anti-1,2-dibromo-1,2-diphenylethane | 13440-24-9

• 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 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: anti-1,2-dibromo-1,2-diphenylethane
• 英文别名: meso-1,2-dibromo-1,2-diphenylethane；1,2-dibromo-1,2-diphenylethane；meso-stilbene dibromide；[(1R,2S)-1,2-dibromo-2-phenylethyl]benzene
• CAS: 13440-24-9
• 化学式: C₁₄H₁₂Br₂
• 分子量: 340.057
• InChiKey: GKESIQQTGWVOLH-OKILXGFUSA-N

物化性质

• 熔点：
  241 °C (dec.)(lit.)
• 沸点：
  323.8±37.0 °C(Predicted)
• 密度：
  1.613±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2903999090
• 危险品运输编号：
  UN 1759 8/PG 3
• 储存条件：
  常温密闭，阴凉通风干燥

SDS

meso-1,2-Dibromo-1,2-diphenylethane Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: meso-1,2-Dibromo-1,2-diphenylethane

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 4
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Harmful if swallowed
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Do not eat, drink or smoke when using this product.
[Prevention]
Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
[Response] IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
IF IN EYES: 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.
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.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: meso-1,2-Dibromo-1,2-diphenylethane
>97.0%(T)
Percent:
CAS Number: 13440-24-9
meso-1,2-Dibromo-1,2-diphenylethane

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Synonyms: meso-Stilbene Dibromide
Chemical Formula: C14H12Br2

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Get medical advice/attention if you feel unwell.
Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
Skin contact:
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Rinse cautiously with water for several minutes. Remove contact lenses, if present
Eye contact:
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
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
generate poisonous fume.
from the chemical:
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
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
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
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
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
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
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.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.
meso-1,2-Dibromo-1,2-diphenylethane

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Slightly pale yellow
No data available
Odour:
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
No data available
Flash point:
Flammability or explosive
limits:
Lower: No data available
No data available
Upper:
Relative density: No data available
Solubility(ies):
[Water] No data available
No data available
[Other solvents]

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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
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
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.
meso-1,2-Dibromo-1,2-diphenylethane

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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

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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

反应信息

• 作为反应物：
  描述：

  anti-1,2-dibromo-1,2-diphenylethane 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 34.0h， 以76%的产率得到联苯甲酰
  参考文献：
  名称：

  Krasnokutskaya; Yusubov; Filimonov, Russian Journal of Organic Chemistry, 1996, vol. 32, # 7, p. 1001 - 1004

  摘要：

  DOI：
• 作为产物：
  描述：

  反式-1,2-二苯乙烯 在 Br₃^(1-)*C₁₉H₁₇PPol⁽¹⁺⁾ 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以95%的产率得到anti-1,2-dibromo-1,2-diphenylethane
  参考文献：
  名称：

  带有三溴甲基三苯基phosph基团的珠子的顺序溴化反应

  摘要：

  已经开发了一种基于聚苯乙烯珠的可重复使用的溴化试剂，该聚苯乙烯珠具有共价连接的三溴化甲基三苯基phosph基团。描述了几种结构上不同的不饱和底物与微珠和非聚合型溴化剂三溴甲基三苯基phosph溶液的溴化反应的结果。结果表明，该反应具有很高的区域选择性和立体选择性，并且易于进行。版权所有©2010 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1694
• 作为试剂：
  描述：

  二苯基甲氧基膦 在 anti-1,2-dibromo-1,2-diphenylethane 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 [甲氧基(苯基)磷酰基]苯
  参考文献：
  名称：

  三价磷化合物脱溴的动力学研究

  摘要：

  各种类型的三价磷化合物 (1) 导致 vic-二溴化物 (2) 的还原脱溴得到烯烃。该反应通过 1 的磷上的释放电子取代基或 2 的 α-碳上的吸电子取代基加速。 取代基效应以及反应的立体化学与 E1CB 类机制一致消除两个溴原子。也就是说，1 最初对溴 2 进行亲核攻击。在过渡态，1 的磷上产生部分正电荷，2 的碳上产生部分负电荷。这种机制表明电子特性的重要性vic-二溴化物在确定亲溴性、亲碳性、三价磷化合物在与二溴化物反应中的磷的碱性和碱性。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:217–222, 2001

  DOI：

  10.1002/hc.1035

文献信息

• Palladium(0) Complex-Catalyzed Debrominative Coupling of (Tribromomethyl)- and (Dibromomethyl)benzenes to Diarylacetylenes and 1,2-Diarylethenes
  作者：Shuntaro Mataka、Guo-Bin Liu、Masashi Tashiro

  DOI：10.1055/s-1995-3878

  日期：1995.2

  Palladium(0)-triphenylphosphine complex-catalyzed debrominative coupling reaction of (tribromomethyl)benzenes gave diarylacetylenes or a mixture of (E)- and (Z)-α,β-dibromostilbenes depending upon the substrate and the solvent being used. On the other hand, (dibromomethyl)benzenes afforded (E)-stilbenes selectively under the same reaction conditions.

