ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /化合物

1,4-ジクロロ-2-ニトロベンゼン

2,5-Dichloronitrobenzene

HCID 6977
ノートを作成反応を作成見積依頼を出す
印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
89-61-2
標準SMILES
O=[N+]([O-])c1cc(Cl)ccc1Cl
InChIKey
RZKKOBGFCAHLCZ-UHFFFAOYSA-N
分子式
C6H3Cl2NO2
平均分子量
192 g/mol
単同位体質量
190.9540837

概要

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

名称と識別子

優先名称
2,5-Dichloronitrobenzene
IUPAC
1,4-dichloro-2-nitrobenzene
現地名
1,4-ジクロロ-2-ニトロベンゼン
英語名
2,5-Dichloronitrobenzene
分子式
C6H3Cl2NO2
分子量
192

名称と別名

1,4-Dichloro-2-nitrobenzene2,5-DICHLORONITROBENZENE89-61-2Benzene, 1,4-dichloro-2-nitro-1-Nitro-2,5-dichlorobenzene2,5-DichlornitrobenzenDTXSID7052602IY18G50FF4DTXCID1031175RefChem:73231201-923-3Nitro-p-dichlorobenzene
名称をさらに表示
1,4-ジクロロ-2-ニトロベンゼン1-ニトロ-2,5-ジクロロベンゼン2,5-ジクロロニトロベンゼン2,5-ジクロロ-1-ニトロベンゼン1,4ジクロロ2ニトロベンゼン2,5-ジクロロニトロベンゼン 塩化物2,5ジクロロニトロベンゼン1,4‐ジクロロ‐2‐ニトロベンゼン1.4-ジクロロ-2-ニトロベンゼン2,5-ジクロロニトロベンゼン IN TOLUENE2,5-ジクロロニトロベンゼン, 100 µg/mL in Toluene2,5-DICHLORO-4-NITROBENZENE2.5-Dichloroni2,5-Dichlornitrobenzol2,5-DICHLORONITROBENZOL2,5-dichlornitrobenzeneDomperidone Impurity 10
Benzene, 2,5-dichloronitro-1,4-Dichloro-2-nitro-benzeneNSC 406125MFCD00007074NSC-6294NSC-406125Benzene,5-dichloronitro-WLN: WNR CG EG

データベース識別子

CAS
89-61-2
PubChem CID
6977
DTXSID
DTXSID7052602
ChEMBL
CHEMBL354761
UNII
IY18G50FF4
EC Number
201-923-3
Nikkaji
J3.548C

物性

構造計算による物性

XLogP
2.9
極性表面積
45.8 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
11
形式電荷
0
複雑度
159

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Nitros, Aromatic
pHpH = 6.9 (80 mg/L water) at 20 °C
SpringerMaterials PropertiesCrystal structure
LogP · 3 件

log Kow = 3.09

2.93

3.09

Density · 4 件

1.669 at 22 °C

Density: 1.479 g/cu cm at 75 °C

1.67 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

Color/FormPlates or prisms from alcohol, plates from ethyl acetate
Solubility · 4 件

In water, 95 mg/L at 25 °C

In water, 92.1 mg/L at 20 °C

Soluble in ethanol, ether, benzene, carbon disulfide; slightly soluble in carbon tetrachloride

Solubility in water, g/100ml at 20 °C: 0.01 (very slightly soluble)

Flash Point135 °C
Boiling Point · 2 件

267 °C

261 °C

DecompositionWhen heated to decomposition it emits very toxic fumes of /hydrogen chloride and nitrogen oxides/.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H350: May cause cancer [Danger Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.1% (1 of 94) of reports.

Warning

H302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information · 5 件

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

Hazard Traits - Carcinogenicity

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

REACH registered substance: 1,4-dichloro-2-nitrobenzene (EC: 201-923-3)

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

Other Safety InformationEvaluation - Benzene, 1,4-dichloro-2-nitro- (2,5-dichloronitrobenzene)
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary · 1 件

No listed effects of short-term or long-term exposure (health effects have not been fully investigated); [ICSC] Can possibly induce methemoglobinemia; Can be absorbed through skin; Not a skin or eye irritant in rabbits; Not sensitizing in guinea pig maximization tests; No mortalities in rats exposed by inhalation to 47.6 mg/m3 for 7 hours; Increased liver weight (accompanied by hepatocellular hypertrophy), damage to the forestomach, increased bilirubin levels, and adverse male reproductive effects (depressed spermatogenesis) observed in 28-day oral study of rats; Cyanosis and methemoglobin formation observed in cats; [IUCLID] A mild skin and strong eye irritant; May induce methemoglobinemia; Harmful by ingestion and skin absorption; [Sigma-Aldrich MSDS] See 3,4-Dichloronitrobenzene.

