4755-77-5

Basic information

• Product Name: Ethyl oxalyl monochloride
• Synonyms: ETHOXALYL CHLORIDE;ETCOX;ETHYL OXALYL CHLORIDE;Ethyl oxalyl monochloride;ETHYL (CHLOROFORMYL)FORMATE;ETHYL CHLOROGLYOXALATE;ETHYL CHLOROGLYOXYLATE;ETHYL CHLOROOXOACETATE
• CAS NO: 4755-77-5
• Molecular Formula: C₄H₅ClO₃
• Molecular Weight: 136.53
• EINECS: 225-285-0
• Product Categories: Pharmaceutical Intermediates;Organics;Indoles
• Mol File: 4755-77-5.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 135 °C
• Flash Point: 41 °C
• Appearance: Clear/Liquid
• Density: 1.222 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.19mmHg at 25°C
• Refractive Index: 1.416-1.418
• Storage Temp.: Flammables area
• Water Solubility: Slightly miscible with water.
• Sensitive: Moisture Sensitive
• BRN: 506725
• CAS DataBase Reference: Ethyl oxalyl monochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl oxalyl monochloride(4755-77-5)
• EPA Substance Registry System: Ethyl oxalyl monochloride(4755-77-5)

Safety Data

• Hazard Codes: C,F
• Statements: 34-29-20/21/22-14-10-37-36
• Safety Statements: 8-45-36/37/39-26-16
• RIDADR: 2920
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 4755-77-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4755-77-5 differently. You can refer to the following data:
1. Ethyl oxalyl monochloride is used in the synthesis of 2-oxo-3-alkenoic esters and alpha-keto ester in good yield. Ethyl oxalyl monochloride acts as a reactant in the preparation of oxyoxalamide derivatives as an epoxide hydrolase inhibitor.
2. Ethyl oxalyl chloride is used in the synthesis of 2-oxo-3-alkenoic esters and alpha-keto ester in good yield. It acts as a reactant in the preparation of oxyoxalamide derivatives as an epoxide hydrolase inhibitor.
3. Ethyl chlorooxoacetate can be used for the synthesis of:α-keto esters.Functionalized 3-pyrolin-2-ones.Substituted arylglyoxylic acids via Friedel–Crafts acylation.Substituted 9,10-phenanthrenequinones.Quinoxalinone derivatives.

Chemical Properties

clear liquid

InChI:InChI=1/C4H5ClO3/c1-2-8-4(7)3(5)6/h2H2,1H3

Synthetic route

oxalic acid diethyl ester (95-92-1) → oxalyl dichloride (79-37-8) + chloroethane (75-00-3) + 1,2-diethoxy-tetrachloro-ethane (63938-37-4) + ethoxy-dichloro-acetyl chloride (98019-44-4) + Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With phosphorus pentachloride; manganese(ll) chloride at 90℃; for 5h; Product distribution; other catalysts (CuCl2, ZnCl2, CdCl2, CrCl3, FeCl3, CoCl2, PdCl2) and temperatures (from 70 to 130 deg C);	A n/a B n/a C n/a D n/a E 83.7%

oxalic acid diethyl ester (95-92-1) → chloroethane (75-00-3) + Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With phosphorus pentachloride at 90℃; for 5h;	A n/a B 83.7%

oxalyl dichloride (79-37-8) + ethanol (64-17-5) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 2.33333h;	81%
at 0 - 20℃; for 3h;	75%
at 0 - 20℃; for 2.33333h;	69.6%

potassium monoethyl oxalate (1906-57-6) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With thionyl chloride In diethyl ether at 60℃; Cooling with ice; Inert atmosphere;	76.2%
With thionyl chloride

potassium cyanate + N-(4-aminophenyl)-3-<4-(2-pyridinyl)-1-piperazinyl>propanamide (86523-76-4) → Ethyl oxalyl chloride (4755-77-5) + N-<4-<(aminocarbonyl)amino>phenyl>-3-<4-(2-pyridinyl)-1-piperazinyl>propanamide (86523-79-7)

Conditions	Yield
With hydrogenchloride for 8h;	A 3% B 16%

oxalic acid monoethyl ester (617-37-8) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With thionyl chloride
With phosphorus pentachloride
With oxalyl dichloride In N,N-dimethyl-formamide at 20℃; for 4h;

