3-羟基-N,N-二乙基苯胺 | 91-68-9

• 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 - 有机氮化合物
• 中文名称: 3-羟基-N,N-二乙基苯胺
• 中文别名: 间羟基-N,N-二乙基苯胺；间二乙氨基苯酚；3-二乙氨基苯酚；3-二乙氨基酚；N,N-二乙基-3-氨基苯酚；3-(二乙基氨基)苯酚；间二乙氨基酚；间羟基二乙苯胺
• 英文名称: 3-diethylaminophenol
• 英文别名: N,N-diethyl-3-aminophenol；3-hydroxy-N,N-diethylaniline；3-(N,N-diethylamino)phenol；m-diethylaminophenol；m-hydroxy-N,N-diethylaniline；3-(Diethylamino)phenol
• CAS: 91-68-9
• 化学式: C₁₀H₁₅NO
• mdl: MFCD00002265
• 分子量: 165.235
• InChiKey: WAVOOWVINKGEHS-UHFFFAOYSA-N

物化性质

• 熔点：
  69-72 °C (lit.)
• 沸点：
  170 °C/15 mmHg (lit.)
• 密度：
  1.0203 (rough estimate)
• 闪点：
  141 °C
• 溶解度：
  20℃有机溶剂中溶解度4.087g/L
• LogP：
  0.929 at 23℃
• 物理描述：
  3-diethylaminophenol is a black solid. (NTP, 1992)
• 稳定性/保质期：

  剧毒物质可通过吸入、食入或皮肤接触吸收而致死。燃烧时会产生刺激性、腐蚀性和毒性气体。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

毒理性

• 副作用

高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为继发性毒性效应。

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险品标志：
  T
• 安全说明：
  S22,S26,S36/37/39,S45
• 危险类别码：
  R25
• WGK Germany：
  2
• 海关编码：
  29222900
• 危险品运输编号：
  UN 2512 6.1/PG 3
• 危险类别：
  6.1
• RTECS号：
  SL0550500
• 包装等级：
  III
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  本品应密封保存于阴凉避光处。需储存在阴凉、通风的仓库内，并远离火种和热源，避免阳光直射。搬运时要轻装轻放，防止容器受损，同时与食用原料隔离贮运。

SDS

Name:	3-Diethylaminophenol granulated 99% Material Safety Data Sheet
Synonym:	N,N-Diethyl-3-aminophenol; Phenol, m-(diethylamino)-; m-(Diethylamino)phenol; Phenol, 3-(diethylamino)
CAS:	91-68-9

Section 1 - Chemical Product MSDS Name:3-Diethylaminophenol granulated 99% Material Safety Data Sheet
Synonym:N,N-Diethyl-3-aminophenol; Phenol, m-(diethylamino)-; m-(Diethylamino)phenol; Phenol, 3-(diethylamino)

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
91-68-9	3-Diethylaminophenol, granulated	99	202-090-9

Hazard Symbols: T
Risk Phrases: 25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
Prolonged exposure can cause damage to the eyes, severe irritation or burns.

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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.
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:
Do not induce vomiting. 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. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Do not breathe dust, vapor, mist, or gas. Keep container tightly closed. Avoid ingestion and inhalation. Use only in a chemical fume hood.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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 only under a chemical fume hood.
Exposure Limits CAS# 91-68-9: 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:
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: Pellets
Color: purple
Odor: Malodorous
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 170 deg C @ 15.00mm Hg
Freezing/Melting Point: 70 - 73 deg C
Autoignition Temperature: Not applicable.
Flash Point: 141 deg C ( 285.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble in ligroin
Specific Gravity/Density:
Molecular Formula: C10H15NO
Molecular Weight: 165.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 91-68-9: SL0550500 LD50/LC50:
Not available.
CAS# 109-89-7: Oral, rat: LD50 = 540 mg/kg. The toxicity of this product is partially based on the hazards associated with Diethylamine (CAS# Carcinogenicity:
3-Diethylaminophenol, granulated - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 25 Toxic if swallowed.
Safety Phrases:
S 22 Do not breathe dust.
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# 91-68-9: 2
Canada
CAS# 91-68-9 is listed on Canada's NDSL List.
CAS# 91-68-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 91-68-9 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
灰棕色至玫瑰色结晶。其熔点为78℃，沸点在276-280℃之间，170℃时蒸汽压为2.13kPa，闪点为141℃。该物质溶于水、醇、醚和氢氧化钠溶液，但不溶于石油类。

