Ethyl acetoacetate | 141-97-9, Ethyl acetoacetate Formula

Description

Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor. Ethyl 3-Oxobutanoate is a colorless liquid with a fruity, ethereal, sweet odor reminiscent of green apples. It is used to create fresh, fruity top notes in feminine fine fragrances. Ethyl acetoacetate occurs in flavors of natural materials such as coffee, strawberries, and yellow passion fruits.This compound is a tautomer at room temperature consisting of about 93% keto form and 7% enol form.The organic c

The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.

Ethyl acetoacetate appears as a colorless liquid with a fruity odor. Flash point 185°F. Boiling point 365°F. May cause adverse health effects if ingested or inhaled. May irritate to skin, eyes and mucous membranes. Used in organic synthesis and in lacquers and paints.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|clear, colourless to yellow mobile liquid; fruity taste; fruity, sweet, and rum-like odour

Ethyl acetoacetate appears as a colorless liquid with a fruity odor. Flash point 185°F. Boiling point 365°F. May cause adverse health effects if ingested or inhaled. May irritate to skin, eyes and mucous membranes. Used in organic synthesis and in lacquers and paints.|Ethyl acetoacetate is an ethyl ester resulting from the formal condensation of the carboxy group of acetoacetic acid with ethanol. It has a role as a flavouring agent, an antibacterial agent and a plant metabolite. It derives from an acetoacetic acid.

Ethyl acetoacetate Basic Attributes

Molecular Weight：

130.14

Exact Mass：

130.14

BRN：

385838

EC Number：

205-516-1

UNII：

IZP61H3TB1

ICSC Number：

1024

NSC Number：

8657

UN Number：

1993

DSSTox ID：

DTXSID2027092

Color/Form：

COLORLESS LIQUID

HScode：

2918300090

Characteristics

PSA：

43.4

XLogP3：

0.2

Appearance：

APHA: ≤15 Liquid

Density：

1.0282 g/cm³ @ Temp: 20 °C

Melting Point：

-45 °C

Boiling Point：

180.8 °C @ Press: 760 Torr

Flash Point：

185 °F

Refractive Index：

n 20/D 1.419

Water Solubility：

H2O: 116 g/L (20 ºC)

Storage Conditions：

Store below +30°C.

Vapor Pressure：

1 mm Hg ( 28.5 °C)

Vapor Density：

4.48 (vs air)

Toxicity：

Oral-Rat LD50: 3980 mg/kg; Oral-Mouse LD50: 5105 mg/kg

Flammability characteristics：

Combustible in case of open flame, high temperature and strong oxidant; burning emits irritating smoke

Explosive limit：

1.0-54%(V)

Odor：

PLEASANT GREEN, FRUITY, RUM ODOR

Taste：

RIPE FRUIT TASTE

Experimental Properties：

CONVERSION FACTOR: 5.31 MG/CU M IS EQUIVALENT TO 1 PPM|CONVERSION FACTOR: 1 MG/L IS EQUIVALENT TO 188 PPM|THIS COMPD IS A TAUTOMER AT ROOM TEMP CONSISTING OF ABOUT 93% KETO FORM & 7% ENOL FORM; COEFFICIENT OF EXPANSION 0.00101/DEG C; FP (ENOL) -80 °C; FP (KETO) -39 °C|MAX ABSORPTION (VAPOR): 238.5 NM (LOG E= 4.21); DENSITY 1.0119 @ 10 °C; INDEX OF REFRACTION 1.4432 @ 20 °C /ENOL FORM/|MAX ABSORPTION (VAPOR): 263 NM (LOG E= 2.47); DENSITY 1.0368 AT 10 °C/4 °C; INDEX OF REFRACTION: 1.4171 AT 20 °C /KETO FORM/|CAN REACT WITH OXIDIZING MATERIALS|UV: 40 (Sadtler Research Laboratories Spectral Collection) /Ethyl acetoacetate (keto form)/

Air and Water Reactions：

Flammable.

Reactive Group：

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Reactivity Alerts：

Highly Flammable

Reactivity Profile：

ETHYL ACETOACETATE, a beta-keto ester, is more reactive than many esters. Undergoes an exothermic cleavage reaction in the presence of concentrated base. Reacts with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Mixing with 2,2,2-tris(bromomethyl)ethanol and zinc led to an explosion [US Patent 3 578 619, Crotonaldehyde may rapidly polymerize with ethyl acetoacetate (Soriano, D.S. et al. 1988. Journal of Chemical Education 65:637.).1971].

