617-36-7

Basic information

• Product Name: ETHYL OXAMATE
• Synonyms: Acetic acid, aminooxo-, ethyl ester;Ethoxalamide;Ethyl amino(oxo)acetate;OXAMETHANE;OXALIC ACID MONOETHYL ESTER AMIDE;OXAMIC ACID ETHYL ESTER;OXAMIDIC ACID ETHYL ESTER;ETHYL OXAMATE
• CAS NO: 617-36-7
• Molecular Formula: C₄H₇NO₃
• Molecular Weight: 117.1
• EINECS: 210-512-8
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks;Building Blocks;C2 to C7;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 617-36-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 112-115 °C
• Boiling Point: 218.88°C (rough estimate)
• Flash Point: 87 °C
• Appearance: White/Crystalline Powder, Crystals, and/or Chunks
• Density: 1.3886 (rough estimate)
• Vapor Pressure: 0.59mmHg at 25°C
• Refractive Index: 1.4540 (estimate)
• Storage Temp.: -20°C
• PKA: 13.37±0.50(Predicted)
• BRN: 506728
• CAS DataBase Reference: ETHYL OXAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL OXAMATE(617-36-7)
• EPA Substance Registry System: ETHYL OXAMATE(617-36-7)

Safety Data

• Safety Statements: 24/25-22
• WGK Germany: 3
• Hazardous Substances Data: 617-36-7(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C4H7NO3/c1-2-8-4(7)3(5)6/h2H2,1H3,(H2,5,6)

Synthetic route

ethyl cyanoformate (623-49-4) → Ethyl oxamate (617-36-7)

Conditions	Yield
With manganese(IV) oxide; water In isopropyl alcohol at 30℃; under 5171.62 Torr; for 0.25h;	96%
Stage #1: ethyl cyanoformate With phosphoric acid In dibutyl ether at 115℃; for 1.5h; Stage #2: With potassium carbonate In ethanol	50%

oxalic acid diethyl ester (95-92-1) + urea (57-13-6) → Ethyl oxamate (617-36-7) + urethane (51-79-6)

Conditions	Yield
With di(n-butyl)tin oxide at 140℃; for 12h; Inert atmosphere;	A 80% B 80%
With di(n-butyl)tin oxide at 140℃; under 2585.81 Torr; for 12h; Inert atmosphere; Autoclave;	A 30 %Chromat. B 60 %Chromat.

diazoacetic acid ethyl ester (623-73-4) → Ethyl oxamate (617-36-7)

Conditions	Yield
With tert.-butylhydroperoxide; ammonium iodide In acetonitrile at 40℃; for 12h;	65%
With tert.-butylhydroperoxide; ammonium iodide In water; acetonitrile at 40℃; for 12h;	65%

ethyl 2-azido-2-hydroxyacetate (1263290-89-6) → ethyl N-carbonylcarbamate (18804-91-6) + Ethyl oxamate (617-36-7)

Conditions	Yield
In chloroform-d1 at -50℃; for 8h; Photolysis;	A 42% B 29%

ethyl (E)-3-(naphthalen-1-yl)-2-nitroacrylate (60859-75-8) → 1-hydroxy-2-naphthaldehyde (574-96-9) + Ethyl oxamate (617-36-7) + ethyl naphthol<1,2-b>furan-2-carboxylate (74222-20-1) + ethyl 3-(1-naphthyl)-3-oximino-2-oxopropionate (74222-18-7) + 2-(ethoxyoxalylaminomethylene)naphthalen-1-one (88472-35-9)

Conditions	Yield
In acetone at 20℃; for 2h; Mechanism; Product distribution; Irradiation;	A 26.8% B 15.8% C 2.2% D 1.6% E 10%

ethyl (E)-3-(naphthalen-1-yl)-2-nitroacrylate (60859-75-8) → 1-hydroxy-2-naphthaldehyde (574-96-9) + Ethyl oxamate (617-36-7) + ethyl naphthol<1,2-b>furan-2-carboxylate (74222-20-1) + 2-(ethoxyoxalylaminomethylene)naphthalen-1-one (88472-35-9)

