基本信息
- 标准SMILES
O=C1c2ccccc2C(=O)c2c(Cl)cccc21- InChIKey
BOCJQSFSGAZAPQ-UHFFFAOYSA-N- 分子式
- C14H7ClO2
- 平均分子量
- 242.65 g/mol
- 单同位素质量
- 242.01345714
名称与标识
- 首选名称
- 1-Chloroanthraquinone
- IUPAC
- 1-chloroanthracene-9,10-dione
- 中文名
- 1-氯蒽醌
- 英文名
- 1-Chloro anthraquinone
- 分子式
- C14H7ClO2
- 分子量
- 242.66
名称与别名
展开更多名称
数据库标识
- CAS
26264-07-3、82-44-0- PubChem CID
- 6709
- DTXSID
DTXSID7052571- ChEMBL
CHEMBL3560876- UNII
- 96S5SQV15V
- EC Number
- 201-421-4
- Nikkaji
- J55.388C
性质
结构计算性质
- XLogP
- 4
- 极性表面积
- 34.1 Ų
- 氢键供体
- 0
- 氢键受体
- 2
- 可旋转键
- 0
- 重原子
- 17
- 形式电荷
- 0
- 复杂度
- 352
实验与物化性质
Solubility
INSOL IN WATER; SLIGHTLY SOL IN HOT ALCOHOL; SOL IN NITROBENZENE & HOT AMYL ALCOHOL
Sol in ethanol, benzene, acetic acid
Soluble in oxygenated solvents
物理化学性质
- 熔点
- 159 · 159-160 °C (lit.)
- 沸点
- 345.65 °C · 345.65°C (rough estimate)
- 密度
- 1.2377 · 1.2377 (rough estimate)
- 折射率
- 1.538 · 1.5380 (estimate)
- 储存条件
- 30 °C · Store below +30°C.
- 溶解度
- Soluble in hot toluene. (almost transparency)
- 形态
- Powder or Chunks
- 颜色
- Light yellow to yellow
- 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 数据库
- 82 · 82-44-0(CAS DataBase Reference)
- NIST化学物质信息
- 9 · 9,10-Anthracenedione, 1-chloro-(82-44-0)
- EPA化学物质信息
- 1 · 1-Chloroanthraquinone (82-44-0)
化学性质
黄色针状结晶。 溶于醋酸、硝基苯、热苯、戊醇,微溶于热乙醇,不溶于水。
安全与法规
GHS分类
GHS Classification
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.
危害信息
Regulatory Information
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
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.
安全与防护
Disposal Methods
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.
Preventive Measures
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.
毒理信息
Environmental Fate
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).
Soil Adsorption/Mobility
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
CAUTION: LOW SYSTEMIC TOXICITY, BUT MAY CAUSE SKIN IRRITATION, SENSITIZATION. /ANTHRAQUINONE/
Chronic neurotoxic effects include vision disturbances. /From table; Quinones/
Artificial Pollution Sources
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 Bioconcentration
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).
Non-Human Toxicity Excerpts
...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
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-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)
安全数据
- wgk
- 3
- tsca
- TSCA listed
- 毒性
- LD50 orally in Rabbit: 15100 mg/kg
- RTECS号
- CB6150000
- 存储类别
- 11 - Combustible Solids
- 安全说明
- 26-37/39-24/25
- 海关编码
- 29147090
- 危险品标志
- Xi
- 危险类别码
- 36/37/38
- 毒害物质数据
- 82-44-0(Hazardous Substances Data)
毒性防护
急性毒性静脉-小鼠 LD50: 56 毫克/公斤
刺激数据眼睛-兔 500 毫克/24小时 轻度
包装储运
可燃性危险特性热分解排出有毒氯化物烟雾
储运特性库房低温通风干燥; 与食品原料分开存放
灭火剂水,二氧化碳, 泡沫, 干粉
化学与工业
药理信息
用途与制造
Uses
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
(1972) 2.91X10+7 G (PRINCPL CUSTMS DISTS)
(1975) 7.09X10+6 G
Methods of Manufacturing
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).
应用领域
用途用作染料中间体
用途1-氯蒽醌可用作蒽醌还原染料及其他蒽醌染料的中间体,如还原棕BR染料。
制备方法
生产方法蒽醌以硫酸、硝酸配成的混酸进行硝化,再以亚硫酸钠进行磺化,生成蒽醌-1-磺酸钠。在沸腾状态下滴入氯酸钠的盐酸溶液进行氯化,过滤,干燥得成品
上下游产品信息
上游原料
下游产品
试剂价格
- C0653 · 25G
- 1-氯蒽醌1-Chloroanthraquinone — 230元
- C0653 · 500G
- 1-氯蒽醌1-Chloroanthraquinone — 1860元
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