trans-1,3-cyclohexanediol | 5515-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1,3-cyclohexanediol
• 英文别名: trans cyclohexan-1,3-diol；trans-cyclohexane-1,3-diol；(1R,3R)-cyclohexane-1,3-diol
• CAS: 5515-64-0
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: RLMGYIOTPQVQJR-PHDIDXHHSA-N

物化性质

• 熔点：
  113.0 to 120.0 °C
• 沸点：
  135°C/13mmHg(lit.)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2906199090
• 储存条件：
  室温

SDS

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Section I.Chemical Product and Company Identification
Chemical Name trans-1,3-Cyclohexanediol
Portland OR
Synonym 1,3-Cyclohexanediol, (1R,3R)-rel- (CA INDEX NAME);
trans-1,3-Dihydroxycyclohexane
Chemical Formula C6H12O2
CAS Number 5515-64-0

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Section II. Composition and Information on Ingredients
Toxicology Data
Chemical Name CAS Number Percent (%) TLV/PEL
trans-1,3-Cyclohexanediol 5515-64-0 Min. 98.0 (GC) Not available. Not available.

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Ingestion
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Not available.
May be combustible at high temperature. Auto-Ignition
Flammability
Flash Points Flammable Limits Not available.
Not available.
These products are toxic carbon oxides (CO, CO2).
Combustion Products
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
trans-1,3-Cyclohexanediol

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Section VI. Accidental Release Measures
Spill Cleanup Use a shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
Instructions
disposal.

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Section VII. Handling and Storage
Handling and Storage Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a dry, cool
place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
Engineering Controls
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Splash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
Personal Protection
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solid. (White ~ very pale yellow, crystal ~ Solubility
Physical state @ 20°C Not available.
powder.)
Not available.
Specific Gravity
Molecular Weight 116.16 Partition Coefficient Not available.
135°C (275°F) @ 13 mmHg Not applicable.
Boiling Point Vapor Pressure
Melting Point 115°C (239°F) Vapor Density Not available.
Not available. Not available.
Refractive Index Volatility
Critical Temperature Not available. Odor Not available.
Not available. Not available.
Viscosity Taste

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Section X. Stability and Reactivity Data

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of Instability Avoid excessive heat and light.
Incompatibilities Reactive with oxidizing agents.

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Section XI. Toxicological Information
Not available.
RTECS Number
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Not available.
Toxicity Data
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
No specific information is available in our data base regarding the toxic effects of this material for humans. However,
Acute Toxic Effects
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling this
compound.

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Section XII. Ecological Information
Ecotoxicity Not available.
Environmental Fate Not available.
Continued on Next Page
trans-1,3-Cyclohexanediol

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Section XIII. Disposal Considerations
Waste Disposal Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
Not a DOT controlled material (United States).
DOT Classification
PIN Number Not applicable.
Proper Shipping Name Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not controlled under WHMIS (Canada).
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  trans-1,3-cyclohexanediol 在 甲基硼酸 、 tetrabutylphosphonium decatungstate 、 二苯二硫醚 、 (1S,2S,3R,5S)-(+)-2,3-蒎烷二醇 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以80%的产率得到cis-1,3-cyclohexanediol
  参考文献：
  名称：

  通过瞬态热力学控制进行选择性异构化：反式二醇动态差向异构化为顺式二醇

  摘要：

  传统的立体选择性合成方法需要在形成新立体中心的每一步中进行高水平的对映体和非对映体控制。在这里，我们报告了一种替代方法，其中有机底物的立体化学被选择性地编辑而无需进一步的结构修饰，这种策略有可能允许新类别的后期立体化学操作并提供稀有或有价值的立体化学构型。在这项工作中，我们描述了通过氢原子转移光催化和硼酸介导的瞬态热力学控制实现环状二醇的选择性差向异构化，选择性地从原本受欢迎的反式异构体生成不太稳定的顺式产物。一系列取代模式和环尺寸适合选择性异构化，包括立体化学复杂的多元醇，例如雌三醇，以及无环邻位二醇的顺式差向异构化。此外，该策略使得糖端基异构体能够发生不同的差向异构化，从而可以从α-或β-构型糖苷获得不同的糖异构体。

  DOI：

  10.1021/jacs.1c11552
• 作为产物：
  描述：

  (+/-)-1α-Methoxy-2α-brom-3β-hydroxy-cyclohexan 在 镍 ion-exchange resin - form> 、 氢溴酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成 trans-1,3-cyclohexanediol
  参考文献：
  名称：

  The utility of the dehalogenation–deetherification sequence for the proof of structure of methoxyhalocyclohexanols and methoxyhalocyclopentanols. Synthesis of the cis- and trans-2- and -3-methoxy-cyclohexanols and -cyclopentanols

  摘要：

  通过用65-70°的68%盐酸脱醚化，然后用雷尼镍和氢气氢解，得到1,2-和1,3-环戊二醇，可以明确证明甲氧基氯环戊醇(I'c-IV'c)的结构，这与甲氧基溴环己醇(I-IV)转化为1,2-和1,3-环己二醇的方式相同。对甲氧基溴环己醇和甲氧基氯环戊醇进行氢解反应，可在80-97%的产率下合成顺式和反式2-和3-甲氧基环己醇和环戊醇。后者化合物用68%盐酸脱醚化后，以70-90%的产率得到相应的1,2-和1,3-环己二醇和1,2-环戊二醇，但只有5-7%的产率得到1,3-环戊二醇。因此，对于甲氧基卤代环烷醇的结构证明，脱醚化应该在去卤化之前进行，而不是之后。

