HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

1,2-Dichloro-4-nitrobenzene

HCID 7443
New noteNew reactionRequest quotes
Print preview

Completing data — refresh the page later to see the latest

Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
99-54-7
Standard SMILES
O=[N+]([O-])c1ccc(Cl)c(Cl)c1
InChIKey
NTBYINQTYWZXLH-UHFFFAOYSA-N
Molecular formula
C6H3Cl2NO2
Average molar mass
192 g/mol
Monoisotopic mass
190.9540837

Overview

3,4-dichloronitrobenzene appears as colorless crystals or light beige solid. (NTP, 1992)

Names & identifiers

Preferred name
1,2-Dichloro-4-nitrobenzene
IUPAC
1,2-dichloro-4-nitrobenzene
English name
3,4-Dichloronitrobenzene
Molecular formula
C6H3Cl2NO2
Molecular weight
192

Names & synonyms

3,4-DICHLORONITROBENZENE1,2-Dichloro-4-nitrobenzene99-54-71-Nitro-3,4-dichlorobenzeneBenzene, 1,2-dichloro-4-nitro-DCNBDTXSID80249993,4-DichloronitrobenzenIJT74JI7FSAI3-03268 (USDA)NSC-6295NSC-99806
Show more names
3,4-DCNB3,4-DICHLORO-1-NITROBENZENEai3-03268(usda)3,4-DichloronitrobenLABOTEST-BB LT004369593,4-Dichlornitrobenzene3,4-Dichluoronitrobenzene
DTXCID504999RefChem:71856202-764-23,4-Dichlornitrobenzen1,2-Dichloro-4-nitro-benzeneMFCD00007207WLN: WNR CG DGBenzene,2-dichloro-4-nitro-

Database identifiers

CAS
99-54-7
PubChem CID
7443
DTXSID
DTXSID8024999
ChEMBL
CHEMBL167468
UNII
IJT74JI7FS
EC Number
202-764-2
Nikkaji
J3.584J

Properties

Computed structural propertiesFilling in

XLogP
3.1
Topological polar surface area
45.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
11
Formal charge
0
Complexity
159

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitros, Aromatic
SpringerMaterials PropertiesBoiling point
LogP · 2 items

log Kow = 3.12

3.12

Density · 3 items

1.4558 at 167 °F (NTP, 1992) - Denser than water; will sink

1.4558 at 75 °C/4 °C

Density (at 15 °C): 1.56 g/cm³

Color/Form · 2 items

Needles from alcohol

SOLID

Solubility · 4 items

less than 0.1 mg/mL at 74.3 °F (NTP, 1992)

Soluble in ether, alcohol; slightly soluble in carbon tetrachloride

In water, 121 mg/L at 20 °C

Solubility in water: none

Flash Point · 3 items

255 °F (NTP, 1992)

124 °C

124 °C

Boiling Point · 3 items

491 to 493 °F at 760 mmHg (NTP, 1992)

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 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 4 items

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

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 20-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12146

1,2-Dichloro-4-nitrobenzene: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzene, 1,2-dichloro-4-nitro-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Fire PotentialFire risk by spontaneous reaction.
Health HazardsSYMPTOMS: Symptoms of exposure to this compound include eye, skin, and mucous membrane irritation; headache; drowsiness; and unsteadiness. Chronic symptoms include liver damage.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 5 items

YIELDS S-(2-CHLORO-4-NITROPHENYL)GLUTATHIONE IN RAT & RABBIT; YIELDS 3,4-DICHLOROANILINE IN RABBIT. /FROM TABLE/

FOLLOWING ORAL ADMINISTRATION OF 3,4-DICHLORONITROBENZENE TO PIGEONS, ANALYSIS OF EXCREMENT SHOWED THAT DCNB IS MAINLY METABOLIZED BY REDUCTION OF THE NITRO GROUP WITH VERY LITTLE FORMATION OF MERCAPTURIC ACID.

