四溴对苯醌 | 488-48-2

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酮(含烯醇)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 四溴对苯醌
• 中文别名: 对四溴苯醌；四溴-1,4-苯醌
• 英文名称: tetrabromobenzoquinone
• 英文别名: tetrabromo-p-benzoquinone；bromanil；2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione
• CAS: 488-48-2
• 化学式: C₆Br₄O₂
• mdl: MFCD00013785
• 分子量: 423.681
• InChiKey: LWHDQPLUIFIFFT-UHFFFAOYSA-N

物化性质

• 熔点：
  292-294 °C(lit.)
• 沸点：
  340.5±42.0 °C(Predicted)
• 密度：
  3.127±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、DMSO（少许）
• 稳定性/保质期：
  按规格使用和储存，不会发生分解，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2914700090
• RTECS号：
  DK6772500
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封保存，并置于通风、干燥的环境当中。

SDS

Bromanil Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Bromanil

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Bromanil
Percent: >98.0%(T)
CAS Number: 488-48-2
Synonyms: Tetrabromo-1,4-benzoquinone
C6Br4O2
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Bromanil

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: Yellow
No data available
Odour:
Bromanil

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] Insoluble
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen bromide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: ipr-mus LD:>500 mg/kg
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
Reproductive toxicity: No data available
RTECS Number: DK6772500

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
Bromanil

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成制备方法

暂无相关信息。

用途

暂无相关信息。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2,3,5-tribromo-1,4-benzoquinone	25779-26-4	C6HBr3O2	344.785
  2,5-二溴-1,4-苯醌	2,5-dibromo-1,4-benzoquinone	1633-14-3	C6H2Br2O2	265.889
  2-溴-1,4-苯醌	2-bromo-1,4-benzoquinone	3958-82-5	C6H3BrO2	186.993

反应信息

• 作为反应物：
  描述：

  四溴对苯醌 在 ammonium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以54%的产率得到2,5-diamino-3,6-dibromo-1,4-benzoquinone
  参考文献：
  名称：

  通过合成后接头交换的金属-二酰氨基苯醌框架

  摘要：

  带有酰胺键的金属-有机骨架通常表现出特殊的物理性质，但由于其强大的金属-氮键，通过直接合成分离非常具有挑战性。在这里，我们报告了一种通过合成后接头交换从其二羟基苯醌对应物获得金属-二氨基苯醌框架的途径。母体化合物 (Me2NH2)2[M2L3]（M = Zn, Mn；H2L = 2,5-dichloro-3,6-dihydroxo-1,4-benzoquinone）在暴露于去质子化 2 ,5-diamino-3,6-dibromo-1,4-benzoquinone 或 2,5-diamino-3,6-dichloro-1,4-benzoquinone，通过晶体到单晶的反应进行。通过 NMR、拉曼和能量色散 X 射线 (EDX) 光谱的组合证实了所得框架中两种类型的接头的存在。而且，使用 13C NMR 光谱对 Zn 骨架中的接头交换程度进行量化，并且空间分辨 EDX 光谱显示两种类型的接头

  DOI：

  10.1021/jacs.9b11952
• 作为产物：
  描述：

  对硝基苯酚 在 溴 、 硝酸 作用下， 生成 四溴对苯醌
  参考文献：
  名称：

  HALOGENATION. XXII. THE ACTION OF BROMINE AND NITRIC ACID ON ORGANIC COMPOUNDS. PREPARATION OF NITROSYL TRIBROMIDE AND THE FORMATION OF TETRABROMOQUINONE

  摘要：

  DOI：

  10.1021/ja01655a025
• 作为试剂：
  描述：

  异喹啉 、 二异己基酮 在 (2,2,6,6-tetramethylpiperidido)₂Cu(CN)Li₂ 、 四溴对苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到N,N-diisopropyl-2-(isoquinolin-1-yl)benzamide
  参考文献：
  名称：

  芳烃的直接，化学和区域选择性交叉偶联反应，通过有序定向邻位氧化和氧化来实现。

  摘要：

  通过使用连续的定向邻位铜（DoCu）与铜酸根（TMP）2Cu（CN）Li2（1，TMP = 2）进行连续的定向邻位配位（DoCu），可以以30-76％的产率实现两个芳烃的Csp2-H / Csp2-H键的直接交叉偶联。 （2,6,6-四甲基哌啶基），然后氧化。利用1的高度化学选择性作用，该方法可轻松从具有各种定向金属化基团（DMG）和辅助官能团的芳烃中获得不对称联芳基。

  DOI：

  10.1021/acs.orglett.9b03719

文献信息

• One-Pot Synthesis of Novel Antiproliferative 9-Aminoacridines
  作者：Gary Gellerman、Sagiv Waintraub、Amnon Albeck、Vladimir Gaisin

  DOI：10.1002/ejoc.201100133

  日期：2011.8

  Highly efficient one-pot syntheses of antiproliferative 9-aminoacridine (9-AA) derivatives are described. Simple SNAr and addition/elimination reactions, using readily accessible starting materials, give a fast entry to novel 9-(pyridylamino)acridines, 9-(pyrimidinylamino)acridines and potential “dual-function” bioreductive 9-(acridinylamino)quinone intercalators. The synthetic routes reported in this

