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Chloranilin, di

2,3-Dichloroaniline

HCID 11844
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Grundinformationen

CAS
27134-27-6
Standard-SMILES
Nc1cccc(Cl)c1Cl
InChIKey
BRPSAOUFIJSKOT-UHFFFAOYSA-N
Summenformel
C6H5Cl2N
Durchschnittliche Molmasse
162,01 g/mol
Monoisotopische Masse
160,97990452

Überblick

Dichloroanilines appears as an amber to brown crystalline solid. Shipped as a solid or in a liquid carrier. Insoluble in water. It is toxic by skin absorption and by inhalation. Produces toxic oxides of nitrogen during combustion. Used in the manufacture of dyes and pesticides.

Namen und Bezeichner

Bevorzugter Name
2,3-Dichloroaniline
IUPAC
2,3-dichloroaniline
Lokaler Name
Chloranilin, di
Englischer Name
Dichloroaniline
Summenformel
C6H5Cl2N
Molmasse
162.02

Namen und Synonyme

2,3-DICHLOROANILINE608-27-5Benzenamine, 2,3-dichloro-2,3-DichlorobenzenamineAniline, 2,3-dichloro-2BL4F1DXVNNSC-60683DTXSID8040696CHEBI:46636RefChem:1059334DTXCID6020696210-157-9
Weitere Namen anzeigen
Benzenamine,ar,ar-dichloro-
2,3-dichlorophenylamineMFCD000076572,3-Dichloranilin2,3-Dichloroaniline (Technical Grade)27134-27-6HSDB 5433EINECS 210-157-9UNII-2BL4F1DXVN

Datenbank-Bezeichner

CAS
27134-27-6、608-27-5
PubChem CID
11844
DTXSID
DTXSID8040696
ChEMBL
CHEMBL1889723
ChEBI
CHEBI:46636
UNII
2BL4F1DXVN
EC Number
210-157-9
Nikkaji
J130.659F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,9
Polarare Oberfläche (TPSA)
26 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
9
Formalladung
0
Komplexität
97,1

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Amines, Aromatic

Textile

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 3 Einträge

log Kow= 2.78

2.78

2.51

Density · 2 Einträge

1.383 @ 25 °C

Relative density (water = 1): 1.383

Color/FormNEEDLES FROM PETROLEUM ETHER
Solubility · 3 Einträge

VERY SOL IN ETHER; SLIGHTLY SOL IN PETROLEUM ETHER, BENZENE

Sol in alcohol, acetone

Solubility in water: none

Flash Point · 2 Einträge

>112 °C (closed cup)

>112 °C c.c.

Boiling Point · 2 Einträge

252 °C

252 °C

Decomposition

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

H301+H311+H331 (34.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P332+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 83 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Danger

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Benzenamine, 2,3-dichloro-

Status: Active Update: 14-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/11877

Benzenamine, 2,3-dichloro-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Dichloroanilines: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 4 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Heating will cause rise in pressure with risk of bursting.

Health Hazards · 3 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

The metabolic fate of propanil in plants was studied. The conversion of this compound in soil to 3,3',4,4'-tetrachloroazobenzene is catalyzed by soil peroxidases. This reaction also occurs in the presence of crystalline horseradish peroxidase. In some plants propanil is rapidly hydrolyzed to give 3,4-dichloroaniline. Crude extracts of barnyard grass, fresh horseradish root, rice, & commercially purified crystalline horseradish enzyme were prepared. It was inferred that the differences in substrate specificity among peroxidases may account for the failure of some plants to convert the aniline to azo compounds such as in the conversion to dichloroaniline to tetrachloroazobenzene. ... Enzymatically catalyzed products of mono- & dichloroanilines were prepared by mixing barnyard grass supernatants or horseradish peroxidase with an acetic buffer, hydrogen peroxide & various aniline substrates & allowed to react for 30 min. Preparations made from fresh horseradish & from horseradish peroxidase gave products with all anilines except 2,5- & 2,6-dichloroanilines. Barnyard grass & rice plants gave products only with 2,3-dichloroaniline of the dichloroaniline substrates studied.

Verwendung und Herstellung

Uses · 3 Einträge

Byproduct of 3,4-dichloroaniline production; Used in dyestuffs, pesticides, pharmaceuticals, and as a research chemical; [HSDB] Used as an intermediate; [ECHA REACH Registrations]

RESEARCH CHEMICAL

Dyestuffs, pesticides and pharmaceuticals.

