2-甲基-6-硝基苯酚 | 13073-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-甲基-6-硝基苯酚
• 中文别名: 6-硝基邻甲酚；6-硝基邻甲酚 OR 2-甲基-6-硝基苯酚
• 英文名称: 2-methyl-6-nitrophenol
• 英文别名: 6-methyl-2-nitrophenol；2-hydroxy-3-methylnitrobenzene
• CAS: 13073-29-5
• 化学式: C₇H₇NO₃
• mdl: MFCD00031116
• 分子量: 153.137
• InChiKey: AQDKZPFDOWHRDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  147℃
• 沸点：
  235.8±20.0℃ (760 Torr)
• 密度：
  1.320±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  104.0±10.2℃
• 亨利常数：
  3.36e-05 atm-m3/mole
• 保留指数：
  1270

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2908999090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P273,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险品运输编号：
  2446
• 危险性描述：
  H301,H315,H319,H412
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methyl-6-nitrophenol
Synonyms: 2-Hydroxy-3-nitrotoluene

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Methyl-6-nitrophenol
CAS number: 13073-29-5

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H7NO3
Molecular weight: 153.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-甲基-6-硝基苯酚 在 sodium hydroxide 、 硝酸 、 potassium carbonate 、 xylene 作用下， 生成 二硝酚
  参考文献：
  名称：

  Robinson, Journal of the Chemical Society, 1916, vol. 109, p. 1087

  摘要：

  DOI：
• 作为产物：
  描述：

  邻甲酚 在 2-氯-1-甲基吡啶碘化物 、 水 、 silica gel 、 sodium nitrite 作用下， 以 正己烷 为溶剂， 反应 4.0h， 以88%的产率得到2-甲基-6-硝基苯酚
  参考文献：
  名称：

  N-Methyl-2-Chloropyridinium Iodide/NaNO₂/Wet SiO₂: Neutral Reagent System for the Nitration of Activated Aromatic Compounds under Very Mild Conditions

  摘要：

  在中性、非常温和和环境友好的反应条件下，开发了使用N-甲基-2-氯吡啶碘化物（Mukaiyama试剂）/NaNO2/湿硅胶反应体系对活化芳香化合物进行单硝化的方法。多种结构多样的芳香环在该条件下进行反应，得到相应的硝基芳香化合物，产率中等较高。

  DOI：

  10.2174/157017861202150213105836
• 作为试剂：
  描述：

  、 邻甲酚 、 硝酸 、 在 乙酸乙酯 、 水 、 碳酸氢钠 、 Sodium sulfate-III 、 silica gel 、 ethyl acetate benzene 、 2-甲基-6-硝基苯酚 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以giving the desired compound, 2-methyl-6-nitrophenol的产率得到2-甲基-6-硝基苯酚
  参考文献：
  名称：

  Acridinium compounds and conjugates thereof

  摘要：

  Acridinium化合物的一般化学式为（I），其中A是介入基团，不具有与特定结合物质结合的活性，Z是标记活性基团，具有与特定结合物质结合的活性，R.sup.1是卤素原子，烷基或芳基；R.sup.2，R.sup.3，R.sup.4和R.sup.5分别是氢原子，烷基，芳基，烷氧基，硝基，卤素原子或羰基，Y是计数离子。Acridinium化合物可以与特定结合物质形成共轭物。Acridinium化合物具有高发射效率和稳定性，因此可用作化学发光标记剂。

  公开号：

  US05594112A1

文献信息

• Palladium-catalyzed C–O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides
  作者：Guoshu Chen、Albert S.C. Chan、Fuk Yee Kwong

  DOI：10.1016/j.tetlet.2006.11.036

  日期：2007.1

  palladium-catalyzed carbon–oxygen bond formation is reported. The palladium-tri-tert-butylphosphine complex was found to be effective in converting haloarenes to corresponding substituted phenols. This methodology offers a direct transformation of aryl halides to phenols, as well as the straightforward application to generate a wide variety of diaryl or alkyl/aryl ethers.

  据报道，形成了一种简单有效的钯催化的碳氧键。钯-三-叔丁基膦配合物被发现是有效的卤代芳烃转化成相应的取代的酚。这种方法可以将芳基卤化物直接转化为苯酚，并且可以直接用于生成各种二芳基或烷基/芳基醚。
• Highly efficient nitration of phenolic compounds by zirconyl nitrate
  作者：J. Jon Paul Selvam、V. Suresh、K. Rajesh、S. Ravinder Reddy、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2006.02.057

  日期：2006.4

  Zirconyl nitrate was found to be an excellent reagent in the nitration of phenol and substituted phenols to give nitrated phenols. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity.

  发现硝酸氧锆是在苯酚和取代的苯酚的硝化中得到硝化的苯酚的极好试剂。该方法在室温下对大多数实施例有效地进行，以高的区域选择性以中等至良好的产率产生硝基衍生物。
• A New Method for Nitration of Phenolic Compounds
  作者：Min Shi、Shi‐Cong Cui

  DOI：10.1002/adsc.200303111

  日期：2003.11

  Phenolic compounds can be nitrated by 65% nitric acid in the presence of catalytic amounts of montmorillonite KSF and bismuth(III) nitrate to give the corresponding nitrated products in good yields in a heterogeneous phase. The co-catalyst of KSF and Bi(NO3)3 can be easily recovered and reused in the next batch of nitration.

  在催化量的蒙脱土KSF和硝酸铋（III）存在下，可以用65％的硝酸将酚类化合物硝化，从而在异相中以良好的收率得到相应的硝化产物。KSF和Bi（NO 3）3的助催化剂可以很容易地回收并在下一批硝化中重复使用。
• Calcium Nitrate—A New Nitrating Agent for Nuclear Nitration of Substituted Phenols
  作者：S. C. Bisarya、S. K. Joshi、A. G. Holkar

  DOI：10.1080/00397919308018590

  日期：1993.4

  Abstract Nitration of selected substituted phenols using Calcium Nitrate as a new nitrating agent is reported, compared with sodium nitrate and the dependance of product selectivity on temperature is demonstrated.

  摘要 报道了使用硝酸钙作为新型硝化剂硝化选定的取代酚，与硝酸钠相比，并证明了产物选择性对温度的依赖性。
• Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride
  作者：Hussni Muathen

  DOI：10.3390/80700593

  日期：——

  Bismuth subnitrate/thionyl chloride have been found to be an efficient combination of reagents for nitration of a wide range of aromatic compounds in dichloromethane. Phenols, in particular, were easily mononitrated and dinitrated with the reagents by controlling the stoichiometry,

  已发现碱式硝酸铋/亚硫酰氯是一种有效的试剂组合，可用于在二氯甲烷中硝化多种芳香族化合物。尤其是酚类，通过控制化学计量，很容易与试剂一起单硝化和二硝化，

表征谱图