioselective reaction;

DOI:10.1002/ardp.201900384

Reference yield: 68.0%

2-Benzoxazolinone (59-49-4) + acetic anhydride (108-24-7) → 6-acetyl-3H-benzooxazol-2-one (54903-09-2)

Guidance literature:

With aluminium trichloride; In N,N-dimethyl-formamide; at 75 ℃; for 2h; regioselectivity in the C-acylation; other substrates;

DOI:10.1016/S0040-4020(01)82317-6

upstream raw materials:

3-acetylbenzo[d]oxazol-2(3H)-one

2-Benzoxazolinone

acetic anhydride

acetyl chloride

Downstream raw materials:

6-acetyl-3-methylbenzoxazolinone

6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone

C₁₆H₁₀FNO₃

C₁₇H₁₁NO₅

Refernces

• 1、 Messaoud, Liacha,Wassila, Yahia,Khemissi, Seddiki,Yasmina, Adjeroud,Hanane, Chabane. "Synthesis of some novel benzoxazolinonylcarboxamides as potential anti-inflammatory agents". . p. 331 - 333. Retrieved 2014.
• 2、 Bilginer, Sinan,Gul, Halise I.,Erdal, Feyza S.,Sakagami, Hiroshi,Gulcin, Ilhami. "New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6-(3-Halogenated phenyl-2-propen-1-oyl)-2(3H)-benzoxazolones". . . Retrieved 2020/04/23.
• 3、 Reinhardt, Christopher J.,Zhou, Effie Y.,Jorgensen, Michael D.,Partipilo, Gina,Chan, Jefferson. "A Ratiometric Acoustogenic Probe for in Vivo Imaging of Endogenous Nitric Oxide". . p. 1011 - 1018. Retrieved 2018/02/07.