Ethyl dichloro-(ethoxy)-acetate (6957-89-7) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With platinum

oxalic acid diethyl ester (95-92-1) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With phosphorus pentachloride anschliessend Destillieren des gebieldeten Aethoxydichloressigsaeure-aethylesters im Vakuum, Erhitzen auf 160-170grad und wiederholt Fraktionieren;
With phosphorus pentachloride at 130℃; darauffolgende Vakuum-Destillation und Zerlegung des Aethoxy-dichloressigsaeureaethylesters durch mehrfache Destillation bei gewoehnlichem Druck;
With phosphorus pentachloride
With phosphorus pentachloride
Stage #1: oxalic acid diethyl ester With potassium acetate In water at 70 - 80℃; for 2h; Stage #2: With thionyl chloride In diethyl ether for 15h; Cooling with ice; Reflux;	12.22 g

Dichlor-isobutyloxy-essigsaeure-ethylester (90952-82-2) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
Heating;

Ethyl dichloro-(ethoxy)-acetate (6957-89-7) → chloroethane (75-00-3) + Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With phosphorus pentachloride Product distribution; 1) 95 deg C to 100 deg C, 4d, 2) 180 deg C to 200 deg C, 6h;

3-isopropyl-5-chloro-5-ethoxyoxazolidine-2,4-dione (91467-21-9) → 3-isopropyloxazolidine-2,4,5-trione (91467-24-2) + Ethyl oxalyl chloride (4755-77-5) + Isopropyl isocyanate (1795-48-8)

Conditions	Yield
at 180 - 190℃; Yield given. Yields of byproduct given;

phosphorus pentachloride (10026-13-8, 874483-75-7) + oxalic acid diethyl ester (95-92-1) → Ethyl oxalyl chloride (4755-77-5)

potassium ethyl oxalate → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With thionyl chloride

potassium salt of oxalic acid monoethyl ester → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
With trichlorophosphate
With phosphorus pentachloride

thionyl chloride (7719-09-7) + oxalic acid monoethyl ester (617-37-8) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
bei Kochen;

oxalic acid monoethyl ester (617-37-8) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
beim Behandeln von aethyloxalsaurem Kalium;

oxalyl dichloride (79-37-8) + ethyl vinyl ether (109-92-2) → (2E)-3-ethoxyprop-2-enoyl chloride (6191-99-7, 99471-66-6) + Ethyl oxalyl chloride (4755-77-5)

Conditions	Yield
Stage #1: oxalyl dichloride; ethyl vinyl ether at 0 - 5℃; for 12h; Stage #2: at 120℃; for 2h;

Ethyl oxalyl chloride (4755-77-5) + N-methylaniline (100-61-8) → ethyl-2-(methyl(phenyl)amino)-2-oxoacetate (1457-86-9)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;	100%
With triethylamine In dichloromethane at 0 - 20℃;	85%
With pyridine
With pyridine In dichloromethane for 5h; Ambient temperature;

5-amino-3-methylisoxazole (14678-02-5) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-((3-methylisoxazol-5-yl)amino)-2-oxoacetate (41230-59-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 5℃; for 2h;	100%
With triethylamine In chloroform
In pyridine at 20℃; for 1.5h;	30.7 g

3-trifluoromethylaniline (98-16-8) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-oxo-2-((3-(trifluoromethyl)phenyl)amino)acetate (17738-86-2)

Conditions	Yield
With triethylamine In ethyl acetate at 0 - 19℃; for 2.5h; Product distribution / selectivity;	100%
With triethylamine In dichloromethane at 0℃; for 0.166667h; Product distribution / selectivity;	99%
With triethylamine In dichloromethane for 0.166667h; Cooling;	99%

2-amino-6-methoxybenzamide (1591-38-4) + Ethyl oxalyl chloride (4755-77-5) → ethyl ((2-(aminocarbonyl)-3-methoxyphenyl)amino)(oxo)acetate (54249-44-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at 35℃; for 2h; Cooling with ice;	100%
With pyridine In dichloromethane

4-trifluoromethylphenylamine (455-14-1) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-oxo-2-((4-(trifluoromethyl)phenyl)amino)acetate (69066-00-8)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 8h;	100%
With triethylamine In tetrahydrofuran at 20℃;	99%
With pyridine In dichloromethane at 0 - 20℃; for 43h; Reflux; Inert atmosphere; Schlenk technique;	96%

2-amino-p-anisamide (38487-91-1) + Ethyl oxalyl chloride (4755-77-5) → ethyl ((2-(aminocarbonyl)-5-methoxyphenyl)amino)(oxo)acetate (54166-80-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 35℃; for 2h; Cooling with ice;	100%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	72%
With pyridine

