2-溴甲基蒽醌 | 7598-10-9

• 物质功能分类: 有机原料 - 醌类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2-溴甲基蒽醌
• 英文名称: 2-(bromomethyl)anthraquinone
• 英文别名: 2-bromomethyl-9,10-anthraquinone；2-(bromomethyl)anthracene-9,10-dione；2-Bromomethyl-anthraquinone
• CAS: 7598-10-9
• 化学式: C₁₅H₉BrO₂
• mdl: MFCD00042958
• 分子量: 301.139
• InChiKey: FCETXLHFBYOVCV-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C (dec.) (lit.)
• 沸点：
  470.8±34.0 °C(Predicted)
• 密度：
  1.597±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会发生分解，目前没有已知的危险情况。 应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  UN 3261 8/PG 2
• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将密闭、阴凉干燥处保存，并确保有良好通风。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Bromomethyl-anthraquinone
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 7598-10-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards
Lachrymator.

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SECTION 3: Composition/information on ingredients
Substances
Chemical characterization : Natural product
Formula : C15H9BrO2
Molecular Weight : 301,13 g/mol
CAS-No. : 7598-10-9
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Bromomethyl-anthraquinone
CAS-No. 7598-10-9 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-Bromomethyl-anthraquinone
CAS-No. 7598-10-9 Xi, R36/37/38 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Hydrogen bromide gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone] test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 203 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and
skin., spasm, inflammation and edema of the larynx, spasm, inflammation and edema of the bronchi,
pneumonitis, pulmonary edema, burning sensation, Cough, wheezing, laryngitis, Shortness of breath,
Headache, Nausea, Vomiting, To the best of our knowledge, the chemical, physical, and toxicological
properties have not been thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 3261 IMDG: 3261 IATA: 3261
UN proper shipping name
ADR/RID: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (2-Bromomethyl-anthraquinone)
IMDG: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (2-Bromomethyl-anthraquinone)
IATA: Corrosive solid, acidic, organic, n.o.s. (2-Bromomethyl-anthraquinone)
Transport hazard class(es)
ADR/RID: 8 IMDG: 8 IATA: 8
Packaging group
ADR/RID: II IMDG: II IATA: II
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Eye Irrit. Eye irritation
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Full text of R-phrases referred to under sections 2 and 3
Xi Irritant
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2-溴甲基蒽醌 在 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以80%的产率得到2-(nitrooxymethyl)-[9,10]-anthraquinone
  参考文献：
  名称：

  Nitrooxyquinones: synthesis, X-ray diffraction and electrochemical studies

  摘要：

  2-Methyl-3-(nitrooxymethyl)-[1,4]-naphthoquinone and 2-(nitrooxymethyl)-[9,10]-anthraquinone, the first representatives of quinone-derived organic nitrates, potential hybrid drugs, were obtained and characterized through X-ray diffraction. Voltammetric studies showed that reductive elimination occurs, after quinone reduction. The NO3- release, leading to electrogenerated quinonemethide, would suggest a quinone-driven biological activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01957-3
• 作为产物：
  描述：

  2-氯乙基蒽 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 2-溴甲基蒽醌
  参考文献：
  名称：

  反应S RN 1剂烷烃蒽醌类

  摘要：

  由S RN 1机理表明，由2-甲基蒽醌与2-硝基丙烷阴离子制备的三种还原性烷基化剂的C-烷基化反应正在进行。通过离去基团效应和双氧，对二硝基苯，氯化铜和二叔丁基硝基氧化物的抑制作用证实了S RN 1机制。该反应可以扩展为1-甲基-3-硝基吡咯烷酮-2-一阴离子。

  DOI：

  10.1016/s0040-4020(01)81811-1
• 作为试剂：
  描述：

  三溴化磷 、 2-羟甲基蒽醌 在 乙酸乙酯 、 水 、 magnesium sulfate 、 2-溴甲基蒽醌 、 silica 作用下， 以 四氢呋喃 为溶剂， 反应 49.17h， 生成 2-溴甲基蒽醌
  参考文献：
  名称：

