Name: Ethyl diazoacetate
SKU: 623-73-4

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Organic Chemicals (4)
Reagent (1)
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Basic Information

Molecular Structure:
CAS No.:	623-73-4
Name:	Ethyl diazoacetate
Article Data:	110

Formula:	C₄H₆N₂O₂
Molecular Weight:	114.104
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;
EINECS:	210-810-8
Density:	1.085 g/cm³
Melting Point:	-22 °C
Boiling Point:	140-141 °C (720 mmHg)
Flash Point:	46 °C
Solubility:	insoluble in water, soluble in organic solvents such as dichloroethane
Appearance:	colourless liquid
Hazard Symbols:	Xn
Risk Codes:	5-10-22-40
Safety:	36/37
Transport Information:	UN 1993
PSA:	63.69000
LogP:	-0.06884

Synthetic route

: 623-33-6
glycine ethyl ester hydrochloride

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
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

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 96%

...Expand

: 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

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 85%

...Expand

: 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

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 85%

...Expand

: 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

Conditions	Yield
In toluene for 1h; Heating;	A 17% B 83%

...Expand

: 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

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 81%

...Expand

: 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

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 81%

...Expand

: 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

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 80%

...Expand

: 10271-27-9
1-(p-nitrophenyl)-3-(ethoxycarbonylmethyl)triazene

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With acetic acid In dichloromethane; water	66%
In chloroform Ambient temperature;

: 2-aminoacetimidate ethyl ester

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With cis-nitrous acid
With cis-nitrous acid

Raw Materials

141-97-9

64-17-5

123-75-1

623-33-6

Downstream Products

372-31-6

3663-80-7

6290-49-9

3938-96-3

101-97-3

401-56-9

14062-19-2

3249-68-1

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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 NO_x. 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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