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(1α,2α,3aα,4β,7β,7aα)-1,2,4,5,6,7,8,8-Octachlor-2,3,3a,4,7,7a-hexahydro-4,7-methano-1H-inden

Alpha-chlordane

HCID 12303038
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Grundinformationen

CAS
5103-71-9
Standard-SMILES
ClC1=C(Cl)[C@]2(Cl)[C@H]3C[C@H](Cl)[C@H](Cl)[C@H]3[C@@]1(Cl)C2(Cl)Cl
InChIKey
BIWJNBZANLAXMG-IQEDOFJGSA-N
Summenformel
C10H6Cl8
Durchschnittliche Molmasse
409,8 g/mol
Monoisotopische Masse
405,797772

Überblick

Chlordane is a manufactured chemical that was used as a pesticide in the United States from 1948 to 1988. Chlordane occurs in two isomers, called cis-chlordane (alpha-chlordane) and trans-chlordane (gamma-chlordane) (L90).

Namen und Bezeichner

Bevorzugter Name
Alpha-chlordane
IUPAC
(1S,2S,3R,4S,6S,7R)-1,3,4,7,8,9,10,10-octachlorotricyclo[5.2.1.02,6]dec-8-ene
Lokaler Name
(1α,2α,3aα,4β,7β,7aα)-1,2,4,5,6,7,8,8-Octachlor-2,3,3a,4,7,7a-hexahydro-4,7-methano-1H-inden
Englischer Name
cis-Chlordane
Summenformel
C10H6Cl8
Molmasse
409.78

Namen und Synonyme

.alpha.-ChlordaneEINECS 225-825-5ALPHA-CHLORDANEAI3-163974,7-Methano-1H-indene, 1,2,4,5,6,7,8,8-octachloro-2,3,3a,4,7,7a-hexahydro-, (1alpha,2alpha,3a alpha,4beta,7beta,7a alpha)-4,7-Methano-1H-indene, 1,2,4,5,6,7,8,8-octachloro-2,3,3a,4,7,7a-hexahydro-, (1R,2S,3aS,4S,7R,7aS)-rel4,7-Methanoindan, 1-alpha,2-alpha,4-beta,5,6,7-beta,8,8-octachloro-3a-alpha,4,7,7a-alpha-tetrahydro-alphaChlordancisChlordancisChlordaneRefChem:5554334,7Methanoindan, 1alpha,2alpha,4beta,5,6,7beta,8,8octachloro3aalpha,4,7,7aalphatetrahydro
Weitere Namen anzeigen
a-Chlordaneα-ChlordaneCIS-CHLORDANE (ALPHA)a-Chlordancis-Chlordanchlordan,cis-Chlordane ciscis-Chlordane
(1alpha,2alpha,3aalpha,4beta,7beta,7aalpha)1,2,4,5,6,7,8,8Octachloro2,3,3a,4,7,7ahexahydro4,7methano1Hindene4,7Methano1Hindene, 1,2,4,5,6,7,8,8octachloro2,3,3a,4,7,7ahexahydro, (1alpha,2alpha,3a alpha,4beta,7beta,7a alpha)4,7Methano1Hindene, 1,2,4,5,6,7,8,8octachloro2,3,3a,4,7,7ahexahydro, (1R,2S,3aS,4S,7R,7aS)relCHEMBL5283219Chlordan, cis-.alpha.-Chlordanalpha-Chlordan4,7-Methano-1H-indene, 1,2,4,5,6,7,8,8-octachloro-2,3,3a,4,7,7a-hexahydro-, (1R,2S,3aS,4S,7R,7aS)-rel-

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,9
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
18
Formalladung
0
Komplexität
459

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesBoiling point
PesticidesPesticides -> Organochlorine Pesticides
Vapor Pressure0.000036 [mmHg]
Physical DescriptionSolid; [Cerilliant MSDS]

