2-[(乙基氨基)甲基]-4-硝基苯酚 | 71130-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-[(乙基氨基)甲基]-4-硝基苯酚
• 中文别名: 1-羟基-6-羰基-1,6-二氢吡啶-3-羧酸
• 英文名称: 2‐(ethylamino)methyl‐4‐nitrophenol
• 英文别名: 2-<(ethylamino)methyl>-4-nitrophenol；2-((ethylamino)methyl)-4-nitrophenol；2-[(ethylazaniumyl)methyl]-4-nitrophenolate
• CAS: 71130-60-4
• 化学式: C₉H₁₂N₂O₃
• mdl: MFCD00142952
• 分子量: 196.206
• InChiKey: BXQBOFZTTUXRNK-UHFFFAOYSA-N

物化性质

• 熔点：
  200-2010C
• 溶解度：
  可溶于DMSO（轻微）、水（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

SDS

Name:	2-((n-ethylamino)methyl)-4-nitrophenol Material Safety Data Sheet
Synonym:
CAS:	71130-60-4

Section 1 - Chemical Product MSDS Name:2-((n-ethylamino)methyl)-4-nitrophenol Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
71130-60-4	Phenol, 2-(ethylamino)methyl-4-nitro-		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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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. Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 71130-60-4: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H12N2O3
Molecular Weight: 196.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 71130-60-4: SL4127500 LD50/LC50:
CAS# 71130-60-4: Oral, rat: LD50 = 1014 mg/kg.
Carcinogenicity:
Phenol, 2-(ethylamino)methyl-4-nitro- - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 71130-60-4: No information available.
Canada
CAS# 71130-60-4 is listed on Canada's NDSL List.
CAS# 71130-60-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 71130-60-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-[(乙基氨基)甲基]-4-硝基苯酚 在 三乙胺 、 三氯氧磷 作用下， 反应 4.25h， 生成 3-ethyl-6-nitro-2-propoxy-2-sulfanylidene-4H-1,3,2lambda5-benzoxazaphosphinine
  参考文献：
  名称：

  Yoshikawa, Hiromichi; Ueno, Ryohei, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 9, p. 1467 - 1469

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基水杨醛 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 2-[(乙基氨基)甲基]-4-硝基苯酚
  参考文献：
  名称：

  Synthesis of stable isotope-labeled chloroquine and amodiaquine and their metabolites

  摘要：

  抗疟疾药物氯喹和阿莫地喹及其代谢物的合成以 U-13C 标记的苯为起点，加入 13C 和 15N，得到 M + 7 同位素。氯喹及其代谢物由 7-氯-1,2,3,4-四氢喹啉-4-酮通过芳基取代相应的胺制备而成；而阿莫地喹及其代谢物则以类似的方式由 4,7-二氯喹啉制备而成。

  DOI：

  10.1002/jlcr.3721

文献信息

• Novel thyroid receptor ligands and method II
  申请人：Hangeland Jon

  公开号：US20050282872A1

  公开（公告）日：2005-12-22

  New thyroid receptor ligands are provided which have general formula (I) in which: n is an integer from 0 to 4; R 1 is halogen, trifluoromethyl, or alkyl of 1 to 6 carbons or cycloalkyl of 3 to 7 carbons; R 2 and R 3 are the same or differential hydrogen, halogen, alkyl of 1 to 4 carbons or cycloalkyl of 3 to 5 carbons, at least one of R 2 and R 3 being other than hydrogen; R 4 is a carboxylic acid thereof; or when n is equal to or greater than one, R 4 may be heteroaromatic moiety which may be substituted or unsubstituted, or an amine (NR′R″). R 5 is hydrogen or an acyl (such as acetyl or benzoyl) or other group capable of bioconversion to generate the free phenol structure (wherein R 5 —H). In addition, a method is provided for preventing, inhibiting or treating a disease associated with metabolism dysfunction or which is dependant upon the expression of a T 3 regulated gene, wherein a compound as described above is administered in a therapeutically effective amount. Examples of such diseases associated with metabolism dysfunction or are dependent upon the expression of a T 3 regulated gene include obesity, hypercholesterolemia, atherosclerosis, cardiac arrhythmias, depression, osteoporosis, hypothyroidism, goiter, thyroid cancer as well as glaucoma, congestive heart failure and skin disorders.