Conditions	Yield
In acetone at 20℃; for 2h; Irradiation; Further byproducts given;	A 26.8% B 15.8% C 2.2% D 10%
In acetone at 20℃; for 2h; Irradiation; Further byproducts given;	A 26.8% B 15.8% C 2.2% D 10%

ethyl (E)-3-(naphthalen-1-yl)-2-nitroacrylate (60859-75-8) → 1-hydroxy-2-naphthaldehyde (574-96-9) + Ethyl oxamate (617-36-7) + ethyl 3-(1-naphthyl)-3-oximino-2-oxopropionate (74222-18-7) + 2-(ethoxyoxalylaminomethylene)naphthalen-1-one (88472-35-9)

Conditions	Yield
In acetone at 20℃; for 2h; Irradiation; Further byproducts given;	A 26.8% B 15.8% C 1.6% D 10%

ethyl 2-nitro-3-(2-naphthyl)acrylate (74222-04-1) → Ethyl oxamate (617-36-7) + ethyl naphthol<1,2-b>furan-2-carboxylate (74222-20-1) + 3-[(E)-Hydroxyimino]-3-naphthalen-2-yl-2-oxo-propionic acid ethyl ester (74222-17-6)

Conditions	Yield
In acetone Irradiation;	A 10.8% B 2.6% C 22%

Dimethyl oxalate (553-90-2) + ethanol (64-17-5) → Ethyl oxamate (617-36-7)

Conditions	Yield
With ammonia

2-ethoxy-2-oxoacetic anhydride (119174-42-4) → Ethyl oxamate (617-36-7)

Conditions	Yield
With diethyl ether; ammonia

oxalic acid ethyl ester ureide → acetylcarbamoyl-oxalamic acid + Ethyl oxamate (617-36-7)

Conditions	Yield
With acetic anhydride

ethanol (64-17-5) + oxalic acid diethyl ester (95-92-1) → Ethyl oxamate (617-36-7)

Conditions	Yield
With ammonia at 0℃;

oxalic acid diethyl ester (95-92-1) → Ethyl oxamate (617-36-7)

Conditions	Yield
With ethanol; ammonia
With ammonium hydroxide In ethanol

oxalic acid diethyl ester (95-92-1) → Oxalamide (471-46-5) + Ethyl oxamate (617-36-7)

Conditions	Yield
With ammonia

glycine (56-40-6) → Ethyl oxamate (617-36-7)

Conditions	Yield
With ammonium sulfate; sulfuric acid elektrolitische Reduktion;

ethanol (64-17-5) + Ethyl oxalyl chloride (4755-77-5) → N-Ethoxy-2-ethoxy-2-oxoacetamid (39183-52-3) + Ethyl oxamate (617-36-7) + diethyl iminodicarboxylate (19617-44-8)

Conditions	Yield
(i) aq. NaN3, CH2Cl2, (ii) /BRN= 1718733/; Multistep reaction;

Ethyl oxalyl chloride (4755-77-5) + isopropyl alcohol (67-63-0) → N-Isopropoxycarbonylurethan (39183-50-1) + N-Isopropoxyethoxalamid (39183-53-4) + Ethyl oxamate (617-36-7)

Conditions	Yield
(i) aq. NaN3, CH2Cl2, (ii) /BRN= 635639/; Multistep reaction;

Ethyl oxalyl chloride (4755-77-5) + cyclohexene (110-83-8) → N-Aethoxalylcyclohexanonimin (39183-57-8) + Ethyl oxamate (617-36-7)

Conditions	Yield
(i) aq. NaN3, CH2Cl2, (ii) /BRN= 906737/; Multistep reaction. Further byproducts given;

ethyl chloronitroacetate (14011-27-9) → Ethyl oxamate (617-36-7)

Conditions	Yield
at 160 - 180℃; for 21h;	1.43 g

ethyl ester of bromonitroacetic acid (6060-97-5) → Ethyl oxamate (617-36-7)

Conditions	Yield
at 160 - 180℃; for 16h;	1.28 g

5-fluoro-1H-imidazole-4-carboxylic acid ethyl ester (33235-31-3) → Ethyl oxamate (617-36-7)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

ammonia (7664-41-7) + Ethyl oxalyl chloride (4755-77-5) → Ethyl oxamate (617-36-7)

4-(2,4-difluorobiphenylyl)-2-methyl-4-oxobutanoic acid + chloroformic acid ethyl ester (541-41-3) + GlyOEt*HCl (459-73-4) → Ethyl oxamate (617-36-7)

