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149837

Sigma-Aldrich

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
Beilstein:
533048
EC Number:
240-418-2
MDL number:
MFCD00006703
UNSPSC Code:
12352005
PubChem Substance ID:
24848976
NACRES:
NA.22

product name

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

Assay

≥99%

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

62-67 °C (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

CCOC1C=Cc2ccccc2N1C(=O)OCC

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

InChI key

GKQLYSROISKDLL-UHFFFAOYSA-N

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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New approach to the quaternization of chitosan and its amphiphilic derivatives
Stepnova EA, et al.
European Polymer Journal, 43(6), 2414-2421 (2007)
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
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
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
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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