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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

Quality Level

200

application(s)

peptide synthesis

functional group

ether

storage temp.

2-8°C

Related Categories

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.

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.

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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George Vaniotis et al.
Journal of molecular and cellular cardiology, 62, 58-68 (2013-05-21)
At the cell surface, βARs and endothelin receptors can regulate nitric oxide (NO) production. β-adrenergic receptors (βARs) and type B endothelin receptors (ETB) are present in cardiac nuclear membranes and regulate transcription. The present study investigated the role of the
New approach to the quaternization of chitosan and its amphiphilic derivatives
Stepnova EA, et al.
European Polymer Journal, 43(6), 2414-2421 (2007)
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
H Gozlan et al.
Neuropharmacology, 33(3-4), 423-431 (1994-03-01)
The effects of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ), an alkylating agent producing irreversible blockade of various membrane bound receptors in brain, were investigated on four different types of serotonin receptors, 5-HT1A, 5-HT1B, 5-HT2A and 5-HT3, in various brain regions in the rat. In
Kenichi Nagase et al.
Colloids and surfaces. B, Biointerfaces, 178, 253-262 (2019-03-16)
There is strong demand for cell separation methods that do not decrease cell activity or modify cell surfaces. Here, new temperature-modulated cell-separation columns not requiring cell-surface premodification are described. The columns were packed with temperature-responsive cationic polymer hydrogel-modified silica beads.
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