(3S,6S)-3,6-辛二醇 | 136705-66-3

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (3S,6S)-3,6-辛二醇
• 中文别名: (S,S)3,6-辛二醇；(3S,6S) - (+)-3,6 - 辛二醇
• 英文名称: (3S,6S)-octane-3,6-diol
• 英文别名: (3S,6S)-3,6-Octanediol
• CAS: 136705-66-3
• 化学式: C₈H₁₈O₂
• 分子量: 146.23
• InChiKey: BCKOQWWRTRBSGR-YUMQZZPRSA-N

物化性质

• 熔点：
  49-51°C
• 比旋光度：
  +15° (c 10, ethanol)
• 沸点：
  243.79°C (rough estimate)
• 密度：
  0.9636 (rough estimate)
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会发生分解，目前没有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• 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

• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	(3S 6S)-3 6-Octanediol 95% (98% e.e.) Material Safety Data Sheet
Synonym:	(3S,6S)-Dihydroxyoctane
CAS:	136705-66-3

Section 1 - Chemical Product MSDS Name:(3S 6S)-3 6-Octanediol 95% (98% e.e.) Material Safety Data Sheet
Synonym:(3S,6S)-Dihydroxyoctane

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
136705-66-3	(3S,6S)-3,6-Octanediol	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.
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:
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.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with 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 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:
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. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. 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# 136705-66-3: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H18O2
Molecular Weight: 146.23

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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:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 136705-66-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(3S,6S)-3,6-Octanediol - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 136705-66-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 136705-66-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 136705-66-3 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

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3,6-辛二醇 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 生成 (S,S)-octane-3,6-diol cyclic sulfate
  参考文献：
  名称：

  Burk, Mark J.; Feaster, John E.; Nugent, William A., Journal of the American Chemical Society, 1993, vol. 115, # 22, p. 10125 - 10138

  摘要：

  DOI：
• 作为产物：
  描述：

  4-辛炔-3,6-二醇 在 platinum on activated charcoal 、 (S)-B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine jones reagent 、 dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (3S,6S)-3,6-辛二醇
  参考文献：
  名称：

  立体选择性还原不饱和的1，4-二酮。制备手性1,4-二醇的实用方法

  摘要：

  基于硼烷介导的恶唑硼烷催化的2-烯-1,4-二酮（2），2-炔-1,4-二酮（2）还原反应的合成C 2对称手性1,4-二醇的新合成路线描述3）和/或共络二酮4。对二酮3和4的还原分别获得了良好或优异的对映异构和非对映异构选择性，分别由恶唑硼烷6和5催化。

  DOI：

  10.1016/s0040-4039(96)02476-8

文献信息

• New chiral phospholanes; Synthesis, characterization, and use in asymmetric hydrogenation reactions
  作者：Mark J. Burk、John E. Feaster、Richard L. Harlow

  DOI：10.1016/s0957-4166(00)86109-1

  日期：1991.1

  5-disubstituted-1-phenylphospholanes which are then employed in the preparation of a new series of C2-symmetric bis- and C3-symmetric tris(phospholane) ligands. A versatile three-step route to the important chiral 1,4-diol intermediates, used in the phosphine syntheses, is outlined. Rhodium complexes bearing the new phosphine ligands were prepared and shown to act as efficient catalyst precursors for the enantioselective

  我们描述了对映体纯的反式-2,5-二取代-1-苯基膦酸酯的实际合成，然后将其用于制备一系列新的C 2对称双-和C 3对称三（膦）配体。概述了用于膦合成的重要手性1,4-二醇中间体的通用三步路线。制备了带有新的膦配体的铑配合物，并显示出它们可作为对各种不饱和底物进行对映选择性氢化的有效催化剂前体。
• Oxazaborolidine-catalysed reduction of alk-2-ene-1,4-diones. A convenient access to chiral 1,4-diols
  作者：Jordi Bach、Ramon Berenguer、Jordi Garcia、Marta López、Judith Manzanal、Jaume Vilarrasa

  DOI：10.1016/s0040-4020(98)00936-3

  日期：1998.12

  An efficient method for the preparation of C2-symmetric, chiral alk-2-ene-1,4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones (2) in the presence of oxazaborolidine (R)-1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction

  基于硼烷介导的对称烷基-2-烯-1,4-的还原反应，已经获得了一种制备C 2对称的手性烷-2-烯-1,4-二醇的有效方法（4）。二酮（2）在oxazaborolidine（R）-1的存在下。通常，2中双键的存在是有益的（与相关的饱和1,4-二酮3相比），不仅就还原步骤中的立体选择性而言，而且还因为它使我们能够去除内消旋- 4通过色谱纯化和/或改善得到的几个二醇的混合物的立体化学纯度4由Sharpless的环氧化作用。富含对映体的化合物4已经容易地还原成饱和二醇，而光学纯度的损失可忽略不计。
• Ligands for asymmetric reactions
  申请人：——

  公开号：US20040260091A1

  公开（公告）日：2004-12-23

  The invention relates to a process for the manufacture of ligands capable of forming metal complexes and such complexes; novel ligands with new backbones, complexes thereof with transition metals, the use of complexes of said ligands with transition metals as catalysts, as well as novel intermediates for the manufacture of said ligands. The ligand complexes are useful in stereoselective synthesis, especially hydrogenation, of various organic molecules. Especially, the process according to the invention is directed to the synthesis of compounds of the formulae IA and IIA, wherein the substituents have the meanings given in the description, and to novel compounds of these formulae as ligands. 1

  本发明涉及一种制备能够形成金属配合物的配体及其配合物的工艺；带有新骨架的新型配体，以及与过渡金属的复合物，所述配体与过渡金属的复合物的用途作为催化剂，以及用于制备所述配体的新型中间体。所述配体复合物在立体选择性合成中特别有用，特别是在各种有机分子的氢化反应中。特别地，本发明的工艺针对式IA和IIA化合物的合成，其中取代基具有所述描述中给出的含义，以及这些式的新型化合物作为配体。
• Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes
  作者：Scott Snyder、Alexandria Brucks、Daniel Treitler、Shu-An Liu

  DOI：10.1055/s-0033-1338865

  日期：——

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.
• A Catalytic Cycle for the Asymmetric Synthesis of Epoxides Using Sulfur Ylides
  作者：Jacques Zanardi、Catherine Leriverend、Dimitri Aubert、Karine Julienne、Patrick Metzner

  DOI：10.1021/jo015588m

  日期：2001.8.1