Methyl benzoylformate

Base Information

• Chemical Name: Methyl benzoylformate
• CAS No.: 15206-55-0
• Deprecated CAS: 71833-42-6,301543-54-4
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 2915.13
• European Community (EC) Number: 239-263-3
• NSC Number: 409881,171206
• UNII: 23F2045STG
• DSSTox Substance ID: DTXSID9065867
• Nikkaji Number: J60.885H
• Wikidata: Q27157623
• Mol file: 15206-55-0.mol

Synonyms:Methyl benzoylformate;15206-55-0;methyl 2-oxo-2-phenylacetate;Methyl phenylglyoxalate;Methyl oxophenylacetate;Methyl phenylglyoxylate;Benzoylformic acid methyl ester;Methylbenzoylformate;Phenylglyoxylic acid methyl ester;Phenylglyoxylic acid, methyl ester;Benzeneacetic acid, .alpha.-oxo-, methyl ester;Vicure 55;methyl oxo(phenyl)acetate;Glyoxylic acid, phenyl-, methyl ester;NSC 171206;alpha-oxobenzeneacetic acid methyl ester;UNII-23F2045STG;81065-82-9;23F2045STG;EINECS 239-263-3;MFCD00008443;Benzeneacetic acid, methyl-alpha-oxo-;NSC-171206;NSC-409881;2-Oxo-2-phenylacetic acid methyl ester;AI3-07037;Benzeneacetic acid, alpha-oxo-, methyl ester;EC 239-263-3;methyl benzoyl formate;Methybenzoylformate;methyl benzoylformic acid;Benzoylformic acid methyl;Benzoylformate methyl ester;Methyl oxophenylacetic acid;Methyl phenylglyoxalic acid;methyl2-oxo-2-phenylacetate;Methyl benzoylformate, 98%;Phenylglyoxylate methyl ester;SCHEMBL42428;METHYL PHENYLOXOACETATE;a-Oxobenzeneacetate methyl ester;benzoyl-formic acid methyl ester;DTXSID9065867;CHEBI:84256;Methyl 2-oxo-2-phenylacetic acid;alpha-Oxobenzeneacetate methyl ester;METHOXYCARBONYL PHENYL KETONE;oxo-phenyl-acetic acid methyl ester;a-Oxobenzeneacetic acid methyl ester;METHYL BENZOYLFORMATE [INCI];NSC171206;NSC409881;METHYL 2-PHENYL-2-OXOACETATE;AKOS015960585;METHYL .ALPHA.-OXOBENZENEACETATE;METHYL PHENYL-.ALPHA.-OXOACETATE;ANGC-15206-55-0;AC-23668;Methyl benzoylformate, analytical standard;SY014788;.alpha.-Oxobenzeneacetic acid methyl ester;B1033;CS-0030595;FT-0637200;EN300-1239558;J-802241;W-108055;Methyl 2-oxo-2-Phenylacetate (Methyl Benzoylformate);Q27157623;F0001-0544;Z3234965409

Chemical Property of Methyl benzoylformate

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 0.0263mmHg at 25°C
• Melting Point: 16 °C
• Refractive Index: 1.5260
• Boiling Point: 247 °C at 760 mmHg
• Flash Point: 103.8 °C
• PSA: 43.37000
• Density: 1.164 g/cm³
• LogP: 1.04230
• Storage Temp.: Store below +30°C.
• Water Solubility.: 2g/L at 20℃
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

＞99% ^*data from raw suppliers

Methyl Benzoylformate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=O)C1=CC=CC=C1
• Uses: Methyl benzoylformate is a useful research chemical. Methyl Benzoylformate is used in preparation of strong chemistry-resistant tin ink for printed circuit board.

