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Ethyl-chloracetat

Ethyl chloroacetate

HCID 7751
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Grundinformationen

CAS
105-39-5
Standard-SMILES
CCOC(=O)CCl
InChIKey
VEUUMBGHMNQHGO-UHFFFAOYSA-N
Summenformel
C4H7ClO2
Durchschnittliche Molmasse
122,55 g/mol
Monoisotopische Masse
122,01345714

Überblick

Ethyl chloroacetate appears as a clear colorless liquid with a pungent odor. Flash point 100 °F. Denser than water and insoluble in water. Vapors heavier than air.

Namen und Bezeichner

Bevorzugter Name
Ethyl chloroacetate
IUPAC
ethyl 2-chloroacetate
Lokaler Name
Ethyl-chloracetat
Englischer Name
Ethyl chloroacetate
Summenformel
C4H7ClO2
Molmasse
122.55

Namen und Synonyme

ETHYL CHLOROACETATE105-39-5Ethyl chloracetateEthyl monochloroacetateAcetic acid, chloro-, ethyl esterEthyl monochloracetateEthyl chloroethanoate2-Chloroacetic Acid Ethyl EsterEthyl alpha-chloroacetateChloroacetic acid, ethyl esterEthylester kyseliny chloroctoveDTXSID4026715
Weitere Namen anzeigen
CHLOROACETIC ACID ETHYL ESTEREthyl chloroacetatETHYL MONO CHLORO ACETATENSC 8833Chloricacidesterethylchloracetate2-chlorobutanoateChloroaceticester
6H07TEH4TFNSC-8833DTXCID306715Monochloroacetic acid ethyl esterEMCARefChem:138892203-294-0ethyl 2-chloroacetate

Datenbank-Bezeichner

CAS
105-39-5
PubChem CID
7751
DTXSID

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,9
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
7
Formalladung
0
Komplexität
62,7

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Chloroacetic Acid Derivatives

Flammable agents - 2nd degree

SpringerMaterials PropertiesBoiling point
LogP · 2 Einträge

log Kow = 0.94

(calculated)

Odor · 2 Einträge

Fruity pungent odor

Pungent odor

Density · 5 Einträge

1.15 at 68 °F (USCG, 1999) - Denser than water; will sink

1.1498 @ 20 °C/4 °C

1.15 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.01

1.145 @25 °C

Viscosity2.93X10-3 Pa.s @ 247.15 K
Color/Form · 2 Einträge

Water-white mobile liq

Liquid

Solubility · 5 Einträge

Insol in water; miscible with alc, ether

Sol in benzene

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H226 (80%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Acetic acid, chloro-, ethyl ester

Acetic acid, 2-chloro-, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2-chloro-, ethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/16030

Acetic acid, chloro-, ethyl ester: HSNO Approval: HSR001147 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison Flammable Liquid
Fire Hazards · 3 Einträge

Special Hazards of Combustion Products: Irritating, toxic hydrogen chloride and phosgene may be generated in fires. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 53 °C explosive vapour/air mixtures may be formed.

Chemie und Industrie

Pharmakologische Informationen

Absorption, Distribution and Excretion...MAY BE ABSORBED PERCUTANEOUSLY...

Verwendung und Herstellung

Uses · 3 Einträge

Used as a solvent, military poison, and to make other organic chemicals; [Hawley]

Solvent, organic synthesis, military poison, vat dyestuffs.

CHEM INT FOR SODIUM FLUOROACETATE, A RODENTICIDE & OTHER DERIVATIVES, EG, DL-ASPARTIC ACID; CHEM INT FOR BENAZOLIN, AN HERBICIDE (NON-U.S. USE)

U.S. Imports(1977) AT LEAST 4.54X10+6 G
U.S. Production · 3 Einträge

2023: 1,000,000 - <5,000,000 lb

(1977) AT LEAST 4.99X10+7 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Consumption PatternsESSENTIALLY 100% AS A CHEM INT
Industry UsesCBI
Methods of Manufacturing · 4 Einträge

Prepn: Vogel, J Chem Soc 1948, 644.

