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Ethyl diazoacetate
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Name

Ethyl diazoacetate

 EINECS 210-810-8
CAS No. 623-73-4 Density 1.085 g/cm3
PSA 63.69000 LogP -0.06884
Solubility insoluble in water, soluble in organic solvents such as dichloroethane Melting Point -22 °C
Formula C4H6N2O2 Boiling Point 140-141 °C (720 mmHg)
Molecular Weight 114.104 Flash Point 46 °C
Transport Information UN 1993 Appearance colourless liquid
Safety 36/37 Risk Codes 5-10-22-40
Molecular Structure Molecular Structure of 623-73-4 (Ethyl diazoacetate) Hazard Symbols HarmfulXn
Synonyms

Aceticacid, diazo-, ethyl ester (6CI,8CI,9CI);DAAE;Diazoacetic acid ethyl ester;Diazoacetic ester;Ethoxycarbonyldiazomethane;Ethyl 2-diazoacetate;Ethyl2-diazoethanoate;Ethyl diazoacetate;NSC 79147;

Article Data 110

Ethyl diazoacetate Synthetic route

623-33-6

glycine ethyl ester hydrochloride

623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfite; sodium nitrite In dichloromethane; water at 3℃; for 4h; pH=4.3; Solvent; Temperature; Reagent/catalyst; pH-value; Large scale;98.4%
With citric acid; sodium hydroxide; sodium nitrite In o-xylene; para-xylene; ethylbenzene; water; m-xylene at 10℃; for 24h;94.4%
Stage #1: glycine ethyl ester hydrochloride With sodium nitrite In dichloromethane; water for 0.5h; Schlenk technique; Cooling with ice;
Stage #2: With sulfuric acid In dichloromethane; water at -10℃; for 0.333333h; Schlenk technique;		87%
70526-06-6

(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

65245-26-3

perfluorobutanesulfonyl azide

A

623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 96%
70526-06-6

(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

144951-87-1

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide

A

623-73-4

diazoacetic acid ethyl ester

B

N-perfluorobutanesulfonyl-1-(pyrrolidin-1-yl)ethylidenamine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 85%
66003-96-1

β-morpholinoethylcrotonate

144951-88-2

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide

A

623-73-4

diazoacetic acid ethyl ester

B

N'-Perfluorobutanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 85%
781-15-7

1,2,3,4-tetrachloro-5,6-dinitrobenzene

459-73-4

GlyOEt*HCl

A

623-73-4

diazoacetic acid ethyl ester

B

121904-46-9

N-(ethylacetoxy)-2,3,4,5-tetrachloro-6-nitroaniline

Conditions
ConditionsYield
In toluene for 1h; Heating;A 17%
B 83%
65245-26-3

perfluorobutanesulfonyl azide

66003-96-1

β-morpholinoethylcrotonate

A

623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)ethanesulfonyl-N,N-cyclobutylacetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 81%
66003-96-1

β-morpholinoethylcrotonate

144951-87-1

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide

A

623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)ethanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 81%
70526-06-6

(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

144951-88-2

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide

A

623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl-N,N-cyclobutylacetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 80%
10271-27-9

1-(p-nitrophenyl)-3-(ethoxycarbonylmethyl)triazene

623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With acetic acid In dichloromethane; water66%
In chloroform Ambient temperature;

2-aminoacetimidate ethyl ester

623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With cis-nitrous acid
With cis-nitrous acid

Ethyl diazoacetate Specification

The systematic name of Diazoacetic ester is 2-diazonio-1-ethoxyethenolate. With the CAS registry number 623-73-4 and EINECS 210-810-8, it is also named as Diazoacetic acid, ethyl ester. The product's categories are Carboxylic; Azo / Diazo Compounds; Nitrogen Compounds; Organic Building Blocks. It is colourless liquid which is insoluble in water, soluble in organic solvents such as dichloroethane. When heated to decomposition it emits toxic fumes of NOx. Additionally, the storage environment should be well-ventilated, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.673; (4)ACD/LogD (pH 7.4): 0.673; (5)ACD/BCF (pH 5.5): 1.912; (6)ACD/BCF (pH 7.4): 1.912; (7)ACD/KOC (pH 5.5): 55.352; (8)ACD/KOC (pH 7.4): 55.352; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2.

Preparation of Diazoacetic ester: It can be obtained by Glycine ethyl ester hydrochloride and sodium nitrite. HCl•NH2CH2CO2C2H5+NaNO2→N2CHCOOC2H5+NaCl+2H2O

Uses of Diazoacetic ester: It is an important intermediate of chrysanthemic acid and DCVA. It also can be used in organic synthesis. For example: it can react with benzo[1,3]dioxole-5-carbaldehyde to get 3-benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester. This reaction needs solvent 1,2-dichloro-ethane by heating. The reaction time is 8 hours. The yield is 68%.

Diazoacetic ester can react with benzo[1,3]dioxole-5-carbaldehyde to get 3-benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester

When you are using this chemical, please be cautious about it as the following:
It is flammable. When heating it may cause an explosion. It is also harmful if swallowed. What's more, it has limited evidence of a carcinogenic effect. If you want to contact this product, you must wear suitable protective clothing and gloves.

People can use the following data to convert to the molecule structure. 
1. SMILES:CCOC(=O)C=[N+]=[N-]
2. InChI:InChI=1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3
3. InChIKey:YVPJCJLMRRTDMQ-UHFFFAOYAC

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intravenous 280mg/kg (280mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 135, Pg. 219, 1970.
rat LD50 oral 400mg/kg (400mg/kg)   Xenobiotica. Vol. 3, Pg. 271, 1973.

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