  提供了新的甲状腺受体配体，其具有以下通式（I）：其中：n是从0到4的整数；R1是卤素、三氟甲基或1至6个碳原子的烷基或3至7个碳原子的环烷基；R2和R3相同或不同，是氢、卤素、1至4个碳原子的烷基或3至5个碳原子的环烷基，其中至少有一个是氢之外的其他基团；R4是其羧酸；或当n等于或大于1时，R4可以是杂环芳基团，可能被取代或未取代，或胺（NR′R″）。R5是氢或酰基（如乙酰基或苯甲酰基）或其他能够生物转化以生成游离酚结构（其中R5-H）的基团。此外，提供了一种方法，用于预防、抑制或治疗与代谢功能障碍相关或依赖于T3调节基因表达的疾病，其中上述描述的化合物以治疗有效剂量给予。与代谢功能障碍相关或依赖于T3调节基因表达的疾病的例子包括肥胖症、高胆固醇血症、动脉粥样硬化、心律失常、抑郁症、骨质疏松症、甲状腺功能减退症、甲状腺肿、甲状腺癌以及青光眼、充血性心力衰竭和皮肤疾病。
• Antimalarial Pyrido[1,2-<i>a</i>]benzimidazole Derivatives with Mannich Base Side Chains: Synthesis, Pharmacological Evaluation, and Reactive Metabolite Trapping Studies
  作者：John Okombo、Christel Brunschwig、Kawaljit Singh、Godwin Akpeko Dziwornu、Linley Barnard、Mathew Njoroge、Sergio Wittlin、Kelly Chibale

  DOI：10.1021/acsinfecdis.8b00279

  日期：2019.3.8

  glutathione adducts only in derivatives bearing 4-aminophenol moiety, with fragmentation signatures showing that this conjugation occurred on the phenyl ring of the Mannich base side chain. As with amodiaquine (AQ), interchanging the positions of the 4-hydroxyl and Mannich base side group or substituting the 4-hydroxyl with fluorine appeared to block bioactivation of the AQ-like derivatives though at the expense

  合成了一系列新型的带有曼尼希碱基侧链的吡啶并[1,2-a]苯并咪唑及其代谢物，并对其在小鼠中的体外抗疟原虫活性，微粒体代谢稳定性，反应性代谢产物（RM）形成和体内抗疟疾功效进行了评估。模型。在伯氏疟原虫感染的小鼠中口服4×50 mg / kg的一种衍生物可将寄生虫病降低95％，平均存活期为治疗后16天。这些衍生物的体内功效可能是其活性代谢产物的结果，其中两种代谢产物显示出对氯喹敏感和多药耐药性恶性疟原虫（P. falciparum）菌株有效的体外抗疟原虫活性。观察到所有< 在肝微粒体中孵育30分钟后，剩余40％的母体化合物。RM捕集研究仅在带有4-氨基苯酚部分的衍生物中检测到了谷胱甘肽加合物，其片段签名表明该缀合发生在曼尼希碱基侧链的苯环上。与氨二喹（AQ）一样，交换4-羟基和曼尼希碱基侧基的位置或用氟取代4-羟基似乎阻止了AQ-like衍生物的生物活化，尽管这是以抗疟原虫活性为代价的，这大大降低了抗疟原虫的活性。
• Synthesis of some novel amodiaquine analogs as potential antimalarial and antifilarial compounds
  作者：Meilin Go、Tonglan Ngiam、Alfred S. C. Wan

  DOI：10.1021/jm00144a020

  日期：1981.12

  Mastomys natalensis. The most active antimalarial compound, 7-chloro-4-[alpha-[[N-(4-methyl-1-piperazinyl)carbonyl]amino]-4-hydroxy-m-toluidino]quinoline, had twice the activity of amodiaquine. O-Methylation and N-ethylation generally reduced antimalarial activity. Analogues which lack a basic tertiary amino function at their side chain were also lacking in both antimalarial and antifilarial activities.

