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44디클로로아조벤젠

4,4'-Dichloroazobenzene

HCID 15340
노트반응
기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
1602-00-2
표준 SMILES
Clc1ccc(N=Nc2ccc(Cl)cc2)cc1
InChIKey
XHQLXCFUPJSGOE-UHFFFAOYSA-N
분자식
C12H8Cl2N2
평균 분자량
251.11 g/mol
단동위원소 질량
250.00645362

이름 및 식별자

우선 이름
4,4'-Dichloroazobenzene
IUPAC
bis(4-chlorophenyl)diazene
현지명
44디클로로아조벤젠
영어명
44Dichloroazobenzene
분자식
C12H8Cl2N2
분자량
251.11

이름 및 동의어

1602-00-21,2-Bis(4-chlorophenyl)diazene4,4'-DICHLOROAZOBENZENEDiazene, bis(4-chlorophenyl)-p,p'-DichloroazobenzeneAzobenzene, 4,4'-dichloro-0TL0OEH9RXHSDB 2720Diazene, 1,2-bis(4-chlorophenyl)-NSC 59160BRN 0745559NSC-59160
이름 더 보기
44디클로로아조벤젠DCAB4,4'-dichloroazabenzeneBis-(4-chloro-phenyl)-diazene
DTXSID7013059432-16-00-00013 (Beilstein Handbook Reference)4,4'-DICHLOROAZOBENZENE [HSDB]p,p'DichloroazobenzeneRefChem:506632Azobenzene, 4,4'dichloroDiazene, bis(4chlorophenyl)DTXCID701735916

데이터베이스 식별자

CAS
1602-00-2
PubChem CID
15340
DTXSID
DTXSID701305943
UNII
0TL0OEH9RX
EC Number
633-903-9
Nikkaji
J30.196E、J83.088G、J88.687D

물성

구조 계산 물성

XLogP
5.3
극성 표면적
24.7 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
2
무거운 원자 수
16
형식 전하
0
복잡도
205

실험 및 물리화학적 성질

Chemical ClassesDyes -> Azo Dyes
Vapor Pressure0.0000657 [mmHg]
Physical DescriptionSolid; [MSDSonline]

물리화학적 성질

녹는점
179 °C · 179 °C
끓는 점
375.2 · 375.2±27.0 °C(Predicted)
밀도
1.27 · 1.27±0.1 g/cm3(Predicted)
Henry's Law Constant
1.2 · 1.2×100 mol/(m3Pa) at 25℃, HSDB (2015)

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazards SummaryEmergency treatment: methemoglobinemia; [HSDB] An eye irritant; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (100%)

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.

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5100(SRC), determined from a structure estimation method(2), indicates that 4,4'-dichloroazobenzene is expected to be immobile in soil(SRC). Volatilization of 4,4'- dichloroazobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.1X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 4,4'-Dichloroazobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.6X10-5 mm Hg(4). Biodegradation of 4,4'-dichloroazobenzene may be important in anaerobic sediment-water environments(5).

화학 및 산업

약리 정보

Metabolism/Metabolites · 3건

THE MICROBIAL OXIDATION OF 4-CHLOROANILINE BY THE SOIL FUNGUS FUSARIUM OXYSPORUM WAS STUDIED...METABOLITES INCLUDED 4,4'-DICHLOROAZOXYBENZENE & 4,4'-DICHLOROAZOBENZENE.

Lignin peroxidase H2 (LP H2) from Phanerochaete chrysosporium oxidized 4 chloroaniline to form several oligomers. Included among the compounds identified were: 4,4' dichloroazobenzene, 2 (4 chloroanilino) 5 hydroxybenzoquinone di 4 chloroanil and 2 amino S (4 chloroanilino) benzoquinone di 4 chloroanil. In contrast to results by others, we showed that oligomers of 4 chloroaniline were also formed by the fungus in vivo. It was also demonstrated that, although these potentially toxic intermediates are made, they are also degraded.

4 chloroaniline was oxidized by soya cell wall peroxidases in the presence of hydrogen peroxide. The main product, an orange compound with a maximal absorbance at 455 nm, was probably 4,4' dichloroazobenzene. The optimum pH of the reaction was 4. Michaelis constants, determined as described by Dalziel, were 21 mM for 4 chloroaniline and 94 uM for hydrogen peroxide. Syringaldazine was an uncompetitive inhibitor of 4 chloroaniline peroxidation (Ki = 46 uM) and modified the progress of the reaction with the appearance of a lag period. By contrast, 4 chloroaniline was a non competitive inhibitor of syringaldazine peroxidation with a Ki value of 21 mmx at pH 7.5. Therefore, these two inhibiting effects were compatible with the presence of two binding sites for two different hydrogen donors. Both sites were linked by allosteric interactions. The inferences on chloroaniline binding are discussed.

