5-甲基-2-硝基苯胺 | 578-46-1

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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: 5-甲基-2-硝基苯胺
• 中文别名: 3-氨基-4-硝基甲苯；5-甲基-2-硝基苯氨；6-硝基间甲苯胺；2-硝基-5-甲基苯胺
• 英文名称: 5-methyl-2-nitroaniline
• 英文别名: 2-nitro-5-methylaniline；5-methyl-o-nitroaniline
• CAS: 578-46-1
• 化学式: C₇H₈N₂O₂
• mdl: MFCD00007814
• 分子量: 152.153
• InChiKey: IGDYNWKWXUCIJB-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C (lit.)
• 沸点：
  312.4±22.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)
• 物理描述：
  5-methyl-2-nitroaniline appears as yellow leaflets (from water) or orange powder. (NTP, 1992)
• 溶解度：
  less than 1 mg/mL at 73° F (NTP, 1992)
• 稳定性/保质期：
  稳定性和反应性： 避免的物料：氧化物。 要分解的产品包括一氧化碳、二氧化碳和氧化氮。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T,N
• 安全说明：
  S28,S36/37,S45,S61
• 危险类别码：
  R23/24/25,R51/53,R33
• WGK Germany：
  3
• 海关编码：
  2921430090
• RTECS号：
  XU8060000
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN 2660 6.1/PG 3
• 危险性防范说明：
  P261,P273,P280,P301+P310,P311
• 危险性描述：
  H301+H311+H331,H373,H411
• 储存条件：
  贮存： 将密器密封后，放入密封的主藏器中，并置于阴凉、干燥处。

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 5-Methyl-2-nitroaniline
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. : 578-46-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Inhalation (Category 3), H331
Acute toxicity, Dermal (Category 3), H311
Acute toxicity, Oral (Category 3), H301
Specific target organ toxicity - repeated exposure (Category 2), H373
Chronic aquatic toxicity (Category 2), H411
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
T Toxic R23/24/25
R33
N Dangerous for the R51/53
environment
T Toxic R23/24/25
R33
N Dangerous for the R51/53
environment
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)
H301 Toxic if swallowed.
H311 Toxic in contact with skin.
H331 Toxic if inhaled.
H373 May cause damage to organs through prolonged or repeated exposure.
H411 Toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P273 Avoid release to the environment.
P280 Wear protective gloves/ protective clothing.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
P311 Call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
Synonyms : 6-Nitro-m-toluidine
Formula : C7H8N2O2
Molecular weight : 152,15 g/mol
CAS-No. : 578-46-1
EC-No. : 209-423-7
Index-No. : 612-025-00-X
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
5-Methyl-o-nitroaniline
CAS-No. 578-46-1 Acute Tox. 3; STOT RE 2; <= 100 %
EC-No. 209-423-7 Aquatic Chronic 2; H301 +
Index-No. 612-025-00-X H311 + H331, H373, H411
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
5-Methyl-o-nitroaniline
CAS-No. 578-46-1 T, N, T, N, R23/24/25 - R33 - <= 100 %
EC-No. 209-423-7 R51/53R23/24/25 - R33 -
Index-No. 612-025-00-X R51/53
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

---

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
Flush eyes with water as a precaution.
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

---

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 firefighting if necessary.
Further information
No data available

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. 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
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.

---

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)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

---

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.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
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 N99 (US) or type P2 (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
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

---

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: orange
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing Melting point/range: 110 - 111 °C - lit.
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- 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
No data available

---

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, Strong bases
Hazardous decomposition products
Other decomposition products - No data available
In the event of fire: see section 5

---

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
May cause damage to organs through prolonged or repeated exposure.
Aspiration hazard
No data available
Additional Information
RTECS: XU8060000
Absorption into the body leads to the formation of methemoglobin which in sufficient concentration causes
cyanosis. Onset may be delayed 2 to 4 hours or longer., To the best of our knowledge, the chemical,
physical, and toxicological properties have not been thoroughly investigated.

---

SECTION 12: Ecological information
Toxicity
Toxicity to fish LC50 - Pimephales promelas (fathead minnow) - 21,8 mg/l - 96,0 h
Toxicity to daphnia and EC50 - Daphnia magna (Water flea) - 5,8 mg/l - 48 h
other aquatic
invertebrates
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
Toxic to aquatic life with long lasting effects.

---

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.

