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Tetraethylammonium Chloride

HCID 5946
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
56-34-8
Standard SMILES
CC[N+](CC)(CC)CC.[Cl-]
InChIKey
YMBCJWGVCUEGHA-UHFFFAOYSA-M
Molecular formula
C8H20N.Cl
Average molar mass
165.7 g/mol
Monoisotopic mass
165.12842732

Overview

Tetraethylammonium chloride is a quarternary ammonium chloride salt in which the cation has four ethyl substituents around the central nitrogen. It has a role as a potassium channel blocker. It is a quaternary ammonium salt and an organic chloride salt. It contains a tetraethylammonium.

Names & identifiers

Preferred name
Tetraethylammonium Chloride
IUPAC
tetraethylazanium chloride
English name
Tetraethylammonium Chloride
Molecular formula
C8H20ClN
Molecular weight
165.7

Names & synonyms

TETRAETHYLAMMONIUM CHLORIDE56-34-8Etamon chlorideTea chlorideTEACN,N,N-Triethylethanaminium chlorideEthanaminium, N,N,N-triethyl-, chloridetetraethylazanium;chlorideDTXSID6041137CHEBI:781618B82Z83XNNDTXCID4021137
Show more names
TetraethylammoniumtetraethylazaniuM chlorideSKL1479N2,2,2,2Clammonium chLEthamon chlorideTetraethylammonium choride
RefChem:188563Chloride, Tetraethylammonium200-267-5Tetraethyl ammonium chloridetetraethylammoniumchlorideEt4NClTetraethylammonium (chloride)EINECS 200-267-5

Database identifiers

CAS
56-34-8
PubChem CID
5946
DTXSID
DTXSID6041137
ChEMBL
CHEMBL434435
ChEBI
CHEBI:78161
UNII
8B82Z83XNN

Properties

Computed structural propertiesFilling in

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
4
Heavy atoms
10
Formal charge
0
Complexity
47.5

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Quaternary Amines
Density1.08 @25 °C
Solubility20.3 [ug/mL] (The mean of the results at pH 7.4)
Vapor Pressure0.00000308 [mmHg]
Physical Description · 2 items

Liquid

Deliquescent solid; [Merck Index] Colorless or light yellow hygroscopic crystals; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
39 °C · 39°C
Boiling point
273.32 °C · 273.32°C (rough estimate)
Density
1.08 · 1.08
refractive index
1.548 · 1.5480 (estimate)
storage temp.
Inert atmosphere,Room Temperature
solubility
0.1 g/mL, · methanol: 0.1 g/mL, clear, colorless
form

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 · 6 items

Warning

H302 (25.2%): 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 103 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H320: Causes eye irritation [Warning Serious eye damage/eye irritation]

Hazard information

Regulatory Information · 4 items

Chemical: Ethanaminium, N,N,N-triethyl-, chloride (1:1)

Ethanaminium, N,N,N-triethyl-, chloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanaminium, N,N,N-triethyl-, chloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 06-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20036

Ethanaminium, N,N,N-triethyl-, chloride: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Tetraethylammonium salts: Human health tier II assessment
Hazards Summary · 1 item

Causes somnolence, tremor, and muscle weakness in oral, intraperitoneal, and intramuscular lethal-dose studies of mice and rats; Human intravenous injection of 5 mg/kg causes paresthesias, mydriasis, and ptosis; [RTECS] A skin and strong eye irritant; Targets the heart and CNS; [Sigma-Aldrich MSDS] See Tetraethylammonium bromide.

Hazard Classes and Categories

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationA class of drugs that act by inhibition of potassium efflux through cell membranes. Blockade of potassium channels prolongs the duration of ACTION POTENTIALS. They are used as ANTI-ARRHYTHMIA AGENTS and VASODILATOR AGENTS.

Uses & manufacturing

UsesUsed as a catalyst (dehydrogenation and polymerization) and electrolyte (membrane transport studies); [Merck Index]
U.S. Production2023: 1,000,000 - <5,000,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Ethanaminium, N,N,N-triethyl-, chloride (1:1): ACTIVE

Applications · 4 items

UsesMedicine (nerve-blocking agent).

UsesTetraethylammonium Chloride can be used as a source of tetraethylammonium ions for various pharmaceutical studies and has the ability to block K+ channels in various tissues. Tetraethylammonium Chloride can also block the transmission of nervous impulses across autonomic ganglions.

UsesTetraethylammonium chloride (TEAC) has been used:used for inhibition of peroxynitrite induced relaxation in rat aorta ringsas a pharmacological blocker of K+ current and Ca2+ induced K+ current in antennal lobe neuronsfor the induction of TEAC sensitive currents in cochlear inner hair cells digested with proteolytic enzymes and analyze its properties

General DescriptionVisit our Sensor Applications portal to learn more.

