3-甲氧基-N,N-二(2-羟基乙基)苯胺 | 17126-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-甲氧基-N,N-二(2-羟基乙基)苯胺
• 中文别名: 2,2’-[(3-甲氧苯基)亚氨基]双乙醇；间甲氧基-N,N-二(β-羟乙基)苯胺；N,N-二(2-羟乙基)-3-甲氧基苯胺；N,N-双(2-羟基乙基)-3-甲氧基苯胺
• 英文名称: 3-methoxy-bisaniline
• 英文别名: N,N-bis(2-hydroxyethyl)-3-methoxylaniline；3-methoxy-N,N-bis(2-hydroxyethyl)aniline；2,2'-[(3-methoxyphenyl)imino]bis-ethanol；N,N-Bis-<2-hydroxy-aethyl>-3-methoxy-anilin；N,N-Bis-(2-hydroxyaethyl)-m-anisidin；N,N-Bis-(2-hydroxyethyl)-m-anisidin；2,2'-((3-Methoxyphenyl)azanediyl)diethanol；2-[N-(2-hydroxyethyl)-3-methoxyanilino]ethanol
• CAS: 17126-75-9
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: FAMIFVQDRQPFPH-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50℃
• 沸点：
  350.94°C (rough estimate)
• 密度：
  1.1240 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090
• 安全说明：
  S24/25
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P501,P270,P264,P280,P332+P313,P301+P312+P330,P305+P351+P338+P310
• 危险品运输编号：
  3259
• 危险性描述：
  H302,H316,H318
• 储存条件：
  存放于室温且使用惰性气体保护。

SDS

Name:	N N-bis(2-Hydroxyethyl)-3-methoxyaniline Material Safety Data Sheet
Synonym:	None Known
CAS:	17126-75-9

Section 1 - Chemical Product MSDS Name:N N-bis(2-Hydroxyethyl)-3-methoxyaniline Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17126-75-9	N,N-bis(2-Hydroxyethyl)-3-methoxyanili	100	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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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 water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 17126-75-9: 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: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 185-191 deg C @ 0.4mmHg
Freezing/Melting Point: 53-57 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: C11H17NO3
Molecular Weight: 211.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 17126-75-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N,N-bis(2-Hydroxyethyl)-3-methoxyaniline - Not listed by ACGIH, IARC, or NTP.

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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# 17126-75-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 17126-75-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 17126-75-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：棕色液体。

用途：作为甲氧芳芥的中间体。

生产方法：通过将间甲氧基苯胺与环氧乙烷在乙酸的参与下进行反应，再进行羟乙基化处理，最终制得所需产品。

反应信息

• 作为反应物：
  描述：

  3-甲氧基-N,N-二(2-羟基乙基)苯胺 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N,N-二(2-氯乙基)-3-甲氧基苯胺
  参考文献：
  名称：

  Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines

  摘要：

  A series of aniline mustards with a wide range of electron-donating and -withdrawing substituents in the 3- and 4-positions has been synthesized and evaluated for cytotoxicity in cell culture to examine the potential of using nitro group deactivated nitrogen mustards for the design of novel hypoxia-selective anticancer drugs (Denny, W. A.; Wilson, W. R. J. Med. Chem. 1986, 29, 879). Hydrolytic half-lives in tissue culture media, determined by bioassay against a cell line (UV4) defective in the repair of DNA interstrand cross-links showed the expected dependence on the Hammett electronic parameter, sigma, varying from 0.13 h for the 4-amino analogue to greater than 100 h for analogues with strongly electron-withdrawing substituents. Cytotoxic potencies in aerobic UV4 cultures showed a similar dependence on sigma. This dependence predicted that the 4-nitroaniline mustard would be 7200-fold less potent than its potential six-electron reduction product, the 4-amino compound, in growth inhibition assays using a 1-h drug exposure. The measured differential was much lower (225-fold) because of the instability of the latter compound, but a differential of 17,500-fold was observed in the initial rate of killing by using a clonogenic assay. The potential for formation of reactive mustards by reduction to the amine or hydroxylamine was demonstrated by the 4-nitroso compound, which had an aerobic toxicity similar to that of the amine. Although these features confirmed the original rationale, the 3-nitro- and 4-nitroaniline mustards had only minimal hypoxic selectivity against UV cells. Toxicity to hypoxic cells appears to be limited by the low reduction potentials of these compounds and consequent lack of enzymatic nitroreduction. However, this study has demonstrated that nitro groups can be used to latentiate aromatic nitrogen mustards and indicates that examples with higher reduction potentials could provide useful hypoxia-selective therapeutic agents.

  DOI：

  10.1021/jm00163a019
• 作为产物：
  描述：

  间氨基苯甲醚 、 2-氯乙醇 在 calcium carbonate 、 potassium iodide 作用下， 以 水 为溶剂， 反应 8.0h， 以85%的产率得到3-甲氧基-N,N-二(2-羟基乙基)苯胺
  参考文献：
  名称：

  Synthesis and structure–analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ)

  摘要：

  A series of monospirocyclopiperazinium salts were designed and synthesized to search for a peripherally-acting analgesic drug with low side effects. Extensive SAR studies revealed that a suitable (NRR3)-R-2 was critical for the analgesic activity, which might be beneficial to expose the cationic nitrogen to bind to the receptor, and possibly interact with the receptor via pi-pi interaction. Introduction of substituting group on the N-4-phenyl ring could improve the activity, and the best position was the 4-position. Compound 14n showed more potent analgesic activity (63%, 20 mu M/kg, sc) and holds promise for development as a mechanically new analgesic drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.052

文献信息

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