---

SECTION 14: Transport information
UN number
ADR/RID: 2660 IMDG: 2660 IATA: 2660
UN proper shipping name
ADR/RID: NITROTOLUIDINES (MONO)
IMDG: NITROTOLUIDINES (MONO)
IATA: Nitrotoluidines (mono)
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: yes IMDG Marine pollutant: yes IATA: no
Special precautions for user
No data available

---

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
For this product a chemical safety assessment was not carried out

---

SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Aquatic Chronic Chronic aquatic toxicity
H301 Toxic if swallowed.
H301 + H311 + Toxic if swallowed, in contact with skin or if inhaled
H331
H311 Toxic in contact with skin.
H331 Toxic if inhaled.
H373 May cause damage to organs through prolonged or repeated exposure.
H411 Toxic to aquatic life with long lasting effects.
Full text of R-phrases referred to under sections 2 and 3
N Dangerous for the environment
T Toxic
R23/24/25 Toxic by inhalation, in contact with skin and if swallowed.
R33 Danger of cumulative effects.
R51/53 Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic
environment.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

制备方法

用于有机合成中间体。

用途简介 用途

用于有机合成中间体。

反应信息

• 作为反应物：
  描述：

  5-甲基-2-硝基苯胺 在 四羟基二硼 、 水 作用下， 反应 8.0h， 以86%的产率得到3,4-二氨基甲苯
  参考文献：
  名称：

  用 B2(OH)4/H2O 将硝基芳烃无金属还原为胺

  摘要：

  已经开发出一种由二硼酸在温和条件下用水作为氢供体和溶剂介导的硝基芳烃的无金属还原。以良好的官能团耐受性和良好的收率获得了一系列芳香胺。

  DOI：

  10.1055/s-0037-1610086
• 作为产物：
  描述：

  5-甲基-2-硝基苯甲醚 在 copper(I) oxide 、 ammonium hydroxide 作用下， 生成 5-甲基-2-硝基苯胺
  参考文献：
  名称：

  黄素合成素VIII。在Flavinreihe中合成6-甲基-9- [ d，1'-核糖基]-异阿洛嗪和合成代谢

  摘要：

  DOI：

  10.1002/hlca.193501801188

文献信息

• Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study
  作者：Julien Pedron、Clotilde Boudot、Sébastien Hutter、Sandra Bourgeade-Delmas、Jean-Luc Stigliani、Alix Sournia-Saquet、Alain Moreau、Elisa Boutet-Robinet、Lucie Paloque、Emmanuelle Mothes、Michèle Laget、Laure Vendier、Geneviève Pratviel、Susan Wyllie、Alan Fairlamb、Nadine Azas、Bertrand Courtioux、Alexis Valentin、Pierre Verhaeghe

  DOI：10.1016/j.ejmech.2018.06.001

  日期：2018.7

  important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from −1.1 to −0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above −0.6 V

  为了研究抗寄生虫8-硝基喹啉-2（1 H）-一药效基团，以1-5个步骤合成了一系列31种衍生物，并在体外针对婴儿利什曼原虫和布鲁氏锥虫进行了评估。。并行地，通过循环伏安法测量所有分子的还原电势。构效关系首先表明，抗菌活性取决于内酰胺官能团与硝基之间的分子内氢键（通过X射线衍射描述），这是氧化还原电势（+0.3 V与氧化还原电势相比重要的变化）的重要原因。 8-硝基喹啉）。在计算化学的帮助下，设计了一组表现出大范围氧化还原电势（从-1.1至-0.45 V）的衍生物，并提供了一系列适合合成和测试的分子。该方法强调了在该系列中，只有氧化还原电势高于-0.6 V的底物才对婴儿乳杆菌具有活性。。然而，在T中未观察到氧化还原电势与体外抗寄生虫活性之间的这种关系。b。布鲁西。化合物22是该系列中的一种新型命中化合物，对人类HepG2细胞系既显示出抗疟原虫活性又具有抗锥虫活性，并且具有较低的细胞毒性。化合物22被L
• Novel N1-substituted 1,3-dihydro-2H-benzimidazol-2-ones as potent non-nucleoside reverse transcriptase inhibitors
  作者：Anna-Maria Monforte、Angela Rao、Patrizia Logoteta、Stefania Ferro、Laura De Luca、Maria Letizia Barreca、Nunzio Iraci、Giovanni Maga、Erik De Clercq、Christophe Pannecouque、Alba Chimirri