WHEN THE DRUG METABOLIZING POTENTIALS OF LUNG AND LIVER WERE COMPARED OF 4 TRANSFERASE, THE ACTIVITIES IN THE LUNG WERE GENERALLY LESS THAN THE ACTIVITIES IN THE LIVER. THE ACTIVITY OF GLUTATHIONE S-ARYLTRANSFERASE TOWARD 1,2-DICHLORO-4-NITROBENZENE IN THE LUNG WAS APPROXIMATELY 20% THAT IN THE LIVER.

Observed that rat liver contains an enzyme that catalyzes the conjugation of glutathione and 3,4-dichloronitrobenzene with loss of the nitro group.

Female rats were dosed by oral intubation with 3,4-dichloronitrobenzene at 500 mg/kg. Six hr after dosing, liver glutathione had decreased to 56% of controls. Blood glutathione although increased by 18%, was not considered to be significantly changed. The effect on liver glutathione was related to formation of mercapturic acid during metabolism.

Absorption, Distribution and Excretion · 2 items

In rats about 19 % (range 4 - 29 %) of the applied dose (approx. 350 mg/kg bw via gavage) was excreted as mercapturic acid via urine within 24 hrs. In a second trial the animals were dosed with approximately 250 or 350 mg/kg bw and the maximum rate for excretion of mercapturic acid via urine 2 - 6 days after dosing was given with approx 2 or 4 mg/kg bw/hr, resp.

In rabbits dosed orally with 400 mg/kg bw via gavage most of the applied dose was excreted via urine within 72 hrs as mercapturic acid derivative N-acetyl-S-(2-chloro-4-nitrophenyl)-L-cysteine (approx. 45 %) followed by conjugates of amino dichlorophenols (approx 13 % as glucuronide and approx. 12 % as sulfate ester)and 3,4-dichloroaniline (approx. 22 %).

Uses & manufacturing

Uses · 3 items

Used to make herbicides, insecticides, and dyes; [HSDB]

CHEM INTERMEDIATE FOR HERBICIDES (EG, PROPANIL) AND INSECTICIDES & DYE INTERMEDIATES

Related reactions

110 records
New reaction record
HRID 26341 reaction equation
HRID 26341As reactantuspto-grants-1979_04
HRID 38506 reaction equation
HRID 38506As reactantuspto-grants-2013_09
HRID 38508 reaction equation
HRID 38508As reactantuspto-grants-2013_09
HRID 46782 reaction equation
HRID 46782As reactantuspto-grants-1979_11
HRID 46793 reaction equation
HRID 46793As reactantuspto-grants-1979_11
HRID 65272 reaction equation
HRID 65272As reactantuspto-grants-1986_09
HRID 65287 reaction equation
HRID 65287As reactantuspto-grants-1986_09
HRID 127529 reaction equation
HRID 127529As reactantuspto-grants-1981_03
Page 1 of 14

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes

255-256 °C

255 °C

Melting Point · 4 items

109 °F (NTP, 1992)

43 °C

Has both a stable and labile form. The stable alpha-form has a melting point of 42-43 °C and beta-form is a liquid which changes to the alpha-form at 15 °C

39-41 °C

Vapor Density · 3 items

6.63 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

6.63

Relative vapor density (air = 1): 6.6

Vapor Pressure · 3 items

0.01 [mmHg]

