2-氨基-3,4,5,6-四溴苯甲酸 | 54098-90-7

• 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: 2-氨基-3,4,5,6-四溴苯甲酸
• 英文名称: tetrabromoanthranilic acid
• 英文别名: 2-Amino-3,4,5,6-tetrabromobenzoic acid
• CAS: 54098-90-7
• 化学式: C₇H₃Br₄NO₂
• 分子量: 452.722
• InChiKey: CLLXPTWYWVRGCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.32
• 氢给体数：
  2.0
• 氢受体数：
  2.0

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-AMINO-3,4,5,6-TETRABROMO-BENZOIC ACID
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. : 54098-90-7
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
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
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 R36/37/38
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 Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
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 : C7H3Br4NO2
Molecular Weight : 452,72 g/mol
CAS-No. : 54098-90-7
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-AMINO-3,4,5,6-TETRABROMO-BENZOIC ACID
Skin Irrit. 2; Eye Irrit. 2; STOT -
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2-AMINO-3,4,5,6-TETRABROMO-BENZOIC ACID
Xi, R36/37/38 -
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
Carbon oxides, nitrogen oxides (NOx), 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
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 contact with skin and eyes. 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
Safety glasses with side-shields conforming to EN166 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
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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 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: 3,389
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
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
Specific target organ toxicity - single exposure
May cause respiratory irritation.
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：

  2-氨基-3,4,5,6-四溴苯甲酸 在 tetrafluoroboric acid 、 亚硝酸正戊酯 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 2-carboxy-3,4,5,6-tetrabromobenzenediazonium fluoroborate
  参考文献：
  名称：

  Aryne formation from 1-(3'-carboxyaryl)-3,3-dimethyl triazenes

  摘要：

  DOI：

  10.1016/0040-4020(95)00115-o
• 作为产物：
  描述：

  四溴苯酐 生成 2-氨基-3,4,5,6-四溴苯甲酸
  参考文献：
  名称：

  芳烃化学。第二十八部分。由四卤代邻氨基苯甲酸产生的四卤代联苯胺的一些其他环加成反应

  摘要：

  可以从相应的四卤代邻氨基苯甲酸高效地生成四溴和四碘联苯胺，并在与芳族底物的溶液中进行环加成反应。竞争数据已与四氯和四氟苯并ne的竞争数据进行了比较。在亚硝酸3-甲基丁基酯的存在下，某些取代的四溴苯并-barrelenes被转化为萘衍生物。

  DOI：

  10.1039/j39710000567

文献信息

• Synthesis of sterically crowded 9-nitrotriptycenes by the Diels–Alder cycloaddition reaction
  作者：Artur Szupiluk

  DOI：10.1016/j.tetlet.2016.10.041

  日期：2016.11

  The synthesis of novel sterically crowded triptycenes as attractive components for the construction of models for various molecular dynamic studies is reported. 9-Nitrotriptycenes were obtained by the Diels–Alder reactions between 9-nitroanthracene and tetrabromobenzyne as well as 1,4-dichloro-9-nitroanthracene and 2,6-dichlorobenzyne. Interesting regioselectivity relative to the central and terminal

  报道了新颖的空间拥挤的三联体的合成，作为构成各种分子动力学研究模型的有吸引力的组分。9-硝基三萜烯是通过9-硝基蒽和四溴苯并ne以及1,4-二氯-9-硝基蒽和2,6-二氯苯并the之间的Diels-Alder反应获得的。观察到相对于中心和末端环有趣的区域选择性。此外，将1,2,3,4-四溴三苯甲基-9-硝基三茂烯进一步官能化以分两步得到1,2,3,4-四溴三苯甲基-9-四氟硼酸铵。基于单晶X射线衍射数据估计了位阻对分子几何形状的影响。
• Restricted Rotation Involving the Tetrahedral Carbon. XXXIX. 9-(2-Methoxy-1-methylethyl)triptycene Derivatives
  作者：Masahiko Suzuki、Gaku Yamamoto、Hiromi Kikuchi、Michinori Oki

  DOI：10.1246/bcsj.54.2383

  日期：1981.8

  benzynes to examine the feasibility of isolating rotational isomers of 9-isopropyltriptycene derivatives at room temperature. They afforded crystalline ap forms which underwent internal rotation with activation energies of ca. 23 kcal/mol. 9-(2-Acetoxy-1-methylethyl)-1,2,3,4-tetrachlorotriptycene gave similar results. Based on the results, the barrier to rotation of 9-isopropyl-1,2,3,4-tetrabromotriptycene