UN Classification

化学と産業

薬理情報

Biological Half-LifeFollowing oral intake the biological half-life in fish is less than 3 days.
Metabolism/Metabolites · 1 件

1,4-Dichloro-2-nitrobenzene is readily absorbed after oral administration or dermal application. The substance is metabolized to a number of products. Following oral application chiefly 2,5-dichloroaniline, the mercapturic acid derivative N-acetyl-S-(4-chloro-2-nitrophenyl)-L-cysteine as well as glucuronic and sulfuric acid conjugates of 4-amino-2,5-dichlorophenol were identified in urine.

Absorption, Distribution and Excretion1,4-Dichloro-2-nitrobenzene is readily absorbed after oral administration or dermal application.

用途と製造

Uses · 3 件

Used as an intermediate in the chemical industry; [IUCLID] Used to make pigments, pesticides, and UV absorbents; [HSDB]

Used extensively in the manufacture of dyestuff intermediates

Used as an intermediate for pigments, pesticides and UV absorbents in closed systems

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7968]
Methods of ManufacturingNitration of 1,4-dichlorobenzene with mixed acid at 35-65 °C results in a 98% yield of essentially pure 1,4-dichloro-2-nitrobenzene.
General Manufacturing InformationBenzene, 1,4-dichloro-2-nitro-: ACTIVE

応用分野

用途染料の中間体、殺虫剤、紫外線吸収剤。

調製方法

関連反応

153 件
反応記録を作成
HRID 3997 の反応式
HRID 3997反応物としてuspto-grants-1988_02
HRID 4003 の反応式
HRID 4003反応物としてuspto-grants-1988_02
HRID 4055 の反応式
HRID 4055反応物としてuspto-grants-1988_02
HRID 4061 の反応式
HRID 4061反応物としてuspto-grants-1988_02
HRID 21680 の反応式
HRID 21680反応物としてuspto-grants-1995_06
HRID 26705 の反応式
HRID 26705反応物としてuspto-grants-1979_04
HRID 34312 の反応式
HRID 34312反応物としてuspto-grants-1988_08
HRID 34317 の反応式
HRID 34317反応物としてuspto-grants-1988_08
1 / 20 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
Melting Point · 2 件

56 °C

55 °C

Vapor DensityRelative vapor density (air = 1): 6.6

物理化学的性質

融点
52 · 52-54 °C(lit.)
沸点
267 °C · 267 °C
比重(密度)
1 · 1,442 g/cm3
蒸気密度
6.6 · 6.6 (vs air)
蒸気圧
0.1 mm · <0.1 mm Hg ( 25 °C)
屈折率
1.439 · 1.4390 (estimate)
闪点
230 °F · >230 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
0.083 g/リットル · 0.083g/リットル
外見
solid
色
ペールイエロー
爆発限界(explosive limit)
2.4 · 2.4-8.5%(V)
水溶解度
水、エタノール、エーテル、ベンゼン、二硫化炭素に可溶。四塩化炭素にわずかに溶ける。
BRN
778109 · 778109
Henry's Law Constant
8.2 · 8.2×10-1 mol/(m3Pa) at 25℃, Altschuh et al. (1999)
InChI
1S/C6H3Cl2NO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H
InChIKey
RZKKOBGFCAHLCZ-UHFFFAOYSA-N
SMILES
[O-][N+](=O)c1cc(Cl)ccc1Cl
LogP
2.87 at · 2.87 at 25℃
CAS データベース
89 · 89-61-2(CAS DataBase Reference)
NISTの化学物質情報
1 · Benzene, 1,4-dichloro-2-nitro-(89-61-2)
EPAの化学物質情報
2 · 2,5-Dichloronitrobenzene (89-61-2)

化学的性質

化学的特性yellow flakes

UN Hazard Class: 6.1; UN Pack Group: II
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 bases.
Packaging and LabellingDo not transport with food and feedstuffs.
Hazard Classes and Categories · 6 件

Acute Tox. 4 (98.9%)

Acute toxicity (ingestion) - category 4

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Carcinogenicity - Category 1B

Carcinogenicity - Category 1B

Explosive Limits and PotentialExplosive limits , vol% in air: 2.4-8.5
Skin, Eye, and Respiratory Irritations · 2 件

A skin and eye irritant.