용도 및 제조

Uses · 2건

Used in the dye industry; [HSDB]

... Used in the dye industry.

상·하류 제품 정보

하류 제품

클로로(4-)-2-플로로아닐린Diazene, (4-bromophenyl)(4-chlorophenyl)- (9CI)

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화합물 노트

불러오는 중…

이 페이지에서기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5100(SRC), determined from an estimation method(2), indicates that 4,4'-dichloroazobenzene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.1X10-6 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 5.4 days and 44 days, respectively(SRC). However, this model underestimates the volatilization half-life of 4,4'-dichloroazobenzene since it does not take into account the effects of adsorption. This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half life = 13 months in a model pond) and one in which adsorption was ignored (half life = 21 days in a model pond)(5). According to a classification scheme(5), an estimated BCF of 10(SRC), from an estimated log Kow of 5.4(6) suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation of 4,4'-dichloroazobenzene may be important in anaerobic sediment-water environments(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4,4'-dichloroazobenzene, which has an estimated vapor pressure of 6.6X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4,4'-dichloroazobenzene 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 15 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). Particulate-phase 4,4'-dichloroazobenzene may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 4,4'-dichloroazobenzene can be estimated to be 5100(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4,4'-dichloroazobenzene is expected to be immobile in soil.

Artificial Pollution Sources · 1건

4,4'-Dichloroazobenzene's production and use in the dye industry(1) may result in its release to the environment through various waste streams(SRC). Formation of asymmetric and symmetric azobenzenes (e.g. 4,4'-dichloroazobenzene) from substituted aniline pairs in soil or peroxidase reaction mixture may also occur(2).

Environmental BiodegradationANAEROBIC: Under anaerobic conditions, 4,4'-dichloroazobenzene was slowly degraded in combined anaerobic sediment-water microcosms with a first-order disappearance rate of 8.6X10-3/day (half-life = 80 days)(1).
Sediment/Soil ConcentrationsFormation of asymmetric and symmetric azobenzenes (eg 4,4'-dichloroazobenzene) from substituted aniline pairs in soil or peroxidase reaction mixture was studied.
Environmental Bioconcentration · 1건

An estimated BCF of 10 was calculated for 4,4'-dichloroazobenzene(SRC), using an estimated log Kow of 5.4(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1건

The Henry's Law constant for 4,4'-dichloroazobenzene is estimated as 8.1X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4,4'-dichloroazobenzene is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3.5 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 44 days(SRC). However, this model underestimates the volatilization half-life of 4,4'-dichloroazobenzene since it does not take into account the effects of adsorption. This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half life = 13 months in a model pond) and one in which adsorption was ignored (half life = 21 days in a model pond)(5). 4,4'-Dichloroazobenzene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). 4,4'-Dichloroazobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated) vapor pressure of 6.6X10-5 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of 4,4'-dichloroazobenzene with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15 days(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4,4'-Dichloroazobenzene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2).

Probable Routes of Human ExposureOccupational exposure to 4,4'-dichloroazobenzene may occur through inhalation and dermal contact with this compound at workplaces where 4,4'-dichloroazobenzene is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1건

4,4'-Dichloroazobenzene's production and use in the dye industry may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 6.6X10-5 mm Hg at 25 °C indicates 4,4'-dichloroazobenzene will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4,4'-dichloroazobenzene will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 15 days. Particulate-phase 4,4'-dichloroazobenzene will be removed from the atmosphere by wet and dry deposition. If released to soil, 4,4'-dichloroazobenzene is expected to be immobile, based upon an estimated Koc of 5100. 4,4'-Dichloroazobenzene will not ionize at environmentally relevant pHs. Volatilization from moist soil surfaces is expected to be somewhat of an important fate process based upon an estimated Henry's Law constant of 8.1X10-6 atm-cu m/mole. Hydrolysis is not expected to occur due to the lack of hydrolyzable functional groups. If released into water, 4,4'-dichloroazobenzene is expected to adsorb to suspended solids and sediment in water, based upon the estimated Koc. 4,4'-Dichloroazobenzene was slowly degraded in combined anaerobic sediment-water microcosms. Volatilization from water surfaces is expected to be an important fate process based upon its estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 5.4 and 44 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. An estimated BCF of 10 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to 4,4'-dichloroazobenzene may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. (SRC)

안전 데이터

rtecs
CN2330000
유해 물질 데이터
1602-00-2(Hazardous Substances Data)
6-클로로-2-메틸렌놀린

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