16648-44-5

Basic information

• Product Name: Benzeneacetic acid, a-acetyl-, methyl ester
• Synonyms: Benzeneacetic acid, a-acetyl-, methyl ester;Benzeneacetic;methyl α-acetylphenylacetate;Benzeneacetic acid,CAS:16648-44-5;BMK POWDER bmk white powder 3-Oxo-2-PhenylbutanaMide BMK;16648-44-5 methyl α-acetylphenylacetate;BMK Glycidate powder 16648-44-5 manufacturer supplier suppliers factory;BMK Glycidate
• CAS NO: 16648-44-5
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21118
• EINECS: 234-232-0
• Product Categories: pharmaceutical intermediate
• Mol File: 16648-44-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 58.5-59.0 °C
• Boiling Point: 92-96 °C(Press: 0.6 Torr)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• PKA: 10.67±0.46(Predicted)
• CAS DataBase Reference: Benzeneacetic acid, a-acetyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-acetyl-, methyl ester(16648-44-5)
• EPA Substance Registry System: Benzeneacetic acid, a-acetyl-, methyl ester(16648-44-5)

Safety Data

• Hazardous Substances Data: 16648-44-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 16648-44-5 differently. You can refer to the following data:
1. Benzeneacetic acid, a-acetyl-, methyl ester can be used as a pharmaceutical raw material.
2. D1, D2 dopamine receptor antagonist; butyrophenone antipsychotic and anti-emetic. Droperidol is a potent antagonist of dopamine subtype 2 receptor. It is an antipsychotic, which is used to treat acute behavioral anomalies. It helps to manage postoperative nausea and vomiting. Endogenous κ1b opioid receptor agonist.

Description

Different sources of media describe the Description of 16648-44-5 differently. You can refer to the following data:
1. Methyl 2-phenylacetoacetate is an analytical reference standard categorized as a precursor in the synthesis of amphetamines and methamphetamines. This product is intended for research and forensic applications.The Drug Enforcement Administration is proposing the control of the chemical methyl alpha-phenylacetoacetate (also known as MAPA; methyl 3-oxo-2-phenylbutanoate; methyl 2-phenylacetoacetate; [alpha]-acetyl-benzeneacetic acid, methyl ester; and CAS Number: 16648-44-5) and its optical isomers as a list I chemical under the Controlled Substances Act (CSA). Methyl alpha-phenylacetoacetate is used in clandestine laboratories to illicitly manufacture the schedule II controlled substances phenylacetone (also known as phenyl-2-propanone or P2P), methamphetamine, and amphetamine and is important to the manufacture of these controlled substances.
2. Methyl 2-phenylacetoacetate (Item No. 28352) is an analytical reference standard categorized as a precursor in the synthesis of amphetamines and methamphetamines. This product is intended for research and forensic applications.

Preparation

Methyl phenyldiazoacetate, precursor to cyclopropanation agents, is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base.

Synthetic route

acetic acid methyl ester (79-20-9) + benzeneacetic acid methyl ester (101-41-7) → methyl α-acetylphenylacetate (16648-44-5)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -78 - 45℃; for 13h; Inert atmosphere;	51%
With potassium tert-butylate 1.) -78 deg C, 2 h, 2.) r.t., 18 h; reflux,1 h;	39%

acetic anhydride (108-24-7) + benzeneacetic acid methyl ester (101-41-7) → methyl α-acetylphenylacetate (16648-44-5)

Conditions	Yield
Stage #1: benzeneacetic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: acetic anhydride In tetrahydrofuran at -78 - 0℃;	50%

methanol (67-56-1) + 2-diazo-1-phenylbutane-1,3-dione (2009-96-3) → methyl 2-benzoylpropionate (32742-19-1, 116782-25-3, 29540-54-3) + methyl 3-oxo-3-phenylpropionate (614-27-7) + methyl α-acetylphenylacetate (16648-44-5) + 2-Methoxy-3-oxo-3-phenylpropionsaeuremethylester (112370-88-4)

