1’,3’,3’-三甲基-6-羟基螺环 | 23001-29-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 1’,3’,3’-三甲基-6-羟基螺环
• 中文别名: 1',3',3'-三甲基-6-羟基螺环
• 英文名称: 6-hydroxy spiropyran
• 英文别名: spiro[2H-1-benzopyran-2,2’-(6-hydroxy-1’,3’,3’-trimethylindoline)]；1',3',3'-trimethyl-6-hydroxyspiro(2H-1-benzopyran-2,2'-indoline)；1',3',3'-trimethyl-6-hydroxyspiro[2H-1-benzopyran-2,2'-indoline]；1,3,3-trimethyl-6'-hydroxy-spiro-[2H-1-benzopyran-2,2'-indoline]；6-hydroxy-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indolin]；1',3',3'-trimethylspiro[chromene-2,2'-indolin]-6-ol；Spiro[2H-1-benzopyran-2,2'-[2H]indol]-6-ol, 1',3'-dihydro-1',3',3'-trimethyl-；1',3',3'-trimethylspiro[chromene-2,2'-indole]-6-ol
• CAS: 23001-29-8
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: UHRBDHPBCHWWAG-UHFFFAOYSA-N

物化性质

• 沸点：
  435.21°C (rough estimate)
• 密度：
  1.1349 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 储存条件：
  室温

SDS

Name:	1 3 3 -Trimethyl-6-hydroxyspiro (2h-1-benzopyran-2 2 -indoline) Material Safety Data Sheet
Synonym:
CAS:	23001-29-8

Section 1 - Chemical Product MSDS Name:1 3 3 -Trimethyl-6-hydroxyspiro (2h-1-benzopyran-2 2 -indoline) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
23001-29-8	1',3',3'-Trimethyl-6-hydrospiro(2h-1-b	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:
Dust may cause mechanical irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause digestive tract disturbances. 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:
No information found.

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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:

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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 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. 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. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 23001-29-8: 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: Solid
Color: purple
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: C19H19NO2
Molecular Weight: 293.36

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 23001-29-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1',3',3'-Trimethyl-6-hydrospiro(2h-1-benzopyran-2,2'-indoline) - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable 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# 23001-29-8: No information available.
Canada
CAS# 23001-29-8 is listed on Canada's NDSL List.
CAS# 23001-29-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 23001-29-8 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：

  1’,3’,3’-三甲基-6-羟基螺环 在 臭氧 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以72%的产率得到2,5-二羟基苯甲醛
  参考文献：
  名称：

  Fischer碱†作为保护基：2-羟基苯甲醛的保护和脱保护

  摘要：

  2-羟基苯甲醛的羟基和醛基可通过与Fischer碱的反应进行保护，并通过在-78°C的甲醇中进行臭氧分解来脱保护，从而以高至高收率得到相应的2-羟基苯甲醛。

  DOI：

  10.1016/s0040-4039(00)00516-5
• 作为产物：
  描述：

  1,3,3-三甲基-2-亚甲基吲哚啉 、 2,5-二羟基苯甲醛 以 乙醇 为溶剂， 反应 2.0h， 以84.8%的产率得到1’,3’,3’-三甲基-6-羟基螺环
  参考文献：
  名称：

  聚合诱导扩散的光开关水凝胶表面形貌

  摘要：

  在本文中，我们描述了通过使用简便的方法制备图案化的光响应水凝胶。这种聚合物网络水凝胶涂层由N组成异丙基丙烯酰胺（NIPAAM），交联剂三丙二醇二丙烯酸酯（TPGDA）和新型光致变色螺吡喃单丙烯酸酯。在预研究中，合成了含有螺吡喃染料的线性NIPAAM共聚物（不含TPGDA），显示出相对较快的光开关性能。随后，包括TPGDA在内的类似单体混合物的光聚合得到了独立的水凝胶聚合物网络。在弱酸性条件下，质子化的花菁在光诱导下异构化为中性螺吡喃，导致整个聚合物膜的亲水性发生宏观变化，即水凝胶收缩。收缩程度可以通过改变丙烯酸酯混合物的化学组成来控制。经过这些预研究之后，通过使用图案化的光掩模，通过聚合诱导的扩散来制造具有空间调节的交联密度的水凝胶薄膜。所得的光滑图案化水凝胶涂层在弱酸性介质中溶胀，并且在交联密度较低的区域中溶胀度更高，因此产生了波纹状表面。暴露于可见光后，表面形貌再次变平，从而表明可以形