(1) action of chloroacetyl chloride on alcohol; (2) by treating chloroacetic acid with alcohol and sulfuric acid

REACTION OF CHLOROACETIC ACID WITH ETHYL ALCOHOL USING SULFURIC ACID CATALYST

Ethanol and chloroacetic acid (esterification)

General Manufacturing Information · 2 Einträge

CBI

Acetic acid, 2-chloro-, ethyl ester: ACTIVE

Anwendungen · 1 Eintrag

Ethyl chloroacetate is a reagent used in the preparation of 5 member heterocycles. It is used as pharmaceutical and organic intermediate. It is used as a solvent for organic synthesis and the production of pesticides (such as sodium fluoroacetate).

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Weitere Aktionen
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DTXSID4026715
ChEMBL
CHEMBL3186148
UNII
6H07TEH4TF
EC Number
203-294-0
Nikkaji
J55.313A

Insoluble in water, miscible in ethanol, acetone and ethyl ether

Miscible in oxygenated solvents

Solubility in water, g/100ml at 20 °C: 1.23

Flash Point · 4 Einträge

100 °F (USCG, 1999)

53 °C

147 °F (64 °C) (OPEN CUP)

53 °C c.c.

Boiling Point · 4 Einträge

289 °F at 760 mmHg (USCG, 1999)

144-146 °C

144.2 °C

144 °C @760 [mm Hg]

DecompositionWHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES OF /HYDROGEN CHLORIDE/.
Melting Point · 4 Einträge

-15 °F (USCG, 1999)

-26 °C

-26 °C

-27 °C

Physikochemische Eigenschaften

Schmelzpunkt
-26 °C · -26 °C (lit.)
Siedepunkt
143 °C · 143 °C (lit.)
Dichte
1.145 g/mL · 1.145 g/mL at 25 °C (lit.)
Dampfdichte
4.23 · 4.23 (vs air)
Dampfdruck
10 mm · 10 mm Hg ( 38 °C)
Brechungsindex
20 · n20/D 1.421(lit.)
Flammpunkt
150 °F · 150 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
12.3 g/l · 12.3g/l
Aggregatzustand
Liquid
Farbe
Clear colorless
Geruch (Odor)
Extremely irritating; fruity; pungent
Explosionsgrenze
2.6 % · 2.6%(V)
Wasserlöslichkeit
20 g/L · 20 g/L (20 ºC)
Merck
14 · 14,3783
BRN
506455 · 506455
Henry's Law Constant
2.6 · 2.6×10-1 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
11.6 · 11.6(20℃)
Stabilität
Stable. Incompatible with acids, bases, oxidizing agents, reducing agents. Flammable.
InChI
1S/C4H7ClO2/c1-2-7-4(6)3-5/h2-3H2,1H3
InChIKey
VEUUMBGHMNQHGO-UHFFFAOYSA-N
SMILES
CCOC(=O)CCl
LogP
0.94 · 0.940
CAS Datenbank
105 · 105-39-5(CAS DataBase Reference)
NIST chemische Informationen
Ethyl chloroacetate(105-39-5)
EPA chemische Informationen
Ethyl chloroacetate (105-39-5)
Fire PotentialFLAMMABLE LIQUID; A DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME ...
Health Hazards · 2 Einträge

Inhalation causes irritation of mucous membrane, headache, and nausea. Contact with liquid causes extreme eye irritation and conjunctivitis; irritates skin if not removed at once. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 1 Eintrag

A skin, eye, and respiratory tract irritant; May cause skin sensitization; [ICSC] Toxic by inhalation, skin absorption, and ingestion; [ESIS] May cause pulmonary edema; Strong lachrymator; [HSDB] No sensitizing effects known; Causes lacrimation; [MSDSonline]

DOT ID and Guide1181 155
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
EC ClassificationSymbol: T, N; R: 23/24/25-50; S: (1/2)-7/9-45-61
UN ClassificationUN Hazard Class: 6.1; UN Subsidiary Risks: 3; UN Pack Group: II
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 Eintrag

ETHYL CHLOROACETATE is a chlorinated ester. Esters react 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. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

Use water spray, dry powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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

Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

INHALATION: remove patient to fresh air; get medical attention.

General First Aid:

Safe StorageFireproof. Separated from incompatible materials and food and feedstuffs. See Chemical Dangers. Dry.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 2 Einträge

To fight fire, use water, foam, carbon dioxide, dry chemical.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water form as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

Nonfire Spill ResponseExcerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 Eintrag

Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in covered plastic containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 3 Einträge

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ...