Peroxide Forming Chemical：

Ethyl acetoacetate|D*: Other compounds that may form peroxides|1 samples had 30 ppm age > 10 yrs|Management of time-sensitive chemicals (JCHAS)

Autoignition Temperature：

563 °F (USCG, 1999)|563 °F (295 °C).|295 °C

Flammable Limits：

FLAMMABLE LIMITS (BY VOL) 1.4% AT 200 °F (93 °C) & 9.5% AT 350 °F (176 °C).

Physical Dangers：

The vapour is heavier than air.

Safety Information

Packing level：

III

Hazard category：

3.2

Transport codes：

UN 1993

wgk germany：

1

hazard class code：

36

safety instructions：

26-24/25

RTECS Number：

AK5250000

Marks：

Xi

Storage features：

Warehouse ventilated, low temperature and dry

Stability/Shelf Life：

Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.

Precautionary statement(s)：

P210, P264, P280, P305+P351+P338, P337+P313, P370+P378, P403+P235, P501

Hazard Statements：

H227

FDA Requirements：

FDA 121.1164.|FDA 172.515. FLAVOR USEFUL IN STRAWBERRY, FRUIT FLAVORS.

Special Reports：

A REVIEW WITH 8 REFERENCES ON ETHYL ACETOACETATE TOXICITY.[OPDYKE DL J; FRAGRANCE RAW MATRIALS. DIPENTENE. ETHYL ACETOACETATE; FOOD COSMET TOXICOL 12(5-6) 713 (1974)]

RIDADR：

UN 1993

Fire Hazards：

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)|Combustible. Above 70 °C explosive vapour/air mixtures may be formed.

GHS Classification：

|Danger|H315 (17.44%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2527 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H227: Combustible liquid [Warning Flammable liquids]|P210, P264, P280, P305+P351+P338, P337+P313, P370+P378, P403+P235, and P501

Isolation and Evacuation：

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Nonfire Spill Response：

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Personal Protective Equipment：

Goggles or face shield; rubber gloves. (USCG, 1999)

Fire Potential：

MODERATE WHEN EXPOSED TO HEAT OR FLAME.

Explosive Limits and Potential：

TRIBROMONEOPENTYL ALCOHOL, ETHYL ACETOACETATE & ZINC WERE BEING REACTED TO PREPARE THE ZINC CHELATE OF TRIBROMONEOPENTYL ACETOACETATE. WHEN REACTION HAD PROCEEDED TO WHERE 80% OF BY-PRODUCT ETHANOL HAD BEEN REMOVED, A VIOLENT DECOMP OCCURRED.|Explosive limits , vol% in air: 1-54

Fire Fighting Procedures：

USE ALCOHOL FOAM, CARBON DIOXIDE, DRY CHEMICAL.

Irritations：

IRRITANT TO EYES.

Spillage Disposal：

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water.

Safe Storage：

Separated from strong oxidants. Ventilation along the floor. Well closed.

Inhalation Risk：

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

Effects of Short Term Exposure：

The substance is irritating to the eyes, skin and respiratory tract.

Fire Prevention：

NO open flames. Above 70 °C use a closed system and ventilation.

Exposure Prevention：

PREVENT GENERATION OF MISTS!

Inhalation Prevention：

Use ventilation.

Skin Prevention：

Protective gloves.

Eye Prevention：

Wear safety spectacles.

Toxicity

Toxicity class：

moderately toxic

Natural Pollution Sources：

NATURALLY OCCURRING IN STRAWBERRY...

Name	Type of Test	Exposure Route	Species Observed	Dose/Duration	Toxic Effects	Reference
ACUTE TOXICITY DATA	LD50 - Lethal dose, 50 percent kill	Oral	Rodent - rat	3980 mg/kg	Details of toxic effects not reported other than lethal dose value--	Journal of Industrial Hygiene and Toxicology. (Cambridge, MA) V.18-31, 1936-49. For publisher information, see AEHLAU. Volume(issue)/page/year: 31,60,1949
ACUTE TOXICITY DATA	LD50 - Lethal dose, 50 percent kill	Oral	Rodent - mouse	5105 mg/kg	Details of toxic effects not reported other than lethal dose value--	Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 60,1810,1971
ACUTE TOXICITY DATA	Mutation in microorganisms			200 ug/plate	--	Osaka-shi Igakkai Zasshi. Journal of Osaka City Medical Association. (Osaka-shi Igakkai, c/o Osaka-shiritsu Daigaku Igakubu, 1-4-54 Asahi-cho, Abeno-ku, Osaka, 545, Japan) V.24- 1975- Volume(issue)/page/year: 34,267,1985

Drug Information

Health Hazards：

Liquid may cause mild irritation of eyes. (USCG, 1999)

First Aid：

EYES: flush with water for 15 min. (USCG, 1999)

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Human Toxicity Excerpts：

MODERATELY IRRITATING TO SKIN, MUCOUS MEMBRANES.|MODERATELY TOXIC BY INGESTION & INHALATION IRRITANT TO...EYES.

