3,6-二溴四甲苯 | 1646-54-4

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,6-二溴四甲苯
• 中文别名: 1,4-二溴-2,3,5,6-四甲基苯
• 英文名称: 1,4-dibromodurene
• 英文别名: 1,4-dibromo-2,3,5,6-tetramethylbenzene；3,6-dibromodurene；1,4-dibromotetramethylbenzene；dibromodurene；3,6-dibromotetramethylbenzene；3,6-Dibrom-durol
• CAS: 1646-54-4
• 化学式: C₁₀H₁₂Br₂
• 分子量: 292.013
• InChiKey: IEWAQZBDJDWANM-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  307.7±37.0 °C(Predicted)
• 密度：
  1.562±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲苯

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903999090

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1,4-DIBROMO-2,3,5,6-TETRAMETHYLBENZENE
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. : 1646-54-4
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
Chronic aquatic toxicity (Category 4), H413
For the full text of the H-Statements mentioned in this Section, see Section 16.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram none
Signal word none
Hazard statement(s)
H413 May cause long lasting harmful effects to aquatic life.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C10H12Br2
Molecular Weight : 292,02 g/mol
CAS-No. : 1646-54-4
No components need to be disclosed according to the applicable regulations.
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
Flush eyes with water as a precaution.
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
Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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
Provide appropriate exhaust ventilation at places where dust is formed.
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
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.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
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- log Pow: 4,807
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
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. 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: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,6-二溴四甲苯 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 生成 三(4-溴-2,3,5,6-四甲基苯基)硼烷
  参考文献：
  名称：

  The equilibria and conversions between three excited states: the LE state and two charge transfer states, in twisted pyrene-substituted tridurylboranes

  摘要：

  观察到一系列扭曲的芘取代三苯硼化合物的激发态转化，分别对应于局部激发（LE）态、具有更高荧光量子效率的更平面的电荷转移（CT）态和更扭曲的CT态。

  DOI：

  10.1039/c2cc17663g
• 作为产物：
  描述：

  1,2,4-三甲基苯 在 溶剂黄146 、 氢化铝 、 mercury dichloride 作用下， 生成 3,6-二溴四甲苯
  参考文献：
  名称：

  Korczynski, Chemische Berichte, 1902, vol. 35, p. 868

  摘要：

  DOI：
• 作为试剂：
  描述：

  二苯胺 、 3,6-二溴四甲苯 、 sodium t-butanolate 、 在 Pd2(dba)3 (t-Bu)3P 环己烷 、 3,6-二溴四甲苯 、 silica gel 作用下， 生成 4-Bromo-2,3,5,6-tetramethylphenyldiphenylamine
  参考文献：
  名称：

  Non-conjugated polymeric perarylated boranes, use thereof as organically semiconductor transmitters and/or transport materials, methods for producing same and uses thereof

  摘要：

  一种K型共聚芳基硼烷：其中氢原子与末端键合；Arn代表Ar1、Ar2和Ar3中的至少一个；Ar1和Ar2各自代表一个芳烃基团；Ar3代表一个杂环芳烃基团；Ar1具有不低于苯的π电子密度；Ar2能够传输空穴；Ar3的π电子密度不大于苯且小于Ar1；x、y和z分别代表Ar1、Ar2和Ar3的摩尔份数；x、y和z均在0-1的范围内，且x+y+z=1；R代表一个芳基基团。这种K型共聚芳基硼烷可用于有机发光二极管（OLED）、有机太阳能电池、有机光电探测器和有机场效应晶体管。

  公开号：

  US07951874B2

文献信息

• The Reaction of Dihalotetramethylbenzenes with Fuming Nitric Acid as a New Convenient Route to Some Dihalotrimethylbenzylic Compounds
  作者：Hitomi Suzuki、Kiyomi Nakamura、Michiko Takeshima

  DOI：10.1246/bcsj.44.2248

  日期：1971.8

  the latter in somewhat greater amount. 5,6-Dihalo-1,2,3,4-tetramethylbenzene (dihaloprehnitene) gave 5,6-dihalo-2,3,4-trimethylbenzyl nitrate as the sole nitrooxylation product. The reaction affords a new convenient route to precursors of various polysubstituted benzylic compounds hitherto not easily obtained by ordinary methods. Physical properties of some dihalotrimethylbenzylic compounds (chloride

  研究了用发烟硝酸硝化三种异构二氯和二溴四甲基苯得到的产物。3,6-二卤-1,2,4,5-四甲基苯（二卤代脲）主要生成 3,6-二卤-2,4,5-三甲基苄基硝酸酯或 1,2-双（硝基氧甲基）-3,6-二卤- 4,5-二甲苯，取决于反应温度和硝化剂的用量。4,6-二卤-1,2,3,5-四甲基苯（二卤代异丁二烯）生成 3,5-二卤-2,4,6-三甲基苄基硝酸酯和 2,6-二卤-3,4,5-三甲基苄基的混合物硝酸盐，后者的量稍大。5,6-二卤-1,2,3,4-四甲基苯（二卤代戊二烯）得到5,6-二卤-2,3,4-三甲基苄基硝酸盐，作为唯一的硝基酰化产物。该反应为迄今为止通过普通方法不易获得的各种多取代苄基化合物的前体提供了新的便利途径。一些二卤代三甲基苄基化合物（氯化物、硝酸盐、醋酸盐、酒精和双苄基醚）的物理特性已被记录。
• Environmentally benign electrophilic and radical bromination ‘on water’: H2O2–HBr system versus N-bromosuccinimide
  作者：Ajda Podgoršek、Stojan Stavber、Marko Zupan、Jernej Iskra