U.S. Imports(1979) 1.50X10+7 G (PRINCIPAL CUSTOMS DISTRIBUTORS)
Methods of ManufacturingPRODUCED AS A BYPRODUCT IN THE PRODUCTION OF 3,4-DICHLOROANILINE BY NITRATION & REDUCTION OF 1,2-DICHLOROBENZENE
General Manufacturing InformationBenzenamine, 2,3-dichloro-: ACTIVE

Zugehörige Reaktionen

66
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 47414
HRID 47414als Eduktuspto-grants-2004_03
Reaktionsgleichung von HRID 65229
HRID 65229als Eduktuspto-grants-1986_09
Reaktionsgleichung von HRID 65731
HRID 65731als Eduktuspto-grants-1978_12
Reaktionsgleichung von HRID 65734
HRID 65734als Eduktuspto-grants-1978_12
Reaktionsgleichung von HRID 116062
HRID 116062als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 118960
HRID 118960als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 181139
HRID 181139als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 209344
HRID 209344als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
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When heated to decomposition it emits highly toxic fumes of /hydrogen chloride/ and nitrogen oxides. /2,5-Dichloroaniline/
Melting Point · 2 Einträge

24 °C

24 °C

Vapor DensityRelative vapor density (air = 1): 5.6
Vapor Pressure · 2 Einträge

0.02 [mmHg]

Vapor pressure, Pa at 25 °C:

Physikochemische Eigenschaften

EPA chemische Informationen
Dichloroaniline (27134-27-6)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 1 Eintrag

Causes somnolence, tremor, and weight loss in inhalation lethal-concentration studies of rats; [RTECS] Eye contact can cause redness and pain; May induce methemoglobinemia; Can be absorbed through skin; [ICSC] An irritant that may cause serious eye injury; May cause skin sensitization; Toxic by ingestion, inhalation, and skin absorption (may induce methemoglobinemia); Suspected mutagen and carcinogen; [ECHA REACH Registrations] An irritant; May induce methemoglobinemia; Highly toxic by ingestion, inhalation, and skin absorption; [Alfa Aesar MSDS] See 3,4-Dichloroaniline.

DOT ID and Guide · 2 Einträge

3442 153

1590 153

Reactive GroupAryl Halides
EC ClassificationSymbol: T, N; R: 23/24/25-33-50/53; S: (1/2)-28-36/37-45-60-61; Note: C
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,3-Dichlorobenzeneamine is included on this list.

Reactivity Profile · 1 Eintrag

A halogenated aromatic amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

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

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 4 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

General First Aid:

Safe StorageSeparated from strong oxidants and food and feedstuffs. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection · 2 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

Fire Fighting Procedures · 2 Einträge

If material on fire or involved in fire: Use dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Use water in flooding quantities as fog. /Dichloroaniline/

Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Dichloroaniline/

Storage ConditionsSTORE IN A COOL, DRY, WELL-VENTILATED LOCATION. SEPARATE FROM ACIDS, OXIDIZING MATERIALS, & COMBUSTIBLES. /DICHLOROANILINES/
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 Eintrag

Personal protection: chemical protection suit including self-contained breathing apparatus. Remove all ignition sources. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 5 Einträge

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

... ANILINE SHOULD BE REACTED IN CLOSED VESSELS AS FAR AS POSSIBLE. IN FACTORIES VENTILATION SHOULD BE SUFFICIENT TO KEEP ATMOSPHERIC ANILINE CONTENT WELL BELOW PERMITTED LEVEL. /Aniline/

Eating and smoking should not be allowed in areas where liquid aniline is handled, processed, or stored. /Aniline/

Clothing which becomes soaked with aniline should be promptly removed. /Aniline/

For more Preventive Measures (Complete) data for 2,3-DICHLOROANILINE (9 total), please visit the HSDB record page.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 2,3-dichloroaniline is expected to have high mobility in soil(SRC). When released to soil, 2,3-dichloroaniline may undergo covalent chemical bonding with humic materials, which can result in its chemical alteration to a latent form and tight adsorption. When covalently bound in this latent form, leaching in soil systems is not generally expected to occur. This covalent bonding proceeds in two steps; a rapid and reversible bonding followed by a slower and much less reversible reaction(3). The effects of dichlorine-substitued anilines on guelph loam were studied under aerobic conditions. It was shown that a linear rate of decomposition over a 12 week period existed for these compounds(4). Volatilization of 2,3-dichloroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2,3-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-2 mm Hg(SRC), determined from a fragment constant method(6). Due to the strong adsorption to humic material in the soil, 2,3-dichloroaniline volatilization is expected to be attunuated(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 2,3-dichloroaniline is not expected to adsorb to suspended solids and sediment in water(SRC). By analogy to other chloro- and dichloroaniline isomers(3), 2,3-dichloroaniline may undergo covalent bonding with humic materials in the water column and in sediment; partitioning from the water column to sediment and suspended material may therefore be important(3). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC) developed using a fragment constant estimation method(5). Volatilization half-lives for a model river and model lake are 30 and 219 days, respectively(SRC), using an estimation method(4). 2,3-Dichloroaniline may undergo a covalent chemical bonding with suspended soil particles resulting in its chemical alteration to a latent form resulting in strong adsorption, attenuating volatilization(6). According to a classification scheme(7), an estimated BCF of 76(4,SRC) suggests the potential for bioconcentration in aquatic organisms is moderate. The first-order rate constant for 2,3-dichloroaniline degradation a sediment slurry was 0.013 day-1 with a half-life of 54 days under anaerobic conditions(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-dichloroanilne, which has an estimated vapor pressure of 2.5X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3-dichloroaniline 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 17 hours(SRC) from its estimated rate constant of 2.2X10-2 cu cm/molecule sec(3).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Signs and Symptoms · 4 Einträge

Blue lips, fingernails and skin. Dizziness. Headache. Nausea. Shortness of breath. Confusion. Convulsions. Unconsciousness.

MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

Abdominal pain. Further see Inhalation.

Effluent Concentrations2,3-Dichloroaniline was found to occur only once in over 4000 samples of wastewaters from 46 industrial categories(1); the detection (concn and source not reported) occurred in a sample from the organic chemicals industry(1).
ICSC Environmental DataThe substance is toxic to aquatic organisms.
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,3-dichloroaniline can be estimated to be about 120(SRC). According to a classification scheme(2), this Koc value suggests that 2,3-dichloroaniline is expected to have high mobility in soil(SRC). Aromatic amines such as various chloro- and dichloroaniline isomers, have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structure followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(3).

Artificial Pollution Sources · 1 Eintrag

2,3-Dichloroaniline's production and use as intermediates in dyestuffs, pesticides, and pharmaceuticals(1) may result in its release to the environment through various waste streams. The chemical and biological reduction of azo dyes and halogenated nitroaromatic herbicides, explosives, and nitropyrenes could result in the formation of chloroaniline compounds in the environment(2).

Environmental Biodegradation · 2 Einträge

The effects of dichlorine-substituted anilines on guelph loam were studied. Several dichloroanilines at concentrations of 5 to 100 ug/g soil was inhibitory against the oxidation of the nitrogen of ammonia to nitrite nitrogen, but not nitrite nitrogen to nitrate nitrogen. It showed almost a linear rate of decomposition over the 12 wk period of the experiment. The dichloroanilines were more persistent than aniline or the monochloroanilines. /Dichloroanilines/

AEROBIC: The effects of dichlorine-substitued anilines on guelph loam were studied under aerobic conditions. It was shown that a linear rate of decomposition over a 12 week period existed for these compounds(1). Incubation of 2,3-dichloroaniline in covered beakers containing a sandy loam soil for 14 days yielded the azo compound 3,4'-dichloroazobenzene; no azo compounds were detected in control incubations using sterilized soil(2). Products other than azo compounds were not isolated or analyzed(2). ANAEROBIC: A study of a sediment slurry taken from an anaerobic estuary collected from the mouth of the Tsuiami River, Japan, revealed that 2,3-dichloroaniline degraded to 3-chloroaniline and further to aniline(3). The first-order rate constant for 2,3-dichloroaniline degradation slurry was 0.013 day-1 with a half-life of 54 days under anaerobic conditions(3). This site has been well characterized and designated as a sulfate-reducing environment based on its sulfate concentration. This supports the idea that dechlorination of chloroanilines occurred under sulfate-reduction(3).

Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 76 was calculated for 2,3-dichloroaniline(SRC), using the log Kow of 2.78(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for 2,3-dichloroaniline is estimated as 1.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3-dichloroaniline is expected to volatilize from water surfaces(2). 2,3-Dichloroaniline may undergo a covalent chemical bonding with suspended humic material resulting in its chemical alteration to a latent form resulting in strong adsorption, attenuating volatilization(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 711 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 219 days(SRC). 2,3-Dichloroaniline's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 2,3-Dichloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-2 mm Hg(SRC), determined from a fragment constant method(4).

Non-Human Toxicity Excerpts · 3 Einträge

TWENTY-ONE HALO-SUBSTITUTED ANILINES WERE COMPARED WITH ANILINE FOR THEIR ABILITY TO STIMULATE METHEMOGLOBIN FORMATION IN CATS. HALO SUBSTITUTIONS IN THE 4-POSITION INCREASED THE ACTIVITY OF ANILINE, WHILE SUBSTITUTIONS IN THE 2 AND 3 POSITIONS DID NOT CHANGE OR REDUCE THE ACTIVITY. POLYHALO SUBSTITUENTS (SUCH AS 2,6-DICHLOROANILINE) REDUCED THE ACTIVITY COMPARED TO ANILINE. /DICHLOROANILINES/

IN GUELPH LOAM, 3,5-DICHLOROANILINE, AT CONCN OF 5-100 UG/G SOIL, WAS INHIBITORY AGAINST THE OXIDN OF THE NITROGEN OF AMMONIA TO NITRITE NITROGEN BY NITROSOMONAS, BUT NOT NITRITE NITROGEN TO NITRATE. THE DICHLOROANILINES SHOWED INCREASED TOXICITY AGAINST NITROSOMONAS. /DICHLOROANILINES/

Dichloroaniline produces methemoglobinemia in rats & mice. /Dichloroaniline/

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,3-Dichlorobenzeneamine is included on this list.

Atmospheric Standards · 1 Eintrag

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 2,3-Dichloroaniline is produced, as an intermediate or a final product, by process units covered under this subpart.

Sicherheitsdaten

ridadr
UN 3442
hazard_class
6.1
packing_group
II