用途
3-羟基-N,N-二乙基苯胺可作为玫瑰精、酸性桃红及碱性蕊香红等染料的中间体，并用于其他有机合成。

生产方法
将间硝基苯磺酸钠用铁粉还原成间氨基苯磺酸钠，随后使用氯乙烷进行烷基化，再通过氢氧化钠进行碱熔，最后酸化得到成品。

反应信息

• 作为反应物：
  描述：

  3-羟基-N,N-二乙基苯胺 以 乙醚 、 乙醇 为溶剂， 反应 7.0h， 生成 3-氰基-7-(二乙基氨基)香豆素
  参考文献：
  名称：

  Il'chenko, A. Ya.; Koval'chuk, R. E.; Krokhtyak, V. I., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 2348 - 2349

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(N,N-二乙基氨基)乙酰苯胺 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 15.0h， 生成 3-羟基-N,N-二乙基苯胺
  参考文献：
  名称：

  间二烷胺基苯酚的合成方法

  摘要：

  间二烷胺基苯酚的合成方法，其特征为：第一步，将间二烷胺基酰基苯胺和硫酸水溶液混合均匀并加热至50~110℃，保温反应得到含间二烷胺基苯胺的硫酸水溶液；第二步，继续滴加亚硝酸钠水溶液，亚硝酸钠水溶液的滴加温度为‑10~20℃，滴毕于5~30℃保温，得到含间二烷胺基苯胺重氮盐的硫酸水溶液；第三步，含间二烷胺基苯胺重氮盐的硫酸水溶液直接加热至45~110℃，保温，发生重氮盐的水解反应，冷却后处理，得产物间二烷胺基苯酚；三步反应所需的硫酸在第一步反应中一次性投加完毕；三步反应在一锅内分步完成。本发明方法具有原料价格低廉、来源充足，合成工艺安全性高，产品收率高，三废污染较少等特点，具有较高工业化价值。

  公开号：

  CN109134281B

文献信息

• A Molecular Chameleon with Fluorescein and Rhodamine Spectroscopic Behaviors
  作者：Ling Li、Chunyan Wang、Jianjian Wu、Yu Chung Tse、Yue-Peng Cai、Keith Man-Chung Wong

  DOI：10.1021/acs.inorgchem.5b02147

  日期：2016.1.4

  A new class of fluorescein/rhodamine hybrids with two spirolactone rings was reported to exhibit dual-output fluorescent behaviors independently. Isolation and characterization for two diastereomers, trans-RhOH and cis-RhOH, have been made and their X-ray crystal structures determined. In a basic environment, the spirolactone ring on the hydroxyl side will be opened to give a fluorescein-like optical

  据报道，具有两个螺内酯环的新型荧光素/若丹明杂化体独立显示出双输出荧光行为。分离和鉴定了两个对映异构体，反式- RHOH和顺- RHOH，已经和他们的X射线晶体结构测定。在碱性环境中，羟基侧的螺内酯环将打开，以产生类似于荧光素的光学输出，在485和530 nm发射时具有最低的吸收率。另一方面，通过H +或Hg 2+可以打开类罗丹明类似的光输出，即528 nm的吸收和575 nm的发射。离子，归因于氨基侧螺内酯开环。在具有不同pH值的甲醇缓冲液系统中，相应的羟基和氨基的p K a值分别确定为5.7和2.3。还讨论了选择性的Hg 2+传感特性，确定的log K s值约为3.60和3.73。发现与RhOH孵育的秀丽隐杆线虫的共聚焦显微镜图像显示出具有Hg 2+离子的增强的荧光强度，表明RhOH在体内生物成像中的潜在应用。
• Coumarin-Caged Rosamine Probes Based on a Unique Intramolecular Carbon-Carbon Spirocyclization
  作者：Weiying Lin、Lingliang Long、Wen Tan、Bingbing Chen、Lin Yuan

  DOI：10.1002/chem.201000015

  日期：2010.4.6

  Caged fluorophore: We report the first caging strategy for rosamine fluorophores based on a unique intramolecular carbon–carbon spirocyclization. The new class of carbon–carbon spirocyclic caged probes exhibit several significant advantages over the traditional nitrobenzyl‐caged xanthene probes and can be employed for spatially controlled fluorescence imaging of living cells (see graphic).

