联苯-3,4-二醇 | 92-05-7

• 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: 联苯-3,4-二醇
• 中文别名: 3.4-联苯二酚
• 英文名称: 3,4-dihydroxybiphenyl
• 英文别名: 4-phenyl pyrocatechol；3',4'-dihydroxy-1,1'-biphenyl；[1,1'-biphenyl]-3,4-diol；4-Phenylpyrocatechol；biphenyl-3,4-diol；4-phenylbenzene-1,2-diol
• CAS: 92-05-7
• 化学式: C₁₂H₁₀O₂
• mdl: MFCD00041746
• 分子量: 186.21
• InChiKey: QDNPCYCBQFHNJC-UHFFFAOYSA-N

物化性质

• 熔点：
  139.35°C
• 沸点：
  280.69°C (rough estimate)
• 密度：
  1.1032 (rough estimate)
• 溶解度：
  0.01 M
• 保留指数：
  1918

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

SDS

Name:	4-Phenylpyrocatechol 98% (Titr.) Material Safety Data Sheet
Synonym:	1,1'-Biphenyl-3,4-Diol
CAS:	92-05-7

Section 1 - Chemical Product MSDS Name:4-Phenylpyrocatechol 98% (Titr.) Material Safety Data Sheet
Synonym:1,1'-Biphenyl-3,4-Diol

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
92-05-7	1,1'-Biphenyl-3,4-Diol	98	202-121-6

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes 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: Immediately 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:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:
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 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. 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:
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# 92-05-7: 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: Solid
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 138 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H10O2
Molecular Weight: 186.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
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# 92-05-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,1'-Biphenyl-3,4-Diol - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
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# 92-05-7: No information available.
Canada
CAS# 92-05-7 is listed on Canada's NDSL List.
CAS# 92-05-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 92-05-7 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：

  联苯-3,4-二醇 在 sodium periodate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 4-苯基-1,2-苯醌
  参考文献：
  名称：

  邻喹啉酮和苯酚的催化剂控制的需氧耦合用于芳醚的合成

  摘要：

  邻-喹诺酮是未充分利用的六碳原子构建基块。我们在本文中描述了一种控制其与铜的反应性的方法，该方法引起了与苯酚的催化好氧交叉偶联。在温和条件下，可在宽范围的底物范围内以高收率生成所得芳基醚。该方法代表了一个独特的例子，其中过渡金属催化了邻醌的共价修饰，为它们在合成中的利用创造了新的机会。

  DOI：

  10.1002/anie.201606359
• 作为产物：
  描述：

  对羟基联苯 在 2-碘酰基苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以54%的产率得到联苯-3,4-二醇
  参考文献：
  名称：

  邻喹啉酮和苯酚的催化剂控制的需氧耦合用于芳醚的合成

  摘要：

  邻-喹诺酮是未充分利用的六碳原子构建基块。我们在本文中描述了一种控制其与铜的反应性的方法，该方法引起了与苯酚的催化好氧交叉偶联。在温和条件下，可在宽范围的底物范围内以高收率生成所得芳基醚。该方法代表了一个独特的例子，其中过渡金属催化了邻醌的共价修饰，为它们在合成中的利用创造了新的机会。

  DOI：

  10.1002/anie.201606359

文献信息

• Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides
  作者：Michelle A. Kroc、Aditi Patil、Anthony Carlos、Josiah Ballantine、Stephanie Aguilar、Dong-Liang Mo、Heng-Yen Wang、Daniel S. Mueller、Donald J. Wink、Laura L. Anderson

  DOI：10.1016/j.tet.2017.01.061

  日期：2017.7

  synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations

  合成α-氧化羰基化合物和邻苯二酚的常用方法是用亲电子氧源处理羰基化合物或苯酚。作为这些重要结构的替代方法，已经研究了N-烯氧基邻苯二甲酰亚胺，N-烯氧基异吲哚满酮和N-芳氧基邻苯二甲酰亚胺的形式[3,3]重排。当与初始Chan-Lam偶联结合使用时，这些转化有助于烯基硼酸的双氧合以合成α-加氧的酮和芳基硼酸的双氧合以合成儿茶酚。N-烯氧基异吲哚啉酮的重排也已显示为非对映选择性的。
• Altering 2-Hydroxybiphenyl 3-Monooxygenase Regioselectivity by Protein Engineering for the Production of a New Antioxidant
  作者：Almog Bregman-Cohen、Batel Deri、Shiran Maimon、Yael Pazy、Ayelet Fishman

