• Chemical structure of EEDQ (N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline), CAS 16357-59-8, ≥95% — the classic Belleau amide coupling reagent (C14H17NO3), a substituted 1,2-dihydroquinoline. It reacts specifically with carboxylic acids, forming a mixed anhydride that couples acyl amino acids with amino esters to amides in high yield and without racemization, in one step for solution- or solid-phase peptide synthesis and bioconjugation. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

EEDQ

CAS 16357-59-8 ≥95%

EEDQ | CAS 16357-59-8 | ≥95%

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Technical Specifications

CAS Number 16357-59-8
EC / EINECS Number 240-418-2
MDL Number MFCD00006703
RTECS Number VB2010000
SMILES CCOC1C=CC2=CC=CC=C2N1C(=O)OCC
InChI 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
InChIKey GKQLYSROISKDLL-UHFFFAOYSA-N
PubChem CID 27833
Molecular Formula C₁₄H₁₇NO₃
Molecular Weight 247.29 g/mol
Melting Point 62–67 °C
Solubility Soluble in ethanol, acetone, and dichloromethane; insoluble in water.
Purity ≥95%
Physical Form White to off-white crystalline powder
HS Code 2933.49
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store refrigerated (2–8 °C) in a tightly sealed container, protected from moisture

Product Description & Scientific Applications

EEDQ — N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline — is a dihydroquinoline condensing reagent for amide and peptide bond formation. It activates a carboxylic acid as a mixed ethyl carbonic anhydride in situ, in the presence of the amine partner and without added tertiary amine base. EEDQ is supplied as an off-white to white crystalline solid, soluble in common organic solvents and aqueous-organic mixtures but insoluble in water.

Common Scientific Applications

  • Direct amide and peptide coupling: EEDQ reacts with the carboxylic acid to form a mixed ethyl carbonic anhydride in situ; the amine attacks this intermediate as it forms, giving the amide with quinoline, ethanol and carbon dioxide as by-products.
  • One-step, low-racemisation coupling: couples acylamino acids with amino acid esters in a single step with suppression of racemisation under standard solution-phase conditions.
  • DNA-compatible amide coupling: reported in on-DNA amide-coupling studies for DNA-encoded library synthesis, with substrate-dependent performance.
  • Polysaccharide and materials modification: employed in the regioselective quaternisation of chitosan and amphiphilic chitosan derivatives, and in the preparation of amide-modified QCM sensor surfaces.
  • Carboxyl-group-selective protein modification: used in biochemical studies to covalently modify accessible protein carboxylates, including enzyme active-site studies such as F1-ATPase labelling.

Further Reading

For guidance on selecting between carbodiimides, aminium/uronium salts, phosphonium salts and other reagent classes for amide and peptide bond formation, see NorrChemica's Lab Journal guide: Choosing a Coupling Reagent for Amide and Peptide Bond Formation.

Shipping Destinations

  • EU & UK: Priority delivery, 2–5 business days.
  • United States (DDP): 3–7 business days, duties and taxes prepaid.
  • EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
  • Worldwide: 7–14 business days, selected locations.

Safety Information

GHS Pictograms
GHS07 Harmful/Irritant
Signal Word Warning
Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
H-Statements H302 - H315 - H319 - H335
P-Statements P101 - P260 - P280 - P301+P330+P331 - P303+P361+P353 - P304+P340 - P305+P351+P338 - P321 - P405 - P501

Documentation

Safety Data Sheet Download PDF
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