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1,3-Dichlor-4-nitrobenzol

2,4-Dichloronitrobenzene

HCID 11899
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Grundinformationen

CAS
611-06-3
Standard-SMILES
O=[N+]([O-])c1ccc(Cl)cc1Cl
InChIKey
QUIMTLZDMCNYGY-UHFFFAOYSA-N
Summenformel
C6H3Cl2NO2
Durchschnittliche Molmasse
192 g/mol
Monoisotopische Masse
190,9540837

Überblick

2,4-Dichloro-1-Nitrobenzene can cause cancer according to California Labor Code.

Namen und Bezeichner

Bevorzugter Name
2,4-Dichloronitrobenzene
IUPAC
2,4-dichloro-1-nitrobenzene
Lokaler Name
1,3-Dichlor-4-nitrobenzol
Englischer Name
2,4-Dichloronitrobenzene
Summenformel
C6H3Cl2NO2
Molmasse
192

Namen und Synonyme

2,4-DICHLORONITROBENZENE611-06-32,4-Dichloro-1-nitrobenzeneBenzene, 2,4-dichloro-1-nitro-1,3-Dichloro-4-nitrobenzeneDTXSID302499885P1A896RRNSC-43196DTXCID104998RefChem:823874-Nitro-1,3-dichlorobenzene210-248-3
Weitere Namen anzeigen
2,4-DCNB2,4-Dichloroni4-DichloronitrobenzeneBifeprunox Impurity 64Nitro-2,4-dichlorobenzene4-Nitro-m-dichlorobenzene1,3-Dichlor-4-nitrobenzol
MFCD00007071CCRIS 3095HSDB 4267EINECS 210-248-3NSC 43196BRN 1451655UNII-85P1A896RR2,4-Dichloro-1-nitro-benzene

Datenbank-Bezeichner

CAS
611-06-3
PubChem CID
11899
DTXSID
DTXSID3024998
ChEMBL
CHEMBL166050
UNII
85P1A896RR

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3,1
Polarare Oberfläche (TPSA)
45,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
11
Formalladung
0
Komplexität
159

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Nitros, Aromatic
SpringerMaterials PropertiesDensity
LogP · 2 Einträge

log Kow = 3.07

3.1

Density · 3 Einträge

1.551 at 172 °F (NTP, 1992) - Denser than water; will sink

1.4790 at 80 °C

Relative density (water = 1): 1.54

Color/FormCrystallizes as pale yellow needles from ethanol.
Solubility · 3 Einträge

less than 0.1 mg/mL at 61 °F (NTP, 1992)

Sol in ethanol and ether; slightly soluble in chloroform

Solubility in water, g/100ml at 20 °C: 1.88 (sparingly soluble)

Flash Point · 3 Einträge

greater than 235 °F (NTP, 1992)

112 °C

112 °C

Boiling Point · 3 Einträge

496 °F at 760 mmHg (NTP, 1992)

Sicherheit und Regulatorisches

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

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302 (28.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 57 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H350: May cause cancer [Danger Carcinogenicity]

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Benzene, 2,4-dichloro-1-nitro-

Hazard Traits - Carcinogenicity

Status: Active Update: 25-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1902

1,3-Dichloro-4-nitrobenzene: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Benzene, 2,4-dichloro-1-nitro- (2,4-dichloronitrobenzene)
DOT LabelPoison
Fire Hazards · 2 Einträge

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards Summary · 1 Eintrag

Emergency treatment: see Nitrobenzene. Mild irritant on rabbit skin; Not a skin sensitizer; [HSDB] No listed effects of short-term or long-term exposure; Insufficient data are available on the effect of this substance on human health, therefore utmost care must be taken. [ICSC] An irritant; May cause skin sensitization; [MSDSonline] See 3,4-Dichloronitrobenzene.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

The metabolism of 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dichloro-1-nitrobenzene by Mucor javanicus was investigated, together with 2,4-dichloro-1-nitrobenzene metabolism by other fungi. The main metabolites were the corresponding dichloroanilines, accompanied by a lesser amt of 2,5-dichloro-1-nitrobenzene and 2,6-dichloro-1-nitrobenzene (3-or4-substituted) from 2,3-dichloro-1-nitrobenzene or 2,4-dichloro-1-nitrobenzene, respectively. Similar metabolic patterns were observed with M griseocyanus, M praini, M hiemalis, or Aspergillus flavus.