  笼状荧光团：我们报告了基于独特的分子内碳-碳螺环化作用的玫瑰红胺荧光团的第一种笼统策略。与传统的硝基苄基笼式cage吨探针相比，新型的碳-碳螺环笼式探针具有多个显着优势，可用于活细胞的空间控制荧光成像（见图）。
• Superoxide Radical Photogenerator with Amplification Effect: Surmounting the Achilles’ Heels of Photodynamic Oncotherapy
  作者：Mingle Li、Tao Xiong、Jianjun Du、Ruisong Tian、Ming Xiao、Lianying Guo、Saran Long、Jiangli Fan、Wen Sun、Kun Shao、Xiangzhi Song、James W. Foley、Xiaojun Peng

  DOI：10.1021/jacs.8b13141

  日期：2019.2.13

  transfer theory, the energy donor successfully endows ENBOS with significantly enhanced NIR absorbance and photon utility, which in turn lead to ENBOS more easily activated and generating more O2-• in deep tissues, that thus dramatically intensifies the type I PDT against hypoxic deep tumors. Moreover, benefiting from the dyad cationic feature, ENBOS achieves superior "structure-inherent targeting"

  氧依赖强、肿瘤靶向性差、治疗深度有限被认为是光动力疗法（PDT）临床应用面临的“致命弱点”。与常见方法不同，在这里，我们提出了一种创新策略，通过使用具有“0 + 1 > 1”放大效应的光子引发的二元阳离子超氧化物自由基 (O2-•) 发生器 (ENBOS) 同时克服这些缺点。特别是，通过利用 Förster 共振能量转移理论，能量供体成功地赋予 ENBOS 显着增强的 NIR 吸收和光子效用，进而导致 ENBOS 更容易激活并在深层组织中产生更多的 O2-•，从而显着增强了针对缺氧深部肿瘤的 I 型 PDT。而且，受益于二元阳离子特征，ENBOS 实现了卓越的“结构固有靶向”能力，静脉注射后 48 小时的信噪比高达 25.2，为精确成像引导的肿瘤治疗提供了机会。同时，瘤内积累和保留性能也显着改善（> 120 h）。基于这些独特的优点，ENBOS 在低光剂量照射下选择性地抑制深部缺氧肿瘤增殖
• BODIPY/Nile-Red-Based Efficient FRET Pair: Selective Assay of Endoplasmic Reticulum Membrane Fluidity
  作者：Zhigang Yang、Youngjin Wi、Young-Min Yoon、Peter Verwilst、Joo Hee Jang、Tae Woo Kim、Chulhun Kang、Jong Seung Kim

  DOI：10.1002/asia.201501060

  日期：2016.2

  We synthesized a boron‐dipyrromethene (BODIPY)/Nile Red hybrid probe capable of selectively recognizing fluidity changes in the endoplasmic reticulum (ER) membrane due to its preferential localization to the ER and strong energy transfer from BODIPY to the Nile Red moiety, emitting only in nonaqueous environments. ER membrane fluidity in HepG2 cells was markedly reduced by a cell model of metabolic

  我们合成了硼-二吡咯亚甲基（BODIPY）/尼罗红杂交探针，能够选择性识别内质网（ER）膜中的流动性变化，这是由于其优先定位于ER以及从BODIPY到尼罗红部分的强大能量转移，仅发射在非水环境中。代谢综合征的细胞模型显着降低了HepG2细胞中的ER膜流动性。
• Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO
  作者：Martin B. Johansen、Oliver R. Gedde、Thea S. Mayer、Troels Skrydstrup

  DOI：10.1021/acs.orglett.0c01117

  日期：2020.6.5

  trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good

  我们报告了从容易获得的芳基溴化物和氟代硫酸盐开始的顺序一锅法制备芳族三氟甲基酮的方法，后者很容易从相应的苯酚制备。该方法利用产生低压一氧化碳易地从热电联产产生的Weinreb酰胺作为经历monotrifluoromethylation得到良好的收率的相应的芳族三氟甲基酮（TFMKs）的活性中间体。通过化学计量使用CO，可以通过切换使用13 COgen来访问13 C同位素标记的TFMK。

表征谱图