Ethyl oxalyl chloride (4755-77-5) + aniline (62-53-3) → Ethyl oxanilate (1457-85-8)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique;	100%
With triethylamine In dichloromethane at 20℃; for 1h;	91%
With triethylamine In dichloromethane at 20℃; for 1h;	91%

Ethyl oxalyl chloride (4755-77-5) + 2,4,6-trimethylaniline (88-05-1) → 2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester (79354-30-6)

Conditions	Yield
With pyridine at 20℃; for 1.5h; Inert atmosphere;	100%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	97%
In tetrahydrofuran at 70℃; for 1h;	96%

1-hydroxy-2(1H)-pyridinethione (1121-30-8) + Ethyl oxalyl chloride (4755-77-5) → N-ethoxyoxalyloxy-2-thiopyridone (133616-54-3)

Conditions	Yield
With pyridine In benzene at 0℃; for 0.5h;	100%

1-indoline (496-15-1) + Ethyl oxalyl chloride (4755-77-5) → ethyl α-oxo-α-(N-indolinyl)-acetate (131328-01-3)

Conditions	Yield
With triethylamine In dichloromethane 1.) 0 deg C, 10 min, 2.) RT, 1 h;	100%
In tetrahydrofuran for 2h; Heating;	63%

9-vinyl-9H-carbazole (1484-13-5) + Ethyl oxalyl chloride (4755-77-5) → (E)-4-Carbazol-9-yl-2-oxo-but-3-enoic acid ethyl ester (105633-64-5)

Conditions	Yield
With pyridine In chloroform for 2.5h; Ambient temperature;	100%

1,1-Bis--ethylen (39837-37-1) + Ethyl oxalyl chloride (4755-77-5) → 2-Oxo-4,4-bis-p-tolylsulfanyl-but-3-enoic acid ethyl ester (105633-48-5)

Conditions	Yield
With pyridine In chloroform for 0.2h; Ambient temperature;	100%

N-methyl(p-chloroaniline) (932-96-7) + Ethyl oxalyl chloride (4755-77-5) → N-(4-Chloro-phenyl)-N-methyl-oxalamic acid ethyl ester (129049-19-0)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;	100%

2-aminonaphthalene-1-carbonitrile (7066-13-9) + Ethyl oxalyl chloride (4755-77-5) → 2-ethoxalylaminonaphthalene-1-carbonitrile (80999-53-7)

Conditions	Yield
In pyridine Ambient temperature;	100%

C14H10Cl2S2 (105633-65-6) + Ethyl oxalyl chloride (4755-77-5) → Ethyl 4,4-bis<4-chlorophenylthio>-2-oxo-3-butenoate (105633-49-6)

Conditions	Yield
With pyridine In chloroform for 24h; Ambient temperature;	100%

Ethyl oxalyl chloride (4755-77-5) → 3,3-Dihydroxy-2-oxo-propionic acid ethyl ester (138380-46-8)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone Ambient temperature;	100%

Ethyl oxalyl chloride (4755-77-5) + ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-hydroxymethyl-2-propylimidazole-5-carboxylate (144690-86-8) → Oxalic acid 1-(2'-tert-butoxycarbonyl-biphenyl-4-ylmethyl)-5-ethoxycarbonyl-2-propyl-1H-imidazol-4-ylmethyl ester ethyl ester (1026694-93-8)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;	100%

Ethyl oxalyl chloride (4755-77-5) + benzyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (188411-47-4) → 2-(Ethoxyoxalyl-amino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid benzyl ester (188411-48-5)

Conditions	Yield
With triethylamine In dichloromethane 0 deg C, 0.5 h; room temperature, 20 h;	100%

(S)-1-phenyl-ethylamine (2627-86-3) + Ethyl oxalyl chloride (4755-77-5) → ethyl (S)-2-oxo-2-((1-phenylethyl)amino)acetate (164219-31-2)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 0.5h;	100%
With triethylamine In dichloromethane at 0 - 20℃;	99%
With potassium carbonate	89%
With pyridine In dichloromethane at 0 - 20℃;

Ethyl oxalyl chloride (4755-77-5) + 1-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-3-hydroxy-propan-2-one (245112-27-0) → oxalic acid 3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-oxo-propyl ester ethyl ester (245112-28-1)