Verwendung und Herstellung

Uses · 4 Einträge

Used as an intermediate in the synthesis of pigments, pesticides, and medicinal drugs; Produced in a closed system and no exposure in consumer products; [eChemPortal: SIDSUNEP]

CHEMICAL INTERMEDIATE FOR DIAZOXIDE (AN ANTIHYPERTENSIVE AGENT)

Used as a chemical intermediate for the synthesis of chlormethoxyfen; 2,4-difluoroaniline.

1,3-Dichloro-4-nitrobenzene is reduced to the intermediate 2,4-dichloroaniline.

U.S. Imports · 2 Einträge

(1977) 4.17X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 1.45X10+8 GRAMS (PRINCPL CUSTMS DISTS)

Methods of Manufacturing1,3-Dichlorobenzene is nitrated with mixed acid, and the product is separated from the resulting isomer mixture.
General Manufacturing Information · 2 Einträge

Benzene, 2,4-dichloro-1-nitro-: ACTIVE

2,4-Dichloronitrobenzene is reduced to the intermediate 2,4-dichloroaniline. Preferential amination in the ortho position can be effected to give 5-chloro-2-nitroaniline ... .

Anwendungen

Verwenden2,4-Dichloro-1-nitrobenzene is used as a reagent in the synthesis of the hepatitis C virus polymerase inhibitor, Deleobuvir (BI 207127).

Zugehörige Reaktionen

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EC Number
210-248-3
Nikkaji
J2.081H

258.5 °C

258.5 °C

Melting Point · 3 Einträge

84 to 90 °F (NTP, 1992)

34 °C

30-33 °C

Vapor DensityRelative vapor density (air = 1): 6.6
Vapor Pressure · 2 Einträge

0.01 [mmHg]

Vapor pressure, Pa at 20 °C: 1

Refractive IndexIndex of refraction: 1.5512 at 70 °C/alpha

Physikochemische Eigenschaften

Schmelzpunkt
29 · 29-32 °C(lit.)
Siedepunkt
258 °C · 258 °C(lit.)
Dichte
1.479 · 1.479
Dampfdruck
0.013 hPa · 0.013 hPa (20 °C)
Brechungsindex
1.5512 · 1.5512 (estimate)
Flammpunkt
230 °F · >230 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
188 g/l · 188g/l
Aggregatzustand
Crystalline Low Melting Solid
Farbe
Yellow-brown
Wasserlöslichkeit
188 mg/L · 188 mg/L (20 ºC)
BRN
1451655 · 1451655
Henry's Law Constant
3.1 · 3.1×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
InChI
1S/C6H3Cl2NO2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H
InChIKey
QUIMTLZDMCNYGY-UHFFFAOYSA-N
SMILES
[O-][N+](=O)c1ccc(Cl)cc1Cl
CAS Datenbank
611 · 611-06-3(CAS DataBase Reference)
NIST chemische Informationen
2 · Benzene, 2,4-dichloro-1-nitro-(611-06-3)
EPA chemische Informationen
2 · 2,4-Dichloronitrobenzene (611-06-3)
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
Special ReportsEuropean Chemicals Bureau; IUCLID Dataset, 1,3-Dichloro-4-nitrobenzene (CAS # 611-06-3) p. 23 (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of July 5, 2007.
Reactivity ProfileCan react vigorously with oxidizing materials. (NTP, 1992)
Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes including hydrogen chloride (see ICSC 0163) and nitrogen oxides (see ICSC 0282). Reacts with strong oxidants and strong bases.
Packaging and LabellingDo not transport with food and feedstuffs.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this chemical can be controlled using a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)

Use water spray, dry powder, foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap. Refer for medical attention .

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Refer for medical attention .

First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from bases, strong oxidants and food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 2 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

The following wastewater treatment technologies have been investigated for nitrobenzene: Activated carbon and stripping. /Nitrobenzene/

Spillage Disposal · 1 Eintrag

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance, protective clothing, protective gloves and face shield. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.
Inhalation RiskA harmful concentration of airborne particles can be reached quickly when dispersed.
Skin PreventionProtective gloves.

Toxikologische Informationen

Interactions · 1 Eintrag

Changes were characterized in the dose mutagenic response curve of 99% 2,4-dinitrochlorobenzene (DNCB) modified by adding 1% concn of known contaminants: 1-chloro-2-nitrobenzene, 1,3-dinitrobenzene, and 2,4-dichloronitrobenzene. Dose response curves were generated by using Salmonella typhimurium testers strains in a modified Ames assay. A linear dose response ralationship was observed with a slight, but nonsignificant, shift to the right when contaminants were added.