Preparation methods

Related reactions

185 records
New reaction record
HRID 11325 reaction equation
HRID 11325As catalystuspto-grants-2006_08
HRID 12290 reaction equation
HRID 12290As catalystuspto-grants-2010_06
HRID 28245 reaction equation
HRID 28245As catalystuspto-grants-1980_09
HRID 28247 reaction equation
HRID 28247As catalystuspto-grants-1980_09
HRID 28249 reaction equation
HRID 28249As catalystuspto-grants-1980_09
HRID 57450 reaction equation
HRID 57450As catalystuspto-grants-2016_09
HRID 84470 reaction equation
HRID 84470As catalystuspto-grants-2014_09
HRID 215746 reaction equation
HRID 215746As catalystuspto-grants-2012_06
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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EC Number
200-267-5
Crystalline Powder
color
white to light yellow
PH
4 to · 4.0 to 7.0(50g/L, 25℃)
biological source
synthetic (organic)
Water Solubility
Soluble in water, ethanol, chloroform, or acetone
λmax
260 nm · λ: 260 nm Amax: 0.03λ: 280 nm Amax: 0.03
Sensitive
Hygroscopic
Merck
14 · 14,9200
BRN
3563247 · 3563247
Stability
Stable. Incompatible with strong oxidizing agents. Protect from moisture.
InChI
1S/C8H20N.ClH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1
InChIKey
YMBCJWGVCUEGHA-UHFFFAOYSA-M
SMILES
[Cl-].CC[N+](CC)(CC)CC
CAS DataBase Reference
56 · 56-34-8(CAS DataBase Reference)
FDA UNII
8 B82Z83XNN · 8B82Z83XNN
EPA Substance Registry System
Tetraethylammonium chloride (56-34-8)
UNSPSC Code
26111700 · 26111700
NACRES
61 · NB.61
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/37/38
Safety Statements
26 · 26-36-37/39
WGK Germany
3 · 3
RTECS
6125000 · BS6125000
F
3 · 3-10
TSCA
TSCA listed
HS Code
29239000 · 29239000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2
Toxicity
50 i.v · LD50 i.v. in dogs: 55.7-72.4 mg/kg (Keith, Jr.)
REACH Registrations
Active
· 2 items

Acute Tox. 4 (25.2%)

Eye irritation - category 2B

Safety & protection

Protective Action Criteria (PAC) · 3 items

0.55 [mg/m3]

6.0 [mg/m3]

30 [mg/m3]

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Safety data

F
3-10
wgk
3
tsca
TSCA listed
rtecs
BS6125000
hs_code
29239000
Toxicity
LD50 i.v. in dogs: 55.7-72.4 mg/kg (Keith, Jr.)
risk_code
22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
safety_code
26-36-37/39
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2
Precautionary statements
P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
· 1 item

Preparation(1) Dissolve 45g of chloroethane in 300g of xylene and set aside; (2) Add 10g of triethylamine, 50g of diethyl ether, and 150g of xylene to a high-pressure reactor. At 70°C, add 250g of chloroethane-xylene solution dropwise to the high-pressure reactor. After the addition is complete, keep the reactor at this temperature for half an hour. Then, introduce gas to maintain the pressure inside the high-pressure reactor at 3MPa. React at 120°C for 12 hours. Stop the gas supply, slowly open the vent valve, and cool down to room temperature; (3) Filter the reaction solution obtained in step (2) to obtain 58.3g of filter cake A, which is crude tetraethylammonium chloride. Add the crude tetraethylammonium chloride to 100g of water and stir at 45°C until most of the crude product dissolves. Filter while hot to obtain 20.2g of filtrate. Add the filtrate to a mixed solvent of 80g of acetonitrile and 120g of pentanediol. Stir and let stand for half an hour, then filter. Dry the filter cake B to obtain 15.9g of tetraethylammonium chloride. The purity is 99.7%, and the yield is 95.5%.

Upstream & downstream products

Downstream products

n-Butylxanthic acid potassium salt2-Chloro-7H-pyrrolo[2,3-d]pyrimidine6-O-BenzylguanineTetraethylammonium trifluoromethanesulfonateDichloro(1,5-cyclooctadiene)platinum(II)
Additional notes · 1 item

DefinitionChEBI: Tetraethylammonium chloride is a quarternary ammonium chloride salt in which the cation has four ethyl substituents around the central nitrogen. It has a role as a potassium channel blocker. It is a quaternary ammonium salt and an organic chloride salt. It contains a tetraethylammonium.