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

---

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.

---

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.

---

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.

---

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.

---

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.

---

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.

---

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

---

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.

---

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.

---

Section 12 - ECOLOGICAL INFORMATION
Other No information available.

---

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

---

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

---

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.

---

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%。

反应信息

• 作为反应物：
  描述：

  2-氨基-4-硝基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium 10% on activated carbon 吡啶 、 氢气 、 sodium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 1,1-dimethylethyl ((1S)-2-{[3-({[3-fluoro-4-(5-methyl-2-furanyl)phenyl]sulfonyl}amino)-4-(methyloxy)phenyl]amino}-1-methyl-2-oxoethyl)methylcarbamate
  参考文献：
  名称：

  WO2007/118852

  摘要：

  公开号：
• 作为产物：
  描述：

  4-甲氧基-3-硝基苯甲酸 在 ammonium sulfide 、 硝酸 作用下， 生成 2-氨基-4-硝基苯甲醚
  参考文献：
  名称：

  Adrenocortical Dysfunction Following Etomidate Induction in Emergency Department Patients

  摘要：

  Abstract. Objective: To assess adrenocortical function following intravenous etomidate use in emergency department (ED) patients requiring intubation. Methods: This was a prospective, randomized, controlled trial of consecutive patients presenting to the ED requiring intubation. Patients were randomized to receive a single bolus induction dose of either 0.05‐0.1 mg/kg midazolam (control group) or 0.3 mg/kg etomidate (etomidate group) during a standardized rapid‐sequence intubation (RSI) with succinylcholine. The primary outcome variable was adrenocortical function at 4, 12, and 24 hours post‐induction as assessed by measured serum cortisol response to exogenous cosyntropin (cosyntropin stimulation test, CST). Fisher's exact test was used to compare CST results between groups. Results: Thirty‐one patients were enrolled: 8 control, 10 etomidate, and 13 excluded from analysis for either incomplete data or steroid use during the study period. The 4‐hour CST results were significantly different between study groups, with a normal response in 100% of control patients vs 30% of etomidate patients (p = 0.004). The 12‐ and 24‐hour CSTs did not differ significantly between groups: normal CST in 100% of control patients at 12 and 24 hours vs 100% and 90% among etomidate patients at 12 and 24 hours, respectively (p = 1.0 at 12 and 24 hours). Measured cortisol levels of patients with abnormal CSTs remained within normal laboratory reference ranges. Conclusion: Use of etomidate in ED patients requiring RSI results in adrenocortical dysfunction. However, cortisol levels remain within normal laboratory levels during this period of dysfunction. Adrenocortical dysfunction appears to resolve within 12 hours of a single bolus dose of 0.3 mg/kg etomidate.

  DOI：

  10.1111/j.1553-2712.2001.tb00537.x

文献信息

• [EN] COMPOUNDS THAT MODULATE EGFR ACTIVITY AND METHODS FOR TREATING OR PREVENTING CONDITIONS THEREWITH<br/>[FR] COMPOSÉS MODULANT L'ACTIVITÉ DES RÉCEPTEURS EGFR ET MÉTHODES POUR TRAITER OU PRÉVENIR DES TROUBLES À L'AIDE DE CEUX-CI
  申请人：GATEKEEPER PHARMACEUTICALS INC

  公开号：WO2011140338A1

  公开（公告）日：2011-11-10

  Provided are compounds and methods for treating or preventing kinase-mediated disorders therewith.

  提供了用于治疗或预防激酶介导的疾病的化合物和方法。
• 吡咯喹啉醌的合成方法
  申请人：常熟理工学院

  公开号：CN104557921B

  公开（公告）日：2018-04-27

  本发明公开了吡咯喹啉醌的合成方法，包括以下步骤：以2‑甲氧基‑5‑硝基苯胺盐酸盐为原料碱处理得化合物1；化合物1以离子液体催化下甲酰化得化合物2；化合物2采用硼氢化钠还原得化合物3；化合物3经重氮化后与HBF4作用得化合物4；化合物4与2‑甲基乙酰乙酸乙酯反应的化合物5；化合物5用甲酸处理得化合物6；化合物6以离子液体催化酰胺交换得化合物7；化合物7与2‑氧代戊烯二酸二甲酯反应得化合物8；化合物8在Cu(OAc)2·H2O作用下通入氯化氢得化合物9；化合物9碱性水解得化合物10。本发明原料便宜，易得，而且稳定；反应产率高，反应速度快，产物容易分离，催化剂可回收使用，绿色环保。
• A novel method for suppression of the abnormal Fischer indole synthesis
  作者：Bruce G. Szczepankiewicz、Clayton H. Heathcock

  DOI：10.1016/s0040-4020(97)90396-3

  日期：1997.6

  A method is described for the use of the Fischer indole synthesis to prepare 7-hydroxy-indoles in good yield. The method involves the construction of a 4-aminobenzoxazine and removal of the N-O tether after the indole has been formed.

  描述了一种利用费歇尔吲哚合成法以高收率制备7-羟基吲哚的方法。该方法包括构建4-氨基苯并恶嗪并在吲哚形成后除去NO系链。
• Tricyclic protein kinase inhibitors
  申请人：American Home Products Corporation

  公开号：US20030065180A1

  公开（公告）日：2003-04-03

  This invention provides compounds of Formula (I), 1 where A″, Z, X and n are defined herein, or a pharmaceutically acceptable salt thereof which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

  这项发明提供了Formula (I)的化合物， 其中A″、Z、X和n的定义如下，或其药学上可接受的盐，这些化合物可用作抗肿瘤剂，并用于多囊肾病的治疗。
• [EN] COMPOUNDS FOR INHIBITING CELL PROLIFERATION IN EGFR-DRIVEN CANCERS<br/>[FR] COMPOSÉS POUR INHIBER LA PROLIFÉRATION CELLULAIRE DANS LES CANCERS INDUITS PAR L'EGFR
  申请人：ARIAD PHARMA INC

  公开号：WO2013169401A1

  公开（公告）日：2013-11-14

  The invention features compounds, pharmaceutical compositions and methods for treating patients who have an EGFR-driven cancer of Formula (I), wherein the variables are as defined herein.

  这项发明涉及化合物、药物组合物和治疗EGFR驱动的Formula (I)癌症患者的方法，其中变量如本文所定义。

表征谱图