  DOI：10.1016/j.bmc.2008.06.012

  日期：2008.8

  synthesized and evaluated as anti-HIV agents. Some of them proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentration as potent non-nucleoside HIV-1 RT inhibitors (NNRTIs) with low cytotoxicity. SAR studies highlighted that the nature of the substituents at N(1) and on the benzene ring of benzimidazolone moiety significantly influenced the anti-HIV activity of this class

  合成了多个N（1）-取代的1,3-二氢-2H-苯并咪唑-2-酮，并作为抗HIV药物进行了评估。它们中的一些被证明在纳摩尔浓度下作为抑制细胞毒性低的有效非核苷HIV-1 RT抑制剂（NNRTIs）能有效抑制HIV-1复制。SAR研究突出表明，苯并咪唑酮部分的N（1）和苯环上的取代基的性质显着影响此类有效的抗逆转录病毒药物的抗HIV活性。
• H ₂ Activation with Co Nanoparticles Encapsulated in N‐Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles
  作者：Chuncheng Lin、Weihao Wan、Xueting Wei、Jinzhu Chen

  DOI：10.1002/cssc.202002344

  日期：2021.1.21

  Co nanoparticles (NPs) encapsulated in N‐doped carbon nanotubes (Co@NC900) are systematically investigated as a potential alternative to precious Pt‐group catalysts for hydrogenative heterocyclization reactions. Co@NC900 can efficiently catalyze hydrogenative coupling of 2‐nitroaniline to benzaldehyde for synthesis of 2‐phenyl‐1H‐benzo[d]imidazole with >99 % yield at ambient temperature in one step

  系统地研究了封装在N掺杂碳纳米管（Co @ NC 900）中的Co纳米颗粒（NPs）作为氢化杂环反应的宝贵Pt基催化剂的潜在替代品。Co @ NC 900可以高效地催化2-硝基苯胺与苯甲醛的加氢偶联，从而在室温下一步一步合成2-苯基-1 H-苯并[ d ]咪唑，收率> 99％。反应后，坚固的Co @ NC 900催化剂可以很容易地通过外部磁场回收，并且可以循环至少六次而活性没有明显下降。动力学实验表明，Co @ NC 900促进氢化是决定速率的步骤，总表观活化能为41±1 kJ mol -1。理论研究进一步表明，Co @ NC 900可以激活H 2和2-硝基苯胺的硝基。由于Co @ NC 900中存在受限的Co NP，在速率确定步骤中观察到的H 2离解的能垒仅为2.70 eV 。还探索了富地球和非贵族过渡金属催化剂的潜在工业应用，以实现绿色高效合成杂环化合物。
• Indium-mediated one-pot benzimidazole synthesis from 2-nitroanilines or 1,2-dinitroarenes with orthoesters
  作者：Jaeho Kim、Jihye Kim、Hyunseung Lee、Byung Min Lee、Byeong Hyo Kim

  DOI：10.1016/j.tet.2011.08.017

  日期：2011.10

  One-pot reduction-triggered heterocyclizations from 2-nitroanilines or 1,2-dinitroarenes to benzimidazoles were investigated in this study. In the presence of indium/AcOH in ethyl acetate at reflux, reaction of 2-nitroanilines or 1,2-dinitroarenes with R–C(OMe)3 (R=Me, Ph) produced excellent yields of the corresponding benzimidazoles within 30 min to 6 h depending on the substituents of the starting

  在此研究中，研究了从2-硝基苯胺或1,2-二硝基芳烃到苯并咪唑的一锅还原触发的杂环化反应。在乙酸乙酯中存在铟/ AcOH的条件下，回流时，2-硝基苯胺或1,2-二硝基芳烃与RC（OMe）3（R = Me，Ph）的反应在30分钟内可得到优异的相应苯并咪唑收率。 6小时取决于起始材料的取代基。在类似的反应条件下，与1,2-二硝基芳烃向苯并咪唑的铟介导的2-硝基苯胺到苯并咪唑的杂环化反应更快，并且产率更高。
• Bicyclic Benzimidazole Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators
  申请人：Egle Ian

  公开号：US20090192169A1

  公开（公告）日：2009-07-30

  Compounds of Formula I: wherein A, B, D, L, R 1 , R 2 , R 3 , R 4 , m, and n are as defined for Formula I in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

  式I的化合物： 其中A、B、D、L、R1、R2、R3、R4、m和n的定义如描述中所定义。本发明还涉及制备这些化合物的方法，以及用于制备的新中间体，含有这些化合物的药物组合物，以及这些化合物在治疗中的应用。