4,N-二羟基苯甲酰胺 | 5941-13-9

• 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,N-二羟基苯甲酰胺
• 英文名称: 4-hydroxyphenylhydroxamic acid
• 英文别名: 4-hydroxy benzhydroxamic acid；4-hydroxybenzohydroxamic acid；p-hydroxybenzohydroxamic acid；p-hydroxybenzhydroxamic acid；N,4-dihydroxybenzamide；4-OH-Pha
• CAS: 5941-13-9
• 化学式: C₇H₇NO₃
• 分子量: 153.137
• InChiKey: QEQCHLVBRHGAQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : P-HYDROXYBENZOHYDROXAMIC ACID
CAS-No. : 5941-13-9

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 3)
Skin irritation (Category 2)
Serious eye damage (Category 1)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Toxic if swallowed. Irritating to respiratory system and skin. Risk of serious damage to eyes.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
Toxic if swallowed.
Causes skin irritation.
Causes serious eye damage.
May cause respiratory irritation.
Precautionary statement(s)
Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
Wear protective gloves/ eye protection/ face protection.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
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
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R25 Toxic if swallowed.
R37/38 Irritating to respiratory system and skin.
R41 Risk of serious damage to eyes.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S39 Wear eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C7H7NO3
Molecular Weight : 153,14 g/mol
Component Concentration
P-HYDROXYBENZOHYDROXAMIC ACID
CAS-No. 5941-13-9 -

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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. Take victim immediately to hospital. 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
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, nitrogen oxides (NOx)
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
Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate
ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
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
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
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).

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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: 1,098
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
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Inhalation: 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
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
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Toxic if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes eye burns.
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
Harmful to aquatic life.
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: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (P-HYDROXYBENZOHYDROXAMIC ACID)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (P-HYDROXYBENZOHYDROXAMIC ACID)
IATA: Toxic solid, organic, n.o.s. (P-HYDROXYBENZOHYDROXAMIC ACID)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4,N-二羟基苯甲酰胺 在 nickel(II) perchlorate hexahydrate 、 2,9-二丁基-1,10-邻二氮杂菲 、 频那醇硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.67h， 生成
  参考文献：
  名称：

  1,4,2-二恶唑-5-酮对烯烃进行硫醚导向的NiH催化远程γ-C(sp3)-H加氢酰胺化

  摘要：

  开发了一种 NiH 催化的硫醚导向的环金属化策略，以实现未活化烯烃的远程亚甲基 C-H 键酰胺化。由于优先形成五元镍环，由 NiH 插入烯烃引发的链式异构化可以在远离烯烃部分的 γ-亚甲基位点终止。通过使用 2,9-二丁基-1,10-菲咯啉 ( L4 ) 作为配体和二恶唑酮作为试剂，酰胺化发生在 γ-C(sp 3 )-H 键上，以提供高达 90% 的酰胺产物产量（> 40 个例子）具有显着的区域选择性（高达 24:1 rr）。

  DOI：

  10.1021/jacs.1c05834
• 作为产物：
  描述：

  4-hydroxy-N-((tetrahydro-2H-pyran-2-yl)oxy)benzamide 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以10%的产率得到4,N-二羟基苯甲酰胺
  参考文献：
  名称：

  受阿司匹林启发的乙酰基供体 HDAC 抑制剂

  摘要：

  阿司匹林是治疗炎症、发烧和疼痛的最古老的药物之一。据报道，通过乙酰化丝氨酸氨基酸残基来共价修饰 COX-2 酶。凭借阿司匹林的乙酰化潜力，我们首次开发了新型乙酰基供体 HDAC 抑制剂。在这项研究中，我们报告了乙酰基供体 HDAC 抑制剂的设计、合成、计算机对接研究和生物学评估。MDA-MB-231 细胞与化合物 4c 的接触显着促进了 α-微管蛋白和组蛋白 H3 的乙酰化，它们分别是 HDAC6 和 HDAC1 的底物。计算机对接模拟还表明，化合物 4c 通过以双齿方式配位活性锌离子并与 Ser531 和 His573 氨基酸残基形成氢键相互作用，与 HDAC6 的深层底物结合口袋紧密结合。特别是，化合物 4c (GI50 = 147 μM) 与其母体化合物 2c (GI50 > 1000 μM) 和乙酰基供体缺陷化合物 6 (GI50) 相比，显着增强了对 MDA-MB-231 细胞的抗增殖作用=