  Reactive anthraquinone derivatives and conjugates thereof

  摘要：

  蒽醌衍生物被构建用于烷基化目标分子。蒽醌衍生物包括一个蒽醌环系统，该环系统已通过在环系统上的位置添加可诱导反应的取代基而改变。蒽醌环系统可以被选择性地激活，以烷基化目标分子。取代基可以是1到4个甲基基团，通过光化学信号实现激活。在另一种替代实施方案中，可诱导反应的取代基可以包括甲基基团和取代亚甲基基团。在这种实施方案中，通过光化学和/或还原信号实现蒽醌衍生物的激活。或者，取代基可以是1到8个甲基基团，经过修饰以包括反应性基团，通过化学或酶促还原信号实现激活。本发明的蒽醌衍生物可用于目标分子的非特异性修饰。或者，蒽醌衍生物可以进一步衍生化，以允许特异性修饰目标分子。蒽醌的进一步衍生化包括通过连接基将探针连接到蒽醌环系统上。选择探针以选择性地定位到目标分子，然后蒽醌衍生物可以被激活以与目标分子反应并烷基化。此外，还提供了使用这种蒽醌衍生物在体外或体内用于烷基化、特异性或非特异性烷基化目标分子的方法。

  公开号：

  US05650399A1

文献信息

• Thiourea-Mediated Halogenation of Alcohols
  作者：Amar R. Mohite、Ravindra S. Phatake、Pooja Dubey、Mohamed Agbaria、Alexander I. Shames、N. Gabriel Lemcoff、Ofer Reany

  DOI：10.1021/acs.joc.0c01431

  日期：2020.10.16

  conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient

  提出了在亚化学计量的硫脲添加剂的存在下加速的在温和条件下醇的卤化。硫脲的添加量决定了反应的途径，该途径可能与所需的卤化反应不同，在没有硫脲的情况下朝着醇的氧化，或者在使用过量的硫脲时朝着原料的回收。溴化和氯化对于伯醇，仲醇，叔醇和苄醇都非常有效，并且可以耐受各种官能团。详细的电子顺磁共振（EPR）研究，同位素标记和其他对照实验表明，基于自由基的机理。反应是在环境条件下进行的，使用的试剂普遍存在且价格便宜，具有广泛的应用范围，并且可以实现高度原子经济，
• [EN] AZOLIUM AND PURINIUM SALT ANTICANCER AND ANTIMICROBIAL AGENTS<br/>[FR] ANTIMICROBIENS ET ANTINÉOPLASIQUES DE SELS D'AZOLIUM ET DE PURINIUM
  申请人：UNIV AKRON

  公开号：WO2012149523A1

  公开（公告）日：2012-11-01

  Singly and multiply charged imidazolium cations (ICs) have been identified as a class of chemical compositions that possess potent antineoplastic, antibacterial and antimicrobial properties. The imidazolium cations disclosed demonstrate greater or equivalent potency towards cancerous cells as the current clinical standard, cisplatin. These imidazolium cations, however, achieve this efficacy without any of the known toxic side effects caused by heavy metal-based antineoplastic drugs such as cisplatin.

  单电荷和多电荷咪唑阳离子（ICs）已被确认为一类具有强效抗肿瘤、抗菌和抗微生物特性的化学成分。所披露的咪唑阳离子对癌细胞表现出比当前临床标准顂铂更高或相等的效力。然而，这些咪唑阳离子在不引起类似顂铂等重金属抗肿瘤药物已知的毒副作用的情况下实现了这种功效。
• Chromo-Fluorogenic Detection of Nerve-Agent Mimics Using Triggered Cyclization Reactions in Push-Pull Dyes
  作者：Ana M. Costero、Margarita Parra、Salvador Gil、Raúl Gotor、Pedro M. E. Mancini、Ramón Martínez-Máñez、Félix Sancenón、Santiago Royo