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and Evacuation · 2 Einträge

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

Immediate precautionary measure

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 0.94(2) and a regression-derived equation(3), indicates that ethyl chloroacetate is expected to have very high mobility in soil(SRC). Volatilization of ethyl chloroacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.20X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of ethyl chloroacetate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 4.87 mm Hg(5). Ethyl chloroacetate is subject to hydrolysis under acidic and alkaline conditions. Acid hydrolysis products could include ethyl alcohol and chloroacetic acid, both very soluble in water. Alkaline hydrolysis of the ester would yield products similar to acid hydrolysates except the chloroacetic acid would be in salt form. In addition, alkaline hydrolysis could result in the substitution of an OH group for the chlorine atom resulting in the production of glycolic acid in its salt form. Glycolic acid is water soluble as well as being susceptible to biodegradation(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 0.94(2) and a regression-derived equation(3), indicates that ethyl chloroacetate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.20X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 hr and 11 days, respectively(SRC). Ethyl chloroacetate is subject to hydrolysis under acidic and alkaline conditions. Acid hydrolysis products could include ethyl alcohol and chloroacetic acid, both very soluble in water. Alkaline hydrolysis of the ester would yield products similar to acid hydrolysates except the chloroacetic acid would be in salt form. In addition, alkaline hydrolysis could result in the substitution of an OH group for the chlorine atom resulting in the production of glycolic acid in its salt form. Glycolic acid is water soluble as well as being susceptible to biodegradation(7). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl chloroacetate, which has a vapor pressure of 4.87 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl chloroacetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3).

Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
Signs and Symptoms · 4 Einträge

Cough. Sore throat.

MAY BE ABSORBED! Redness. Pain.

Watering of the eyes. Redness. Pain.

Burning sensation of the tongue. Nausea. Abdominal pain. Vomiting.

ICSC Environmental DataThe substance is toxic to aquatic organisms.
Soil Adsorption/MobilityThe Koc of ethyl chloroacetate is estimated as 12(SRC), using a log Kow of 0.94(1). According to a classification scheme(3), this estimated Koc value suggests that ethyl chloroacetate is expected to have very high mobility in soil.
TSCA Test Submissions · 1 Eintrag

Ethyl chloroacetate (CAS# 105-39-5) was evaluated for acute inhalation toxicity in male and female rats at dose levels of 2.20, 3.81, 5.84, and 4.44 mg/L for one-hour. Mortality ratios were 0/5 M, 0/5 F; 1/5 M, 3/5 F; 2/5 M, 3/5 F; and 5/5 M, 5/5 F, respectively. The estimated LC50 value was 4.65 mg/L (927 ppm).

Human Toxicity Excerpts · 3 Einträge

.../ETHYL CHLOROACETATE IS AMONG HALOGENATED ACID ESTERS WHICH HAVE/ POTENTIAL FOR PRODUCING PULMONARY EDEMA.

...POTENT LACRIMATOR.

SUMMARY TOXICITY STATEMENT /ACUTE/ MODERATE IRRITATION VIA ORAL & INHALATION ROUTES. MODERATE= MAY CAUSE REVERSIBLE OR IRREVERSIBLE CHANGES TO EXPOSED TISSUE, NOT PERMANENT INJURY OR DEATH; CAN CAUSE CONSIDERABLE DISCOMFORT.

Artificial Pollution SourcesEthyl chloroacetate's production and use in organic synthesis, vat dyestuff, and military poison(1) may result in its release to the environment through various waste streams.
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 3 was calculated for ethyl chloroacetate(SRC), using a log Kow of 0.94(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for ethyl chloroacetate is estimated as 8.20X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethyl chloroacetate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 15 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 11 days(SRC). Ethyl chloroacetate's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of ethyl chloroacetate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 4.87 mm Hg(3).

Non-Human Toxicity Excerpts · 3 Einträge

IT IS MODERATELY STRONG IRRITANT TO GUINEA PIG SKIN...

.../ETHYL CHLOROACETATE/ TESTED BY DROP APPLICATION TO RABBIT EYES CAUSED SEVERE DAMAGE SIMILAR TO THAT CAUSED BY AMMONIA, GRADED 9 ON SCALE OF 1 TO 10 AFTER 24 HR... RATED ACCORDING TO DEGREE OF INJURY...PAYING PARTICULAR ATTENTION TO CONDITION OF CORNEA. MOST SEVERE INJURIES HAVE BEEN RATED 10.

