2-氨基-4-硝基苯甲醚 | 99-59-2

• 物质功能分类: 化学试剂 - 有机试剂 - 硝基化合物
• 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: 2-氨基-4-硝基苯甲醚
• 中文别名: 邻氨基对硝基苯甲醚；5-硝基邻茴香胺；大红色基R；5-硝基邻甲氧基苯胺；粗色基R；2-氨基-4-硝基茴香醚；2-甲氧基-5-硝基苯胺
• 英文名称: 3-amino-4-methoxynitrobenzene
• 英文别名: 2-Methoxy-5-nitroaniline
• CAS: 99-59-2
• 化学式: C₇H₈N₂O₃
• mdl: MFCD00007261
• 分子量: 168.152
• InChiKey: NIPDVSLAMPAWTP-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C(lit.)
• 沸点：
  337.07°C (rough estimate)
• 密度：
  1.2068
• 闪点：
  119℃
• 溶解度：
  20℃有机溶剂中的溶解度为382mg/L
• LogP：
  1.16 at 23℃
• 物理描述：
  5-nitro-o-anisidine appears as orange-red needles or orange powder. (NTP, 1992)
• 颜色/状态：
  ORANGE-RED NEEDLES FROM ALC, ETHER, WATER
• 分解：
  When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
• 解离常数：
  pKa = 2.49 (conjugate acid)
• 保留指数：
  1764.4
• 稳定性/保质期：

  避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

毒理性

• 致癌性证据

没有关于人类的数据可用。动物致癌性证据有限。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

5-硝基邻甲苯胺：因合理预期为人类致癌物而被除名。

5-Nitro-o-anisidine: delisted as reasonably anticipated to be a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：5-硝基-邻-茴香胺

IARC Carcinogenic Agent:5-Nitro-ortho-anisidine

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专论：第27卷（1982年）一些芳香胺、蒽醌和亚硝基化合物，以及用于饮用水和牙科制剂的无机氟化物

IARC Monographs:Volume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations

来源:International Agency for Research on Cancer (IARC)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S36/37,S45
• 危险类别码：
  R20/21/22
• WGK Germany：
  2
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2922299090
• 危险类别：
  6.1
• RTECS号：
  BZ7175000
• 包装等级：
  I; II; III
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335,H351,H361
• 储存条件：
  储存于阴凉、通风的库房，远离火种、热源，避免阳光直射，并进行密封包装。与氧化剂分开存放，禁止混储。配备相应种类和数量的消防器材。存储区应备有合适的材料以处理泄漏物。

SDS

Name:	2-Methoxy-5-nitroaniline 99% Material Safety Data Sheet
Synonym:	5-Nitro-o-anisidine; 3-Amino-4-Methoxynitrobenzene; 3-Nitro-6-Methoxyaniline
CAS:	99-59-2

Section 1 - Chemical Product MSDS Name:2-Methoxy-5-nitroaniline 99% Material Safety Data Sheet
Synonym:5-Nitro-o-anisidine; 3-Amino-4-Methoxynitrobenzene; 3-Nitro-6-Methoxyaniline

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
99-59-2	2-Methoxy-5-nitroaniline	99.0	202-770-5

Hazard Symbols: T+
Risk Phrases: 26/27/28 33

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Very toxic by inhalation, in contact with skin and if swallowed.
Danger of cumulative effects.Moisture sensitive.
Potential Health Effects
Eye:
Dust may cause mechanical irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract.
Inhalation:
May cause respiratory tract irritation.
Chronic:
May cause cancer according to animal studies.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.
Antidote: None reported.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Combustible material; may burn but does not ignite readily.
Extinguishing Media:
Water or foam may cause frothing. Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use only in a well-ventilated area.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 99-59-2: Russia: 1 mg/m3 TWA Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: orange to brown
Odor: None reported.
pH: Not available.
Vapor Pressure: 1.3104 mm Hg @25C
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 117.0 - 119.0 deg C
Autoignition Temperature: Not available.
Flash Point: 200 deg C ( 392.00 deg F)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature: 200 deg C
Solubility in water: 2206 mg/L @25C
Specific Gravity/Density: 1.207 @156C
Molecular Formula: C7H8N2O3
Molecular Weight: 168.15

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, liquid anisidine.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 99-59-2: BZ7175000 LD50/LC50:
CAS# 99-59-2: Oral, mouse: LD50 = 1060 mg/kg; Oral, rabbit: LD50 = 1 gm/kg; Oral, rat: LD50 = 2250 mg/kg.
Carcinogenicity:
2-Methoxy-5-nitroaniline - California: carcinogen, initial date 10/1/89 Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T+
Risk Phrases:
R 26/27/28 Very toxic by inhalation, in contact with
skin and if swallowed.
R 33 Danger of cumulative effects.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37 Wear suitable protective clothing and
gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 99-59-2: No information available.
Canada
CAS# 99-59-2 is listed on Canada's NDSL List.
CAS# 99-59-2 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 99-59-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
橙红色针状晶体，易溶于丙酮、甲醇、乙醇、苯、乙酸乙酯等，而不溶于石油醚。

用途
该物质用作染料、颜料及有机合成中间体。

生产方法
2,4-二硝基氯苯经甲氧基化和还原而得。具体步骤如下：

1. 甲氧基化：将熔融的2,4-二硝基氯苯加入反应锅，再加入适量的甲醇。加热至约40℃，在4小时内逐步加入30%氢氧化钠溶液（开始快加后慢加），温度控制在58-60℃。当酚酞试纸对料液显橘红色时，即为终点，得到2,4-二硝基苯甲醚，收率为95%。

2. 还原：将上述甲氧基化生成物冷却至30℃，然后在4小时内逐步加入18%的二硫化钠溶液。反应温度逐渐上升至50℃，保持此温度下保温半小时。反应完成后，冷却至20℃，进行压滤、洗涤和干燥处理，最终得到2-甲氧基-5-硝基苯胺，收率为76%。