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벤젠,디클로로니트로-

2,3-Dichloronitrobenzene

HCID 18555
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
27900-75-0
표준 SMILES
O=[N+]([O-])c1cccc(Cl)c1Cl
InChIKey
CMVQZRLQEOAYSW-UHFFFAOYSA-N
분자식
C6H3Cl2NO2
평균 분자량
192 g/mol
단동위원소 질량
190.9540837

개요

2,3-dichloronitrobenzene appears as light yellow crystals or yellow crystalline solid. (NTP, 1992)

이름 및 식별자

우선 이름
2,3-Dichloronitrobenzene
IUPAC
1,2-dichloro-3-nitrobenzene
현지명
벤젠,디클로로니트로-
영어명
Benzene, dichloronitro-
분자량
0

이름 및 동의어

2,3-DICHLORONITROBENZENE1,2-Dichloro-3-nitrobenzene3209-22-12,3-Dichloro-1-nitrobenzeneBenzene, 1,2-dichloro-3-nitro-CCRIS 5901DTXSID8024997HSDB 4279EINECS 221-717-7NSC 60641BRN 2048029985EWS35KG
이름 더 보기
벤젠,디클로로니트로-AI315074AI3-15074AI3 15074Benzene, dichloronitro-
NSC-60641DTXCID704997EC 221-717-7DICHLORONITROBENZENE, 2,3-2,3-DICHLORONITROBENZENE [HSDB]1-Nitro-2,3-dichlorobenzene1,2Dichloro3nitrobenzene2,3Dichloro1nitrobenzene

데이터베이스 식별자

CAS
27900-75-0、3209-22-1
PubChem CID
18555
DTXSID
DTXSID8024997
ChEMBL
CHEMBL168024
UNII
985EWS35KG
EC Number
221-717-7
Nikkaji
J2.176H

물성

구조 계산 물성보충 중

XLogP
3
극성 표면적
45.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
11
형식 전하
0
복잡도
159

실험 및 물리화학적 성질

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

log Kow = 3.05

3.05

Density · 3건

1.72 (NTP, 1992) - Denser than water; will sink

1.721 at 14 °C

1.7 g/cm³

Color/Form · 2건

Monoclinic needles from petroleum ether, acetic acid

Crystallizes as yellow monoclinic needles.

Solubility · 4건

less than 0.1 mg/mL at 77 °F (NTP, 1992)

Very soluble in organic solvents; soluble in ethanol, ether, acetone, benzene, petroleum ether; slightly soluble in chloroform

In water, 62.4 mg/L at 20 °C.

Solubility in water: none

Flash Point · 3건

255 °F (NTP, 1992)

123 °C

123 °C

Boiling Point · 3건

495 to 496 °F at 760 mmHg (NTP, 1992)

257.5 °C

257-258 °C

Melting Point

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H301 (81.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P273, P301+P316, P301+P317, P319, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 2건

Benzene, 1,2-dichloro-3-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,2-dichloro-3-nitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 20-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/1956

DOT LabelClass 9
Fire Hazards · 2건

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.

Health HazardsACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. (NTP, 1992)
Hazards Summary · 1건

A mutagen; [RTECS] Emergency treatment: Nitrobenzene. [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; [MSDSonline] See 3,4-Dichloronitrobenzene.

Reactive Group

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

2,3-Dichloronitrobenzene undergoes extensive biotransformation in the rabbit. The animals were dosed orally with 2,3-dichloronitrobenzene (0.1 g/kg) and their urine and feces were collected for 72 hr. About 5% of the dose was recovered in feces as 2,3-dichloronitrobenzene and dichloroaniline. About 84% of the dose was recovered in urine, in the form of amino and nitrodichlorophenols: mercapturic acid (0% of dose), glucuronides (47%), sulfates (17%), dichloroaniline-free (15%), dichloroaniline-conjugated (5%), and chlorazoxybenzene (0%).

Absorption, Distribution and Excretion/Rabbits/ were dosed orally with 2,3-dichloronitrobenzene (0.1 g/kg) and their urine and feces were collected for 72 hr. About 5% of the dose was recovered in feces /and/ ... about 84% of the dose was recovered in urine ... .

용도 및 제조

Uses · 6건

Used to make agricultural chemicals and antibacterial/antiprotozoal agents; [HSDB]

Using Disinfectants or Biocides [Category: Clean]

RESEARCH CHEMICAL

Intermediate reagents in the chemical industry.

Agricultural chemicals.

Antibacterial and antiprotozoal agents.

U.S. Production · 3건

2023: 550,000 - <1,000,000 lb

(1977) NOT PRODUCED COMMERCIALLY IN USA

(1979) NOT PRODUCED COMMERCIALLY IN USA

Industry UsesProcessing aids not otherwise specified
Methods of Manufacturing · 2건

PROBABLY BY CHLORINATION OF O-CHLORONITROBENZENE IN THE PRESENCE OF AN ANTIMONY CHLORIDE CATALYST

1,2--Dichloro-3-nitrobenzene is a byproduct of the nitration of 1,2-dichlorobenzene.