  描述了抗增殖 9-氨基吖啶 (9-AA) 衍生物的高效一锅合成。简单的 SNAr 和加成/消除反应，使用容易获得的起始材料，快速进入新型 9-（吡啶氨基）吖啶、9-（嘧啶氨基）吖啶和潜在的“双功能”生物还原性 9-（吖啶氨基）醌嵌入剂。这项工作中报道的合成路线是通用且易于应用的，显着扩大了潜在 9-AA 抗癌候选物的范围和范围。
• Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
  作者：Henian Peng、Tiejun Li、Duanshuai Tian、He Yang、Guangqing Xu、Wenjun Tang

  DOI：10.1039/d1ob00300c

  日期：——

  A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from

  一系列不饱和羰基、醌和吡啶盐已被有效地还原为相应的饱和羰基、二羟基苯和氢吡啶，其中四羟基二硼/水是一种温和、方便且无金属的还原体系，其产率中等至高。氘标记实验表明，该协议是一种从水中进行的独家转移氢化过程。
• Synthesis, Structure, and Photochemistry of 2,3,5,6-Tetrasilyl-1,4-benzoquinones and Related Compounds
  作者：Shinobu Tsutsui、Kenkichi Sakamoto、Keisuke Ebata、Chizuko Kabuto、Hideki Sakurai

  DOI：10.1246/bcsj.75.2571

  日期：2002.12

  3,5,6-tetrakis(trimethylsilyl)-1,4-benzoquinone (1a) was distorted into a chair form. The deformed quinone ring allowed a σ(Cquinone-Si)–π* electronic transition in 1a. Photolysis of 1a resulted in an isomerization, creating a ketene derivative, 4-carbonyl-2,3,5,5-tetrakis(trimethylsilyl)-2-cyclopenten-1-one.

  通过用氯铬酸吡啶鎓氧化相应的 1,4-二甲氧基苯衍生物，获得 2,3,5,6-四甲硅烷基-和 2,3,5,6-tetragermyl-1,4-苯醌。X 射线晶体学分析表明，2,3,5,6-四(三甲基甲硅烷基)-1,4-苯醌 (1a) 的醌环扭曲成椅子形式。变形的醌环允许 1a 中的 σ(Cquinone-Si)-π* 电子跃迁。1a 的光解导致异构化，产生乙烯酮衍生物 4-carbonyl-2,3,5,5-tetrakis(trimethylsilyl)-2-cyclopenten-1-one。
• 一种给-受体型化合物及其有机电致发光器件 应用
  申请人：西安瑞联新材料股份有限公司

  公开号：CN111574428B

  公开（公告）日：2021-10-22

  本发明提供一种给‑受体型化合物，属于有机电致发光材料技术领域。该化合物由下述通式(Ⅰ)表示，式(Ⅰ)中，X1、X2均为氧原子或丙二腈基团；D1、D4为相同给电子基团或H，或者D1、D4为不同给电子基团，或者D2、D3为相同给电子基团或H，D2、D3为不同给电子基团，当D1、D4相同，且D2、D3相同时，D1、D4与D2、D3不同时为H；所述给电子基团选自取代或未被取代的咔唑基、吖啶基、吩噁嗪基、吩唖嗪基、吩嗪基、吩噻嗪基中的一种；本发明还提供了一种给‑受体型化合物的应用以及有机电致发光器件。本发明通过引入特定的给电子基团修饰构成的全新化合物，具有较高的热稳定性，可显著提高发光器件的发光稳定性。通式(Ⅰ)表示如下：
• A novel, versatile synthetic approach to linearly fused tricyclopentanoids via photo-thermal olefin metathesis
  作者：Goverdhan Mehta、A. Srikrishna、A.Veera Reddy、Mangalam S. Nair

  DOI：10.1016/0040-4020(81)80021-x

  日期：1981.1

  the cyclobutane ring gave cis, syn, cis-tricyclo [6.3.0.02,6]undeca-4,9-dien-3,11-diones (11a–11j, 15a,b in just three steps and in exceptionally good yields. A few interesting transformations of the readily available parent bis-enone 11a which indicates its wider uses in syntheses, are described. Finally, a smooth thermal isomerisation of cis, syn, cis-bis-enones to cis, anti, cis-bis-enones is reported

  描绘了十五种新的，快速且通用的方法，以线性融合的三环戊烷为载体，其具有当代高度关注的三环[6.3.0.0 2,6 ]十一烷（三喹烷）骨架。在我们合成三喹烷的过程中，关键概念是廉价的，可大量利用的1,3环戊二烯与对苯醌的Diels-Alder加合物的新颖光热烯烃复分解反应。因此，内-三环[6.2.1.0 2,7 ]十一烷-4,9-二烯-3,6-二酮（9a – 9j，13a，b）的光解提供了五环[5.4.0.0 2,6 .0 3,10 .0 5,9 ] undecan-8,11-diones（10a – 10j，14a，b），其在环丁烷环热裂解后得到顺，顺，顺-三环[6.3.0.0 2,6 ] undeca -4,9-dien-3,11-二酮（11a – 11j，15a，b在只需三个步骤和在特别好的产率。在容易获得的亲双烯酮的一些有趣的转换部11a，其指示在合成其更为广泛的用途，进行了描述。最

表征谱图