2H-Azirine-2-carboxylic acid, 3-phenyl-, methyl ester

Base Information

• Chemical Name: 2H-Azirine-2-carboxylic acid, 3-phenyl-, methyl ester
• CAS No.: 18709-45-0
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• DSSTox Substance ID: DTXSID50330647
• Nikkaji Number: J102.517A
• Mol file: 18709-45-0.mol

Synonyms:methyl 3-phenyl-2H-azirine-2-carboxylate;18709-45-0;2H-Azirine-2-carboxylic acid, 3-phenyl-, methyl ester;DTXSID50330647;AC4984;MFCD29923958;AKOS016038710;methyl3-phenyl-2H-azirine-2-carboxylate;SY037180;Methyl 3-phenyl-2H-azirene-2-carboxylate #;2-Phenyl-3H-azirine-3-carboxylic acid methyl ester

Chemical Property of 2H-Azirine-2-carboxylic acid, 3-phenyl-, methyl ester

Chemical Property:

• Boiling Point: 262.7±50.0 °C(Predicted)
• PKA: 1.68±0.40(Predicted)
• PSA: 38.66000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 0.46650
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 241

Purity/Quality:

97% ^*data from raw suppliers

Methyl3-phenyl-2H-azirine-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1C(=N1)C2=CC=CC=C2

Technology Process of 2H-Azirine-2-carboxylic acid, 3-phenyl-, methyl ester

There total 11 articles about 2H-Azirine-2-carboxylic acid, 3-phenyl-, methyl ester 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%

5-methoxy-3-phenylisoxazole (18803-02-6) → methyl 3-phenyl-2H-azirine-2-carboxylate (18709-45-0)

Guidance literature:

With rhodium(II) pivalate; In toluene; for 3h; Reflux;

DOI:10.1055/s-0036-1590822

Reference yield: 80.0%

methyl 3-amino-3-phenylacrylate (70272-01-4) → methyl 3-phenyl-2H-azirine-2-carboxylate (18709-45-0)

Guidance literature:

With C₁₂H₈I₂N₂O₇; In 1,2-dichloro-ethane; at 60 ℃; for 3.5h; Reagent/catalyst; Solvent; Temperature;

DOI:10.1039/c9sc05536c

Reference yield: 55.0%

methanol (67-56-1) + 3-phenyl-2H-azirine-2-carbonyl azide → methyl 2-(5-phenyl-1H-tetrazole-1-yl)acetate (131647-65-9) + methyl 3-phenyl-2H-azirine-2-carboxylate (18709-45-0)

Guidance literature:

With triethylamine; at 25 ℃; for 24h; Reagent/catalyst;

DOI:10.1021/acs.orglett.1c02157

upstream raw materials:

methyl 1-chloro-trans-3-phenylaziridine-2-carboxylate

5-methoxy-3-phenylisoxazole

methyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate

rac Methyl (2R^*,3S^*)-3-phenyl-1H-aziridine-2-carboxylate

Downstream raw materials:

(S)-(+)-2-carbomethoxy-3-phenyl-2H-azirine

Refernces

• 1、 Komendantov,Bekmukhametov. "-". . . Retrieved 1975.
• 2、 Zhang, Guangtao,Wang, Yuanxun,Xu, Jun,Sun, Jiyun,Sun, Fengxia,Zhang, Yilin,Zhang, Chenglin,Du, Yunfei. "A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2: H -azirines". . p. 947 - 953. Retrieved 2020/02/11.
• 3、 Rostovskii, Nikolai V.,Agafonova, Anastasiya V.,Smetanin, Ilia A.,Novikov, Mikhail S.,Khlebnikov, Alexander F.,Ruvinskaya, Julia O.,Starova, Galina L.. "Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines". . p. 4478 - 4488. Retrieved 2017/09/26.