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2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline

HCID 27833
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Basic information

CAS
16357-59-8
Standard SMILES
CCOC(=O)N1c2ccccc2C=CC1OCC
InChIKey
GKQLYSROISKDLL-UHFFFAOYSA-N
Molecular formula
C14H17NO3
Average molar mass
247.29 g/mol
Monoisotopic mass
247.1208434

Overview

peptide coupling reagent

Names & identifiers

Preferred name
2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline
IUPAC
ethyl 2-ethoxy-2H-quinoline-1-carboxylate
English name
N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline
Molecular formula
C14H17NO3
Molecular weight
247.29

Names & synonyms

16357-59-8EEDQ1(2H)-QUINOLINECARBOXYLIC ACID, 2-ETHOXY-, ETHYL ESTER2-Ethoxy-1(2H)-quinolinecarboxylic acid, ethyl esterN-carbethoxy-2-ethoxy-1,2-dihydroquinolineDTXSID5087196960O971AN192-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineRefChem:471395DTXCID408195772-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinolineN-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline
Show more names
ETHYL 1,2-DIHYDRO-2-ETHOXY-1-QUINOLINECARBOXYLATEETHYL 2-ETHOXY-1,2-DIHYDRO-1-QUINOLINECARBOXYLATE2-Ethoxy-2H-quinoline-1-carboxylic acid ethyl esterEEDQ extrapure
ethyl 2-ethoxyquinoline-1(2H)-carboxylateethyl 2-ethoxy-2H-quinoline-1-carboxylateethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate1-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinolineMFCD00006703MLS000069601BC 681NSC 147831

Database identifiers

CAS
16357-59-8
PubChem CID
27833
DTXSID
DTXSID50871969
ChEMBL
CHEMBL1527785
UNII
60O971AN19
EC Number
240-418-2
Nikkaji
J14.768K

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
38.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
18
Formal charge
0
Complexity
316

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biochemical Research
Solubility8 [ug/mL] (The mean of the results at pH 7.4)
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionOff-white powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
62 · 62-67 °C(lit.)
Boiling point
125 · 125-128 °C (0.1 mmHg)
Density
1.1173 · 1.1173 (rough estimate)
refractive index
1.53 · 1.5300 (estimate)
Flash point
125 · 125-128°C/0.1mm
storage temp.
2 · 2-8°C
solubility
Chlorofrom (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka
-1.27 · -1.27±0.40(Predicted)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.1% (1 of 87) of reports.

Warning

H302 (90.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 87 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information1(2H)-Quinolinecarboxylic acid, 2-ethoxy-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses other degenerative changes to brain and effects on proteins in acute intraperitoneal studies of rats; Intraperitoneal LD50 (mouse) = 32 mg/kg; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (90.8%)

Safety data

F
9-21
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
VB2010000
hs_code
29334990
Toxicity
mouse,LD50,intraperitoneal,32mg/kg (32mg/kg),Journal of Medicinal Chemistry. Vol. 14, Pg. 49, 1971.
risk_code

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 4 items

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.

Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases.

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Uses & manufacturing

UsesUsed as a coupling agent in peptide synthesis; [Merck Index]
General Manufacturing Information1(2H)-Quinolinecarboxylic acid, 2-ethoxy-, ethyl ester: ACTIVE
Applications · 3 items

UsesPeptide condensing agent with little or no racemization. Amidation coupling reagent.

Uses2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline is an irreversible membrane-bound receptor antagonist. It is used in synthetic chemistry, discovery, process R&D. It also acts as coupling reagents.

Related reactions

776 records
New reaction record
HRID 79561 reaction equation
HRID 79561As reactantuspto-grants-2014_09
HRID 79577 reaction equation
HRID 79577As reactantuspto-grants-2014_09
HRID 97083 reaction equation
HRID 97083As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 97945 reaction equation
HRID 97945As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 103237 reaction equation
HRID 103237As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 110055 reaction equation
HRID 110055As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 116812 reaction equation
HRID 116812As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 128513 reaction equation
HRID 128513As reactantuspto-grants-1995_11
Page 1 of 97

Compound notes

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form
Crystalline Powder
color
White to beige
Water Solubility
insoluble
Sensitive
Moisture Sensitive
Merck
14 · 14,3518
BRN
533048 · 533048
Major Application
peptide synthesis
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
SMILES
CCOC1C=Cc2ccccc2N1C(=O)OCC
CAS DataBase Reference
16357 · 16357-59-8(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
60 O971AN19 · 60O971AN19
EPA Substance Registry System
1 · 1(2H)-Quinolinecarboxylic acid, 2-ethoxy-, ethyl ester (16357-59-8)
UNSPSC Code
12352005 · 12352005
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi,Xn
Risk Statements
38 · 38-36/37/38-20/21/22
Safety Statements
22 · 22-24/25-36/37/39-26-36
WGK Germany
3 · 3
RTECS
2010000 · VB2010000
F
9 · 9-21
TSCA
TSCA listed
HS Code
29334990 · 29334990
Storage Class
11 · 11 - Combustible Solids
Toxicity
50 · mouse,LD50,intraperitoneal,32mg/kg (32mg/kg),Journal of Medicinal Chemistry. Vol. 14, Pg. 49, 1971.
38-36/37/38-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
22-24/25-36/37/39-26-36
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a

UsesIn the synthesis of peptides.

Upstream & downstream products

Upstream raw materials

QuinolineN,N-DimethylformamidePotassium hydroxideEthyl chloroformateBoron trifluoride diethyl etherateDiethyl etherDichloromethaneMagnesium sulfate