  DOI：10.1002/asia.201000058

  日期：——

  results in a hypsochromic shift of the absorption band of the dyes. Similar reactivity studies are also carried out with other “non‐toxic” organophosphorus compounds, but no changes in the UV/Vis spectra were observed. The emission behaviour of the reagents in acetonitrile and water–acetonitrile 3:1 v/v mixtures is also studied in the presence of nerve‐agent simulants and other organophosphorous derivatives

  偶氮和二苯乙烯衍生物（的家族1，2，3，4，5，6，7，8，9）的合成，并且在神经剂模拟物，磷酸二乙酯的存在下（DCP）其色光荧光行为，二异丙基（DFP）和乙腈中的氰基磷酸二乙酯（DCNP），以及用MES缓冲的pH 5.6的水/乙腈（3：1 v / v）混合溶液。制备的化合物包含2-（2- N，N-二甲基氨基苯基）乙醇或2-[（2- N，N-二甲基氨基）苯氧基]乙醇反应性基团，是染料共轭π-系统的一部分，能够与膦酸酯底物发生酰化反应，随后发生快速的分子内N反应烷基化。神经药模拟触发的环化反应将二甲基氨基基团转变为季铵盐，从而引起离域系统电子性质的变化，从而导致染料吸收带的变色移动。其他“无毒”有机磷化合物也进行了类似的反应性研究，但未观察到UV /​​ Vis光谱的变化。在存在神经试剂模拟剂和其他有机磷衍生物的情况下，还研究了乙腈和水-乙腈3：1 v / v混合物中试剂的发射行为。之间的反
• Retinoids and Related Compounds; 18: A Convenient Synthesis of Retinoic Acid Analogs Having an Anthraquinone Ring
  作者：Akimori Wada、Chisato Tode、Saeko Hiraishi、Yukiko Tanaka、Tomoko Ohfusa、Masayoshi Ito

  DOI：10.1055/s-1995-4063

  日期：1995.9

  Synthesis of retinoic acid analogs involving an anthraquinone ring is described. The reaction of p-toluenesulfonylmethylanthraquinones 8 with ethyl 8-chloro-3,7-dimethyl-2,4,6-octatrienoate (6) and subsequent desulfonylation afforded the esters 10 and 11 as a mixture of terminal double bond isomers. After separation of these isomers, basic hydrolysis using 10% potassium hydroxide gave the corresponding acids 12 and 13, respectively, without isomerization of the terminal double bond in excellent yields.

  描述了涉及蒽醌环的类视黄酸类似物的合成。通过对甲苯磺酰甲基蒽醌8与乙基8-氯-3,7-二甲基-2,4,6-辛三烯酸酯（6）反应，随后进行脱磺酰化，得到了末端双键异构体的酯混合物10和11。通过分离这些异构体，使用10%氢氧化钾进行碱性水解，分别在优异的产率下得到相应的酸12和13，且末端双键没有发生异构化。
• Discovery and biological evaluation of some (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety as potent xanthine oxidase inhibitors
  作者：Ting-jian Zhang、Song-ye Li、Wei-yan Yuan、Qing-xia Wu、Lin Wang、Su Yang、Qi Sun、Fan-hao Meng

  DOI：10.1016/j.bmcl.2017.01.049

  日期：2017.2

  A series of (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety were synthesized and identified as novel xanthine oxidase inhibitors. Among them, the most promising compounds 1h and 1k were obtained with IC50 values of 0.6 μM and 0.8 μM, respectively, which were more than 10-fold potent compared with allopurinol. The Lineweaver-Burk plot revealed that compound

  合成了一系列含有蒽醌部分的（1 H -1,2,3-三唑-4-基）甲氧基苯甲醛衍生物，并将其鉴定为新型黄嘌呤氧化酶抑制剂。其中，获得最有前途的化合物1h和1k的IC 50值分别为0.6μM和0.8μM，与别嘌呤醇相比，具有50倍以上的效力。Lineweaver-Burk图显示化合物1h充当了混合型黄嘌呤氧化酶抑制剂。SAR分析表明，对于抑制效力，苯甲醛部分比蒽醌部分起着更重要的作用。黄嘌呤氧化酶被1h显着抑制的基础 通过分子模型研究合理化。