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Cas Database

623-73-4

623-73-4

Identification

  • Product Name:Ethyl diazoacetate

  • CAS Number: 623-73-4

  • EINECS:210-810-8

  • Molecular Weight:114.104

  • Molecular Formula: C4H6N2O2

  • HS Code:29270000

  • Mol File:623-73-4.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn,F

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

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  • Manufacture/Brand:TRC
  • Product Description:EthylDiazoacetate(>90%)
  • Packaging:20g
  • Price:$ 80
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl diazoacetate contains ≥13 wt. % dichloromethane
  • Packaging:1kg
  • Price:$ 1330
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl diazoacetate contains ≥13 wt. % dichloromethane
  • Packaging:20g
  • Price:$ 78.3
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl diazoacetate contains ≥13 wt. % dichloromethane
  • Packaging:5g
  • Price:$ 26.7
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl diazoacetate contains ≥13 wt. % dichloromethane
  • Packaging:100g
  • Price:$ 244
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Ethyl diazoacetate
  • Packaging:10 g
  • Price:$ 620
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Ethyl 2-diazoacetate (diluted with ~10% dichloromethane wt/wt)97%
  • Packaging:250g
  • Price:$ 864
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Ethyl 2-diazoacetate (diluted with ~10% dichloromethane wt/wt)97%
  • Packaging:500g
  • Price:$ 1440
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:ETHYL DIAZOACETATE 95.00%
  • Packaging:100G
  • Price:$ 2823.28
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:ETHYL DIAZOACETATE 95.00%
  • Packaging:20G
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Relevant articles and documentsAll total 62 Articles be found

-

La Forge et al.

, p. 391 (1952)

-

-

Clusius,Luehti

, p. 445 (1957)

-

A pilot-scale synthesis of (1R)-trans-2-(2,3-dihydro-4-benzofuranyl) cyclopropanecarboxylic acid: A practical application of asymmetric cyclopropanation using a styrene as a limiting reagent

Simpson, James H.,Godfrey, Jollie,Fox, Rita,Kotnis, Atul,Kacsur, David,Hamm, Jason,Totelben, Michael,Rosso, Victor,Mueller, Richard,Delaney, Edward,Deshpande, Rajendra P.

, p. 3569 - 3574 (2003)

Asymmetric cyclopropanation of styrene 1 (as the limiting reagent) was demonstrated using excess ethyl diazoacetate and catalytic Ru(ip-Pybox). Selective hydrolysis of the resulting 90:10 trans:cis mixture of cyclopropane 4 generated cyclopropyl acid 2 as a 96:4 trans:cis mixture with 84% e.e. for the trans-cyclopropane. Further purification and enantiomeric enrichment was achieved by diastereoselective crystallization with (+)-dehydroabeitylamine to afford the (R,R)-isomer with ≥99.9% e.e in 60-65 M% yield starting from styrene 1.

-

Womack,Nelson

, p. 392 (1955)

-

METHOD OF PRODUCING NITRO COMPOUND

-

Paragraph 0041, (2021/06/25)

PROBLEM TO BE SOLVED: To provide a production method which can efficiently provide a nitro compound in an industrial scale. SOLUTION: A method of producing a compound represented by formula (2) comprises using nitric acid to nitrate a compound represented by formula (1) in the presence of concentrated sulfuric acid that weighs 1.5-5.0 times more than the compound represented by formula (1). [In formulas (1) and (2), X1 and X2 are identical or different and represent halogen atoms, and R represents an optionally substituted 6-membered heterocyclic group.] SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Guo, Jing,Mandal, Dipendu,Stephan, Douglas W.,Wu, Yile,Zhao, Yunbo

supporting information, p. 7758 - 7761 (2021/08/13)

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.