  DOI：

  10.1007/s12272-018-1045-z

文献信息

• 히스톤 탈아세틸효소 억제제 및 이의 용도
  申请人：INDUSTRY ACADEMIC COOPERATION FOUNDATION KEIMYUNG UNIVERSITY 계명대학교 산학협력단(220040180743) BRN ▼503-82-09622

  公开号：KR102023845B1

  公开（公告）日：2019-11-04

  본 발명은 신규한 히스톤 탈아세틸효소 억제제 및 이의 의학적 용도에 관한 것으로, 보다 상세하게 신규한 아스피린 유도체는 히스톤 탈아세틸효소(HDAC)의 기질 결합 주머니에 결합함으로써 HDAC의 활성을 억제시키고 세포 내 α -튜불린 및 히스톤 H3의 아세틸화를 유의적으로 증가시켜 암세포 증식을 억제하는 효과를 나타내는 것이 확인됨에 따라, 상기 신규한 아스피린 유도체는 HDAC 억제제로 제공되어 HDAC과 관련된 암질환 및 중추신경계 질환에 효과적인 치료제로 제공될 수 있다.

  本发明涉及一种新型的组蛋白脱乙酰酶抑制剂及其医学用途，更具体地说，是一种新型的阿司匹林衍生物，它通过结合到组蛋白脱乙酰酶（HDAC）的天然结合口袋中来抑制HDAC的活性，并且显著增加细胞内α-微管蛋白和组蛋白H3的乙酰化，从而抑制癌细胞的增殖。因此，这种新型的阿司匹林衍生物可以作为HDAC抑制剂提供，用于治疗与HDAC相关的癌症和中枢神经系统疾病。
• Antimicrobial Activity of Hydroxamic Acids
  作者：JUNICHI HASE、KYOICHI KOBASHI、NOBUO KAWAGUCHI、KIYONORI SAKAMOTO

  DOI：10.1248/cpb.19.363

  日期：——

  o-, m- and p-alkyloxybenzohydroxamic acids were synthesized and subjected to the examination for antibacterial and antifungal activity. All the hydroxamic acids tested were almost ineffective for pathogens examined of Enterobacteriaceae, but some of alkyloxybenzo- and fatty acyl-hydroxamic acid were found to be as highly effective for pathogenic fungi as butyl p-hydroxybenzoate being used as a comparison. The increase of carbon number of p-alkyloxybenzo- and fatty acyl-hydroxamic acid led to the increase in their antifungal activity, reached to the maximum at C6 in alkyloxy moiety and C10 in fatty acyl derivatives, and then the gradual decrease in both series. Considering the inhibitory power of hydroxamic acid on plant and bacterial urease, we discussed the possible correlation between antimicrobial activity and inhibitory powers on urease activity of the compounds.

  o-、m- 和 p-烷氧基苯甲酰羟肟酸被合成并进行了抗菌和抗真菌活性的检测。所有测试的羟肟酸对所检测的肠杆菌科病原体几乎无效，但某些烷氧基苯甲酰和脂肪酸酰基羟肟酸被发现对病原真菌具有与作为比较标准的丁基对羟基苯甲酸酯相当的高效性。随着p-烷氧基苯甲酰和脂肪酸酰基羟肟酸中碳数的增加，其抗真菌活性也随之增强，在烷氧基部分达到C6和脂肪酸酰基衍生物部分达到C10时达到最高，随后在这两系列中逐渐下降。鉴于羟肟酸对植物和细菌脲酶的抑制作用，我们讨论了抗微生物活性与这些化合物对脲酶活性抑制能力之间可能的相关性。
• Benzoic hydroxamate-based iron complexes as model compounds for humic substances: synthesis, characterization and algal growth experiments
  作者：Ewelina Orlowska、Alexander Roller、Hubert Wiesinger、Marc Pignitter、Franz Jirsa、Regina Krachler、Wolfgang Kandioller、Bernhard K. Keppler

  DOI：10.1039/c5ra25256c

  日期：——

  complexes in pure water and seawater was monitored over 24 h by means of UV-Vis spectrometry. The ability to release iron from the synthesized model complexes has been investigated with algae growth experiments.