  DOI：

  10.1002/chem.201300852

文献信息

• Characteristic Phase Transition of Aqueous Solution of Poly(<i>N</i>-isopropylacrylamide) Functionalized with Spirobenzopyran
  作者：Kimio Sumaru、Mitsuyoshi Kameda、Toshiyuki Kanamori、Toshio Shinbo

  DOI：10.1021/ma049661x

  日期：2004.6.1

  synthesized by modifying poly(N-isopropylacrylamide) with spirobenzopyran. The phase transition properties of the aqueous solution of this copolymer exhibited a logic-gate response to the light irradiation and to increased temperature, which has three different modes depending on the pH of the solution. Especially, a great increase in turbidity was observed even in dilute aqueous solution containing only 0

  通过用螺并苯并吡喃改性聚（N-异丙基丙烯酰胺）合成了一种新型的功能共聚物。该共聚物水溶液的相变性能表现出对光照射和温度升高的逻辑门响应，取决于溶液的pH值，其具有三种不同的模式。特别是，即使共聚物仅含有1.1摩尔％的螺并苯并吡喃，即使在仅含有0.10重量％的共聚物的稀水溶液中，也观察到浊度的极大增加。还证实了在相同系统的热诱导相变的影响下，螺并苯并吡喃残基被异构化。紧密连接在一起的热响应性聚合物和光响应性发色团的主链相互影响。
• Spiropyran-based liquid crystals: the formation of columnar phases via acid-induced spiro–merocyanine isomerisation
  作者：Boon-Hooi Tan、Masafumi Yoshio、Takahiro Ichikawa、Tomohiro Mukai、Hiroyuki Ohno、Takashi Kato

  DOI：10.1039/b610903a

  日期：——

  Hexagonal columnar liquid-crystalline phases are induced for a new fan-shaped spiropyran compound as the result of an acidichromism effect of spiro–merocyanine isomerisation through protonation upon incorporation of 4-methylbenzenesulfonic acid.

  由于螺-部花青异构化通过掺入 4-甲基苯磺酸后的质子化产生酸变色效应，从而诱导出一种新的扇形螺吡喃化合物，从而产生六方柱状液晶相。
• Synthesis of Photochromic Monomers with Silyloxy Substituents
  作者：Bhaskar D. Hosangadi、Sharmila K. Thakur

  DOI：10.1055/s-1997-1331

  日期：1997.10

  The preparation of photochromic spirobenzopyrans with silyloxy groups is described.

  描述了具有甲硅烷氧基的光致变色螺苯并吡喃的制备。
• Self-Assembly of Graphene Oxide with a Silyl-Appended Spiropyran Dye for Rapid and Sensitive Colorimetric Detection of Fluoride Ions
  作者：Yinhui Li、Yu Duan、Jing Zheng、Jishan Li、Wenjie Zhao、Sheng Yang、Ronghua Yang

  DOI：10.1021/ac402592c

  日期：2013.12.3

  Fluoride ion (F–), the smallest anion, exhibits considerable significance in a wide range of environmental and biochemical processes. To address the two fundamental and unsolved issues of current F– sensors based on the specific chemical reaction (i.e., the long response time and low sensitivity) and as a part of our ongoing interest in the spiropyran sensor design, we reported here a new F– sensing approach that, via assembly of a F–-specific silyl-appended spiropyran dye with graphene oxide (GO), allows rapid and sensitive detection of F– in aqueous solution. 6-(tert-Butyldimethylsilyloxy)-1′,3′,3′-trimethylspiro [chromene- 2,2′-indoline] (SPS), a spiropyran-based silylated dye with a unique reaction activity for F–, was designed and synthesized. The nucleophilic substitution reaction between SPS and F– triggers cleavage of the Si–O bond to promote the closed spiropyran to convert to its opened merocyanine form, leading to the color changing from colorless to orange-yellow with good selectivity over other anions. With the aid of GO, the response time of SPS for F– was shortened from 180 to 30 min, and the detection limit was lowered more than 1 order of magnitude compared to the free SPS. Furthermore, due to the protective effect of nanomaterials, the SPS/GO nanocomposite can function in a complex biological environment. The SPS/GO nanocomposite was characterized by XPS and AFM, etc., and the mechanism for sensing F– was studied by 1H NMR and ESI-MS. Finally, this SPS/GO nanocomposite was successfully applied to monitoring F– in the serum.