Conditions	Yield
In 1,4-dioxane at 10℃; Product distribution; Mechanism; Irradiation; also thermolysis at 80 deg C, other 2-diazo-1,3-dicarbonyl compounds;	A 23.9 % Chromat. B n/a C 12.5 % Chromat. D 27.2 % Chromat.

acetyl chloride (75-36-5) + benzeneacetic acid methyl ester (101-41-7) → methyl α-acetylphenylacetate (16648-44-5)

Conditions	Yield
Stage #1: benzeneacetic acid methyl ester With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: acetyl chloride In tetrahydrofuran; hexane at -78 - 20℃;	1.5 g

methyl α-acetylphenylacetate (16648-44-5) + p-toluenesulfonyl chloride (98-59-9) → C18H18O5S

Conditions	Yield
With 1-methyl-1H-imidazole; triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 2h; stereoselective reaction;	94%

methyl α-acetylphenylacetate (16648-44-5) + p-toluenesulfonyl chloride (98-59-9) → C18H18O5S

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; lithium chloride In acetonitrile at 0 - 25℃; for 2h; stereoselective reaction;	93%

methyl α-acetylphenylacetate (16648-44-5) + 3-phenyl-4-(piperidin-1-yl)-1H-pyrazol-5-amine → 5-methyl-2,6-diphenyl-3-(piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one

Conditions	Yield
With acetic acid for 0.5h; Reflux; Inert atmosphere;	88%

methyl α-acetylphenylacetate (16648-44-5) + chlorophosphoric acid diphenyl ester (2524-64-3) → (Z)-methyl 2-phenyl-3-(diphenoxyphosphoryloxy)but-2-enoate

Conditions	Yield
With 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine; lithium chloride at 0 - 5℃; for 1h; Inert atmosphere; stereoselective reaction;	86%

methyl α-acetylphenylacetate (16648-44-5) + chlorophosphoric acid diphenyl ester (2524-64-3) → (E)-methyl 2-phenyl-3-(diphenoxyphosphoryloxy)but-2-enoate

Conditions	Yield
With 1-methyl-1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0 - 5℃; for 1h; Inert atmosphere; stereoselective reaction;	74%

methyl α-acetylphenylacetate (16648-44-5) + 1-Phenyl-2-propyn-1-ol (4187-87-5) → 3-oxo-2-phenylbutyric acid 1-phenylprop-2-ynyl ester

Conditions	Yield
In toluene at 20℃; for 122h; Reflux; Inert atmosphere;	68%

2-bromo-4-methyl-2H-furan-5-one (59488-94-7) + methyl α-acetylphenylacetate (16648-44-5) → 2-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-3-oxo-2-phenyl-butyric acid methyl ester

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide for 15h; Ambient temperature;	65%

methyl α-acetylphenylacetate (16648-44-5) + thiophenol (108-98-5) → methyl 3-oxo-2-phenyl-2-(phenylthio)butanoate

Conditions	Yield
With oxygen; potassium iodide; sodium hydroxide In acetonitrile at 80℃; under 760.051 Torr; for 18h; Green chemistry;	61%

3-amino-1-phenylpyrazin-2(1H)-one (1425864-74-9) + methyl α-acetylphenylacetate (16648-44-5) → C20H15N3O2 (1425865-18-4)

Conditions	Yield
With methanesulfonic acid In acetonitrile at 180℃; for 0.5h; Conrad-Limpach Synthesis; Microwave irradiation;	60%

methyl α-acetylphenylacetate (16648-44-5) → 3-methyl-4-phenyl-1H-pyrazol-5-ol (64754-67-2)

Conditions	Yield
With ethanol; hydrazine hydrate for 4h; Reflux;	55%

methyl α-acetylphenylacetate (16648-44-5) + dibenzoyl peroxide (94-36-0) → C18H16O5

