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CAS No.: | 623-73-4 |
---|---|
Name: | Ethyl diazoacetate |
Article Data: | 110 |
Molecular Structure: | |
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 |
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% |
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
perfluorobutanesulfonyl azide
A
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; | A n/a B 96% |
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide
A
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; | A n/a B 85% |
β-morpholinoethylcrotonate
1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide
A
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; | A n/a B 85% |
1,2,3,4-tetrachloro-5,6-dinitrobenzene
GlyOEt*HCl
A
diazoacetic acid ethyl ester
B
N-(ethylacetoxy)-2,3,4,5-tetrachloro-6-nitroaniline
Conditions | Yield |
---|---|
In toluene for 1h; Heating; | A 17% B 83% |
perfluorobutanesulfonyl azide
β-morpholinoethylcrotonate
A
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; | A n/a B 81% |
β-morpholinoethylcrotonate
1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide
A
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; | A n/a B 81% |
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide
A
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; | A n/a B 80% |
1-(p-nitrophenyl)-3-(ethoxycarbonylmethyl)triazene
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
With acetic acid In dichloromethane; water | 66% |
In chloroform Ambient temperature; |
diazoacetic acid ethyl ester
Conditions | Yield |
---|---|
With cis-nitrous acid | |
With cis-nitrous acid |
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%.
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. |