1,4-Dichloro-2-nitrobenzene is mildly irritating to eyes and non-irritating to skin.

安全と保護具

Fire FightingUse water spray, dry powder, foam, carbon dioxide.
First Aid Measures · 4 件

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 .

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.
Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

Personal protection: particulate filter respirator 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.

Preventive Measures · 1 件

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.
Inhalation RiskA harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT DISPERSION OF DUST! STRICT HYGIENE!
Ingestion PreventionDo not eat, drink, or smoke during work.

毒性情報

Ecotoxicity Values · 5 件

EC50; Species: Chlorella pyrenoidosa (Green Algae) exponential growth phase, 2 X10+8 cells/mL; Conditions: freshwater, static, 25 °C, pH 6.6; Concentration: 2100 ug/L for 96 hr (95% confidence interval: 1500-2800 ug/L); Effect: growth, general />98% purity formulation/

LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3. dissolved oxygen >6.5 mg/L; Concentration: 11000 ug/L for 48 hr (95% confidence interval: 5600-18000 ug/L) />98% purity formulation/

LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3. dissolved oxygen >6.5 mg/L; Concentration: 3800 ug/L for 21 days (95% confidence interval: 3600-4000 ug/L) />98% purity formulation/

LC50; Species: Poecilia reticulata (Guppy) age 3-4 weeks; Conditions: freshwater, static, 25 °C, pH 8.2, hardness 250 mg/L CaCO3; Concentration: 4900 ug/L for 14 days />98% purity formulation/

For more Ecotoxicity Values (Complete) data for 1,4-Dichloro-2-nitrobenzene (6 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 590(SRC), determined from a structure estimation method(2), indicates that 1,4-dichloro-2-nitrobenzene is expected to have low mobility in soil(SRC). Volatilization of 1,4-dichloro-2-nitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.5X10-5 atm-cu m/mole(3). 1,4-Dichloro-2-nitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00383 mm Hg at 25 °C(4). 1,4-Dichloro-2-nitrobenzene absorbs UV light above 290 nm and will photodegrade in sunlight(4). Utilizing the Japanese MITI test, 4% of the theoretical BOD was reached in four weeks(5) indicating 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 590(SRC), determined from a structure estimation method(2), indicates that 1,4-dichloro-2-nitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.5X10-5 atm-cu m/mole at 25 °C(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.4 and 36 days, respectively(SRC). According to a classification scheme(5), observed BCF values of 18-118, measured in carp and rainbow trout(6,7), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). 1,4-Dichloro-2-nitrobenzene has an epilson of 0.00126 at 300 nm in aqueous solution(8) which indicates the compound may be susceptible to direct photolysis(SRC); an approximated quantum yield of 0.01 can be used to estimate a half-life of 34 days in a model sunlit body of water with a 500 cm depth(2). In an aqueous hydrolysis test (OECD Test guideline 111), benzene, 1,4-dichloro-2-nitro was stable to abiotic hydroylsis at pHs 4, 7 and 9 at 25 °C(8). Utilizing the Japanese MITI test, 4% of the theoretical BOD was reached in four weeks(6) indicating 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), 1,4-dichloro-2-nitrobenzene, which has a vapor pressure of 0.00383 mm Hg at 25 °C(2), expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-dichloro-2-nitrobenzene 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 5X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,4-Dichloro-2-nitrobenzene absorbs UV light above 290 nm and therefore is photodegraded in sunlight(2).