  制备了一系列带有苯氧异羟肟酸酯为O，O-螯合物的Fe III单体和二聚体配合物，并通过元素分析，IR光谱，UV-Vis光谱，电喷雾电离质谱（ESI-MS），循环伏安法，EPR光谱进行了表征对于某些示例，通过X射线衍射分析。通过UV-Vis光谱法监测合成的配合物在纯水和海水中的稳定性，历时24小时。已经通过藻类生长实验研究了从合成的模型配合物中释放铁的能力。
• A general concept for the introduction of hydroxamic acids into polymers
  作者：Tobias Johann、Jennifer Keth、Matthias Bros、Holger Frey

  DOI：10.1039/c9sc02557j

  日期：——

  Hydroxamic acids (HA) form stable complexes with a large variety of metal-ions, affording hydroxamates with high complexation constants. Hydroxamic acid moieties play a crucial role in the natural iron metabolism. In this work, 1,4,2-dioxazoles linked to a hydroxyl group are introduced as key compounds for the installation of hydroxamic acids at synthetic polymers in well-defined positions. A general

  异羟肟酸 (HA) 可与多种金属离子形成稳定的络合物，从而提供具有高络合常数的异羟肟酸盐。异羟肟酸部分在天然铁代谢中起着至关重要的作用。在这项工作中，与羟基相连的 1,4,2-二恶唑作为关键化合物被引入，用于将异羟肟酸安装在合成聚合物的明确位置。开发了一种通用合成方案，该方案提供了一系列新的功能性关键构件，可普遍用于获得基于异羟肟酸的单体和聚合物，例如作为受保护的 HA 功能引发剂或用于合成各种新型基于 HA 的单体，例如环氧化物或甲基丙烯酸酯。为了证明二恶唑保护的异羟肟酸具有优异的稳定性，通过氧阴离子聚合。在温和的酸性条件下，方便的后续脱保护是可行的。α-功能性HA-聚醚，即聚乙二醇、聚丙二醇和基于环氧乙烷、环氧丙烷和乙氧基乙基缩水甘油醚的聚甘油，分别在1000-8500 g mol 分子量范围内具有低分散度（<1.2）-1。水溶性异羟肟酸功能聚（乙二醇）（HA-PEG）被探索用于各种生物医学应用和表面涂层。Fe(
• Synthesis, structures and speciation studies of ruthenium(<scp>iii</scp>) hydroxamate/hydroximato complexes. Crystal and molecular structure of hydrated [Ru(H₂edta)(2-methoxyphenylhydroxamate)], the first structurally characterised ruthenium(<scp>iii</scp>)–hydroxamate complex
  作者：Jedd Comiskey、Etelka Farkas、Krystyna A. Krot-Lacina、Robin G. Pritchard、Charles A. McAuliffe (the late)、Kevin B. Nolan

  DOI：10.1039/b310193m

  日期：——

  first reported structure of a Ru(III)–hydroxamate, the carboxylato groups of the tetradentate H2edta are trans to each other and the amino nitrogen and hydroxamate oxygen donor atoms are roughly coplanar. Relevant bond lengths (Å) are: Ru–O(carboxylato) 2.016(4) and 2.044(3), Ru–O(hydroxamato O−) 1.964(4), Ru–O (hydroxamato CO) 2.019(4), Ru–N 2.060(4) and 2.156(4). Addition of R-PhaH to an aqueous solution

  K [Ru（Hedta）Cl]·1.5H 2 O与各种苯基异羟肟酸R-PhaH在水溶液中反应，得到异羟肟酸酯络合物[Ru（H 2 edta）（R-Pha）]· x H 2 O，已经确定其中之一即水合的[Ru（H 2 edta）（2-OMe-Pha）]的晶体和分子结构，其中2-OMe-Pha = 2-甲氧基苯基异羟肟酸酯。在这个复合物中，Ru（III）–的第一个报告结构异羟肟酸酯中，四齿H的羧酸根基团2 EDTA是反式于彼此和氨基 氮和异羟肟酸酯的氧供体原子大致共面。相关的键长（A）为：钌-O（羧酸根）2.016（4）和2.044（3），RU-O（hydroxamatoø -）1.964（4），RU-O（hydroxamato CO）2.019（4），钌–N 2.060（4）和2.156（4）。在K [Ru（Hedta）Cl]·1.5H 2 O的水溶液中添加R-PhaH导致[Ru（edta）（R-Pha）]