MeSH Entry Terms：

ethyl 3-oxobutanoate

Exposure Routes：

The substance can be absorbed into the body by inhalation.

Symptoms：

Cough. Sore throat.

Redness.

Redness. Pain.

Ethyl acetoacetate Use and Manufacturing

Methods of Manufacturing

The preparation method commonly used in industry is that diketene and absolute ethanol are esterified under concentrated sulfuric acid catalysis to obtain crude ethyl acetoacetate, which is then rectified under reduced pressure to obtain a finished product. Add ethanol and sulfuric acid to the esterification pot according to the proportion, stir and heat. When the temperature rises to 82 ℃, start adding diketene dropwise, and the esterification temperature should not exceed 130 ℃. Continue to reflux until the reaction temperature no longer changes and the esterification solution is free of diketene to end the reaction. Reduce the temperature of the feed liquid to within 120℃, and remove the low boilers under the condition of controlling the reflux ratio of 1:1. When the low boilers no longer distill, increase the vacuum degree to 86.6kPa, continue to remove the low boilers, when the tower When the top temperature rises above 100°C, the vacuum degree is increased to 97.3 kPa, and the finished product is distilled with the content greater than 97%. Self-condensation reaction with ethyl acetate can also be used. 2CH3COOC3H5[Na]→CH3COCH2COOC2H5 Add 250g of sodium metal to 4240mL of ethyl acetate. The reaction starts very slowly. It needs to be warmed on the water bath. Once the reaction starts, it is very violent and needs to be cooled. After refluxing, ethyl acetate was recovered by distillation. Add 1375mL of 56% acetic acid solution and stir to reflux, add 250g of common salt, separate the oil, extract with ether, recover ether from the extract, and wash with 10% sodium bicarbonate solution until it is acid-free. After drying with calcium chloride, it is distilled under reduced pressure, and the 76-78°C/2.4kPa fraction is collected as the finished product, and the yield is close to 30%.

Uses

Ethyl acetoacetate (EAA) is used as starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives as well as intermediate for vitamins and pharmaceuticals. Product Data Sheet

Intermediates

Air care products

Production

10,000,000 - 50,000,000 lb|(1972) GREATER THAN 9.08X10+5 GRAMS|(1975) GREATER THAN 4.54X10+5 GRAMS|(1986) No Data

Formulations：

GRADES: TECHNICAL; 98%.

Manufacturing Info：

All other basic organic chemical manufacturing|Butanoic acid, 3-oxo-, ethyl ester: ACTIVE|17 PPM IN NON-ALCOHOLIC BEVERAGES; 24 PPM IN ICE CREAM, ICES, ETC; 110 PPM IN CANDY; 120 PPM IN BAKED GOODS; 93 PPM IN GELATINS & PUDDINGS; & 530 PPM IN CHEWING GUM.|USEFUL AS STRAWBERRY, FRUIT FLAVORS. FEMA NUMBER 2415.

Use Classification：

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

Food Additive Classes：

Flavoring Agents

Analysis Methods

Name	Column Shape	Active Phase(℃)	Retention index	Temperature Control	Method	Comments	Reference
Kovats' RI, non-polar column, isothermal	Capillary	SE-30	903.0	100.	isothermal	40. m/0.35 mm/0.35 μm	Tudor, E.Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equationsJ. Chromatogr. A1997, 779, 1-2, 287-297.
Kovats' RI, non-polar column, isothermal	Packed	SE-30	910.	150.	isothermal	Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m	Tiess, D.Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe1984, 33, 6-9.
Kovats' RI, non-polar column, isothermal	Capillary	Carbowax 20M	1496.	150.	isothermal	Phase thickness: 0.08 μm	Tudor, E.Moldovan, D.Zârna, N.Temperature dependence of the retention index for perfumery compounds on two carbowax-20M glass capillary columns with different film thickness. 2Rev. Roum. Chim.1999, 44, 7, 665-675.
Kovats' RI, non-polar column, isothermal	Capillary	HP-5MS	954.		temperature ramp	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min	Pino, J.A.Mesa, J.Muñoz, Y.Martí, M.P.Marbot, R.Volatile components from mango (Mangifera indica L.) cultivarsJ. Agric. Food Chem.2005, 53, 6, 2213-2223.
Kovats' RI, non-polar column, isothermal	Capillary	HP-5	944.		temperature ramp	50. m/0.32 mm/1.05 μm, He, 2. K/min; T_start: 50. C; T_end: 290. C	David, F.Scanlan, F.Sandra, P.Retention time locking in flavor analysisProceedings 23rd ISCC; CD-ROM, 2000, retrieved from http://www.richrom.com/assets/CD23PDF.