1.03X10-2 mm Hg at 25 °C

Vapor pressure, Pa at 25 °C: 2

Henry's Law ConstantHenry's Law constant = 8.07X10-6 amt-cu m/mol at 25 °C

Physicochemical properties

Melting point
39 · 39-41 °C(lit.)
Boiling point
255 · 255-256 °C(lit.)
Density
1.48 g/cm3 · 1.48 g/cm3 (55℃)
bulk density
750 kg/m3 · 750kg/m3
vapor pressure
0.01 hPa · 0.01 hPa (20 °C)
refractive index
1.5929 · 1.5929 (estimate)
Flash point
255 °F · 255 °F
storage temp.
30 °C · Store below +30°C.
solubility
0.151 g/l · 0.151g/l
form
Crystalline Mass
color
Yellow to brown
Water Solubility
151 mg/L · 151 mg/L (20 ºC)
FreezingPoint
30 · 30~31℃
BRN
1818163 · 1818163
Henry's Law Constant
1.2 · 1.2×100 mol/(m3Pa) at 25℃, Altschuh et al. (1999)
Stability
Stable. Incompatible with strong oxidizing agents, strong bases.
InChI
1S/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H
InChIKey
NTBYINQTYWZXLH-UHFFFAOYSA-N
SMILES
[O-][N+](=O)c1ccc(Cl)c(Cl)c1
CAS DataBase Reference
99 · 99-54-7(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
74 JI7FS · IJT74JI7FS
NIST Chemistry Reference
1 · Benzene, 1,2-dichloro-4-nitro-(99-54-7)
EPA Substance Registry System
3 · 3,4-Dichloronitrobenzene (99-54-7)
UNSPSC Code
12352101 · 12352101
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H317-H319
Precautionary statements
280 · P280-P301+P312+P330-P302+P352-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn,N
Risk Statements
22 · 22-36-43-51/53
Safety Statements
26 · 26-36/37-61-39-24/25
RIDADR
2811 · 2811
WGK Germany
3 · 3
RTECS
5250000 · CZ5250000
Autoignition Temperature
420 °C · 420 °C
TSCA
TSCA listed
HazardClass
9 · 9
PackingGroup
III
HS Code
29049085 · 29049085
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Sens. 1
Hazardous Substances Data
99 · 99-54-7(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 643 mg/kg LD50 dermal Rat > 2000 mg/kg
REACH Registrations
Active
Hazards Summary · 1 item

A skin and eye irritant; May cause effects on the blood; [ICSC] May cause liver damage; [CAMEO] Causes methemoglobinemia in high-dose animals experiments; Methemoglobinemia also reported in exposed workers; Dermal LD50 (rats) >2000 mg/kg; Oral LDLo (rabbits) = 950 mg/kg; [HSDB] An eye irritant; Can be absorbed through skin; May cause skin sensitization; May induce methemoglobinemia; Effects in high-dose animal studies include cyanosis; [MSDSonline] No evidence of skin sensitization; [INCHEM: SIDS] Danger of cutaneous absorption; Could be carcinogenic for man but not conclusive because of insufficient data; [MAK]

Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
Special Reports · 2 items

Organisation for Economic Cooperation and Development; Screening Information Data Set for 1,2-Dichloro-4-nitrobenzene, CAS # 99-54-7 (2003). A compliation of the chemical properties, toxicity and pharmacokinetics of 1,2-dichloro-4-nitrobenzene used for the initial assesment of the test compound. Includes an IUCLID dataset updated in 2004 as an appendix.

European Chemicals Bureau; IUCLID Dataset, 1,2-Dichloro-4-Nitrobenzene (CAS # 99-54-7) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of July 5, 2007. A report on the ecotoxicity, toxicity, and pharmacokinetics of 1,2-dichlor-4-nitrobenzene.

TSCA Requirements · 2 items

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. 3,4-Dichloronitrobenzene is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Reactivity ProfileCan react vigorously with oxidizing materials. (NTP, 1992)

Safety & protection

Fire Fighting · 2 items

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

Use powder, water spray, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Rinse and then wash skin with water and soap.

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

Rinse mouth.

First Aid · 1 item

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 strong oxidants, strong bases and food and feedstuffs. Provision to contain effluent from fire extinguishing.
Nonfire Spill Response · 1 item

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 items

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 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames. Prevent deposition of dust. Closed system, dust explosion-proof electrical equipment and lighting.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves.

Toxicology

InteractionsKinetic studies of glutathione transferase activites in which nafenopin was mixed with normal rat liver cytosols in the assay system revealed competitive type inhibition toward 3,4-dichloronitrobenzene.
Ecotoxicity Values · 4 items

LC50 Leuciscus idus /(Ide)/ 3.1 mg/L for 48 hr /Conditions of bioassay not specified in source examined/

LC50 Leuciscus idus /(Ide)/ 5.6 mg/L for 96 hr /Conditions of bioassay not specified in source examined/

LC50 Leusiscus Idus melanotus /golden orfe/ 5.2 mg/L for 96 hr /Static bioassay/

LC50 Oryzias latipes /Japanese medaka/ 7 mg/L for 48 hr/ Static bioassay

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 390 to 393(2,3), indicate that 3,4-dichloronitrobenzene is expected to have moderate mobility in soil(SRC). Volatilization of 3,4-dichloronitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 8.07X10-6 atm-cu m/mole(4). 3,4-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.03X10-2 mm Hg(5). Lack of biodegradation of 3,4-dichloronitrobenzene incubated in an aquifer slurry over an unspecified time frame(6) suggests that biodegradation is not an important environmental fate process in soil(SRC). However, under anaerobic conditions using a river sediment, a half-life of 2.4 days has been reported(7).

AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 390 to 393 in silt loams(2,3), indicate that 3,4-dichloronitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 8.07X10-6 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 6 days and 51 days, respectively(SRC). According to a classification scheme(6), a BCF values ranging from 104 to 130(7,8) suggest the potential for bioconcentration in aquatic organisms is high(SRC). Lack of biodegradation of 3,4-dichloronitrobenzene incubated in an aquifer slurry over an unspecified time frame(9) suggests that biodegradation is not an important environmental fate process in water(SRC). However, under anaerobic conditions using a river sediment, a half-life of 2.4 days has been reported(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,4-dichloronitrobenzene, which has a /an estimated vapor pressure of 1.03X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,4-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 321 days(SRC), calculated from its rate constant of 5.0X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3,4-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.
Toxicity Summary · 1 item

Human Health: 1,2-Dichloro-4-nitrobenzene is absorbed from the gastro-intestinal tract and although there are some species differences in experimental animals from the available data it can be concluded that 1,2-dichloro-4-nitrobenzene is excreted mainly via urine in the form of the mercapturic acid derivative N-acetyl-S-(2-chloro-4-nitrophenyl)-Lcysteine. ... Based on the results of the acute dermal toxicity study with rats the LD50 is > 2000 mg/kg bw. From studies with rabbits no LD50 could be derived, the lowest Lethal Dose Level (LDLo) was 950 mg/kg bw. The acute oral toxicity in rats ranges from 625 to 950 mg/kg bw. 1,2-Dichloro-4- nitrobenzene causes the formation of methemoglobin. ... 1,2-Dichloro-4-nitrobenzene gave no skin irritation effects when tested for 4 hours under semiocclusive conditions ... and showed slightly irritating effects, which disappeared within 72 hours under occlusive conditions ... 1,2-Dichloro-4-nitrobenzene is slightly irritating to the eyes /but/ ... was not found to induce dermal sensitization ... . In addition, 1,2-dichloro-4-nitrobenzene was not found to induce dermal sensitization in humans in a limited study. The main targets identified in animal studies after repeated oral administration as well as after inhalation exposure are the hematological system and in addition the kidneys after oral application and the liver after inhalation. From a 28- day oral study ... a NOAEL of 4 mg/kg bw/day was derived. The NOAEL following subchronic inhalation exposure study of limited validity (limited documentation) was 0.4 mg/cu m (4 hours per day). Changes in hematological parameters (e.g. methemoglobinaemia, Heinz bodies) are the main target in the only available report on exposure of workers. As these findings relate to mixed exposures they cannot be clearly attributed to 1,2-dichloro-4-nitrobenzene, but would be plausible, because they were also observed in animal experiments. In the recent open literature reports of human poisoning could not be identified. 1,2-Dichloro-4-nitrobenzene exhibits mutagenic activity in Salmonella typhimurium but not in the HPRT test in Chinese Hamster Ovary (CHO) cells. 1,2-Dichloro-4-nitrobenzene induced chromosomal aberrations in V79 cells with metabolic activation only at the highest concentration, which was cytotoxic. In insects (Drosophila melanogaster) 1,2-dichloro-4-nitrobenzene revealed no mutagenic activity in the SLRL-test after application over 3 days with slight increased toxicity, but revealed mutagenic activity following a single ip injection of a clearly toxic dose. 1,2-Dichloro-4-nitrobenzene showed no clastogenic activity in vivo in a chromosomal aberrations test with rats. Overall in non-toxic doses, there was no evidence for genotoxicity in vivo under the conditions tested. Studies dealing specifically with toxicity to reproduction were not identified. The subacute study with 1,2-dichloro-4- nitrobenzene yielded no damage of the reproductive organs in rats despite clear systemic toxicity up to the maximum tolerated dose of 100 mg/kg bw. 1,2-Dichloro-4-nitrobenzene commercial grade (85% 1,2-dichloro-4-nitrobenzene and 15% 1,2-dichloro-3- nitrobenzene) caused effects on development at maternally toxic doses probably due to methemoglobinemia in dams and fetuses. A significant dose-response trend for variations (dilated ureters) was seen in the fetuses of the >= 30 mg/kg bw/day-groups and significant reduced body weight gain of dams at dose levels of 30 mg/kg bw/day on gd 6-10 with an even stronger effect at 100 mg/kg bw/day. Thus, 10 mg/kg bw/day was determined as the NOAEL for maternal and developmental toxicity. Environment: ... Concerning the acute toxicity of 1.2-dichloro-4-nitrobenzene towards aquatic species reliable experimental results of tests with fish, Daphnia, and algae are available. The acute toxicity determined for fish (Leuciscus idus) was of 3.1 mg/L (48 hr LC50) ... and Daphnia (Daphnia magna) of 3 mg/L (24 hr-EC50) ... . In the growth inhibition test with algae (Scenedesmus obliquus) the value 5.8 mg/L was achieved after 48 hr (48 hr-ErC50)... . For the algae Chlorella fusca a value of 0.32 mg/L was found after 24 hr (24 hr-ErC50). In a chronic (21 d) study with Daphnia magna a NOEC of 0.025 mg/L was determined for the most sensitive endpoint reproduction rate. An ErC10 > 0.1 mg/L was reported for the algae Scenedesmus subspicatus after 48 hours. For terrestrial organisms the lowest measured 6d-EC50 was 27 mg/L for the plant Phaseolus aureus. Applying an assessment factor of 50 to the lowest available chronic value of 25 ug/L (21d reproduction in D. magna), a PNECaqua of 0.5 ug/lL is obtained.

