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1-클로로-9,10-안트라퀴논

1-Chloroanthraquinone

HCID 6709
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기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
26264-07-3
표준 SMILES
O=C1c2ccccc2C(=O)c2c(Cl)cccc21
InChIKey
BOCJQSFSGAZAPQ-UHFFFAOYSA-N
분자식
C14H7ClO2
평균 분자량
242.65 g/mol
단동위원소 질량
242.01345714

이름 및 식별자

우선 이름
1-Chloroanthraquinone
IUPAC
1-chloroanthracene-9,10-dione
현지명
1-클로로-9,10-안트라퀴논
영어명
1-Chloro anthraquinone
분자식
C14H7ClO2
분자량
242.66

이름 및 동의어

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
이름 더 보기
1-클로로-9,10-안트라퀴논1-클로로안트라센-9,10-다이온1-클로로안트라퀴논알파-모노클로로안트라퀴논알파-클로로안트라퀴논1-CHLOROANTHRACENE-9,10-DIONE1-CHLORO AQTIMTEC-BB SBB0008251-Chloro anthraquino-Chloroanthraquinone1-Chloroantraquinone1-chloro-anthraquinon
HSDB 2565EINECS 201-421-4NSC 30428BRN 191275296S5SQV15VAI3-38116NSC-5138NSC-30428

데이터베이스 식별자

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

물성

구조 계산 물성보충 중

XLogP
4
극성 표면적
34.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
17
형식 전하
0
복잡도
352

실험 및 물리화학적 성질

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

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/

안전 및 규제

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

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 2건

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 · 1건

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.

안전 및 보호

Disposal Methods · 1건

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.

화학 및 산업

약리 정보

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/

용도 및 제조

Uses · 3건

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 · 2건

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

(1975) 7.09X10+6 G

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

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

응용 분야

용도1-Chloroanthraquinone is an intermediate for manufacturing vat dyes such as CI Vat Brown 1.

상·하류 제품 정보

상류 원료

1-Anthraquinonesulfonic acid sodium salt

관련 반응

27건
반응 기록 만들기
HRID 226253 반응식
HRID 226253반응물로uspto-grants-2009_07
HRID 256135 반응식
HRID 256135반응물로uspto-grants-1987_10
HRID 256278 반응식
HRID 256278반응물로uspto-grants-1987_10
HRID 260814 반응식
HRID 260814반응물로uspto-grants-1996_06
HRID 260815 반응식
HRID 260815반응물로uspto-grants-1996_06
HRID 260817 반응식
HRID 260817반응물로uspto-grants-1996_06
HRID 441106 반응식
HRID 441106반응물로uspto-grants-1996_05
HRID 496966 반응식
HRID 496966반응물로uspto-grants-2005_09
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물리화학적 성질

녹는점
159 · 159-160 °C (lit.)
끓는 점
345.65 °C · 345.65°C (rough estimate)
밀도
1.2377 · 1.2377 (rough estimate)
굴절률
1.538 · 1.5380 (estimate)
저장 조건
30 °C · Store below +30°C.
용해도
뜨거운 톨루엔에 용해됩니다. (거의 투명함)
물리적 상태
분말 또는 덩어리
색상
밝은 노란색에서 노란색까지
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
NIST
9 · 9,10-Anthracenedione, 1-chloro-(82-44-0)
EPA
1 · 1-Chloroanthraquinone (82-44-0)

화학적 성질

light yellow to yellow powder or chunks

Preventive Measures · 1건

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.

독성 정보

Environmental Fate · 3건

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 · 1건

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 · 2건

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

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

Artificial Pollution Sources · 2건

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 · 1건

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 · 4건

...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 · 1건

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 · 1건

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)

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
CB6150000
독성
LD50 orally in Rabbit: 15100 mg/kg
HS 번호
29147090
risk_code
36/37/38
hazard_code
Xi
safety_code
26-37/39-24/25
기존화학 물질
KE-05518
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
82-44-0(Hazardous Substances Data)
아황산나트륨
안트라퀴논
소다의 염산
9(10H)-Anthracenone, 4-chloro-
1-Anthracenecarboxylic acid, 4-chloro-9,10-dihydro-9,10-dioxo-
2-벤조일-3-클로로벤조산
1-클로로안트라센-9(10H)-온
칼륨9,10-디하이드로-9,10-디옥소안트라센-1-설포네이트
o-Phenanthroline monohydrochloride monohydrate
1,5-DICHLOROANTHRAQUINONE
3-클로로-N-페닐벤자미드
3 클로로프탈산 무수물

하류 제품

Vat Orange 166,10,12-트리클로로나프트[2,3-c]아크리딘-5,8,14(13H)-트리온VAT BLACK 27C.I. 용제 적 111Vat Orange 11Vat Brown 11,9-Pyrazoloanthrone6,10,12-트리클로로나프트[2,3-c]아크리딘-5,8,14(13H)-트리온Solvent Red 138