Computed Properties

Molecular Weight:130.14
XLogP3:0.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:130.062994177
Monoisotopic Mass:130.062994177
Topological Polar Surface Area:43.4
Heavy Atom Count:9
Complexity:118
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

1

304479-42-3

=

+

2

115479-06-6

=

+

3

+

=

+

Material

Methyl acetoacetate

Ethyl acetate

Ethanol

Recommended Suppliers of Ethyl acetoacetate

Shaanxi Dideu Medichem Co. Ltd Contact Supplier

CN
5 YRS

Business licensed Certified factory

Manufactory Supplier of Chemical Pesticides,Food Additives,Agrochemicals,Active Pharm Ingredients,Flavors and Fragrances,Chemical Catalyst,Chemical Materials,Chem&Pharm Intermediates,Organic Intermediates,Feed Additive

Ethyl acetoacetate 99% liquid Dideu

CAS No.: 141-97-9

Grade: Industrial Grade

Content: 99%

Inquiry
QINGDAO EAST CHEMSOURCES TRADE CO.,LTD Contact Supplier

CN
8 YRS

Business licensed

Trader Supplier of Food additives,Pharmaceutical raw materials,Chemicals,Comestic raw materials

Ethyl acetoacetate cas 141-97-9 Hot Selling High Quality Ethyl Acetoacetate colorless clear liquid Acetoacetic ester; EAA

CAS No.: 141-97-9

Grade: Different Grade

Content: 99%

Inquiry
Henan Lihao Chem Plant Limited Contact Supplier

CN
5 YRS

Business licensed

Trader Supplier of PVC resin,pvc paste resin,melamine

high purity hot sale Ethyl acetoacetate 99% high quality see COA KANBEI

CAS No.: 141-97-9

Grade: Industrial Grade

Content: 99%

Inquiry
Honour Enterprise Company Limited Contact Supplier

CN
4 YRS

Business licensed

Trader Supplier of Semaglutide,Tirzepatide,API,Enzyme

More than 15 years GMP Factory Suppy 99.5% Ethyl acetoacetate Medical Grade CAS141-97-9

CAS No.: 141-97-9

Grade: Pharmaceutical Grade

Content: 99.5%

Inquiry
ZhengZhou YiBang Industry Co,. Ltd Contact Supplier

CN
5 YRS

Business licensed

Trader Supplier of L-ethyl lactate,Ethyl butyrate,glacial acetate acid

Factory Supply Ethyl acetoacetate Safe Delivery Ethyl 3-oxobutanoate 99%

Unit Price: $6-7 /MT FOB

CAS No.: 141-97-9

Content: 99%

Inquiry

Learn More Other Chemicals

Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, ethyl ester, (1alpha,3R,4alpha,5R)- (9CI)

463325-95-3
Cyclopropanecarboxylic acid, 1-formyl-2-methyl-, ethyl ester (9CI)

260261-27-6
3-CYCLOPROPYL-2-METHYL-3-OXO-PROPIONIC ACID ETHYL ESTER

21741-37-7
Cyclopropanecarboxylic acid, 1-amino-2-phenyl-, ethyl ester, (1R,2R)-rel- (9CI) Formula

669058-57-5
Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, (1R,2S)-rel- (9CI) Formula

213316-32-6
Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, hydrochloride (9CI) Formula

681807-60-3
3-Cyclopentene-1-carboxylic acid, 1-(chlorocarbonyl)-, ethyl ester (9CI) Structure

76910-09-3
Cyclopropanecarboxylic acid, 2-propyl-, ethyl ester, (1R,2S)- (9CI) Structure

492468-18-5
What is Cyclopentanecarboxylic acid, 2-(formylhydrazono)-, ethyl ester, (Z)- (9CI)

163352-99-6
What is 2-[(2,6-Dichlorophenyl)sulfonyl]acetic acid ethyl ester

1154228-17-7