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1-クロロアントラキノン

1-Chloroanthraquinone

HCID 6709
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基本情報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
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基本情報

CAS
26264-07-3
標準SMILES
O=C1c2ccccc2C(=O)c2c(Cl)cccc21
InChIKey
BOCJQSFSGAZAPQ-UHFFFAOYSA-N
分子式
C14H7ClO2
平均分子量
242.65 g/mol
単同位体質量
242.01345714

名称と識別子

優先名称
1-Chloroanthraquinone
IUPAC
1-chloroanthracene-9,10-dione
現地名
1-クロロアントラキノン
英語名
1-Chloro anthraquinone
分子式
C14H7ClO2
分子量
242.66

名称と別名

1-CHLOROANTHRAQUINONE82-44-0Anthraquinone, 1-chloro-1-Chloro-9,10-anthraquinone9,10-Anthracenedione, 1-chloro-1-Chloranthrachinon1-Chloranthrachinon [Czech]alpha-Chloroanthraquinone1-chloro-9,10-Anthracenedionealpha-Monochloroanthraquinone.alpha.-MonochloroanthraquinoneDTXSID7052571
名称をさらに表示
1-クロロアントラキノン1-クロロ-9,10-アントラキノン1-クロロ-9,10-アントラセンジオン1クロロアントラキノン1-クロロアンスラキノン1‐クロロアントラキノン1-クロロアントラセン-9,10-ジオンクロロアントラキノン1-CHLOROANTHRACENE-9,10-DIONE1-CHLORO AQTIMTEC-BB SBB0008251-Chloro anthraquino-Chloroanthraquinone1-Chloroantraquinone1-chloro-anthraquinon
HSDB 2565EINECS 201-421-4NSC 30428BRN 191275296S5SQV15VAI3-38116NSC-5138NSC-30428

データベース識別子

CAS
26264-07-3、82-44-0
PubChem CID
6709
DTXSID
DTXSID7052571
ChEMBL
CHEMBL3560876
UNII
96S5SQV15V
EC Number
201-421-4
Nikkaji
J55.388C

物性

構造計算による物性補完中

XLogP
4
極性表面積
34.1 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
17
形式電荷
0
複雑度
352

実験および物理化学的性質

Chemical ClassesOther Classes -> Aromatic Ketones
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Color/FormYELLOW NEEDLES FROM TOLUENE OR ALCOHOL
Solubility · 3 件

INSOL IN WATER; SLIGHTLY SOL IN HOT ALCOHOL; SOL IN NITROBENZENE & HOT AMYL ALCOHOL

Sol in ethanol, benzene, acetic acid

Soluble in oxygenated solvents

Boiling PointSublimes
DecompositionWhen heated to decomp it emits very toxic fumes of /hydrogen chloride and nitrogen oxides/.
Melting Point162 °C
Vapor Pressure0.00000087 [mmHg]
Physical DescriptionYellow solid; [HSDB] Yellow powder; [MSDSonline]
Other Experimental PropertiesUV: 15813 (Sadtler Research Laboratories Spectral Collection) /2-Chloroanthraquinone/

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 · 5 件

This chemical does not meet GHS hazard criteria for 8.5% (4 of 47) of reports.

Warning

H315 (89.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Chemical: 9,10-Anthracenedione, 1-chloro-

9,10-Anthracenedione, 1-chloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards Summary · 1 件

A skin and eye irritant; [HSDB] Causes abnormal liver function test results after subcutaneous injection of experimental animals; [RTECS] An irritant; Effects in high-dose animal studies include impaired liver function tests; [MSDSonline] See Anthraquinone.

Hazard Classes and CategoriesSkin Irrit. 2 (89.4%)
Skin, Eye, and Respiratory IrritationsA skin, eye irritant.

安全と保護具

Disposal Methods · 1 件

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.

化学と産業

薬理情報

Metabolism/MetabolitesQuinones (ie, 6,12-dione) have been shown to undergo oxidation-reduction cycles involving quinone, hydroquinone, and molecular oxygen, resulting in the formation of oxygen radicals and semiquinone radicals. /Quinones/

用途と製造

Uses · 3 件

Used as a chemical intermediate for dyes; [HSDB]

CHEM INTERMEDIATE FOR THE DYES DISPERSE RED 9, VAT BROWN 1, VAT ORANGE 11

Derivatives of 1-chloroanthraquinone include Disperse Red 9, Disperse Red 22, Vat Brown 1, Vat Brown 44, Vat Yellow 28.