Conditions	Yield
With triethylamine In tetrahydrofuran Acylation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-propan-1-one → N-(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-N-(2-propionyl-phenyl)-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-3-furan-3-yl-propan-1-one → N-(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-N-[2-(3-furan-3-yl-propionyl)-phenyl]-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-3-furan-2-yl-propan-1-one → N-(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-N-[2-(3-furan-2-yl-propionyl)-phenyl]-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-3-phenyl-propan-1-one → N-(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-N-[2-(3-phenyl-propionyl)-phenyl]-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-3-(4-methoxy-phenyl)-propan-1-one (292859-75-7) → N-benzo[1,3]dioxol-5-ylmethyl-N-{2-[3-(4-methoxy-phenyl)-propionyl]-phenyl}-oxalamic acid ethyl ester (292859-74-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 3-benzo[1,3]dioxol-5-yl-1-[2-(4-methoxy-benzylamino)-phenyl]-propan-1-one → N-[2-(3-benzo[1,3]dioxol-5-yl-propionyl)-phenyl]-N-(4-methoxy-benzyl)-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-3-pyridin-3-yl-propan-1-one → N-(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-N-[2-(3-pyridin-3-yl-propionyl)-phenyl]-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(7-bromo-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-3-(4-methoxy-phenyl)-propan-1-one → N-(7-bromo-benzo[1,3]dioxol-5-ylmethyl)-N-{2-[3-(4-methoxy-phenyl)-propionyl]-phenyl}-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 3-(4-bromo-phenyl)-1-{2-[(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-propan-1-one → N-{2-[3-(4-bromo-phenyl)-propionyl]-phenyl}-N-(6-chloro-benzo[1,3]dioxol-5-ylmethyl)-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Ethyl oxalyl chloride (4755-77-5) + 1-{2-[(7-methoxy-benzo[1,3]dioxol-5-ylmethyl)-amino]-phenyl}-3-(4-methoxy-phenyl)-propan-1-one → N-(7-methoxy-benzo[1,3]dioxol-5-ylmethyl)-N-{2-[3-(4-methoxy-phenyl)-propionyl]-phenyl}-oxalamic acid ethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Condensation;	100%

Upstream product

• 6957-89-7 Ethyl dichloro-(ethoxy)-acetate 
• 79-37-8 oxalyl dichloride 
• 64-17-5 ethanol 
• 91467-21-9 3-isopropyl-5-chloro-5-ethoxyoxazolidine-2,4-dione 
• 10026-13-8 phosphorus pentachloride 
• 95-92-1 oxalic acid diethyl ester 
• 7719-09-7 thionyl chloride 
• 617-37-8 oxalic acid monoethyl ester 
• 10025-87-3 trichlorophosphate 
• 109-92-2 ethyl vinyl ether 
• 86523-76-4 N-(4-aminophenyl)-3-<4-(2-pyridinyl)-1-piperazinyl>propanamide 
• 1906-57-6 potassium monoethyl oxalate 
• 90952-82-2 Dichlor-isobutyloxy-essigsaeure-ethylester 

Downstream Products

• 41374-72-5 ethyl 2-oxo-2-(2-pyridylamino)acetate 
• 5432-10-0 1,2,3,4-tetrahydro-2-methyl-1,3,4-trioxopyrazino[1,2-a]indole 
• 101103-89-3 [4-(3-chloro-4-methyl-phenyl)-piperazino]-oxo-acetic acid ethyl ester 
• 401640-33-3 (2-acetyl-phenyl)-oxalamic acid ethyl ester 
• 13326-56-2 ethyl N-[2-(3,4-dimethoxyphenyl)ethyl]oxamate 
• 64837-53-2 ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate 
• 41230-59-5 ethyl 2-((3-methylisoxazol-5-yl)amino)-2-oxoacetate 
• 53117-15-0 ethyl 2-[(3-methoxyphenyl)amino]-2-oxoacetate 
• 18522-99-1 ethyl 4'-methoxyoxanilate 
• 53074-84-3 O-ethyl S-phenyl monothiooxalate 
• 101110-21-8 ethyl 2-(1,2-dihydroacenaphthylen-5-yl)-2-oxoacetate 
• 4075-59-6 2-thiopheneglyoxylic acid 
• 4075-58-5 thienylglycoxylate dethyle 
• 100519-34-4 (4-acetoxy-phenyl)-glyoxylic acid ethyl ester 

Relevant articles and documents

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