3,3′,5,5′-四溴-1,1′-联苯 | 16400-50-3

• 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: 3,3′,5,5′-四溴-1,1′-联苯
• 中文别名: 3,5,3',5'-四溴联苯；1,3-二溴-苯基苯；3,3,5,5-四溴联苯
• 英文名称: 3,3',5,5'-tetrabromo-1,1'-biphenyl
• 英文别名: 3,3',5,5'-tetrabromobiphenyl；3,3’,5,5’-tetrabromobiphenyl；1,3-dibromo-5-(3,5-dibromophenyl)benzene
• CAS: 16400-50-3
• 化学式: C₁₂H₆Br₄
• 分子量: 469.796
• InChiKey: FXJXZYWFJAXIJX-UHFFFAOYSA-N

物化性质

• 熔点：
  185-190℃
• 沸点：
  401.8±40.0 °C(Predicted)
• 密度：
  2.140±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、二氯甲烷（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

多溴联苯（PBBs）可以通过口服、吸入和皮肤途径被吸收。由于它们的亲脂性，尤其是高溴代的多溴联苯，倾向于在富含脂质的组织中积累，如肝脏、脂肪、皮肤和母乳。某些多溴联苯化合物通过由苯巴比妥诱导的细胞色素P-450类型的微粒体单加氧酶系统进行代谢。代谢速率可能取决于溴取代模式。低溴含量的多溴联苯同系物转化为主要在尿液中排出的羟基衍生物。高溴代同系物要么被保留，要么在粪便中不变排出。(L628)

PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

多氯联苯（PBBs）的毒性机制因具体同系物而异。主要的相互作用被认为是涉及芳基烃受体（AhR）。PBBs与AhR结合并激活它，进而启动一系列基因的转录上调，影响生化途径和内分泌途径、细胞周期调节、形态发生、氧化应激反应以及各种其他过程。这导致PBBs特有的多种毒性反应。一些已知的诱导基因包括细胞色素P-450依赖性单加氧酶CYP1A1和CYP1A2。

The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

2A，可能对人类致癌。（L135）

2A, probably carcinogenic to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

PBB暴露可能会导致体重减轻、皮肤问题（如痤疮）、神经和免疫系统的影响，以及对肝脏、肾脏和甲状腺的影响。

PBB exposure may cause weight loss, skin disorders (such as acne), nervous and immune systems effects, and effects on the liver, kidneys, and thyroid gland. (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L628）；吸入（L628）；皮肤给药（L628）

Oral (L628) ; inhalation (L628) ; dermal (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

PBB暴露的症状可能包括恶心、腹痛、食欲不振、关节痛、疲劳和虚弱。

Symptoms of PBB exposure may include nausea, abdominal pain, loss of appetite, joint pain, fatigue, and weakness. (L629)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R41
• WGK Germany：
  3
• 海关编码：
  2903999090
• 储存条件：
  室温且干燥

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: 3,3′,5,5′-Tetrabromo-1,1′-biphenyl
Product name
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. : 16400-50-3
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
Serious eye damage (Category 1), H318
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 R41
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 Danger
Hazard statement(s)
H318 Causes serious eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ eye protection/ face protection.
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 - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C12H6Br4
Molecular Weight : 469,79 g/mol
CAS-No. : 16400-50-3
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3,3',5,5'-Tetrabromo-1,1'-biphenyl
CAS-No. 16400-50-3 Eye Dam. 1; H318 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
3,3',5,5'-Tetrabromo-1,1'-biphenyl
CAS-No. 16400-50-3 Xi, R41 <= 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
no data available
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 formation of dust and aerosols.
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
Face shield and safety glasses 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. 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: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 185 - 190 °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 16,22 - (Air = 1.0)
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
Relative vapour density 16,22 - (Air = 1.0)

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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

制备方法与用途

3,3,5,5-四溴联苯是一种烃类衍生物，主要用作医药原料。

反应信息

• 作为反应物：
  描述：

  3,3′,5,5′-四溴-1,1′-联苯 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 氯仿 、 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Tetraarylbiphenyl as a New Lattice Inclusion Host by Structure Reductionism: Shape and Size Complementarity Based on Torsional Flexibility

  摘要：

  3,3',5,5'-Tetrakis(2,6-dimethyl-4-methoxyphenyl)biphenyl (TB) was designed as a lattice inclusion host based on a structure reductionistic approach. TB binds guests in two different domains based on the premise that the two phenyl rings of the biphenyl core remain coplanar in the solid state. The versatility of TB as a host has been demonstrated by its ability to include different guest molecules in the crystal lattice, as revealed by X-ray crystal structure analyses. One observes preference for guest location in the concave domain with the trough domain compromised. The host TB is found to exploit torsional freedom about the central c-bond between the two phenyl rings of the biphenyl core to adopt discrete structures that are complementary in terms of shape and size to include a given guest. In other words, TB behaves like a "molecular chameleon" that undergoes structural adaptation in response to the guest via torsional twist about the central sigma-bond. Quite remarkably, the inclusion compounds with different guests having similar torsional angles between the phenyl rings of the biphenyl core are found to be isostructural. The torsion-induced structural morphosis in response to the guest is found to completely offset binding in the trough region.