Conditions	Yield
With 1-ethyl-piperidine In N-methyl-acetamide; hydrogenchloride; dichloromethane; water; sodium hydrogencarbonate	4.3 g (67.2 % theor.)

ethyl acetamidate-HCl salt + 3-aminomethyl-3-hydroxy-1-azabicyclo[2.2.2]octane (128200-13-5) → 2-Methyl-spiro(1,3 oxazoline-5,3')quinuclidine + Ethyl oxamate (617-36-7)

Conditions	Yield
With Hg In dichloromethane

oxalic acid diethyl ester (95-92-1) + urea (57-13-6) → Ethyl oxamate (617-36-7) + urethane (51-79-6) + diethyl iminodicarboxylate (19617-44-8)

Conditions	Yield
With di(n-butyl)tin oxide at 140℃; for 2h; Inert atmosphere;	A 63 %Chromat. B 63.5 %Chromat. C 15 %Chromat.

Ethyl oxalyl chloride (4755-77-5) → Ethyl oxamate (617-36-7)

Conditions	Yield
With ammonia; triethylamine at 0 - 20℃;

methyl 3,3,3-trifluoropyruvate (13089-11-7) + Ethyl oxamate (617-36-7) → 2-(ethoxyoxalyl-amino)-3,3,3-trifluoro-2-hydroxy-propionic acid methyl ester (915033-02-2)

Conditions	Yield
at 20℃; for 16h;	98%

Ethyl oxamate (617-36-7) + 4,5-Dichloro-3-nitro-1,2-diaminobenzene (276238-86-9) → 3-Amino-6,7-dichloro-8-nitroquinoxalin-2(1H)-one

Conditions	Yield
In ethanol	96%

Ethyl oxamate (617-36-7) + 1,2-diamino-benzene (95-54-5) → 3-amino-2(1H)-quinoxalinone (35015-91-9)

Conditions	Yield
With pyridine for 24h; Reflux;	95%
With pyridine for 8h; Reflux;

4-methyl-2-oxo-2H-chromen-7-yl-1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (93131-78-3) + Ethyl oxamate (617-36-7) → ethyl 2-((4-methyl-2-oxo-2H-chromen-7-yl)amino)-2-oxoacetate

Conditions	Yield
With potassium phosphate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In toluene at 100℃; for 48h; Buchwald-Hartwig Coupling;	94%

1,2-Diphenylethylenediamine (5700-60-7) + Ethyl oxamate (617-36-7) → 3-amino-5,6-diphenyl-2(1H)-pyrazinone (39213-73-5)

Conditions	Yield
With pyridine for 12h; Reflux;	93.5%

Ethyl oxamate (617-36-7) + methylamine (74-89-5) → N-methyloxamide (22509-04-2)

Conditions	Yield
In ethanol for 0.0833333h; Heating;	93%
In ethanol Heating;

Ethyl oxamate (617-36-7) + anthranilic acid amide (28144-70-9) → ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate (29113-33-5)

Conditions	Yield
With acetic acid for 0.5h; Heating;	92%

N-(4-methoxybenzyl)hydrazinecarbothioamide (16735-76-5) + Ethyl oxamate (617-36-7) → 1-oxamoyl-4-(p-methoxybenzyl)-3-thiosemicarbazide (61320-96-5)

Conditions	Yield
With sodium methylate In methanol; water	91%

Ethyl oxamate (617-36-7) + 2,2-dimethoxyethylamine (22483-09-6) → N'-(2,2-dimethoxyethyl)oxamide (68797-27-3)

Conditions	Yield
Stage #1: 2,2-dimethoxyethylamine In ethanol at 50℃; for 0.166667h; Stage #2: Ethyl oxamate In ethanol at 80℃;	90%
In ethanol

Ethyl oxamate (617-36-7) + zinc(II) chloride (7646-85-7) → {Zn(Hoxm)2(H2O)2} (172342-91-5, 34383-62-5)

Conditions	Yield
With H2O In ethanol; water byproducts: C2H5OH, HCl; 50°C, 3 h;	90%

Ethyl oxamate (617-36-7) + cobalt(II) chloride (7646-79-9) → {Co(Hoxm)2(H2O)2}*2H2O

Conditions	Yield
With H2O In ethanol; water byproducts: C2H5OH, HCl; 50°C, 3 h;	90%