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; CHF3O3S*C10H24N2 In chloroform at 20℃; Schlenk technique; Inert atmosphere; enantioselective reaction;	40%

methyl α-acetylphenylacetate (16648-44-5) + phenylhydrazine (100-63-0) → 3-methyl-1,4-diphenyl-1H-pyrazol-5-ol

Conditions	Yield
With ethanol at 70℃; for 4h;	23%

2-bromo-4-methyl-2H-furan-5-one (59488-94-7) + methyl α-acetylphenylacetate (16648-44-5) → 2-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-3-oxo-2-phenyl-butyric acid methyl ester + (Z)-3-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yloxy)-2-phenyl-but-2-enoic acid methyl ester

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In toluene for 15h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

methyl α-acetylphenylacetate (16648-44-5) → (E)-3-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yloxy)-2-phenyl-but-2-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: KOBu-t, 18-crown-6 / toluene / 15 h / Ambient temperature 2: benzophenone / acetone / 0.5 h / Irradiation View Scheme

methyl α-acetylphenylacetate (16648-44-5) → (E)-methyl 2,3-diphenyl-2-butenoate (42443-37-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: 1-methyl-1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 0 - 5 °C / Inert atmosphere 2.1: zinc(II) chloride / tetrahydrofuran; acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 2 h / 0 - 65 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → α carbomethoxy β methyl stilbene cis (42443-38-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: lithium chloride; 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / 1 h / 0 - 5 °C / Inert atmosphere 2.1: zinc(II) chloride / tetrahydrofuran; acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere 2.2: 2 h / 0 - 65 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C18H18O2

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C18H18O2

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → (E)-3-(4-Methoxy-phenyl)-2-phenyl-but-2-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → (Z)-3-(4-Methoxy-phenyl)-2-phenyl-but-2-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C17H15ClO2 + C17H15ClO2

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / isopropyl alcohol; water / 4 h / 60 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C17H15ClO2 + C23H19ClO2

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C17H15ClO2

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / isopropyl alcohol; water / 1 h / 60 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C15H14O3

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C15H14O3

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

methyl α-acetylphenylacetate (16648-44-5) → C15H14O2S

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere View Scheme

Upstream product

• 67-56-1 methanol 
• 2009-96-3 2-diazo-1-phenylbutane-1,3-dione 
• 108-24-7 acetic anhydride 
• 101-41-7 benzeneacetic acid methyl ester 
• 75-36-5 acetyl chloride 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 1425865-18-4 C₂₀H₁₅N₃O₂ 
• 64754-67-2 3-methyl-4-phenyl-1H-pyrazol-5-ol 
• 7713-62-4 5-methoxy-3-methyl-4-phenylisoxazole 

Relevant articles and documents

Synthesis of Substituted Indole-3-carboxylates by Iron(II)-Catalyzed Domino Isomerization of 3-Alkyl/aryl-4-aryl-5-methoxyisoxazoles

The iron(II)-catalyzed domino isomerization of 3-alkyl/aryl-4-arylisoxazoles provides a selective access to a wide range of structurally diverse highly substituted indole-3-carboxylates. The operational simplicity, high atom efficiency, and the use of stable starting materials and an inexpensive and low-toxicity catalyst are some of the attractive features of this tandem double ring-opening-ring-closure strategy.

PYRAZOLONE DERIVATIVES AS NITROXYL DONORS

The disclosed subject matter provides pyrazolone derivative compounds, pharmaceutical compositions comprising such compounds, kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

Mechanism of the Photochemical and Thermal Wolff Rearrangement of 2-Diazo-1,3-dicarbonyl Compounds

Thermolysis and photolysis of diazo-1,3-dicarbonyl compounds were investigated as a fuction of methanol concentration.As the methanol concentration decreased, methyl group migration increased concomitant with the suppresion of O-H insertion into methanol, whereas aryl group migration was essentially uanaltered with the methanol concentration.The results are interpreted as indicating that aryl migration occurs directly from the excited state of diazo compounds, but that methyl migration takes place un the singlet carbene in competition with O-H insertion.