General Manufacturing Information · 2건

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

관련 반응

103건
반응 기록 만들기
HRID 18503 반응식
HRID 18503반응물로uspto-grants-2010_06
HRID 32902 반응식
HRID 32902반응물로uspto-grants-2008_09
HRID 33591 반응식
HRID 33591반응물로uspto-grants-2008_09
HRID 46853 반응식
HRID 46853반응물로uspto-grants-1979_11
HRID 50963 반응식
HRID 50963반응물로uspto-grants-2004_03
HRID 132912 반응식
HRID 132912반응물로uspto-grants-2008_06
HRID 132920 반응식
HRID 132920반응물로uspto-grants-2008_06
HRID 132924 반응식
HRID 132924반응물로uspto-grants-2008_06
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· 3건

142 to 144 °F (NTP, 1992)

61.5 °C

61 °C

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

0.00505 [mmHg]

Vapor pressure at 20 °C: negligible

Physical Description · 4건

2,3-dichloronitrobenzene appears as light yellow crystals or yellow crystalline solid. (NTP, 1992)

Other Solid

Colorless solid; [ICSC] Light yellow solid; [CHEMINFO] Light yellow powder; [MSDSonline]

COLOURLESS-TO-YELLOW CRYSTALS.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: II
Special Reports · 1건

Organisation for Economic Cooperation and Development; Screening Information Data Set for 2,3-dichloronitrobenzene, CAS # 3209-22-1 (1994). Available from the Database Query page at: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html as of June 26, 2007.

Reactivity ProfileCan react vigorously with oxidizing materials. (NTP, 1992)
Chemical DangersDecomposes on contact with hot surfaces or flames. This produces toxic and corrosive fumes of nitrogen oxides and hydrogen chloride (see ICSC 0163). Reacts with strong oxidants and bases.
Packaging and LabellingDo not transport with food and feedstuffs.
Air and Water ReactionsInsoluble in water.

안전 및 보호

Fire Fighting · 2건

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

Use foam, dry powder, carbon dioxide.

First Aid Measures · 4건

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 · 1건

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.
Nonfire Spill Response · 1건

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 · 3건

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: Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment (extra personal protection: P3 filter respirator for toxic particles).

Spillage Disposal · 1건

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. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.

Preventive MeasuresEyes: Safety spectacles, or eye protection in combination with breathing protection.
Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
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.

독성 정보

Ecotoxicity Values · 5건

LC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static; Concentration: 4900 ug/L for 48 hr

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: 3500 ug/L for 21 days (95% confidence interval: 3400-3600 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: 7500 ug/L for 7 days (95% confidence interval: 3200-32000 ug/L) />98% purity/

For more Ecotoxicity Values (Complete) data for 2,3-DICHLORONITROBENZENE (6 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.05(2) and a regression-derived equation(3), indicates that 2,3-dichloronitrobenzene is expected to have low mobility in soil(SRC). Volatilization of 2,3-dichloronitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2,3-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.0X10-3 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation half-lives in excess of 4 weeks using activated sludge(6) suggest 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 3.05(2) and a regression-derived equation(3), indicates that 2,3-dichloronitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-5 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 42 hours and 17 days, respectively(SRC). According to a classification scheme(5), a BCF range of 82-151(6,7) suggests bioconcentration in aquatic organisms is moderate to high(SRC). Biodegradation half-lives in excess of 4 weeks using activated sludge(8) suggest 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), 2,3-dichloronitrobenzene, which has an estimated vapor pressure of 5.9X10-3 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 2,3-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 320 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). 2,3-Dichloronitrobenzene absorbs light at wavelengths of 310 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.
Signs and Symptoms · 2건

Cough.

Redness.

Effluent Concentrations · 1건

In an analysis of over 4000 industrial wastewater samples from 46 industrial categories, 2,3-dichloronitrobenzene was detected in only one sample (the sample was collected from the organic chemicals industry)(1); concn of the sample and origin of the sample were not reported(SRC).

ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.
Soil Adsorption/Mobility · 1건

The Koc of 2,3-dichloronitrobenzene is estimated as 1,100(SRC), using a log Kow of 3,05(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,3-dichloronitrobenzene is expected to have low mobility in soil.

TSCA Test Submissions · 2건

2,3-Dichloronitrobenzene (CAS# 3209-22-1) was evaluated for primary dermal irritation. The test substance was applied undiluted to the skin of 6 New Zealand albino rabbits at a dose level of 0.5 ml for 24-hours. Toxic effects included a slight defatting effect where the skin flaked off in 7-10 days. At 24 hours, severe erythema and edema was evident. Irritation gradually subsided and there was no injury in depth. The test substance was determined to be severe skin irritant.

2,3-Dichloronitrobenzene (CAS# 3209-22-1) was evaluated for teratogenicity. The test substance was administered via gavage to 8 mated Sprague-Dawley rats at a dose level of 100 mg/kg/day for gestation days 6-12. Clinical signs included wet fur, red nasal and oral staining, and yellow urogenital staining. Maternal toxicity included reduced body weight and body weight gain. All dams survived and were pregnant with viable fetuses. A significant reduction in total hemoglobin and a five-fold increase in blood methemoglobin was noted. There were no treatment-related effects on fetal survival.

Fish/Seafood Concentrations · 1건

A 2,3-dichloronitrobenzene concn of 0.024 ppm was detected in a composite sample of carp/sucker taken from the Mississippi River at St. Louis (collection date not reported)(1). Identified, not quantified in fish from the River Main in Germany(2). 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(3).

Artificial Pollution Sources2,3-Dichloronitrobenzene's former production and use as a chemical intermdiate(1) and production as a byproduct of the nitration of 1,2-dichlorobenzene(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1건

AEROBIC: In biodegradability tests using both a semistatic (revised OECD test) and dynamic system (sole carbon source, activated sludge), the half-life of 2,3-dichloronitrobenzene was determined to be greatly in excess of 4 weeks using both adapted and non-adapted inoculum(1). However, since bacteria capable of degrading unspecified chloronitrobenzene isomers have been isolated, these compounds are not expected to be inherently recalcitrant(2).

Benzene, 1,2-dichloro-3-nitro-: ACTIVE