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Cloethocarb

HCID 40032
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Basic information

CAS
51487-69-5
Standard SMILES
CNC(=O)Oc1ccccc1OC(CCl)OC
InChIKey
PITWUHDDNUVBPT-UHFFFAOYSA-N
Molecular formula
C11H14ClNO4
Average molar mass
259.68 g/mol
Monoisotopic mass
259.0611356

Overview

Cloethocarb is an aromatic ether.

Names & identifiers

Preferred name
Cloethocarb
IUPAC
[2-(2-chloro-1-methoxyethoxy)phenyl] N-methylcarbamate
English name
o-(2-chloro-1-methoxyethoxy)phenyl methylcarbamate
Molecular formula
C11H14ClNO4
Molecular weight
259.69

Names & synonyms

CLOETHOCARBLanceo-(2-Chloro-1-methoxyethoxy)phenyl methylcarbamateCloethocarb [BSI:ISO]BAS 263EINECS 257-236-4BAS 263IBASF 2632-(2-Chloro-1-methoxyethoxy)phenyl methylcarbamateUNII-BVH4P57R5OBAS 263-51IBAS 263-52I
Show more names
BAS263IBAS-263IFenobucarb Impurity 2Phenol, 2-(2-chloro-1-methoxyethoxy)-, 1-(N-methylcarbamate)Methylcarbamic acid 2-(2-chloro-1-methoxyethoxy)phenyl ester
BVH4P57R5OBRN 2219139AI3-29534CLOETHOCARB [ISO]2-(2-Chloro-1-methoxyethoxy)phenol methylcarbamatePhenol, 2-(2-chloro-1-methoxyethoxy)-, methylcarbamateBASF-263DTXSID8041791

Database identifiers

CAS
51487-69-5
PubChem CID
40032
DTXSID
DTXSID8041791
ChEBI
CHEBI:82091
UNII
BVH4P57R5O
EC Number
257-236-4
Nikkaji
J261.737D

Properties

Computed structural properties

XLogP
1.3
Topological polar surface area
56.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
6
Heavy atoms
17
Formal charge
0
Complexity
240

Physicochemical properties

Melting point
80 °C · 80 °C
Boiling point
366.1 · 366.1±42.0 °C(Predicted)
Density
1.291 · 1.2910 (rough estimate)
refractive index
1.6 · 1.6000 (estimate)
storage temp.
-20 °C · -20°C
pka
12.17 · 12.17±0.46(Predicted)
BRN
2219139 · 2219139
Henry's Law Constant
5 · 5.0×105 mol/(m3Pa) at 25℃, MacBean (2012)
Major Application
agricultureenvironmental
InChI
1S/C11H14ClNO4/c1-13-11(14)17-9-6-4-3-5-8(9)16-10(7-12)15-2/h3-6,10H,7H2,1-2H3,(H,13,14)
InChIKey
PITWUHDDNUVBPT-UHFFFAOYSA-N
SMILES
CNC(=O)Oc1ccccc1OC(CCl)OC
FDA UNII
4 P57R5O · BVH4P57R5O
EPA Substance Registry System
Cloethocarb (51487-69-5)
UNSPSC Code
41116107 · 41116107

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 · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Toxicology

Treatment · 1 item

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects · 1 item

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Uses & manufacturing

UsesCloethocarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
Applications · 2 items

DescriptionCloethocarb is an obsolete insecticide. It has a high aqueous solubility and is non-volatile. It is not usually persistent in soil systems. Little data is available regarding its ecotoxicology. It is highly toxic to mammals if ingested and is an acetyl cholinesterase inhibitor.

UsesRefer to the productμs Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Additional notes

DefinitionChEBI: Cloethocarb is an aromatic ether.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
NACRES
24 · NA.24
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
300 · H300
Precautionary statements
264 · P264-P301+P310
Hazard Codes
T
Risk Statements
25 · 25
Safety Statements
45 · 45
RIDADR
2757 · 2757
WGK Germany
3 · 3
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
2 Oral · Acute Tox. 2 Oral
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 item

Cloethocarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Signs and Symptoms · 1 item

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
3
ridadr
2757
risk_code
25
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T
safety_code
45
hazard_class
6.1(b)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
III
Hazard statements
H300
Hazard Classifications
Acute Tox. 2 Oral
Precautionary statements
P264-P301+P310