  通过铂(0)-三苯膦络合物催化的去溴偶联反应，（三溴甲基）苯类物质会生成二取代乙炔或者根据所用底物和溶剂的不同，产生（E）-和（Z）-α，β-二溴代联苯乙烯混合物。另一方面，（二溴甲基）苯类物质在相同的反应条件下，会优先得到（E）-联苯乙烯。
• Mild and Efficient Vicinal Dibromination of Olefins Mediated by Aqueous Ammonium Fluoride
  作者：Tony Shing、Ying-Yeung Yeung、Wing Ng

  DOI：10.1055/s-0036-1588506

  日期：2018.3

  A mild and efficient vicinal dibromination of olefins has been developed by using saturated aqueous ammonium fluoride solution as the promoter. Inexpensive and commercially available N -bromosuccinimide (NBS) was used as the brominating reagent. The corresponding vicinal dibromoalkanes could be obtained in good to excellent yields.

  以饱和氟化铵水溶液为促进剂，开发了温和高效的烯烃邻位二溴化反应。使用廉价且可商购的 N-溴代琥珀酰亚胺 (NBS) 作为溴化试剂。可以以良好到极好的产率获得相应的邻位二溴烷烃。
• Magnetic‐Nanoparticle‐Supported 2,2′‐Bis[3‐(triethoxysilyl)propyl]imidazolium‐Substituted Diethyl Ether Bis(tribromide): A Convenient Recyclable Reagent for Bromination
  作者：Liqiang Wu、Zhikui Yin

  DOI：10.1002/ejic.201300755

  日期：2013.12.9

  A new magnetic-nanoparticle-supported bromination reagent was synthesized by anchoring a 2,2′-bis[3-(triethoxysilyl)propyl]imidazolium-substituted diethyl ether bis(tribromide) onto the surface of γ-Fe2O3 nanoparticles and subsequently treating this new ionic liquid with bromine. The nanoparticle reagent was obtained with good loading levels and has been successfully used for the efficient bromination

  通过将 2,2'-双[3-（三乙氧基甲硅烷基）丙基]咪唑鎓取代的二乙醚双（三溴化物）锚定在 γ-Fe2O3 纳米颗粒的表面上并随后处理这种新的磁性纳米颗粒负载溴化试剂含溴离子液体。纳米颗粒试剂具有良好的负载水平，并已成功用于各种烯烃、炔烃、酮和芳香族底物的有效溴化。更重要的是，该试剂可以通过外部磁铁轻松回收并重复使用六次而不会显着降低活性。
• From 4-nitrotoluene and 4,4′-dinitrobibenzyl to <i>E</i>-4,4′-dinitrostilbene: an electrochemical approach
  作者：Iluminada Gallardo、Ana Belén Gómez、Gonzalo Guirado、Adrián Lariño、Miquel Moreno、Manuel Ortigosa、Sergio Soler

  DOI：10.1039/c8nj00131f

  日期：——

  The dianions formed by the electroreduction of Z-O2NC6H4CHCHC6H4NO2, E-O2NC6H4CHCHC6H4NO2, O2NC6H4CH2–CH2C6H4NO2 or O2NC6H4CMeH–CMeHC6H4NO2, as well as the anion radical arising from 4-nitrotoluene, are stable, in the time scale of cyclic voltammetry (DMF + 0.10 M NBu4BF4). However, in the electrolysis time scale (from minutes to hours), only the dianion O2NC6H4CMeH–CMeHC6H4NO22− remains stable, since

  通过Z -O 2 NC 6 H 4 CH CHC 6 H 4 NO 2，E -O 2 NC 6 H 4 CH CHC 6 H 4 NO 2，O 2 NC 6 H 4 CH 2 -CH 2的电还原形成的阴离子。C 6 H 4 NO 2或O 2 NC 6 H 4 CMeH–CMeHC 6 H在循环伏安法（DMF + 0.10 M NBu 4 BF 4）的时间范围内， 4 NO 2以及由4-硝基甲苯产生的阴离子自由基是稳定的。但是，在电解时间范围内（从几分钟到几小时），只有二价阴离子O 2 NC 6 H 4 CMeH–CMeHC 6 H 4 NO 2 2-保持稳定，因为还原的物质Z -O 2 NC 6 H 4 CHCHC 6 H 4 NO 2 2-，O 2 NC 6 H4 CH 2 -CH 2 C ^ 6 ħ 4 NO 2 2-或O的2 NC 6 H ^ 4 ME - ，进化以形成ë -O 2 NC
• Reduction with Samarium(0). Debromination of<i>vic</i>-Dibromides to Alkenes
  作者：Reiko Yanada、Kiyoshi Bessho、Kazuo Yanada

  DOI：10.1246/cl.1994.1279

  日期：1994.7

  Three electrons from Sm(0) to Sm(III) can be available during the title reduction which was achieved in 90–95% yield with vic-dibromides such as trans-10,11-dibromodibenzosuberone, meso- and dl-1,2-dibromo-1,2-diphenylethane, ethyl 2,3-dibromo-3-phenylpropionate, 2,3-dibromo-3-phenylpropionic acid, and cholesterol dibromide. These reductions were accelerated with a catalytic amount of acid.

  在标题还原过程中，Sm(0)向Sm(III)转移三个电子的操作可以通过使用诸如反式-10,11-二溴二苯并苏勃酮、内消旋和外消旋-1,2-二溴-1,2-二苯基乙烷、乙基2,3-二溴-3-苯基丙酸酯、2,3-二溴-3-苯基丙酸以及胆固醇二溴化物等邻二溴化物来实现，产率高达90-95%。这些还原过程可通过加入少量酸催化加速。