Physikochemische Eigenschaften

Schmelzpunkt
106 °C · 106°C (estimate)
Siedepunkt
492.46 °C · 492.46°C (rough estimate)
Dichte
1.8 · 1.80
Dampfdruck
3.6 x · 3.60 x 10-5 mmHg at 25 °C (subcooled liquid vapor pressure calculated from GC retention time data,Hinckley et al., 1990)
Brechungsindex
1.6 · 1.6000 (estimate)
Flammpunkt
-18 °C · -18 °C
storage temp.
4 °C · APPROX 4°C
Löslichkeit
Miscible with aliphatic and aromatic solvents (Windholz et al., 1983)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Gefahrenhinweise

Hazards SummaryA skin and strong eye irritant; Harmful by ingestion and inhalation; Toxic by skin absorption; Targets the CNS; May cause liver and kidney injury; [Cerilliant MSDS] See Chlordane.

Sicherheit und Schutzausrüstung

Minimum Risk Level · 2 Einträge

Intermediate Inhalation: 0.0002 mg/m3 (L134) Chronic Inhalation: 0.00002 mg/m3 (L134) Acute Oral: 0.001 mg/kg/day (L134) Intermediate Oral: 0.0006 mg/kg/day (L134) Chronic Oral: 0.0006 mg/kg/day (L134)

Intermediate Inhalation: 0.0002 mg/m3 (L134) Chronic Inhalation: 0.00002 mg/m3 (L134) Acute Oral: 0.001 mg/kg/day (L134) Intermediate Oral: 0.0006 mg/kg/day (L134) Chronic Oral: 0.0006 mg/kg/day (L134)

Toxikologische Informationen

Treatment · 2 Einträge

Treatment is symptomatic. It is aimed at controlling convulsions, coma, and respiratory depression. Gastric lavage, followed by the administration of activated charcoal, may be performed following ingestion. (L146)

Treatment is symptomatic. It is aimed at controlling convulsions, coma, and respiratory depression. Gastric lavage, followed by the administration of activated charcoal, may be performed following ingestion. (L146)

Health Effects · 2 Einträge

Chlordane is a central nervous system stimulant, and can also damage the digestive system and the liver. Large doses have been known to cause convulsions, respiratory failure, and death. Chlordane is also known to have adverse reproductive and developmental effects. (L91)

Chlordane is a central nervous system stimulant, and can also damage the digestive system and the liver. Large doses have been known to cause convulsions, respiratory failure, and death. Chlordane is also known to have adverse reproductive and developmental effects. (L91)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Chlordane is highly lipophilic and is thus easily absorbed by ingestion, inhalation, and dermal exposure, then stored mainly in the fat. Chlordane is metabolized mainly in the liver and kidney. Metabolism is slow, and is believed to occur by multiple pathways involving cytochrome P-450 enzymes, glutathione-S-transferase type enzymes, and microsomal mixed-function oxidase systems. The metabolites are generally less toxic and include chlordene chlorohydrin, monohydroxylated dihydrochlordene, and oxychlordane. They are excreted in the urine and faeces. (L91)

Chlordane is highly lipophilic and is thus easily absorbed by ingestion, inhalation, and dermal exposure, then stored mainly in the fat. Chlordane is metabolized mainly in the liver and kidney. Metabolism is slow, and is believed to occur by multiple pathways involving cytochrome P-450 enzymes, glutathione-S-transferase type enzymes, and microsomal mixed-function oxidase systems. The metabolites are generally less toxic and include chlordene chlorohydrin, monohydroxylated dihydrochlordene, and oxychlordane. They are excreted in the urine and faeces. (L91)

Verwendung und Herstellung

Uses · 3 Einträge

Comprises approximately 19% of technical chlordane (according to one description); [IARC]

Chlordane was used as a pesticide. (L90)

Chlordane was used as a pesticide. (L90)