  DOI：10.1002/cbic.201700648

  日期：2018.3.16

  New regiospecificity→new antioxidant: One single mutation, M321A, changed 2‐hydroxybiphenyl 3‐monooxygenase (HbpA) regioselectivity from oxidizing 2‐substituted phenols to 3‐substituted phenols. The crystal structure provided an explanation for the new activity. The antioxidant produced, 3,4‐dihydroxybiphenyl, had similar ferric reducing capacity to the well‐studied piceatannol.

  新的区域特异性→新的抗氧化剂：一个单一突变M321A改变了2-羟基联苯3-单加氧酶（HbpA）的区域选择性，从将2-取代的苯酚氧化为3-取代的酚。晶体结构为新活性提供了解释。产生的抗氧化剂3,4-二羟基联苯与经过充分研究的皮卡季诺醇具有类似的三价铁还原能力。
• Photoinduced reactions—XXXV
  作者：K. Omura、T. Matsuura

  DOI：10.1016/0040-4020(70)85026-8

  日期：——

  compounds as the main product. Relative reactivity of representative substituted phenols and the effect of the phenols on the decomposition rate of hydrogen peroxide were examined by a competition reaction with p-cresol. The apparent reactivity of phenols was found to decrease in the following order; p-Ph >p-Ac, p-Me, p-Cl > p-COOH, o-NO2, p-CN, p-t-Bu > m-COOH, p-NO2 > 2,4-(COOMe)2 > 2,4(NO2)2. The

  通过过氧化氢的光分解，发现乙腈是制备各种苯酚的规模水垢羟化反应的最佳有机溶剂。用2537Å的光照射系统，形成了邻位和对位二羟基化合物的主要产物。通过与对甲酚的竞争反应研究了代表性取代酚的相对反应性和酚对过氧化氢分解速率的影响。发现苯酚的表观反应性按以下顺序降低。p -Ph> p -Ac，p -Me，p -Cl> p -COOH，o -NO2，p -CN，p -吨-Bu>米-COOH，p -NO 2 > 2,4-（COOMe）2 > -2,4（NO 2）2。对过氧化氢的分解速度的影响倾向于以相同的顺序降低，但是没有发现明显的关系。讨论了将OH自由基加到苯酚中的机理。
• Conversion of Simple Cyclohexanones into Catechols
  作者：Yu-Feng Liang、Xinyao Li、Xiaoyang Wang、Miancheng Zou、Conghui Tang、Yujie Liang、Song Song、Ning Jiao

  DOI：10.1021/jacs.6b07269

  日期：2016.9.21

  A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis

  描述了在温和和简单的条件下，一种新型的 I2 催化的环己酮直接转化为取代的儿茶酚。仅使用 DMSO 作为溶剂、氧化剂和氧源即可实现多重氧化和脱氢芳构化过程，这种新颖的转变是显着的。这种不含金属的简单系统展示了一种合成高价值取代儿茶酚的通用方案，因此简化了用于药物发现的生物重要分子的合成和修饰。
• Melanin concentrating hormone antagonists
  申请人：Hu Eric Xiufeng

  公开号：US20050075324A1

  公开（公告）日：2005-04-07

  The present invention relates to compounds capable of serving as moderators of human and mammalian appetite and as such provides a means for reducing body mass. The compounds of the present invention are selective against melanin concentrating hormone and do not have the pernicious side effects resulting from compounds which interact with other appetite related brain receptors.

  本发明涉及能够作为人类和哺乳动物食欲调节剂的化合物，从而提供了一种减少体重的手段。本发明的化合物对黑色素浓缩激素具有选择性，并且不具有与与其他食欲相关的脑受体相互作用的化合物导致的有害副作用。

表征谱图