  氟离子 (F–) 是最小的阴离子，在广泛的环境和生化过程中具有相当重要的意义。为了解决当前基于特定化学反应的 F 传感器的两个基本且未解决的问题（即响应时间长和灵敏度低），并且作为我们对螺吡喃传感器设计持续兴趣的一部分，我们在此报告了一种新的 F 传感器– 通过将 F– 特异性附加甲硅烷基的螺吡喃染料与氧化石墨烯 (GO) 组装在一起的传感方法，可以快速、灵敏地检测水溶液中的 F–。 6-(叔丁基二甲基硅氧基)-1′,3′,3′-三甲基螺[色烯- 2,2′-二氢吲哚] (SPS) 是一种螺吡喃基甲硅烷基化染料，对 F– 具有独特的反应活性。合成的。 SPS和F-之间的亲核取代反应触发Si-O键断裂，促进封闭的螺吡喃转化为开放的部花青形式，导致颜色从无色变为橙黄色，与其他阴离子相比具有良好的选择性。在GO的帮助下，SPS对F–的响应时间从180 min缩短至30 min，检测限比游离SPS降低了1个数量级以上。此外，由于纳米材料的保护作用，SPS/GO纳米复合材料可以在复杂的生物环境中发挥作用。采用XPS、AFM等手段对SPS/GO纳米复合材料进行表征，并利用1H NMR、ESI-MS研究其传感F-的机理。最后，这种SPS/GO纳米复合材料成功应用于监测血清中的F-。
• Photo-reversible and selective Cu2+ complexation of a spiropyran-carrying sulfobetaine copolymer in saline solution
  作者：Takayuki Suzuki、Yuki Hirahara、Kaori Bunya、Hiraku Shinozaki

  DOI：10.1039/b921169a

  日期：——

  A sulfobetaine copolymer (1) carrying a photochromic spiropyran residue was synthesized, which reversibly isomerized between the closed and open forms in pure water and in saline by irradiation with visible light. The thermodynamic stability of the open form of the spiropyran methacrylate (SPMA) units of compound 1 was reduced upon increasing NaCl concentration. In addition, photo-reversible and selective Cu2+ complexation in saline solution ([NaCl] = 1.0 wt%) was achieved using compound 1 with metal ions (Cu2+, Zn2+, Ni2+, or Co2+). Covalently cross-linked compound 1 showed selective Cu2+ adsorption in pure water. In contrast, the other metal ions were increasingly adsorbed as NaCl concentration increased, resulting in lower selectivity of Cu2+ ion adsorption with 1, e.g., the ratios of adsorption of Cu2+, Zn2+, Ni2+, and Co2+ with 1 in 10 wt% saline were 73, 20, 10, and 3%, respectively, while only Cu2+ adsorption was observed in a solution of 1.0 wt% NaCl. Because the stability of the open form of the SPMA units and the metal complexation of 1 were influenced by NaCl concentration, the electrostatically cross-linked networks of the zwitterionic sulfobetaine units of 1 may be loosened by NaCl addition, resulting in easy entry of metal ions into the network. The order of metal complexation among the four metals corresponded to the Irving–Williams series. Hydrogen-bonded networks of water molecules also may contribute to the relatively ineffective selective adsorption of Cu2+ ions by 1 compared to the electrically neutral spiropyran-carrying copolymer of N-isopropylacrylamide, 2.

  合成了带有光致变色螺吡喃残基的磺基甜菜碱共聚物(1)，该共聚物在纯水和盐水中通过可见光照射在闭合和开放形式之间可逆地异构化。化合物 1 的螺吡喃甲基丙烯酸酯 (SPMA) 单元的开放形式的热力学稳定性随着 NaCl 浓度的增加而降低。此外，使用化合物 1 与金属离子（Cu2+、Zn2+、Ni2+ 或 Co2+）在盐水溶液（[NaCl] = 1.0 wt%）中实现了光可逆和选择性 Cu2+ 络合。共价交联的化合物 1 在纯水中表现出选择性吸附 Cu2+。相反，随着 NaCl 浓度的增加，其他金属离子的吸附量增加，导致 Cu2+ 离子对 1 的吸附选择性较低，例如，10 wt% 盐水中 Cu2+、Zn2+、Ni2+ 和 Co2+ 对 1 的吸附比例为 73分别为 20%、10% 和 3%，而在 1.0 wt% NaCl 溶液中仅观察到 Cu2+ 吸附。由于SPMA单元开放形式的稳定性和1的金属络合受到NaCl浓度的影响，1的两性离子磺基甜菜碱单元的静电交联网络可能会因NaCl的添加而松弛，导致金属离子容易进入进入网络。四种金属之间的金属络合顺序对应于欧文-威廉姆斯系列。与电中性的带有螺吡喃的 N-异丙基丙烯酰胺共聚物 2 相比，水分子的氢键网络也可能导致 Cu2+ 离子 1 的选择性吸附相对无效。