Ethyl oxamate (617-36-7) + copper dichloride → Cu(Hoxm)2(H2O)2 (131345-69-2, 152102-97-1, 312904-31-7)

Conditions	Yield
With H2O In ethanol; water byproducts: C2H5OH, HCl; 50°C, 3 h;	90%

Ethyl oxamate (617-36-7) + nickel dichloride → Ni(Hoxm)2(H2O)2 (131345-68-1, 152075-74-6)

Conditions	Yield
With H2O In ethanol; water byproducts: C2H5OH, HCl; 50°C, 3 h;	90%

Ethyl oxamate (617-36-7) + manganese(ll) chloride → Mn(Hoxm)2(H2O)2 (131345-67-0)

Conditions	Yield
With H2O In ethanol; water byproducts: C2H5OH, HCl; 50°C, 3 h;	90%

oxalyl dichloride (79-37-8) + Ethyl oxamate (617-36-7) → Glycine ethyl ester isocyanate (2949-22-6)

Conditions	Yield
In dichloromethane Reflux;	90%

Ethyl oxamate (617-36-7) → 2-amino(2H4)ethan-1-ol (85047-08-1)

Conditions	Yield
With lithium aluminium deuteride In tetrahydrofuran	90%
With lithium aluminium deuteride In tetrahydrofuran at 0℃; for 10h; Reflux;	4.4 g

1-benzofurane (271-89-6) + glyoxylic acid ethyl ester (924-44-7) + Ethyl oxamate (617-36-7) → ethyl 2-(benzofuran-2-yl)-2-((ethoxycarbonyl)amino)acetate

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; for 16h;	88%

Ethyl oxamate (617-36-7) → ethyl 2-amino-2-thioxoacetate (16982-21-1)

Conditions	Yield
With Lawessons reagent In toluene at 80℃; for 1h;	87%
With Lawessons reagent In tetrahydrofuran Reflux;	83%
With Lawessons reagent In tetrahydrofuran for 2h; Heating / reflux;	80%

4-[(2-aminoethyl)amino]-3-penten-2-one (89376-43-2) + Ethyl oxamate (617-36-7) → N-[2-((Z)-1-Methyl-3-oxo-but-1-enylamino)-ethyl]-oxalamide (122054-71-1)

Conditions	Yield
In dichloromethane for 0.25h; Heating;	86%

Ethyl oxamate (617-36-7) + 4,4'-Dimethoxybenzhydrol (728-87-0) → ethyl N-(4,4'-dimethoxybenzhydryl)oxamate

Conditions	Yield
With sulfuric acid In acetic acid at 20℃; for 24h;	83%

oxalyl dichloride (79-37-8) + Ethyl oxamate (617-36-7) → ethoxycarbonylcarbonyl isocyanate (66913-88-0)

Conditions	Yield
With 1,2-dichloro-ethane Heating;	82%
In 1,2-dichloro-ethane for 5h; Carbonylation; Heating;	82%
In 1,2-dichloro-ethane for 16h; Condensation; Heating;	68%
In dichloromethane at 0 - 25℃; for 12h;	39%

4-(2,4,6-trimethylphenyl)-5-aminotriazole (202580-66-3) + Ethyl oxamate (617-36-7) → 4-(2,4,6-trimethylphenyl)-5-acetamidinotriazole, acetic acid salt

Conditions	Yield
In acetic acid; acetonitrile	82%

Ethyl oxamate (617-36-7) + (Diethoxymethyl)triethylammoniumtetrafluoroborat → <(Ethoxymethylen)amino>oxoessigsaeure-ethylester (79437-79-9)

Conditions	Yield
In dichloromethane 1) 1 h, 0 deg C, 2) 2 h, r.t.;	81%

Lawessons reagent (19172-47-5) + sodium hydrogencarbonate (144-55-8) + Ethyl oxamate (617-36-7) → ethyl 2-amino-2-thioxoacetate (16982-21-1)

Conditions	Yield
In tetrahydrofuran	80%

3-hydrazineylidene-3,4-dihydroquinoxalin-2(1H)-one (31595-63-8) + Ethyl oxamate (617-36-7) → 2-hydroxy-1-imino-1H-[1,2,4]triazino[4,3-a]quinoxalin-5(6H)-one (1489264-69-8)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 8h;	79%