Ecotoxicity Values · 5 Einträge

LC50 Daphnia magna /(Water flea)/ 6.6 mg/L for 14 day /Conditions of bioassay not specified in source examined/

LC50; Species: Daphnia magna (Water flea, <24 hr old); Conditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3, dissolved oxygen >6.5 mg/L; Concentration: 4200 ug/L for 48 hr (95% confidence interval: 3200-5600 ug/L) />98% purity/

LC50; Species: Daphnia magna (Water flea, <24 hr old); Conditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3, dissolved oxygen >6.5 mg/L; Concentration: 610 ug/L for 21 days (95% confidence interval: 560-670 ug/L) />98% purity/

LC50; Species: Danio rerio (Zebra danio, <4 hr old); Conditions: freshwater, static, 25 °C, pH 8.2, hardness 250 mg/L CaCO3; Concentration: 7200 ug/L for 7 days (95% confidence interval: 4700-11000 ug/L) />98% purity/

For more Ecotoxicity Values (Complete) data for 2,4-DICHLORONITROBENZENE (11 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.07(2) and a regression-derived equation(3), indicates that 2,4-dichloronitrobenzene is expected to have low mobility in soil(SRC). Volatilization of 2,4-dichloronitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.2X10-6 atm-cu m/mole(4). 2,4-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-2 mm Hg(SRC), determined from a fragment constant method(5). A less than 0.1% biodegradation loss in a 5-day BOD test using activated sludge(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.07(2) and a regression-derived equation(3), indicates that 2,4-dichloronitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a estimated Henry's Law constant of 3.2X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 17 days, respectively(SRC). According to a classification scheme(5), experimental BCF values of 80 to 120(2,6,7) suggests bioconcentration in aquatic organisms is moderate to high. A less than 0.1% biodegradation loss in a 5-day BOD test using activated sludge(7) suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-dichloronitrobenzene, which has an estimated vapor pressure of 1.4X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dichloronitrobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 130 days(SRC), calculated from its rate constant of 1.2X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2,4-Dichloronitrobenzene contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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 RoutesThe substance can be absorbed into the body by ingestion and through the skin.
Average Daily Intake · 1 Eintrag

Based on the FDA Total Diet Study, the average daily intake of 2,4-dichloronitrobenzene was determined for 6-11 months, 2 years, 14-16 yr female, 14-16 yr male, 25-30 yr female, 25-30 yr male, 60-65 yr female, and 60-65 yr male as 2.5, 3.1, 1.0, 0.6, 0.9, 0.7, 1.6 and 1.3 ng/kg body weight/day, respectively(1).

Signs and Symptoms · 2 Einträge

Cough.

Redness.

ICSC Environmental DataThe substance is toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment.
Soil Adsorption/Mobility · 1 Eintrag

The Koc of 2,4-dichloronitrobenzene is estimated as 1,100(SRC), using a log Kow of 3.07(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4-dichloronitrobenzene is expected to have low mobility in soil.

Fish/Seafood Concentrations · 1 Eintrag

2,4-Dichloronitrobenzene was detected not quantified in fish from the River Main in Germany(1). Zebra mussel (Dreissena polymorpha) and eel (Anguilla anguilla) collected from the Rhine and Meuse Rivers in Germany tested positive for chloronitrobenzenes (isomers not specified) at average concentrations up to 0.00009 and 0.0001 mmol/kg fat weight, respectively, sampling conducted in 1993 through 1994(2).

Artificial Pollution Sources2,4-Dichloronitrobenzene's production and use as a chemical intermediate(1) and in the production of 2,4-dichloroaniline(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

AEROBIC: Less than 0.1% of applied 2,4-dichloronitrobenzene was degraded in a 5 day biodegradation study using activated sludge from a municipal sewage treatment plant(1). However, since bacteria capable of degrading unspecified chloronitrobenzene isomers have been isolated, these compounds are not expected to be inherently recalcitrant(2).

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
2811
hs_code
29049085
RTECS-Nr.
CZ5420000
risk_code
36/37/38-51/53-43-21/22
Toxizität
LD50 orally in Rabbit: 380 mg/kg LD50 dermal Rat 920 mg/kg
hazard_code
Xi,N,Xn
safety_code
26-36-61-36/37-24
hazard_class
9
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
611-06-3(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 2Carc. 1BMuta. 2Skin Sens. 1B
Selbstentzündungstemperatur
500 °C

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

1,3-Dichlorbenzol1-Chlor-3-nitrobenzol1,3-Dichlor-2-nitrobenzol

Nachgelagerte Produkte

2,4-DifluorphenolDiuron2-Chlor-4-fluor-1-nitrobenzol1,3-Difluor-4-nitrobenzol4-(4-Nitrophenoxy)anilin5-Chlor-2-nitrodiphenylamin