藤黄盐 | 491-45-2

• 物质功能分类: 化学试剂 - 有机试剂 - 酚类
• 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: 藤黄盐
• 英文名称: phloroglucide
• 英文别名: NSC65069；2-(3,5-dihydroxyphenyl)benzene-1,3,5-triol
• CAS: 491-45-2
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: KICYRZIVKKYRFS-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C
• 沸点：
  529.5±40.0 °C(Predicted)
• 密度：
  1.594±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 海关编码：
  29072900,2906299090

SDS

Name:	Phloroglucide 95+% Material Safety Data Sheet
Synonym:	PHB
CAS:	491-45-2

Section 1 - Chemical Product MSDS Name:Phloroglucide 95+% Material Safety Data Sheet
Synonym:PHB

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
491-45-2	Phloroglucide	95+	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.Hygroscopic (absorbs moisture from the air).Light sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
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:
Not available.

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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 if irritation develops or persists. Flush skin with plenty of soap and water.
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.
Inhalation:
Remove from exposure and move to fresh air immediately. Get medical aid if cough or other symptoms appear.
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.
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:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. 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. Dark room.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 491-45-2: 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: slightly brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 300 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: C12H10O5
Molecular Weight: 234.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures. May discolor on exposure to light.
Conditions to Avoid:
Incompatible materials, light, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 491-45-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Phloroglucide - 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# 491-45-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 491-45-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 491-45-2 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

藤黄盐是一种极其重要的医药中间体，其应用范围广泛。制备步骤如下：

1. 将47.6摩尔（6千克）间三苯酚加入24升三氟醋酸中，加热回流搅拌20小时。

2. 减压蒸出15升三氟醋酸，得到残留固体。

3. 在残留固体中加入10升二氯甲烷，搅拌成均匀浆状物后过滤，用二氯甲烷洗涤干燥后的5千克粉红色粗品，如图1所示为该粗品的HPLC图。

4. 取2千克粗产品，加入20升水，用碳酸钠调节pH至8-9，加热回流搅拌18小时后冷却至室温。过滤出固体，干燥后得到淡土黄色固体产品1.5千克。

反应信息

• 作为反应物：
  描述：

  藤黄盐 在 溴 、 1,2-二氯乙烷 作用下， 生成 3,5,2',4',6'-pentabromo-biphenyl-2,4,6,3',5'-pentaol
  参考文献：
  名称：

  Herzig; Kohn, Monatshefte fur Chemie, 1908, vol. 29, p. 683

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三羟基-苯-1,3,5-三磺酸 在 盐酸 作用下， 生成 藤黄盐
  参考文献：
  名称：

  Pollak; Gebauer-Fuelnegg, Monatshefte fur Chemie, 1926, vol. 47, p. 549

  摘要：

  DOI：

文献信息

• Increasing Structural Diversity of Natural Products by Michael Addition with <i>ortho</i>-Quinone Methide as the Acceptor
  作者：Ge Liao、Jie Fan、Lena Ludwig-Radtke、Katja Backhaus、Shu-Ming Li

  DOI：10.1021/acs.joc.9b02971

  日期：2020.1.17

  form of clavatol, ortho-quinone methide, can be generated from hydroxyclavatol in an aqueous system and used as a highly reactive intermediate for coupling with diverse natural products under very mild conditions. These include flavonoids, hydroxynaphthalenes, coumarins, xanthones, anthraquinones, phloroglucinols, phenolic acids, indole derivatives, tyrosine analogues, and quinolines. The clavatol moiety

  克拉维醇的活性形式，邻醌甲基化物，可以在水性系统中由羟基克拉维醇产生，并用作在非常温和的条件下与各种天然产物偶联的高反应性中间体。这些包括类黄酮，羟基萘，香豆素，氧杂蒽酮，蒽醌，间苯三酚，酚酸，吲哚衍生物，酪氨酸类似物和喹啉。克拉法醇部分主要通过CC键与酚羟基/氨​​基的邻位或对位以及吲哚环的C2位相连。
• BIS(AMINOPHENOL) DERIVATIVE, PROCESS FOR PRODUCING SAME, POLYAMIDE RESIN, POSITIVE PHOTOSENSITIVE RESIN COMPOSITION, PROTECTIVE FILM, INTERLAYER DIELECTRIC FILM, SEMICONDUCTOR DEVICE, AND DISPLAY ELEMENT
  申请人：Terakawa Koji

  公开号：US20100044888A1

  公开（公告）日：2010-02-25

  A bis(aminophenol) derivative having substituents at positions adjacent to two amino groups is provided. The bis(aminophenol) derivative is used as a raw material of a polyamide resin for a positive-tone photosensitive resin composition. A polyamide resin comprising bis(aminophenol) and a structure derived from a carboxylic acid is also provided, the bis(aminophenol) having substituents at positions adjacent to the two amino groups. A positive-tone photosensitive resin composition comprising a polybenzooxazole precursor resin, exhibiting high sensitivity and a high cyclization rate even when cured at a low temperature is provided. Also provided is a positive-tone photosensitive resin composition comprising a polyamide resin having an imide structure, an imide precursor structure, or an amide acid ester structure. The composition exhibits high sensitivity and produces a cured product having low water absorption even when cured at a low temperature.

