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Merck
CN

149837

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline

≥99%, for peptide synthesis

Synonym(s):

N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, EEDQ, Ethyl 1,2-dihydro-2-ethoxyquinoline-1-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C14H17NO3
CAS Number:
16357-59-8
Molecular Weight:
247.29
NACRES:
NA.22
PubChem Substance ID:
24848976
UNSPSC Code:
12352005
EC Number:
240-418-2
MDL number:
MFCD00006703
Beilstein/REAXYS Number:
533048

Key Documents

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Product Name

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline, ≥99%

InChI key

GKQLYSROISKDLL-UHFFFAOYSA-N

InChI

1S/C14H17NO3/c1-3-17-13-10-9-11-7-5-6-8-12(11)15(13)14(16)18-4-2/h5-10,13H,3-4H2,1-2H3

SMILES string

CCOC1C=Cc2ccccc2N1C(=O)OCC

assay

≥99%

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

62-67 °C (lit.)

application(s)

peptide synthesis

functional group

ether

storage temp.

2-8°C

Quality Level

200

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Related Categories

Application

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline is used as a coupling agent:
  • In the regioselective quaternization of chitosan and its amphiphilic derivatives.
  • In the preparation of amide-type S-MA derivative-modified QCM sensors.

General description

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline(EEDQ) is a stable, and readily available reagent used to prepare amides and peptides in high yields. At ambient temperature, EEDQ is soluble in an aqueous medium containing organic solvents but insoluble in water. It is used as a coupling agent in peptide synthesis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR1121
MKCP0630
MKCN7854
MKCN8013
MKCN7852

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Toshiaki Miki et al.
Journal of biochemistry, 141(3), 377-387 (2007-01-20)
Chemical modification of the bovine heart cytochrome bc1 complex with N-(ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline (EEDQ) has been reported to inhibit the proton pumping activity without affecting the rate of electron transfer to ferricytochrome c. This study aims to examine the effect of EEDQ
S Kapur et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 23(5), 595-598 (2000-10-12)
Two techniques are commonly used to measure antipsychotic induced dopamine D(2) occupancy in animals: competition with a reversible radioligand (3H-raclopride) or with an irreversible receptor inactivator (EEDQ). While both of these techniques have been used in the past, there is
Development of real-time sensitive chiral analysis technique using quartz crystal analyzer
Kim JM, et al.
Sensors and Actuators B, Chemical, 171, 478-485 (2012)
Didier Cussac et al.
Molecular pharmacology, 62(3), 578-589 (2002-08-16)
As determined by a guanosine 5'-O-(3-[(35)S]thio)triphosphate ([(35)S]GTPgammaS) binding assay, which does not distinguish G protein subtypes, 5-hydroxytryptamine (5-HT) and 2(S)- 1-(6-chloro-5-fluoro-1H-indol-1-yl)-2-propanamine fumarate (Ro600175) behaved as full agonists at human 5-HT(2C) (h5-HT(2C)) receptors (VSV isoform) stably expressed in Chinese hamster ovary
G D Stanwood et al.
The Journal of pharmacology and experimental therapeutics, 295(3), 1232-1240 (2000-11-18)
Regulation of the expression of dopamine D2 and D3 receptors in the rat brain was examined using quantitative autoradiography after chronic (14 day) drug treatments designed to increase or decrease dopamine receptor stimulation. Reserpine treatment depleted endogenous dopamine by more
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