Ecotoxicity Excerpts · 1 item

/AQUATIC SPECIES/ In a reproduction (21 d) study with Daphnia magna performed in a semistatic system in closed vessels /the authors/ found a NOEC of 0.025 mg/L for the most sensitive endpoint reproduction rate. The stability of the test substance concentration was confirmed by analytical monitoring.

Signs and Symptoms · 2 items

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 item

An experimentally determined mean Koc value of 393 for 3,4-dichloronitrobenzene was reported using 4 silt loam soils(1). A log Koc value of 2.62 was reported following adsorption studies using sediment from the Yangste River in China(2), corresponding to a Koc of 390(SRC). According to a classification scheme(3), these Koc values suggest that 3,4-dichloronitrobenzene is expected to have moderate mobility in soil. Using a modified organo montmorillonite clay from Jiangning Jinagsu Province, China, a log Koc of 3.76 was determined(3), corresponding to a Koc of 5,754(SRC).

TSCA Test Submissions · 5 items

3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute oral toxicity. The test substance was administered orally to 10 rats (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Signs of toxicity included weakness (moderate to very weak), labored respiration, cyanosis, dark eyes, and prostration. Time of death was between 45 minutes and 2 days. The approximate LD50 was determined to be between 1600 and 3200 mg/kg b.w. The test substance was determined to be slightly toxic.

3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute intraperitoneal toxicity. The test substance was administered intraperitoneally to 10 rats (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Signs of toxicity included weakness (moderate to very weak), labored respiration, cyanosis, dark eyes, and prostration. Time of death was between 2 hours and 1 day. The approximate LD50 was determined to be between 400 mg/kg b.w. The test substance was determined to be moderately toxic.

3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute oral toxicity. The test substance was administered orally to 10 mice (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Clinical signs included weakness (normal to very weak), decreased activity, slow respiration, cyanosis, dark eyes, slight tremor, prostration, and yellow-orange urine. Time of death was 1 day. The approximate LD50 was determined to be between 800-1600 mg/kg b.w. The test substance was determined to be slightly toxic.