IN STRAIN A MICE, ETHYL CHLOROACETATE WAS CONSIDERED BORDERLINE TUMORIGENIC COMPD, PRODUCING ELEVATED LUNG TUMOR RESPONSE WHICH WAS SIGNIFICANT BY ONLY 1 STATISTICAL TEST USED.

Regulatorische Informationen

Atmospheric Standards · 1 Eintrag

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethyl chloroacetate is produced, as an intermediate or a final product, by process units covered under this subpart.

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 1181
hs_code
2915 40 00
RTECS-Nr.
AF9110000
risk_code
23/24/25-50-10
Toxizität
LD50 orally in Rabbit: 180 mg/kg LD50 dermal Rat 161 mg/kg
hazard_code
T,N
safety_code
45-61-7/9-16
hazard_class
6.1
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
105-39-5(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 3 OralAquatic Acute 1Eye Dam. 1Flam. Liq. 3Skin Irrit. 2
Selbstentzündungstemperatur
452 °C
Verwenden
Darstellung · 1 Eintrag

synthetischeEthyl chloroacetate is synthesized by esterification of chloroacetic acid and ethanol under the catalysis of sulfuric acid. The reaction equation is as follows:ClCH2COOH+C2H5OH[H2SO4]→ClCH2COOC2H5+H2OReaction: Add chloroacetic acid, ethanol and benzene into the esterification pot, turn on the stirrer, slowly add sulfuric acid, heat to reflux, continuously steam out the benzene-water azeotrope, and de-esterify the water generated by condensation and separator layering, Benzene is refluxed into the esterification pot, cooled and discharged when there is no more water to steam out, the crude ester is washed with saturated sodium bicarbonate solution and water to neutrality, dried with anhydrous calcium chloride, distilled, and collected The fraction at 144-146°C is the finished product of ethyl chloroacetate, the content is ≥99.0%, and the yield is 85%.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

AcetateCalciumchloridNatriumhydrogencarbonat

Nachgelagerte Produkte

HydratropaldehydEthyl-[[3-[2-(diethylamino)ethyl]-4-methyl-2-oxo-2H-1-benzopyran-7-yl]oxy]acetathydrochloridN-ethyl perfluorooctylsulfonylaminoacetate3-(1,1-dimethylethyl)-5-(ethoxycarboxy)-methylthio-1,2,4-triazole(4-Oxo-6,7-dihydro-4H,5H-cyclopenta[4,5]thieno-[2,3-d]pyrimidin-3-yl)-acetic acidPiroxicam2-(4-Isobutylphenyl)propionaldehyd1-(Hydrazinocarbonylmethyl)pyridiniumchlorid7-Methoxybenzofuran-2-carboxylic acidPiracetam4-(Acetylamino)phenoxyacetic acid ethyl ester2-MethylundecanalEthyl 3-(4-isobutylphenyl)-3-methyl glycidateMenazon6-Bromoindole-2-carboxylic acidEthylfluoracetat1-Boc-3-oxopiperazine2-PiperazinoneEtomidatEthyl 5-bromothiophene-2-carboxylate2-Imino-1,3-thiazol-4-on2-(4-Isobutylphenyl)propionaldehydoximSodium 3-4-isobutylphenyl)-2,3-epoxybutyurateEthyl 6-bromoindole-2-carboxylateEthyl-3-phenyloxiran-2-carboxylat2-Chloracetamid5-Bromothiophene-2-carbohydrazideCloricromene(6-Ethyl-4-oxo-4H-thieno[2,3-d]pyrimidin-3-yl)-acetic acid6-Amino-chromen-2-one7-Propoxy-chromen-2-one1-(((5-Nitro-2-furanyl)methylen)-amino)-2,4-imidazolidindionα-Methyl-3-phenoxybenzeneacetaldehydeVitamin-A-alkoholTriethylethan-1,1,2-tricarboxylatEthyl 2-aminothiazole-5-carboxylateMethyl-3-methyl-2-butenoatEthyl-2,3-epoxy-3-phenylbutyrat2-(2-thienyl)propionic acid(Hydrazinocarbonylmethyl)trimethylammoniumchlorid