  DOI：

  10.1021/cg501711t
• 作为产物：
  描述：

  4,4'-二氨基-3,3'，5,5'-四溴联苯 在 硫酸 作用下， 生成 3,3′,5,5′-四溴-1,1′-联苯
  参考文献：
  名称：

  van Roosmalen, Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 359,362

  摘要：

  DOI：

文献信息

• [EN] PHOTOALIGNING MATERIAL<br/>[FR] MATÉRIAU DE PHOTOALIGNEMENT
  申请人：ROLIC AG

  公开号：WO2013017467A1

  公开（公告）日：2013-02-07

  The present invention relates to a copolymer for the photoalignment of liquid crystals comprising a photoreactive group as given below in formula (I), compositions thereof, and its use for optical and electro optical devices, especially liquid crystal devices (LCDs).

  本发明涉及一种共聚物，用于液晶的光调向，包括如下所示的具有光反应性基团的化合物（I）的公式，以及其组合物，以及其在光学和电光设备，特别是液晶设备（LCD）中的使用。
• PHOTOREACTIVE COMPOUNDS
  申请人：Lincker Frederic

  公开号：US20140192305A1

  公开（公告）日：2014-07-10

  The present invention relates to photoreactive compounds that are particularly useful in materials for the alignment of liquid crystals.

  本发明涉及光反应性化合物，特别适用于液晶对准材料的制作。
• Sterically controlled C–H/C–H homocoupling of arenes <i>via</i> C–H borylation
  作者：Xiaocong Pei、Guan Zhou、Xuejing Li、Yuchen Xu、Resmi C. Panicker、Rajavel Srinivasan

  DOI：10.1039/c9ob00995g

  日期：——

  A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain

  描述了一种温和的一锅法方案，该方案通过顺序的Ir催化的CH硼酸酯化和Cu催化的芳烃均偶联合成对称的联芳基。所形成的联芳基的区域化学空间上受CH硼酸酯化步骤的控制。该方法还成功地扩展到了杂芳烃。通过这种方法获得的某些产品无法通过Ullmann或Suzuki耦合协议获得。最后，我们显示了一锅序列描述了CH硼化/ Cu催化的均偶联/ Pd催化的Suzuki偶联以获得π扩展的芳烃骨架。
• Scalable synthesis of multi-substituted aryl-phosphonates: Exploring the limits of isoretical expansion and the synthesis of new triazene-based phosphonates
  作者：Derek Barbee、Andrew R. Barron

  DOI：10.1080/10426507.2019.1673750

  日期：2020.3.3

  the efficiency of the palladium-catalyzed Hirao cross-coupling reaction in the synthesis of substituted phosphonates; however, attempts to prepare derivatives with isoretical expansion through the cyclization of 4-(4′-bromophenyl)acetophenone resulted in an extremely low yield, with the isolation of the dimer intermediate. Ab initio calculations showed that while the trimerization of acetophenone is

  摘要 新型多取代芳基膦酸酯化合物的开发有望成为具有优异孔隙率和气体吸附性能的金属有机骨架 (MOF) 材料的新构件。我们证明了钯催化的 Hirao 交叉偶联反应在取代膦酸酯的合成中的效率；然而，尝试通过 4-(4'-溴苯基) 苯乙酮的环化制备具有等距扩展的衍生物的尝试导致极低的产率，并分离出二聚体中间体。从头算计算表明，虽然苯乙酮的三聚是放热的，但 4-苯基苯乙酮的三聚是吸热的。相比之下，4-(4'-溴苯基) 苄腈的环化是放热的，并允许形成适当的膦酸。苄腈方法还允许形成具有高位阻的邻甲基衍生物。本文报道的所有多取代芳基膦酸酯化合物都可以在多克规模上制备，使研究人员能够为膦酸酯 MOF 提供更广泛的构建模块。图形概要
• [EN] PHOTOALIGNING MATERIALS<br/>[FR] MATÉRIAUX DE PHOTOALIGNEMENT
  申请人：ROLIC AG

  公开号：WO2013050122A1

  公开（公告）日：2013-04-11

  The present invention relates to polymer, homo- or copolymer or oligomer, which, when irradiated with polarised light orients perpendicular to the polarization direction of polarized actinic light, for the photoalignment of liquid crystals, especially for the planar orientation of liquid crystals, and which derives from at least one monomer (I), compositions thereof, and its use for optical and electro optical devices, such as, liquid crystal devices (LCDs), especially for planar orientation of liquid crystals.

  本发明涉及与极化光辐照时垂直于极化作用光的极化方向定向的聚合物、同聚物或寡聚物，用于液晶的光配向，特别是用于液晶的平行定向，其来源于至少一种单体(I)，以及其组成物和其在光学和电光设备中的使用，例如液晶装置（LCDs），特别是用于液晶的平行定向。

表征谱图