Skip to Content
Merck
All Photos(4)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(4)

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

Looking for similar products? Visit Product Comparison Guide

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.
C Ribas et al.
British journal of pharmacology, 132(7), 1467-1476 (2001-03-27)
1. This study was designed to assess the molecular and cellular events involved in the up-regulation (and receptor supersensitivity) of brain alpha(2)-adrenoceptors as a result of chronic depletion of noradrenaline (and other monoamines) by reserpine. 2. Chronic reserpine (0.25 mg
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
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
View All Related Papers

Protocols

cAMP Assays

cAMP Assays protocol from cold spring harbor

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service