4,5-二溴-1,2-二甲氧基苯 | 37895-73-1

• 物质功能分类: 有机原料 - 醚类化合物及其衍生物
• 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: 4,5-二溴-1,2-二甲氧基苯
• 中文别名: 4,5-二溴藜芦醚
• 英文名称: 1,2-dibromo-4,5-dimethoxybenzene
• 英文别名: 4,5-dibromoveratrole；4,5-dibromo-1,2-dimethoxybenzene；4,5-dibromoveratrol；1,2-dimethoxy-4,5-dibromobenzene
• CAS: 37895-73-1
• 化学式: C₈H₈Br₂O₂
• mdl: MFCD00014894
• 分子量: 295.958
• InChiKey: ZYCLQXMMFJREPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92°C
• 沸点：
  286.6±35.0 °C(Predicted)
• 密度：
  1.742±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S22,S24/25
• 海关编码：
  2909309090
• 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、阴凉、干燥保存

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,2-DIBROMO-4,5-DIMETHOXYBENZENE
CAS-No. : 37895-73-1
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
This substance is not classified as dangerous according to Directive 67/548/EEC.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C8H8Br2O2
Molecular Weight : 295,96 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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 vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
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).

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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) Evaporation 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: 3,395
octanol/water
p) Autoignition 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
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products

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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 sensitization
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
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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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
no data available
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.
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

制备方法与用途

概述

含有二溴苯结构的化合物在有机合成中有着一些应用，其中4,5-二溴藜芦醚作为此类物质之一，可用作有机合成中间体。

应用

4,5-二溴藜芦醚广泛应用于医药合成反应，例如用于制备伊伐布雷定。该化合物及其与可药用酸形成的加成盐（特别是其盐酸盐）具有非常有价值的药理学和治疗性能。

反应信息

• 作为反应物：
  描述：

  4,5-二溴-1,2-二甲氧基苯 在 tetrabutylammonium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.4h， 以77%的产率得到邻苯二甲醚
  参考文献：
  名称：

  通过直接电解对芳基卤化物进行加氢脱卤

  摘要：

  公开了无催化剂和无金属的芳基卤化物的电化学加氢脱卤。我们通过灵活的协议进行的反应在配备了廉价石墨棒阳极和阴极的不分隔电池中进行。三烷基胺n Bu 3 N / Et 3 N充当该电化学还原反应的有效还原剂和氢原子供体。各种芳基和杂芳基溴有效地起作用。通常反应性较低的芳基氯化物和氟化物也可以顺利转化。克农药规模的有害农药排毒和二溴代联苯的加氢溴化（阻燃剂类似物）证明了我们方法的实用性。

  DOI：

  10.1002/chem.201901082
• 作为产物：
  描述：

  邻苯二甲醚 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以40.38%的产率得到4,5-二溴-1,2-二甲氧基苯
  参考文献：
  名称：

  Mono-oxo-bis-dithioveratrol-molybdate - 在溶液中是亚砷酸氧化酶的模型，在固态中是具有前所未有的结合基序的配位聚合物

  摘要：

  Mono-oxo-bis-dithioveratrol-molybdate 被合成、结构表征和研究其氧化转移活性。后者与类似的钨配合物的活性进行了比较。标题复合物是含有亚砷酸氧化酶的钼蝶呤的结构模型，两种复合物均成功催化氧转移反应达到 100% 转化率。使用二硫藜芦醇配体，对于钨络合物，三苯基膦的氧化被证明更快，这是不典型的。钼复合物的固态结构表现出意想不到且非常不寻常的聚合物结构基序，由复合阴离子单氧代双二硫藜芦醇钼酸盐、钠阳离子和甲醇组成。

  DOI：

  10.1002/zaac.201300076

文献信息

• Synthesis of Fluorene and Indenofluorene Compounds: Tandem Palladium-Catalyzed Suzuki Cross-Coupling and Cyclization
  作者：Tao-Ping Liu、Chun-Hui Xing、Qiao-Sheng Hu

  DOI：10.1002/anie.201000327

  日期：2010.4.6

  “Fluor” it: Palladium‐catalyzed tandem reactions, in which C(sp3)H bond activation is the key step (see scheme; DMA=dimethylacetamide), lead to substituted fluorenes and indenofluorenes through annulation in high yield and in one step. This method has potential for the preparation of other cyclic compounds, as well as substituted oligofluorenes and polyfluorenes.

  “ Fluor”：钯催化的串联反应，其中C（sp 3）H键的活化是关键步骤（请参阅方案； DMA =二甲基乙酰胺），通过高产率环合反应可生成取代的芴和茚并芴。该方法具有制备其他环状化合物以及取代的低聚芴和聚芴的潜力。
• Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
  作者：Wen Yang、Renshi Luo、Dingqiao Yang

  DOI：10.3390/molecules201219748

  日期：——

  Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i.

