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16357-59-8

Basic Information
CAS No.: 16357-59-8
Name: N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline
Article Data: 13
Molecular Structure:
Molecular Structure of 16357-59-8 (N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline)
Formula: C14H17NO3
Molecular Weight: 247.294
Synonyms: 1-(Ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline;2-Ethoxy-1(2H)-quinolinecarboxylic acid ethyl ester;2-Ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline;EEDQ;Ethyl2-ethoxy-1(2H)-quinolinecarboxylate;N-Carbethoxy-2-ethoxy-1,2-dihydroquinoline;NSC 147831;
EINECS: 240-418-2
Density: 1.16 g/cm3
Melting Point: 62-67 °C(lit.)
Boiling Point: 355.9 °C at 760 mmHg
Flash Point: 169 °C
Solubility: insoluble in water
Appearance: White to pale yellow solid
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 38-36/37/38-20/21/22
Safety: 22-24/25-36/37/39-26-36
PSA: 38.77000
LogP: 3.10390
Synthetic route
91-22-5

quinoline

64-17-5

ethanol

541-41-3

chloroformic acid ethyl ester

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water at 0℃; for 1.33333h;69%
16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

67-64-1

acetone

ethyl 4-(2-hydroxypropan-2-yl)quinoline-1(4H)-carboxylate

Conditions
ConditionsYield
With diethylzinc; palladium diacetate; triphenylphosphine In toluene at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; regioselective reaction;100%
107-10-8

propylamine

3050-37-1

indole-3-glycolic acid

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

carbonic acid ethyl ester (1H-indol-3-yl)-propylcarbamoyl-methyl ester

Conditions
ConditionsYield
In dichloromethane for 5h; Ambient temperature;99%
3050-37-1

indole-3-glycolic acid

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

62-53-3

aniline

carbonic acid ethyl ester (1H-indol-3-yl)-phenylcarbamoyl-methyl ester

Conditions
ConditionsYield
In dichloromethane for 5h; Ambient temperature;99%
3050-37-1

indole-3-glycolic acid

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

ethoxycarbonyloxy-(1H-indol-3-yl)-acetic acid

Conditions
ConditionsYield
In dichloromethane for 5h; Ambient temperature;99%
107-10-8

propylamine

617-73-2

2-hydroxy-octanoic acid

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

carbonic acid ethyl ester 1-propylcarbamoyl-heptyl ester

Conditions
ConditionsYield
In dichloromethane for 5h; Ambient temperature;99%
107-10-8

propylamine

828-01-3

phenyllactic acid

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

carbonic acid ethyl ester 2-phenyl-1-propylcarbamoyl-ethyl ester

Conditions
ConditionsYield
In dichloromethane for 5h; Ambient temperature;99%
828-01-3

phenyllactic acid

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

2-ethoxycarbonyloxy-3-phenyl-propionic acid

Conditions
ConditionsYield
In dichloromethane for 5h; Ambient temperature;99%
828-01-3

phenyllactic acid

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

100-46-9

benzylamine

carbonic acid 1-benzylcarbamoyl-2-phenyl-ethyl ester ethyl ester

Conditions
ConditionsYield
In dichloromethane for 5h; Ambient temperature;99%
4224-69-5

methyl 2-(bromomethyl)propenoate

16357-59-8

N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

2-(2-methoxycarbonyl-allyl)-2H-quinoline-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With indium; acetic acid In tetrahydrofuran for 0.5h;99%
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Chemistry

Molecular Formula: C14H17NO3
Molar mass: 247.29 g/mol
Density: 1.16 g/cm3
Flash Point: 169 °C
Index of Refraction: 1.564
Boiling Point: 355.9 °C at 760 mmHg
Vapour Pressure: 3.04E-05 mmHg at 25°C
Melting point: 62-67 °C(lit.)
storage temp: 0-6°C
Water solubility: insoluble
Sensitive: Moisture Sensitive
Appearance: White to pale yellow solid
Structure of N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline(16357-59-8):
                 
Synonyms: EEDQ;Ethyl 2-ethoxy-1(2H)-quinolinecarboxylate;1(2H)-quinolinecarboxylic acid, 2-ethoxy-, ethyl ester;2-Ethoxy-1(2H)-quinolinecarboxylic Acid Ethyl Ester;Ethyl-2-ethoxychinolin-1(2H)-carboxylat
Product Categories: Heterocycles;Coupling Reagent;Acids and Derivatives;Biochemistry;Condensation & Active Esterification;Synthetic Organic Chemistry;Coupling Reactions (Peptide Synthesis);Peptide Synthesis

Toxicity Data With Reference

1.   

ipr-mus LD50:32 mg/kg

   JMCMAR    Journal of Medicinal Chemistry. 14 (1971),49.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.
Hazard Codes: Xi,Xn
Risk Statements:
20:  Harmful by inhalation
21:  Harmful in contact with skin
22:  Harmful if swallowed 
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
22:  Do not breathe dust
24:  Avoid contact with skin
25:  Avoid contact with eyes
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
39:  Wear eye/face protection

Specification

N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline(16357-59-8) is hazardous,so the first aid measures and others should be known .Such as:
Skin: Get medical aid. Should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing and shoes.
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon. 
Inhalation: Remove from exposure and move to fresh air immediately.Give artificial respiration While not breathing. when breathing is difficult, give oxygen.And as soon as to get medical aid if cough or other symptoms appear.
Ingestion: Do not induce vomiting.If victim is conscious and alert, give 2-4 cupfuls of milk or water.If conscious drink water, then induce vomiting. If unconscious, immediately take victim to a physician and do not attempt to induce vomiting. Wash mouth out with water,and get medical aid immediately.
Notes to Physician: Treat supportively and symptomatically.
Stability and Reactivity of N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline(16357-59-8): 
Incompatibilities with Other Materials: Strong oxidizing agents.
Conditions to Avoid: Incompatible materials.
Hazardous Decomposition Products: Nitrogen oxides, carbon dioxide,carbon monoxide.