Anwendungen

VerwendenInsecticide

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Datenbank-Bezeichner

CAS
5103-71-9
PubChem CID
12303038
ChEMBL
CHEMBL5283219
UNII
832600T9WH
Aggregatzustand
Solid
Farbe
Yellow
Wasserlöslichkeit
51 μg/L · 51 μg/L at 20–25 °C (Geyer et al., 1984)
BRN
7079209 · 7079209
Henry's Law Constant
0.18 at · In distilled water: 0.18 at 5 °C, 0.34 at 15 °C, 0.39 at 20 °C, 0.54 at 25 °C, 1.59 at 35 °C:in 3% NaCl solution: 0.41 at 5 °C, 0.71 at 15 °C, 2.45 at 25 °C, 7.87 at 35 °C (gas stripping-GC, Cetin et al., 2006)(x 10-4 atmm3/mol)
Stabilität
Light Sensitive
CAS Datenbank
5103 · 5103-71-9
EPA chemische Informationen
cis-Chlordane (5103-71-9)
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 Einträge

Oral (L281) ; inhalation (A105)

Oral (A105) ; inhalation (A105)

Toxicity Summary · 2 Einträge

Chlordane is believed to bind irreversibly to DNA, leading to cell death or altered cellular function. It also affects transcription by antagonizing estrogen-related receptors. Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. Chlordane has also been shown to bind and activate retinoic acid receptor, causing various developmental defects, and inhibit alkaline phosphatases in hepatic and renal tissues. (L91, A52, A53, A68, A69)

Chlordane is believed to bind irreversibly to DNA, leading to cell death or altered cellular function. It also affects transcription by antagonizing estrogen-related receptors. Chlordane induces hepatic cytochrome P-450, causing a large increase in the volume of the smooth endoplasmic reticulum, which results in hepatocellular enlargement and hypertrophy. Chlordane has also been shown to bind and activate retinoic acid receptor, causing various developmental defects, and inhibit alkaline phosphatases in hepatic and renal tissues. (L91, A52, A53, A68, A69)

Signs and Symptoms · 2 Einträge

Ingestion and inhalation of chlordane cause headaches, irritability, confusion, weakness, vision problems, vomiting, stomach cramps, diarrhea, and jaundice. (L91)

Ingestion and inhalation of chlordane cause headaches, irritability, confusion, weakness, vision problems, vomiting, stomach cramps, diarrhea, and jaundice. (L91)

Carcinogen Classification · 2 Einträge

2B, possibly carcinogenic to humans. (L135)

Chlordane is possibly carcinogenic to humans (Group 2B). (L135)

Toxicity Data · 2 Einträge

LD50: 200 mg/kg (Oral, Rat) (T13) LD50: 343 mg/kg (Intraperitoneal, Rat) (T13) LD50: 10 mg/kg (Intravenous, Mouse) (T14) LD50: 780 mg/kg (Dermal, Rat) (T14) LC50: 100 mg/m3 over 4 hours (Inhalation, Cat) (T14)

LD50: 200 mg/kg (Oral, Rat) (T13) LD50: 343 mg/kg (Intraperitoneal, Rat) (T13) LD50: 10 mg/kg (Intravenous, Mouse) (T14) LD50: 780 mg/kg (Dermal, Rat) (T14) LC50: 100 mg/m3 over 4 hours (Inhalation, Cat) (T14)

Sicherheitsdaten

wgk
3
ridadr
2761
RTECS-Nr.
PB9705000
risk_code
11-38-50/53-65-67-48-36/37/38-24/25-20-62-51/53-48/20-22-24-20/22
Toxizität
LC50 (96-hour) for rainbow trout 90 mg/L and bluegill sunfish 70 mg/L (Hartley and Kidd, 1987); EC50 (96-hour) for goldfish 0.5 mg/L; acute oral LD50 for rats 365–590 mg/kg (Hartley and Kidd, 1987), 343 mg/kg (RTECS, 1985).
hazard_code
F,Xn,N,T
safety_code
16-33-60-61-62-45-36/37-26-9-29-25
hazard_class
6.1(b)
packing_group
III