3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute intraperitoneal toxicity. The test substance was administered intraperitoneally to 10 mice (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Clinical signs included weakness (normal to very weak), decreased activity, slow respiration, cyanosis, dark eyes, slight tremor, prostration, and yellow-orange urine. Time of death was between 4-1/2 hours and 1 day. The approximate LD50 was determined to be between 400-800 mg/kg b.w. The test substance was determined to be moderately toxic.

For more TSCA Test Submissions (Complete) data for 3,4-DICHLORONITROBENZENE (14 total), please visit the HSDB record page.

Human Toxicity Excerpts · 2 items

/HUMAN EXPOSURE STUDIES/ In a study with 10 female subjects the single dermal application of a 10 % solution of 1,2-dichloro- 4-nitrobenzene in acetone followed by a challenge with a 10 or 0.01 - 1 % solution in acetone on day 28 and 49 caused no skin sensitization.

/BIOMONITORING/ 3,4-Dichloronitrobenzene, like other nitro and amino aromatics, is responsible for methemoglobin formation in humans. Levels of 10 mg/L of 3,4-dichloronitrobenzene metabolites in human urine may be considered to be warning levels of overexposure.

Regulatory information

TSCA Requirements · 2 items

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. 3,4-Dichloronitrobenzene is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
CZ5250000
ridadr
2811
hs_code
29049085
Toxicity
LD50 orally in Rabbit: 643 mg/kg LD50 dermal Rat > 2000 mg/kg
risk_code
22-36-43-51/53
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,N
safety_code
26-36/37-61-39-24/25
hazard_class
9
Storage Class
11 - Combustible Solids
packing_group
III
Hazard statements
H302-H317-H319
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Sens. 1
Autoignition Temperature
420 °C
Precautionary statements
P280-P301+P312+P330-P302+P352-P305+P351+P338
Hazardous Substances Data
99-54-7(Hazardous Substances Data)

Iron reduction of 1,2-dichloro-4-nitrobenzene yields 3,4-dichloroaniline, an important agrochemical intermediate. Amination produces 2-chloro-4-nitroaniline, which is an important diazo component and intermediate.

Impurities1,2-dichloro-3-nitrobenzene (< 1 % w/w); water (ca. 0.1 % w/w)
U.S. Imports · 2 items

(1977) 1.19X10+6 GRAMS (PRINCPL CUSTMS DISTS)

(1978) 2.05X10+7 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 4 items

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4889]

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Methods of Manufacturing · 2 items

Nitration of 1,2-dichlorobenzene with mixed acid at 35 - 60 °C results in a mixture of 3-nitro (10 %) and 4-nitro (90 %) isomers, which are separated by crystallization. A more expensive process (two stages from chlorobenzene) is based on chlorination of molten 4-chloronitrobenzene (90 - 100 °C) by a process similar to that used for 3-chloronitrobenzene production. Chlorination has the advantage of giving a pure product, but it cannot be used if the isomeric 1,2-dichloro-3-nitrobenzene is also required.

CHLORINATION OF P-NITROCHLOROBENZENE; NITRATION OF O-DICHLOROBENZENE

General Manufacturing InformationBenzene, 1,2-dichloro-4-nitro-: ACTIVE

Applications

Uses1,2-Dichloro-4-nitrobenzene is an intermediate in the synthesis of agrochemicals. Studies have been conducted to use 1,2-Dichloro-4-nitrobenzene as an organic intermediate for the synthetic preparation of ciprofloxacin (C482500).

General DescriptionColorless crystals or light beige solid.

Upstream & downstream products

Upstream raw materials

4-Chloronitrobenzene1,2-Dichlorobenzene2,5-Dinitroaniline3,4-Dichlorophenylboronic acid, pinacol ester2,3-Dichloro-6-nitrobenzonitrile2,3-Dichloro-6-nitrobenzaldehyde2,3,4-Trichloronitrobenzene2-Chloro-5-nitrobenzoic acid2,3-Dichlorobenzaldehyde1,2,4-Trichloro-5-nitrobenzene2,3-Dichloronitrobenzene1-Chloro-3-nitrobenzene2,5-Dichloronitrobenzene

Downstream products

3-Chloro-4-phenoxyanilinePropanilNorfloxacinDiuron3,4-Dichloroaniline2-Chloro-4-nitrophenol2,4-DinitrophenolRafoxanide