  报道了铱催化的氧杂苯并降冰片二烯与N-取代哌嗪的不对称开环反应。在2.5 mol% [Ir(COD)Cl]2和5.0 mol% (S)-对甲苯-BINAP的存在下，该反应以高产率和中等对映选择性提供了相应的开环产物。还研究了各种手性双齿配体、催化剂用量、溶剂和温度对产率和对映选择性的影响。基于产物2i的X射线结构，提出了一个合理的机理来解释相应反式开环产物的形成。
• Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide
  作者：Tomohiro Maegawa、Ayako Shibata、Sara Kitamoto、Kazuma Fujimura、Yuuka Hirose、Hiromi Hamamoto、Akira Nakamura、Yasuyoshi Miki

  DOI：10.1055/s-0037-1610980

  日期：2018.10

  We describe the dehydroxymethylbromination of alkoxybenzyl alcohol by using a hypervalent iodine reagent and lithium bromide in F3CCH2OH at room temperature. Selective monobromination or dibromination was possible by adjusting the molar ratios of hypervalent iodine reagent and lithium bromide.

  我们描述了在室温下在 F3CCH2OH 中使用高价碘试剂和溴化​​锂对烷氧基苄醇进行脱羟甲基溴化。通过调节高价碘试剂和溴化​​锂的摩尔比，可以选择性地单溴化或二溴化。
• Directing Selectivity to Aldehydes, Alcohols, or Esters with Diphobane Ligands in Pd-Catalyzed Alkene Carbonylations
  作者：Dillon W. P. Tay、James D. Nobbs、Srinivasulu Aitipamula、George J. P. Britovsek、Martin van Meurs

  DOI：10.1021/acs.organomet.1c00228

  日期：2021.6.28

  trifluoromethylphenylene-bridged diphobane L1 with an electron-withdrawing substituent, lead to ester products via alkoxycarbonylation, whereas BCOPE gives predominantly alcohol products (n-nonanol and isomers) via reductive hydroformylation. The preference of BCOPE for reductive hydroformylation is also seen in the hydroformylation of 1-hexene in diglyme as the solvent, producing heptanol as the major product, whereas

  已经合成了具有不同取代基（CF 3、H、OMe、（OMe）2、t Bu）的亚苯基桥连二恶烷配体，并将其用作钯催化的各种烯烃羰基化反应中的配体。已经使用 1-己烯、1-辛烯和戊烯酸甲酯作为底物研究了这些配体在加氢甲酰化与烷氧基羰基化选择性方面的性能，并将结果与​​乙烯桥连二恶烷配体 ( BCOPE ) 进行了比较。1-辛烯在质子溶剂 2-乙基己醇中的加氢甲酰化导致加氢甲酰化和烷氧基羰基化之间的竞争，其中亚苯基桥连的配体，特别是三氟甲基亚苯基桥连的二恶烷L1带有吸电子取代基，通过烷氧基羰基化产生酯产物，而BCOPE通过还原加氢甲酰化产生主要的醇产物（正壬醇和异构体）。在以二甘醇二甲醚为溶剂的 1-己烯的加氢甲酰化中也可以看到BCOPE对还原加氢甲酰化的偏好，生成庚醇作为主要产物，而在这种情况下，亚苯基桥连的配体显示出低得多的活性。亚苯基桥连配体在 1-辛烯甲氧基羰基化生成壬酸甲酯方面表现出优异
• Diastereoselective [3+2] Annulation of Aromatic/Vinylic Amides with Bicyclic Alkenes through Cobalt-Catalyzed C−H Activation and Intramolecular Nucleophilic Addition
  作者：Parthasarathy Gandeepan、Pachaiyappan Rajamalli、Chien-Hong Cheng

  DOI：10.1002/anie.201512018

  日期：2016.3.18

  dihydroepoxybenzofluorenone derivatives from aromatic/vinylic amides and bicyclic alkenes is described. This new transformation proceeds through cobalt‐catalyzed C−H activation and intramolecular nucleophilic addition to the amide functional group. Transition‐metal‐catalyzed C−H activation reactions of secondary amides with alkenes usually lead to [4+2] or [4+1] annulation; to the best of our knowledge

  描述了由芳族/乙烯基酰胺和双环烯烃合成二氢环氧苯并芴酮衍生物的高度非对映选择性的方法。这种新的转化过程是通过钴催化的CH活化和分子内亲核加成到酰胺官能团上而进行的。仲酰胺与烯烃的过渡金属催化的CH活化反应通常导致[4 + 2]或[4 + 1]环化；据我们所知，这是第一次在这种情况下描述[3 + 2]环加成反应。反应在温和的条件下进行，并能耐受各种官能团。机理研究表明，CH键断裂可能是限速步骤。

表征谱图