  从 9-(2-甲氧基-1-甲基乙基) 蒽和相应的苄制备 9-(2-甲氧基-1-甲基乙基)triptycenes 以检查在室温下分离 9-isopropyltriptycene 衍生物的旋转异构体的可行性。他们提供了结晶 ap 形式，该形式经历了内部旋转，活化能约为。23 大卡/摩尔。9-(2-乙酰氧基-1-甲基乙基)-1,2,3,4-四氯三苯产生类似的结果。根据结果​​，重新检查了 9-异丙基-1,2,3,4-四溴三苯环烯的旋转障碍，表明它必须在 175 °C 下校正为 23.5 kcal/mol。
• Restricted Rotation Involving the Tetrahedral Carbon. LIX. Stereodynamics of Singly<i>peri</i>-Substituted 9-(3,5-Dimethylphenoxy)triptycene Derivatives
  作者：Gaku Yamamoto、Michinori Oki

  DOI：10.1246/bcsj.59.3597

  日期：1986.11

  mol−1 for the C(CH3)3 one. Molecular mechanics calculations (MM2) were performed on closely related model compounds to obtain the relative steric energies of the ground states and the possible transition states. The results from the dynamic NMR and the molecular mechanics studies suggest the following: When the peri-substituent is small (F and OCH3), the complete gear rotational circuit with the passing

  以 F、OCH3、CH3、Br 和 C(CH3)3 作为周围取代基的 9-(3,5-二甲基苯氧基)triptycene 的五个单周围取代衍生物被合成，并研究了它们的动态核磁共振行为。在任何一种化合物中，苯氧基部分中的两个间甲基基团在低温下是不等时的，并且在升高温度时信号合并成一个单峰。线形分析为速率过程提供了能量势垒，范围从 F 化合物的 10.1 kcal mol-1 (1 calth=4.184 J) 到 C(CH3)3 化合物的 17.6 kcal mol-1。对密切相关的模型化合物进行分子力学计算 (MM2)，以获得基态和可能的过渡态的相对空间能。动态核磁共振和分子力学研究的结果表明：
• Restricted Rotation Involving the Tetrahedral Carbon. XIV. Conformational Equilibria and Attractive Interactions in Substituted 9-Benzyltriptycenes
  作者：Fumio Suzuki、Michinori Oki

  DOI：10.1246/bcsj.48.596

  日期：1975.2

  Several 9-benzyltriptycene derivatives were prepared by addition of benzynes to 9-benzylanthracenes. Rotation about the C9–Cbenzyl bond of compounds with a substituent at a peri-position to the benzyl group was found to be frozen at low temperatures on the NMR time scale but not at room temperature. In contrast, compounds with two substituents at two peri-positions to the benzyl group showed a frozen rotation about the C9–Cbenzyl bond at room temperature. Distribution of the conformers, as judged from the PMR intensities, showed preference to the dl-isomers in spite of the fact that they are the ones which are highly disfavored by steric effects. Interpretation of the phenomenon was based on the fact that attractive interactions, mainly charge-transfer type, exist between the substituted benzo group in the triptycene skeleton and the benzene ring in the benzyl group.

  通过将苄基加到 9-苄基蒽中，制备了几种 9-苄基三联苯衍生物。在核磁共振时间尺度上发现，在低温下，苄基的一个周边位置上有一个取代基的化合物围绕 C9-Cbenzyl 键的旋转被冻结，而在室温下则没有。与此相反，在苄基的两个周边位置上有两个取代基的化合物在室温下显示出围绕 C9-Cbenzyl 键的冻结旋转。根据 PMR 强度判断，尽管 dl-异构体受立体效应的影响很大，但其构象的分布却偏向于 dl-异构体。对这一现象的解释是，三庚烯骨架中的取代苯并基和苄基中的苯环之间存在吸引力相互作用，主要是电荷转移类型的相互作用。
• Restricted Rotation Involving the Tetrahedral Carbon. L. Rotamer Distributions and Rotational Barriers in Some 9-(1-Methoxyethyl)triptycene Derivatives
  作者：Yoshiyuki Tanaka、Gaku Yamamoto、Michinori Oki

  DOI：10.1246/bcsj.56.3023

  日期：1983.10

  appropriate benzynes. Rotamer distributions and rotational barriers about the bridgehead-to-substituent bond were studied by NMR spectroscopy. Rotamer distributions are governed mainly by the steric effect; the major rotamer is assigned to sc*(S*), the minor one to ap, and the third one found only in the tetrafluoro derivative to sc*(R*). Rotational barriers are 21–23 kcal mol−1 which are slightly lower

  1,4-二甲基-和 1,2,3,4-四卤-9-(1-甲氧基乙基)triptycenes (卤素 = F、Cl 和 Br) 是通过 9-(1-甲氧基乙基) 蒽与适当的反应合成的苯。通过核磁共振光谱研究了桥头-取代基键的旋转异构体分布和旋转势垒。旋转异构体分布主要受空间效应控制；主要旋转异构体分配给 sc*(S*)，次要旋转异构体分配给 ap，第三个仅在四氟衍生物中发现的分配给 sc*(R*)。旋转势垒为 21-23 kcal mol-1，略低于相应的 9-异丙基三苯环。