  本发明提供了一种在两个氨基团相邻位置上具有取代基的双(氨基酚)衍生物。该双(氨基酚)衍生物用作聚酰胺树脂的原材料，用于制备正向感光树脂组合物。还提供了一种聚酰胺树脂，包括双(氨基酚)和由羧酸衍生的结构，其中双(氨基酚)在两个氨基团相邻位置上具有取代基。提供了一种正向感光树脂组合物，包括聚苯并噁唑前体树脂，即使在低温下固化，也表现出高灵敏度和高环化速率。还提供了一种正向感光树脂组合物，包括具有酰亚胺结构、酰亚胺前体结构或酰胺酸酯结构的聚酰胺树脂。该组合物表现出高灵敏度，即使在低温下固化，也能产生低吸水性的固化产物。
• [EN] SQUARYLIUM COMPOUNDS FOR USE IN DISPLAY DEVICES<br/>[FR] COMPOSÉS DE SQUARYLIUM DESTINÉS À ÊTRE UTILISÉS DANS DES DISPOSITIFS D'AFFICHAGE
  申请人：NITTO DENKO CORP

  公开号：WO2018227145A1

  公开（公告）日：2018-12-13

  Optionally substituted squarylium compounds, such as those depicted in Formula 1, may be useful in filters for display devices.

  可选择替代苯并四氮杂环化合物，例如公式1中所示的化合物，在显示器滤光片中可能是有用的。
• Structure-activity relationship in advanced glycation end products formation inhibitory activity of phlorotannins
  作者：Mitsuhiro Sekiguchi、Seiya Shinoda、Arisa Uno、Tomoya Masaki、Tetsuya Sasaki、Haruaki Ishiyama

  DOI：10.1093/bbb/zbac106

  日期：2022.8.24

  The structure and inhibitory activity of advanced glycation end products (AGEs) formation were studied using six model compounds and seven phlorotannins isolated from brown alga Ecklonia stolonifera. As a result, it was inferred that AGEs formation inhibitory activity was stronger when electron-rich groups were present because of the addition of many oxygen atoms to the phlorotannins.

  使用从褐藻 Ecklonia stolonifera 中分离出的六种模型化合物和七种草单宁，研究了晚期糖基化终产物 (AGE) 形成的结构和抑制活性。结果推断，由于在叶皮单宁中添加了许多氧原子，当存在富电子基团时，AGEs形成抑制活性更强。
• Positive type photoresist composition
  申请人：FUJI PHOTO FILM CO., LTD.

  公开号：EP0445680A2

  公开（公告）日：1991-09-11

  A positive type photoresist composition which is superior in the prevention of pattern break and scumming during development, comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound, wherein said novolak resin is a condensate of a mixture of m-cresol and p-cresol with at least one of formaldehyde, formaldehyde polymer and formaldehyde precursor and wherein the relationship between X = A/(A+B+C) and the content of m-cresol in said novolak resin falls within the shaded part (including the straight lines surrounding this part) in Figure 1, said A representing an integrated value of peak area between 23.0 ppm and 31.0 ppm , B representing an integrated value of peak area between 31.0 ppm and 34.0 ppm and C representing an integrated value of peak area between 34.0 ppm and 37.0 ppm in a ¹³C-NMR spectrum of a dimethyl sulfoxide-d₆ solution of said novolak resin.

  一种正型光刻胶组合物，在显影过程中可有效防止图案破裂和浮渣，该组合物由碱溶性酚醛树脂和 1,2-醌噻嗪化合物组成，其中所述酚醛树脂是间甲酚和对甲酚与甲醛、甲醛聚合物和甲醛前体中至少一种的混合物的缩合物、其中，X = A/(A+B+C) 与间甲酚在所述酚醛树脂中的含量之间的关系在图 1 中的阴影部分（包括围绕该部分的直线）内，所述 A 代表峰面积的综合值，介于 23.在所述酚醛树脂的二甲亚砜-d₆溶液的¹³C-NMR 光谱中，A 代表峰面积的综合值在 23.0 ppm 和 31.0 ppm 之间，B 代表峰面积的综合值在 31.0 ppm 和 34.0 ppm 之间，C 代表峰面积的综合值在 34.0 ppm 和 37.0 ppm 之间。