U.S. Imports · 2 件

(1972) 2.91X10+7 G (PRINCPL CUSTMS DISTS)

(1975) 7.09X10+6 G

U.S. Production(1972) 5.17X10+7 G
Methods of Manufacturing · 3 件

REACTION OF 1-HYDROXYANTHRAQUINONE WITH PHOSPHORUS PENTACHLORIDE IN NITROBENZENE

1-Chloroanthraquinone is prepared from anthraquinone-1-sulfonic acid or from 1-nitro-anthraquinone. Purification by high temperature distillation.

1-Chloroanthraquinone is prepared from anthraquinone-1-sulfonic acid, sodium salt and sodium chlorate (sulfonate displacement).

General Manufacturing Information9,10-Anthracenedione, 1-chloro-: ACTIVE

応用分野

使用1-Chloroanthraquinone is an intermediate for manufacturing vat dyes such as CI Vat Brown 1.

上流・下流製品情報

上流原料

アントラキノン-1-スルホン酸ナトリウム

関連反応

27 件
反応記録を作成
HRID 226253 の反応式
HRID 226253反応物としてuspto-grants-2009_07
HRID 256135 の反応式
HRID 256135反応物としてuspto-grants-1987_10
HRID 256278 の反応式
HRID 256278反応物としてuspto-grants-1987_10
HRID 260814 の反応式
HRID 260814反応物としてuspto-grants-1996_06
HRID 260815 の反応式
HRID 260815反応物としてuspto-grants-1996_06
HRID 260817 の反応式
HRID 260817反応物としてuspto-grants-1996_06
HRID 441106 の反応式
HRID 441106反応物としてuspto-grants-1996_05
HRID 496966 の反応式
HRID 496966反応物としてuspto-grants-2005_09
1 / 4 ページ

化合物ノート

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物理化学的性質

融点
159 · 159-160 °C (lit.)
沸点
345.65 °C · 345.65°C (rough estimate)
比重(密度)
1.2377 · 1.2377 (rough estimate)
屈折率
1.538 · 1.5380 (estimate)
貯蔵温度
30 °C · Store below +30°C.
溶解性
熱トルエンに可溶。 (ほぼ透明)
外見
粉末またはチャンク
色
薄黄色~黄色
BRN
1912752 · 1912752
Henry's Law Constant
4.3 · 4.3×102 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
InChI
InChI=1S/C14H7ClO2/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7H
InChIKey
BOCJQSFSGAZAPQ-UHFFFAOYSA-N
SMILES
C1(Cl)=C2C(C(=O)C3=C(C2=O)C=CC=C3)=CC=C1
CAS データベース
82 · 82-44-0(CAS DataBase Reference)
NISTの化学物質情報
9 · 9,10-Anthracenedione, 1-chloro-(82-44-0)
EPAの化学物質情報
1 · 1-Chloroanthraquinone (82-44-0)

化学的性質

化学的特性light yellow to yellow powder or chunks

Preventive Measures · 1 件

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: An estimated Koc value of 3500(1,SRC), based on an estimated log Kow of 3.99(2,SRC) suggests that 1-chloroanthraquinone will have only slight mobility in soil(SRC), based upon a recommended classification scheme(3). Under reducing conditions, this compound has been shown to form the chloroanthrone with measured half-lives of <0.4 to 2.4 daysin sediments(4) and this may also occur in soils(SRC). Incomplete information is available regarding the biodegradation potential of 1-chloroanthraquinone; however, this compound was resistant to biodegradation under aerobic conditions using an activated sludge inoculum; only 2.8% of the theoretical BOD was reported following 2 weeks incubation(5). 1-Chloroanthraquinone is not expected to volatilize from moist soil surfaces based on an estimated Henry's Law constant of 2.4X10-9 atm-cu m/mole(6,SRC).

