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

Key Documents

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Product Name

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

Quality Level

200

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

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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1 of 4

This Item
792873151936650
2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline ≥99%

Sigma-Aldrich

149837

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

Ethoxyquin-(ethoxy-d5) PESTANAL®, analytical standard

Supelco

79287

Ethoxyquin-(ethoxy-d5)

Ethoxyquin PESTANAL®, analytical standard

Supelco

31519

Ethoxyquin

DCC puriss., ≥99.0% (GC)

Sigma-Aldrich

36650

DCC

form

solid

form

-

form

-

form

solid

functional group

ether

functional group

-

functional group

-

functional group

-

assay

≥99%

assay

≥98.0% (HPLC)

assay

-

assay

≥99.0% (GC)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

mp

62-67 °C (lit.)

mp

-

mp

-

mp

32.0-37.0 °C, 34-35 °C (lit.)

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

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.[1]

Application

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

Storage Class

11 - Combustible Solids

wgk_germany

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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Analía Bortolozzi et al.
The international journal of neuropsychopharmacology, 13(10), 1299-1314 (2010-02-18)
Atypical antipsychotic drugs (APDs) increase dopamine (DA) release in prefrontal cortex (PFC), an effect probably mediated by the direct or indirect activation of the 5-HT(1A) receptor (5-HT(1A)R). Given the very low in-vitro affinity of most APDs for 5-HT(1A)Rs and the
Chunmei You et al.
Scientific reports, 10(1), 8400-8400 (2020-05-23)
Two unique housefly strains, PSS and N-PRS (near-isogenic line with the PSS), were used to clarify the mechanisms associated with propoxur resistance in the housefly, Musca domestica. The propoxur-selected resistant (N-PRS) strain exhibited >1035-fold resistance to propoxur and 1.70-, 12.06-
L Carbonell et al.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, 14(6), 497-502 (2004-12-14)
One of the most effective psychotherapeutic agents in the treatment of bipolar disease is lithium. Chronic lithium treatment affects some signal transduction mechanisms such as cAMP, cGMP, inositol 1,4,5 P(3), Gi protein, protein kinase C and can also modify gene
Eur. J. Pharmacol., Molec. Pharmacol. Sec., 269, 25-25 (1994)
New approach to the quaternization of chitosan and its amphiphilic derivatives
Stepnova EA, et al.
European Polymer Journal, 43(6), 2414-2421 (2007)
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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