  设计并合成了十个氨二喹类似物，它们是氨二喹和二乙基氨基甲嗪的杂交分子。六种类似物均在其侧链上具有基本的叔氨基功能，它们在小鼠中对伯氏疟原虫具有活性，并在体外抑制成虫的活动性和Breinlia booliati的微丝虫。它们对纳塔氏乳杆菌中的Litomosoides carinii没有活性。最具活性的抗疟疾化合物7-氯-4- [α-[[N-（4-甲基-1-哌嗪基）羰基]氨基] -4-羟基-间甲苯基]喹啉的活性是氨二喹的两倍。O-甲基化和N-乙基化通常会降低抗疟活性。在其侧链上缺乏基本叔氨基功能的类似物在抗疟和抗孝活性上也都缺乏。
• Photographic material and process comprising a coupler capable of forming a wash-out dye (Q/C)
  申请人：EASTMAN KODAK COMPANY

  公开号：EP0576087A1

  公开（公告）日：1993-12-29

  A photographic element comprises a support bearing at least one photographic silver halide emulsion layer and at least one coupler (A) having a water solubilizing group wherein coupler (A) forms a compound that is washed out of the photographic element during photographic processing and forms a coupling-off group represented by the formula:         -X - Rel⁴ - T⁴ - INH wherein;    X is selected from oxygen, nitrogen or sulfur;    Rel⁴ contains a ballast and is a releasing group for releasing T⁴-INH from Rel⁴ by elimination electron transfer reaction during photographic processing without substantial delay of releasing;    T⁴ is a timing group that releases INH by intramolecular displacement reaction with timing delay during photographic processing; and    INH is a development inhibitor group. The photographic coupler (A) enables formation of easily removable dyes in photographic elements and processes that provide images having improved acutance, stability and interimage effects.

  一种感光元件包括一个至少带有一个感光卤化银乳剂层的支架和至少一个具有水溶性基团的耦合剂 (A)，其中耦合剂 (A) 形成一种化合物，该化合物在摄影冲洗过程中被冲出感光元件，并形成一个由式表示的耦合基团： -X - Rel⁴ - T⁴ - INH 其中 X 选自氧、氮或硫； Rel⁴ 含有镇流器，是释放基团，用于在照相处理过程中通过消除电子转移反应将 T⁴-INH 从 Rel⁴ 中释放出来，释放过程不会出现严重延迟； T⁴ 是一个定时基团，在照相冲洗过程中通过分子内置换反应释放 INH，具有定时延迟；以及 INH 是显影抑制基团。 感光耦合剂（A）能够在感光元件和感光过程中形成易于去除的染料，使图像具有更好的清晰度、稳定性和临时效果。
• Photographic material and process comprising a coupler capable of forming a wash-out dye (C/C)
  申请人：EASTMAN KODAK COMPANY

  公开号：EP0576088A1

  公开（公告）日：1993-12-29

  A photographic element comprises a support bearing at least one photographic silver halide emulsion layer and at least one coupler (A) having a water solubilizing group wherein coupler (A) forms a compound that is washed out of the photographic element during photographic processing and forms a coupling-off group represented by the formula:         -X - Rel³ - T³ - INH wherein:    X is selected from oxygen, nitrogen or sulfur    X-Rel³ contains a photographic ballast and is a releasing group for releasing T³-INH from X-Rel³ by intramolecular displacement reaction during photographic processing without substantial delay of releasing;    T³ is a timing group that releases INH by intramolecular displacement reaction with timing delay during photographic processing;    INH is a development inhibitor group;    The photographic coupler (A) enables formation of easily removable dyes in photographic elements and processes that provide images having improved acutance, stability and interimage effects.

  一种感光元件包括一个至少带有一个感光卤化银乳剂层的支架和至少一个具有水溶性基团的耦合剂 (A)，其中耦合剂 (A) 形成一种化合物，该化合物在摄影冲洗过程中被冲出感光元件，并形成一个由式表示的耦合基团： -X - Rel³ - T³ - INH 其中 X 选自氧、氮或硫 X-Rel³ 含有感光镇流器，是一种释放基团，用于在感光冲洗过程中通过分子内置换反应从 X-Rel³ 中释放 T³-INH 而不会对释放造成实质性延迟； T³ 是一种定时基团，可在照相冲洗过程中通过分子内置换反应释放 INH，并有定时延迟； INH 是显影抑制基团； 感光耦合剂（A）可以在感光元件和感光过程中形成易于去除的染料，从而提供具有更好的清晰度、稳定性和临时效果的图像。