AQUATIC FATE: Based upon an estimated Koc value of 3500(SRC) from an estimated log Kow(2,SRC), 1-chloroanthraquinone may adsorb to suspended solids and sediments(SRC) based upon a recommended classification scheme(1). In anoxic sediments, 1-chloroanthraquinone has been shown to quickly reduce resulting in the formation of an unspecified chloroanthrone(4). Half-lives of <0.4 to 2.4 days are reported for this compound dependent on the source of the sediment(4). An estimated BCF value of 630(3,SRC), based on an estimated log Kow(2,SRC) and measured BCF values of 118-351 in carp(5) indicate that 1-chloroanthraquinone may bioconcentrate in aquatic organisms(SRC). Incomplete information is available regarding the biodegradation potential of 1-chloroanthraquinone; however, this compound was resistant to biodegradation under aerobic conditions using an activated sludge inoculum; only 2.8% of theoretical BOD was reported following 2 weeks incubation(5). 1-Chloroanthraquinone is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 2.2X10-12 atm-cu m/mole(SRC), developed using a fragment constant method(6).

ATMOSPHERIC FATE: Based on an estimated vapor pressure value of 8.74X10-7 mm Hg at 25 °C(1,SRC), 1-chloroanthraquinone will exist in both the vapor phase and the particulate phase in the ambient atmosphere(2,SRC). 1-Chloroanthraquinone will degrade fairly rapidly in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 13 days(3,SRC). Particulate phase 1-chloroanthraquinone may be physically removed from the air by wet and dry deposition(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.
Effluent Concentrations1-Chloroanthraquinone was detected in an extract of flyash from a municipal incinerator in Ontario, Canada at unreported concentrations(1).
Soil Adsorption/Mobility · 1 件

Based on an estimated log Kow of 3.99(1,SRC), the Koc of 1-chloroanthraquinone is estimated as approximately 3500(SRC) using a regression-derived equation(2). According to a suggested classification scheme(3), this estimated Koc value suggests that 1-chloroanthraquinone will have only slight mobility in soil(SRC).

Human Toxicity Excerpts · 2 件

CAUTION: LOW SYSTEMIC TOXICITY, BUT MAY CAUSE SKIN IRRITATION, SENSITIZATION. /ANTHRAQUINONE/

Chronic neurotoxic effects include vision disturbances. /From table; Quinones/

Artificial Pollution Sources · 2 件

WASTE WATERS FROM ALPHA-DISULFATION OF ANTHRAQUINONE, WHICH CONTAIN ANTHRAQUINONESULFONIC ACIDS, ARE TREATED TO FORM HALOANTHRAQUINONES.

1-Chloroanthraquinone's production and subsequent use as an intermediate in the production of dyes, including Disperse Red 9, Disperse Red 22, Vat Brown 1, Vat Brown 44, Vat Yellow 28(1), may result in its release to the environment through various waste streams(SRC).

Environmental Biodegradation1-Chloroanthraquinone (100 mg/l), inoculated with activated sludge, had a theoretical BOD of 2.8% after a two week period(1). This suggests that 1-chloroanthraquinone may be resistant to biodegradation(1).
Environmental Bioconcentration · 1 件

Experimental BCF values of 118-351 were measured using carp(1). An estimated BCF value of 630 was calculated for 1-chloroanthraquinone(SRC), using an estimated log Kow of 3.99(2,SRC) and a recommended regression-derived equation(3). These BCF values suggest that 1-chloroanthraquinone may bioconcentrate in aquatic organisms(SRC).

Volatilization from Water/SoilThe Henry's Law constant for 1-chloroanthraquinone is estimated as 2.36X10-9 atm-cu m/mole(1,SRC). This indicates that 1-chloroanthraquinone will essentially not volatilize from water surfaces(2,SRC).
Non-Human Toxicity Excerpts · 4 件

...MICE...UNHARMED BY SINGLE ORAL DOSES OF 5,000 MG/KG. /ANTHRAQUINONE/

ANTHRAQUINONE...HAS BEEN NOTED ONLY IN EXPTL ANIMAL EYES TO CAUSE IRRITATION & INFLAMMATION WHEN APPLIED TO THE EYE. ...IT IS POSSIBLE THAT IRRITATION IS DUE TO MECH ACTION OF POWDER RATHER THAN TO TOXIC EFFECT... /ANTHRAQUINONE/

Anthraquinones (incl 1-chloroanthraquinone) admin orally at 100-200 mg/kg to mice and at 200-400 mg/kg to rats were effective laxatives. Anthraquinones were weak laxatives in mice. In the range tested (100-400 mg/kg), the cmpd were not toxic in rats and mice.