  DOI：10.1016/j.tet.2009.03.034

  日期：2009.5

  brominating systems reveals the H2O2–HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2–HBr ‘on water’. Bromination of styrene reveals that not just the structure of the brominating reagent

  AH 2 O 2 -HBr系统和N-溴琥珀酰亚胺在水性介质中被用作亲电和自由基溴化的“绿色”方法。使用两种体系，在环境温度下且不添加金属或酸催化剂的情况下，几种活化和活化程度较低的芳族分子，苯基取代的酮和苯乙烯都可以在水中“有效”溴化，而各种未活化的甲苯则在存在可见光作为自由基活化剂。两种溴化系统的反应性和选择性的比较表明，H 2 O 2-HBr系统在苄基溴化和酮的溴化方面比NBS具有更高的反应性，而对于甲氧基取代的四氢萘酮的亲电芳香取代，NBS则更高。另外，使用H 2 O 2时，溴化芳烃的收率更高。–HBr“上水”。苯乙烯的溴化揭示了不仅溴化试剂的结构，而且反应条件：水量，有机溶剂，搅拌速率和界面结构也对定义溴化的结果（二溴化与溴羟基化）起着关键作用。此外，温和的反应条件，简单的分离程序，廉价的试剂以及对环境的较低影响，使得水性溴化方法可以替代其他已报道的溴化方法。
• In Situ Formation of Frustrated Lewis Pairs in a Water‐Tolerant Metal‐Organic Framework for the Transformation of CO ₂
  作者：Serhii Shyshkanov、Tu N. Nguyen、Fatmah Mish Ebrahim、Kyriakos C. Stylianou、Paul J. Dyson

  DOI：10.1002/anie.201901171

  日期：2019.4.8

  Frustrated Lewis pairs (FLPs) consist of sterically hindered Lewis acids and Lewis bases, which provide high catalytic activity towards non‐metal‐mediated activation of “inert” small molecules, including CO2 among others. One critical issue of homogeneous FLPs, however, is their instability upon recycling, leading to catalytic deactivation. Herein, we provide a solution to this issue by incorporating

  沮丧的路易斯对（FLP）由位阻的路易斯酸和路易斯碱组成，它们对非金属介导的“惰性”小分子（包括CO 2等）的非金属活化提供了高催化活性。但是，均相FLP的一个关键问题是它们在回收后的不稳定性，从而导致催化失活。本文中，我们通过将庞大的路易斯酸官能化配体并入耐水金属有机骨架（MOF）（名为SION-105）中，并使用路易斯碱性二胺底物在其中原位形成FLP，从而为该问题提供了解决方案财政部。使用CO 2作为C1原料，这种结合可以有效地将多种二胺底物有效转化为苯并咪唑。可以通过用MeOH洗涤轻松地重新使用SION‐105，并多次重复使用而不会失去其身份和催化活性，这突出了MOF方法在FLP化学中的优势。
• Merging<i>N</i>‐Hydroxyphthalimide into Metal‐Organic Frameworks for Highly Efficient and Environmentally Benign Aerobic Oxidation
  作者：Man Wang、Gan Liang、Yunhao Wang、Tao Fan、Baoling Yuan、Mingxian Liu、Ying Yin、Liangchun Li

  DOI：10.1002/chem.202100987

  日期：2021.7.2

  metal-organic framework catalysts TJU-68-NHPI and TJU-68-NDHPI have been successfully synthesized through solvothermal reactions of which the frameworks are merged with N-hydroxyphthalimide (NHPI) units, resulting in the decoration of pore surfaces with highly active nitroxyl catalytic sites. When t-butyl nitrite (TBN) is used as co-catalyst, the as-synthesized MOFs are demonstrated to be highly efficient and recyclable

  通过溶剂热反应成功合成了两种高效金属有机骨架催化剂 TJU-68-NHPI 和 TJU-68-NDHPI，其中骨架与N-羟基邻苯二甲酰亚胺(NHPI) 单元合并，使孔隙表面具有高度的装饰性。活性硝酰基催化位点。当t亚硝酸丁酯 (TBN) 用作助催化剂，所合成的 MOF 被证明是一种高效且可回收的催化剂，可用于伯醇和仲醇和苄基化合物的活化 CH 键的新型三相多相氧化在温和的条件下。基于高效率和选择性，已经建立了一个环境友好的系统，具有良好的可持续性、温和的条件、简单的后处理程序，可用于各种底物的实际氧化。
• Solid-State Organic Reactions Proceeding by Pulverization of Inorganic Solid-Supports. Reactions of lodosobenzene with Unsaturated Hydrocarbons on Acid-Treated Silica Gel
  作者：Hajime Sohmiya、Takahide Kimura、Patrick Bauchat、Mitsue Fujita、Takashi Ando

  DOI：10.1246/cl.1991.1391

  日期：1991.8

  Pulverization of solid mixtures of hydrogen halide-treated silica gels, iodosobenzene, and alkenes or an alkyne in the absence of a solvent brings about smooth and rapid reaction to give halogenated or oxidized products in good yields.

  无溶剂条件下，经过卤化氢处理的硅胶与碘亚苯和烯烃或炔烃的固体混合物的粉碎会产生平滑快速的反应，以良好产率生成卤代或氧化产物。