  DOI：

  10.1139/v67-423

文献信息

• Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions
  作者：Tomohiro Maegawa、Akira Akashi、Kiichiro Yaguchi、Yohei Iwasaki、Masahiro Shigetsura、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1002/chem.200900361

  日期：2009.7.13

  An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H2 pressures (<10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are

  已经开发了基于使用异质铂族催化剂的有效和实用的芳烃加氢方法。Rh / C是最有效的芳环加氢催化剂，可以在中性条件下，在常压至中等H 2压力（<10 atm）下在i PrOH中进行。将各种芳烃（如烷基苯，苯甲酸，吡啶，呋喃）以良好或极好的收率氢化成相应的环己基和杂环化合物。Ru / C的使用比Rh / C便宜，它为氢化包括苯酚在内的芳烃提供了一种有效而实用的方法。在简单过滤后，两种催化剂都可以重复使用数次，而催化活性没有任何重大损失。
• Chiral-Substituted Poly-<i>N</i>-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions
  作者：Bo Hao、Medha J. Gunaratna、Man Zhang、Sahani Weerasekara、Sarah N. Seiwald、Vu T. Nguyen、Alex Meier、Duy H. Hua

  DOI：10.1021/jacs.6b12113

  日期：2016.12.28

  synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1

  由L-氨基酸合成了在吡咯烷酮环的C5处含有不对称中心的一类新的聚-N-乙烯基吡咯烷酮。这些聚合物，特别是17，用于稳定纳米团簇，例如Pd/Au，用于1,3-和1,2-环烷二醇和烯烃的催化不对称氧化，而Cu/Au用于环烷烃的CH氧化。研究发现，吡咯烷酮环中的C5取代基体积越大，产生的光学产率越大。 (±)-1,3- 和 1,2-反式环烷二醇的氧化动力学拆分以及内消旋顺式二醇的去对称化均在水中的氧气气氛下用 0.15 mol% Pd/Au (3:1)-17 进行，提供优异的 (S)-羟基酮的化学和光学收率。在 30 psi 氧气水中，用 0.5 mol% Pd/Au (3:1)-17 氧化各种烯烃，得到 >93% ee 的二羟基化产物。 (R)-柠檬烯在 25 °C 下在 C-1,2-环烯官能团处发生氧化，产生 (1S,2R,4R)-二羟基柠檬烯 49，产率 92%。重要的是，环烷烃用乙腈中的
• Catalytic 1,3-Difunctionalisation of Organic Backbones through a Highly Stereoselective, One-Pot, Boron Conjugate-Addition/Reduction/Oxidation Process
  作者：Cristina Solé、Amolak Tatla、Jose A. Mata、Andrew Whiting、Henrik Gulyás、Elena Fernández

  DOI：10.1002/chem.201102081

  日期：2011.12.9

  enantioselectivity provided by the CuI catalyst modified with Josiphos‐ and Mandyphos‐type ligands has been examined. The oxidative substitution of the boryl unit with a hydroxyl group proceeds with complete retention of configuration at the Cβ‐atom. In parallel, the stoichiometric reduction of the imino or carbonyl group provides a second stereogenic centre. Depending on the nature of the reducing reagent

  建立了简单的一锅三步合成路线，制备手性1,3-氨基醇和1,3-二醇。考虑到合成方案的整体立体控制，第一步和关键步骤分别是对映选择性的α，β-不饱和亚胺和酮的β-硼酸酯。研究了用Josiphos和Mandyphos型配体改性的Cu I催化剂提供的对映选择性。的甲硼烷基单元的氧化性取代与在C配置的完全保留的羟基进行β -原子。同时，亚氨基或羰基的化学计量还原提供了第二个立体定向中心。根据还原剂的性质，可以实现极高的非对映选择性，特别是对于合成试剂而言。-1,3-氨基醇和1,3-二醇
• Synthesis of cyclic 1,3-diols as scaffolds for spatially directed libraries
  作者：Gurpreet Singh、Jeffrey Aubé

  DOI：10.1039/c6ob00598e

  日期：——

  A series of 1,3-diols has been synthesized and used to create a pilot library of spatially diverse compounds.

  一系列1,3-二醇已经合成并用于创建一个空间多样化化合物的试验库。
• [EN] DI-VANILLOYL AND TRI-VANILLOYL DERIVATIVES FOR USE IN ANTI-CANCER THERAPY<br/>[FR] DÉRIVÉS DE DI-VANILLOYLE ET DE TRI-VANILLOYLE POUR UNE UTILISATION DANS UNE THÉRAPIE ANTI-CANCÉREUSE
  申请人：UNIV BRUXELLES

  公开号：WO2010043631A1

  公开（公告）日：2010-04-22

  The invention relates to the medical field, more precisely in the field of anti-cancer treatment and treatment of Alzheimer's disease, Parkinson's disease or Pick's disease or for ameliorating symptoms of Down syndrome, providing newly synthesised multi-vanilloyl derivative compounds and their use in the treatment of said disorders.

  这项发明涉及医学领域，更准确地说是在抗癌治疗和治疗阿尔茨海默病、帕金森病或皮克氏病，或改善唐氏综合征症状方面，提供新合成的多香豆酰衍生物化合物及其在治疗上述疾病中的用途。

表征谱图