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 IntakeFor indirect exposure to 1,4-dichloro-2-nitrobenzene via the environment, the daily intake through drinking water is estimated to be 2.6X10-5 mg/kg/day and through fish is calculated as 1.2X10-3 mg/kg/day(1).
Ecotoxicity Excerpts · 2 件

/AQUATIC SPECIES/ Following the exposure of algae (Chlorella pyrenoidosa) for 96 hours to 2.1 mg/L, 50% inhibition of growth has been observed... For water fleas (Daphnia magna), 48-hr EC50 value (immobilization) amounts to 11 mg/L and the 21-day EC50 value to 3.8 mg/L. In a semi-static 21-day reproduction test the lowest concentrations at which the population growth rate and mean length of the animals significantly (p<0.01) decreased were 1.8 mg/L and 3.2 mg/L respectively. For fish (Leuciscus idus), the value of acute toxicity (96-hr LC50) in an open system under semi-static conditions is 6.3 mg/L and the corresponding value (48-hr LC50) in a closed system under static conditions is 4.5 mg/L. The lowest 96-hr LC0 was 3.15 mg/L. In the prolonged fish toxicity test under semi-static conditions a 14 day LC50 value of 4.9 mg/L has been found for Poecilia reticulata.

/PLANTS/ 1,4-Dichloro-2-nitrobenzene at concentrations > 42.2 mg/L is phytotoxic (6-day EC50; reduction in fresh weight) to higher plants (seedlings of cucumber and bean).

Animal Concentrations1,4-Dichloro-2-nitrobenzene was detected in zebra mussels (Dreissena polymorpha) collected from the Rhine-Meuse delta in 1994 at concentrations of 0.021-0.030 mg/kg wet weight(1).
Signs and Symptoms · 2 件

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 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,4-dichloro-2-nitrobenzene can be estimated to be 590(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,4-dichloro-2-nitrobenzene is expected to have low mobility in soil. 1,4-Dichloro-2-nitrobenzene did not leach in column leachate tests designed to assess leaching potential from wastes in landfill sites(3).

Human Toxicity Excerpts · 1 件

/OTHER TOXICITY INFORMATION/ 1,4-Dichloro-2-nitrobenzene is mildly irritating to eyes and non-irritating to skin. When tested in animals the product has been proved to be a non-sensitizer; however, there are indications of skin sensitization in man.

Artificial Pollution Sources1,4-Dichloro-2-nitrobenzene's production and use in the manufacture of dyestuff intermediates, pesticides and UV absorbents(1,2) may result in its release to the environment through various waste streams(SRC).

安全データ

wgk
2
tsca
TSCA listed
rtecs
CZ5260000
ridadr
UN 3077 9/PG 3
PRTR法
第一種指定化学物質
hs_code
29049085
risk_code
22-36-51/53
化審法
(3)-455
安衛法
変異原性物質
hazard_code
Xn,N
safety_code
26-60
hazard_class
9
packing_group
III
環境リスク評価
1,4-ジクロロ-2-ニトロベンゼン(89-61-2)
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2
ストレージクラス
11 - Combustible Solids
有毒物質データの
89-61-2(Hazardous Substances Data)

Nitration of 1,4-dichlorobenzene with mixed acid at 35 – 65 ℃ results in a 98 % yield of essentially pure 2,5-Dichloronitrobenzene.

純化方法Crystallise the nitrobenzene from absolute EtOH. [Beilstein 5 IV 726.]

上流・下流製品情報

上流原料

水和物p-Dichlorobenzene硝酸1,4-ジクロロベンゼン硫酸水素Benzaldehyde, 3,6-dichloro-2-nitro-3,4-ジニトロアニリン4'-クロロ-2'-ニトロアセトフェノン3-クロロ-4-ニトロアニリン4-クロロ-2-ニトロ安息香酸

下流製品

4-クロロ-2-ニトロアニリンクロザピン6-クロロオキシインドール2,5-ジクロロアニリン2-[(2-アミノ-4-クロロフェニル)アミノ]安息香酸4-クロロ-2-ニトロフェノール2,5-ジクロロフェニルヒドラジン塩酸塩4-クロロ-2-ニトロトルエン5-クロロ-2-[(4-クロロフェニル)オキシ]アニリン5-クロロ-2-メトキシアニリン5-クロロ-2-フェノキシベンゼンアミンAzoic Diazo Component 334-クロロ-N-(4-メトキシフェニル)-2-ニトロアニリン4-クロロ-2-ニトロ-N-フェニルベンゼンアミン