Acute neurotoxic effects reported in animals include convulsions; medullary paralysis. /From table; Quinones/

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor phase reaction of 1-chloroanthraquinone with photochemically produced hydroxyl radicals has been estimated as 1.3X10-12 cu cm/molecule-sec at 25 °C(1). The half-life of 1-chloroanthraquinone is approximately 13 days based on a concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 1-Chloroanthraquinone, added to lake bottom sediments, resulted in the formation of a chlorine containing anthrone(2). 1-Chloroanthraquinone had measured first-order rate constants of 1.2X10-2 to 6.5X10-2/hr giving half-lives from <0.4 to 2.4 days for this anoxic sediment-water system(2).

Environmental Fate/Exposure Summary · 1 件

1-Chloroanthraquinone's production and subsequent use as an intermediate in the production of dyes may result in its release to the environment through various waste streams. 1-Chloroanthraquinone may also be introduced directly to the environment as a product of the treatment of waste waters from the alpha-disulfation of anthraquinone. If released to the atmosphere, 1-chloroanthraquinone should exist in both the vapor phase and the particulate phase based on an estimated vapor pressure of 8.7X10-7 mm Hg. In the vapor phase, 1-chloroanthraquinone will react with hydroxyl radicals with an estimated half-life of about 13 days. Particulate phase 1-chloroanthraquinone may be physically removed from the atmosphere by wet and dry deposition. An estimated Koc of 3500 suggests that 1-chloroanthraquinone will have only slight mobility in soil. It is not expected to volatilize from moist soil surfaces given an estimated Henry's Law constant of 2.4X10-9 atm-cu m/mol. Incomplete information is available regarding the biodegradation potential of 1-chloroanthraquinone; however, this compound was resistant to biodegradation under aerobic conditions using an activated sludge inoculum; only 2.8% BOD was reported following 2 weeks incubation. In water, 1-chloroanthraquinone is expected to adsorb to organic matter and suspended solids in the water column based on its Koc value. In reducing sediments, this compound will rapidly form the chloroanthrone with measured half-lives for the parent compound of <0.4 to 2.4 days. 1-Chloroanthraquinone may bioconcentrate in aquatic organisms; BCF values of 118-351 were measured in carp, an estimated BCF value of 630 was calculated using an estimated log Kow. (SRC)

安全データ

wgk
3
tsca
TSCA listed
rtecs
CB6150000
毒性
LD50 orally in Rabbit: 15100 mg/kg
hs_code
29147090
risk_code
36/37/38
化審法
(4)-688
hazard_code
Xi
safety_code
26-37/39-24/25
ストレージクラス
11 - Combustible Solids
有毒物質データの
82-44-0(Hazardous Substances Data)
亜硫酸ナトリウム
アントラキノン
塩素酸ナトリウム
9(10H)-Anthracenone, 4-chloro-
1-Anthracenecarboxylic acid, 4-chloro-9,10-dihydro-9,10-dioxo-
2-ベンゾイル-3-クロロ安息香酸
2-クロロ-9(10H)-アントラセノン
potassium 9,10-dihydro-9,10-dioxoanthracene-1-sulphonate
塩化 1,10-フェナントロリニウム 一水和物
1,5-ジクロロアントラキノン
3-クロロ-N-フェニルベンズアミド
4-クロロ-1,3-イソベンゾフランジオン

下流製品

ジナフト[2,3-a:2',3'-h]アクリジン-5,9,14,15,18(6H)-ペンタオン6,10,12-トリクロロナフト[2,3-c]アクリジン-5,8,14(13H)-トリオンバット ブラック-271-(メチルアミノ)アントラキノンC.I.バットオレンジ11:1バットブラウン442,6-ジヒドロ-1,2-ジアザアセアントリレン-6-オン6,10,12-トリクロロナフト[2,3-c]アクリジン-5,8,14(13H)-トリオンSolvent Red 138