Ethyl oxamate (617-36-7) + anthranilic acid hydrazide (1904-58-1) → ethyl 3-amino-4-oxo-3,4-dihydroquinazoline-2-carboxylate (34127-27-0)

Conditions	Yield
With acetic acid for 0.5h; Heating;	78%

Ethyl oxamate (617-36-7) + phenylacetylene (536-74-3) → ethyl oxo{[(Z)-2-phenylvinyl]amino}acetate (1095320-58-3)

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,4-bis(dicyclohexylphosphino)butane; ytterbium(III) triflate In N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere; optical yield given as %de; stereoselective reaction;	78%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,4-bis(dicyclohexylphosphino)butane; ytterbium(III) triflate In N,N-dimethyl-formamide at 60℃; for 6h; anti-Markovnikov hydroamidation; Inert atmosphere; optical yield given as %de; stereoselective reaction;	78%

glyoxylic acid ethyl ester (924-44-7) + 1-(p-toluenesulfonyl)-1H-indole (31271-90-6) + Ethyl oxamate (617-36-7) → ethyl 2-((ethoxycarbonyl)amino)-2-(1-tosyl-1H-indol-3-yl)acetate

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; for 16h;	78%

Upstream product

• 119174-42-4 2-ethoxy-2-oxoacetic anhydride 
• 95-92-1 oxalic acid diethyl ester 
• 56-40-6 glycine 
• 64-17-5 ethanol 
• 4755-77-5 Ethyl oxalyl chloride 
• 67-63-0 isopropyl alcohol 
• 110-83-8 cyclohexene 
• 7664-41-7 ammonia 
• 541-41-3 chloroformic acid ethyl ester 
• 459-73-4 GlyOEt*HCl 
• 128200-13-5 3-aminomethyl-3-hydroxy-1-azabicyclo[2.2.2]octane 
• 623-73-4 diazoacetic acid ethyl ester 
• 623-49-4 ethyl cyanoformate 
• 1263290-89-6 ethyl 2-azido-2-hydroxyacetate 

Downstream Products

• 76-84-6 triphenylmethyl alcohol 
• 92-52-4 biphenyl 
• 623-49-4 ethyl cyanoformate 
• 46297-10-3 2-p-tolyl-1H-imidazole-4,5-dione 
• 4474-17-3 Cyanformylchlorid 
• 471-47-6 oxamic acid 
• 617-49-2 oxalic acid amide ureide 
• 49715-78-8 piperazine-2,3,5,6-tetraone 
• 51-79-6 urethane 
• 3232-84-6 urazole 
• 64-17-5 ethanol 
• 471-46-5 Oxalamide 
• 627-70-3 propan-2-one azine 
• 16982-21-1 ethyl 2-amino-2-thioxoacetate 

Relevant articles and documents

Synthetic route to isotopically labelled-oxamate

Since none of the available methods was suitable for the synthesis of isotopically labelled oxamate, a new procedure has been developed in our laboratory, based on the known procedures, but with substantial modifications. The method is convenient and gives reproducibly 17% yield based on KCN used. The strategy is considered suitable for labelling oxamate with 15N and 13C or 14C when starting with labelled KCN and can be easily modified for the synthesis of 18O-carbonyl-labelled oxamate. Copyright 2011 John Wiley & Sons, Ltd. Synthesis route to sodium oxamate labelled with various isotopes has been proposed. Copyright

Method for preparing oxamide ester

The invention discloses a method for preparing oxamide ester. A diazonium ester compound and ammonium iodide are adopted as reaction substrates, t-butylhydroperoxide (TBHP) is adopted as an environment-friendly oxidant under the condition of having no transition metal and alkali, and the oxamide ester is obtained through an oxidative coupling reaction in an organic solvent. Compared with the priorart, the method has the following advantages that the range of the reaction substrates is wide, reaction conditions are mild, the operation is simple, and the environment is protected. According to the method, TBHP is used as the oxidant, tert-butanol and water are produced after the reaction, the use of oxidants such as iodobenzene acetate and sodium hypochlorite is avoided, no harm is caused tothe environment, and the requirements of contemporary environment-friendly chemistry are met. In addition, the method can be used for post-modification of natural active molecules, such as cholesterol and epiandrosterone, a final target product with a high yield can be obtained, and a foundation is laid for practical application.

Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide

A sustainable flow chemistry process for the hydration of nitriles, whereby an aqueous solution of the nitrile is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.