Process route upstream and downstream products

Process route

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

diazoacetic acid ethyl ester
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%
glycine ethyl ester hydrochloride; With sodium nitrite; In dichloromethane; water; for 0.5h; Schlenk technique; Cooling with ice;
With sulfuric acid; In dichloromethane; water; at -10 ℃; for 0.333333h; Schlenk technique;
87%
glycine ethyl ester hydrochloride; With sodium azide; sulfuric acid; In dichloromethane; water; at -10 ℃;
With sodium carbonate; In dichloromethane; water; at 0 ℃;
82%
With sulfuric acid; sodium nitrite;
With dichloromethane; sulfuric acid; sodium nitrite;
Darstellung nach Curtius;
With sulfuric acid; sodium nitrite; In dichloromethane; at -20 ℃; for 0.25h;
With borax; sodium tetraborate decahydrate; phosphoric acid; sodium nitrite; In water; toluene; at 10 ℃;
128 g
With sulfuric acid; sodium nitrite; In dichloromethane; water; at -5 ℃; for 0.166667h;
glycine ethyl ester hydrochloride; With sodium hydroxide; citric acid; sodium nitrite; In water; at 8 - 12 ℃; for 12h; pH=4.5 - 4.8; Acidic aqueous solution;
With sodium carbonate; In water; at 8 - 12 ℃; pH=<= 9.2;
With sodium nitrite; In water; 1,2-dichloro-ethane; at -5 ℃; for 1.5h;
With sodium acetate; sodium nitrite;
glycine ethyl ester hydrochloride; With sodium nitrite; In dichloromethane; water; at -5 ℃;
With sulfuric acid; In dichloromethane; water; at -5 - 1 ℃; for 0.166667h;
With phosphoric acid; sodium nitrite; sodium tetraborate decahydrate; In water; toluene; at 0 - 20 ℃; for 0.5h; pH=3.7 - 4.5; Product distribution / selectivity;
With hydrogenchloride; sodium nitrite; In water; Product distribution / selectivity; Industry scale;
With sulfuric acid; sodium nitrite; In dichloromethane; water; at -10 ℃; Inert atmosphere;
With hydrogenchloride; water; sodium nitrite; at -5 ℃; for 0.5h;
glycine ethyl ester hydrochloride; With sodium acetate; sodium nitrite; In water; at 0 - 20 ℃; for 0.166667h;
With sulfuric acid; In water;
9 g
With sodium acetate; sodium nitrite; In water; at 20 ℃; for 0.166667h;
9 g
With sodium acetate; sodium nitrite; In water; at 0 - 20 ℃;
9 g
With sulfuric acid; sodium nitrite; In water; at -5 ℃; for 0.25h;
With sodium tetraborate decahydrate; sodium nitrite; In water; at 25 ℃;
With sodium nitrite; In dichloromethane; at 50 ℃; for 0.0333333h; pH=3.5; Temperature; Concentration; Time; Flow reactor;
With hydrogenchloride; sodium acetate trihydrate; sodium nitrite; In water; toluene; at 10 - 15 ℃; for 1.5h; Ionic liquid; Large scale;
With sodium tetraborate decahydrate; sodium nitrite; In water; at 25 ℃; Inert atmosphere;
With hydrogenchloride; sodium nitrite; In toluene; at 20 ℃; pH=3.5; Time; Temperature; Flow reactor;
99 %Chromat.
With sulfuric acid; sodium nitrite; In water;
With sodium acetate; sodium nitrite; In water; at 2 ℃;
With sulfuric acid; sodium nitrite; In dichloromethane; water; at 0 ℃; Solvent; Temperature;
With phosphoric acid; sodium nitrite; In water; toluene;
GlyOEt*HCl
459-73-4

GlyOEt*HCl

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
Conditions Yield
With cis-nitrous acid;
With cis-nitrous acid;
With isopentyl nitrite; var. reag.: NaNO2;
With cis-nitrous acid; In tetrachloromethane;
With thiophene; sulfuric acid; sodium nitrite; In water; at 5 ℃;
70 %Chromat.
With sodium nitrite; Acidic conditions;
ethyl acetate
141-78-6

ethyl acetate

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
Conditions Yield
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 20 ℃; for 12h;
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;
With 4-acetamidobenzenesulfonyl azide; In acetonitrile; at 0 - 20 ℃; Inert atmosphere; Schlenk technique; Alkaline conditions;
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 40 ℃; for 1h; Microwave irradiation;
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 - 40 ℃; for 1h; Irradiation;
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; Inert atmosphere;
1-(p-nitrophenyl)-3-(ethoxycarbonylmethyl)triazene
10271-27-9

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

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
Conditions Yield
With acetic acid; In dichloromethane; water;
66%
In chloroform; Ambient temperature;
ethyl bromoacetate
105-36-2

ethyl bromoacetate

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
Conditions Yield
ethyl bromoacetate; With sodium hydrogencarbonate; In acetonitrile; benzyl alcohol; at 0 - 20 ℃; for 1h; Inert atmosphere;
With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20 ℃; for 0.583333h; Inert atmosphere;
With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.5h;
With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.5h;
With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.5h;
With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.5h;
ethyl 2-diazo-3-oxobutanoate
2009-97-4

ethyl 2-diazo-3-oxobutanoate

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
Conditions Yield
With potassium hydroxide; In diethyl ether; water; at 25 ℃; for 1h;
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
70526-06-6

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

perfluorobutanesulfonyl azide
65245-26-3

perfluorobutanesulfonyl azide

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

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;
96%
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
70526-06-6

(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
144951-87-1

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

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

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

Conditions
Conditions Yield
In dichloromethane; at 20 ℃; for 0.5h;
85%
β-morpholinoethylcrotonate
66003-96-1

β-morpholinoethylcrotonate

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide
144951-88-2

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

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

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

Conditions
Conditions Yield
In dichloromethane; at 20 ℃; for 0.5h;
85%
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
70526-06-6

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

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide
144951-88-2

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

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

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;
80%

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