Technology Process of Methyl benzoylformate

There total 268 articles about Methyl benzoylformate 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: 82.0%

di-isopropyl azodicarboxylate (2446-83-5) + N-benzyloxyphenylglycine (120225-99-2) → methyl 2-oxo-2-phenylacetate (15206-55-0) + O-benzyloxime of phenolglyoxalic acid methyl ester (120226-05-3) + benzaldehyde (100-52-7)

Guidance literature:

With triphenylphosphine;

DOI:10.1016/S0040-4039(00)80574-2

Reference yield: 62.1%

phenylacetaldehyde (122-78-1) → methyl 2-oxo-2-phenylacetate (15206-55-0) + benzaldehyde (100-52-7) + Benzoylformic acid (611-73-4) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With pyridine; water; oxygen; triethylamine; pyridine; compound with copper (II)-nitrate; In methanol; at 25 ℃; for 12h; under 1748 Torr; Further byproducts given. Title compound not separated from byproducts;

DOI:10.1021/jo00297a013

Reference yield: 58.3%

3-phenyl-propionaldehyde (104-53-0) → methyl 2-oxo-2-phenylacetate (15206-55-0) + benzaldehyde (100-52-7) + Benzoylformic acid (611-73-4) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With pyridine; water; oxygen; triethylamine; pyridine; compound with copper (II)-nitrate; In methanol; at 25 ℃; for 12h; under 1748 Torr; Further byproducts given. Title compound not separated from byproducts;

DOI:10.1021/jo00297a013

upstream raw materials:

benzoyl cyanide

methanol

(RS)-methyl mandelate

methyl 2-methoxy-2-phenylacetate

Downstream raw materials:

methyl benzoylformate semicarbazone

Benzoylformic acid

methyl benzoyl formate phenylhydrazone

3-cyano-2-hydroxy-2-phenyl-succinic acid dimethyl ester

Refernces

• 1、 Oba, Makoto,Endo, Masaki,Nishiyama, Kozaburo,Ouchi, Akihiko,Ando, Wataru. "Photosensitized oxygenation of diaryl tellurides to telluroxides and their oxidizing properties". . p. 1672 - 1673. Retrieved 2004.
• 2、 Jefford,Barchietto. "-". . p. 4531,4532. Retrieved 1977.
• 3、 Sun, Wei-Yin,Ueyama, Norikazu,Nakamura, Akira. "Air oxidation of p-substituted benzoin to the corresponding benzil catalyzed by Fe(II)-cysteine peptide complexes". . p. 1557 - 1566. Retrieved 1992.
• 4、 Schaefer,Corey. "-". . p. 1825. Retrieved 1959.
• 5、 Jiang, Xiaoying,Gan, Bing,Liu, Jiwei,Xie, Yuanyuan. "Novel Synthesis of α-Keto Esters and Amides by an sp3 C-H Oxidation of Nitromethyl Aryl Ketones Promoted by Ion-Supported (Diacetoxyiodo)benzene". . p. 2737 - 2741. Retrieved 2016.
• 6、 Clerici, Angelo,Clerici, Laura,Porta, Ombretta. "A Tricomponent Reaction Promoted by a Titanium Trichloride/Pyridine System Diastereoselective Synthesis of β-Amino-α-hydroxyesters". . p. 5955 - 5958. Retrieved 1995.
• 7、 Zhuang, Jing,Wang, Changqing,Xie, Fang,Zhang, Wanbin. "One-pot efficient synthesis of aryl α-keto esters from aryl-ketones". . p. 9797 - 9800. Retrieved 2009.
• 8、 Maity, Rajib,Naskar, Sandip,Mal, Kanchan,Biswas, Sandipa,Das, Indrajit. "Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from α-Keto Thioesters through Thiolate Transfer". . p. 4405 - 4410. Retrieved 2017.
• 9、 Yadav, Ganapati D.,Bhagat, Ramesh D.. "Synthesis of methyl phenyl glyoxylate via clean oxidation of methyl mandelate over a nanocatalyst based on heteropolyacid supported on clay". . p. 879 - 882. Retrieved 2004.
• 10、 Xie, Yangla,Sun, Moran,Zhou, Hang,Cao, Qiwei,Gao, Kaige,Niu, Changling,Yang, Hua. "Enantiospecific total synthesis of (+)-tanikolide via a key [2,3]-meisenheimer rearrangement with an allylic amine N-oxide-directed epoxidation and a one-pot trichloroisocyanuric acid N-debenzylation and N-chlorination". . p. 10251 - 10263. Retrieved 2013.