3-环己基-1,1-二甲醇 | 2160-94-3

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-环己基-1,1-二甲醇
• 中文别名: 环己烯-1,1-二甲基醇；3-环己烯-1,1-二甲醇
• 英文名称: 4,4-bis(hydroxylmethyl)cyclohexene
• 英文别名: 4,4-bis-hydroxymethyl-cyclohexene；1,1-bis(hydroxymethyl)-cyclohex-3-ene；3-Cyclohexene-1,1-dimethanol；[1-(hydroxymethyl)cyclohex-3-en-1-yl]methanol
• CAS: 2160-94-3
• 化学式: C₈H₁₄O₂
• mdl: MFCD00001575
• 分子量: 142.198
• InChiKey: YXEBFFWTZWGHEY-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C(lit.)
• 沸点：
  115 °C (0.4 mmHg)
• 密度：
  1.0037 (rough estimate)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与不相容的材料及强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25,S36
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2906199090
• 储存条件：
  密封储存，应存放在阴凉干燥的库房中。

SDS

Name:	3-Cyclohexene-1 1-dimethanol 98% Material Safety Data Sheet
Synonym:	4,4-Bis(hydroxymethyl)-1-cyclohexene; 1,1-bis(Hydroxymethyl)-3-cyclohexene; 4,4-bis(Hydroxymethyl)cyclohexen
CAS:	2160-94-3

Section 1 - Chemical Product MSDS Name:3-Cyclohexene-1 1-dimethanol 98% Material Safety Data Sheet
Synonym:4,4-Bis(hydroxymethyl)-1-cyclohexene; 1,1-bis(Hydroxymethyl)-3-cyclohexene; 4,4-bis(Hydroxymethyl)cyclohexen

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2160-94-3	3-Cyclohexene-1,1-dimethanol	98.0	218-481-2

Hazard Symbols: XN
Risk Phrases: 20/21

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation and in contact with skin.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May be harmful if absorbed through the skin.
Ingestion:
May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation.
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:
Antidote: None reported.

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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, then place into a suitable 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. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. 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# 2160-94-3: 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 gloves to prevent skin exposure.
Clothing:
Wear appropriate 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: Crystalline powder
Color: White - Beige Crystalline Powder
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 88.00 - 90.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H14O2
Molecular Weight: 142.20

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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:
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# 2160-94-3: GW6050000 LD50/LC50:
CAS# 2160-94-3: Oral, mouse: LD50 = 1750 mg/kg; Oral, rabbit: LD50 = 3400 mg/kg; Oral, rat: LD50 = 1750 mg/kg.
Carcinogenicity:
3-Cyclohexene-1,1-dimethanol - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: XN
Risk Phrases:
R 20/21 Harmful by inhalation and in contact with
skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 2160-94-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2160-94-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2160-94-3 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：

  3-环己基-1,1-二甲醇 在 甲醇 、 三溴化磷 、 镍 作用下， 45.0~150.0 ℃ 、6.86 MPa 条件下， 生成 1,1-双(溴甲基)环己烷
  参考文献：
  名称：

  Shortridge et al., Journal of the American Chemical Society, 1948, vol. 70, p. 948

  摘要：

  DOI：
• 作为产物：
  描述：

  cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 3-环己基-1,1-二甲醇
  参考文献：
  名称：

  Synthesis of 4,4-Disubstituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into 12-Helical β-Peptides

  摘要：

  An enantioselective synthetic route is reported for trans-2-aminocyclopentanecarboxylic acids (ACPC) bearing geminal side chain pairs at the 4-position. beta-Peptides containing the 4,4-disubstituted ACPC residues adopt the 12-helical conformation, as demonstrated by 2D NMR analysis in aqueous solution. These 4,4-disubstituted ACPC residues display functional groups, including acidic and hydrogen bond donating groups, in a geometrically defined fashion, which should be useful for the design of beta-peptides for specific applications.

  DOI：

  10.1021/ol0483293

文献信息

• Stereochemistry of cyclic compounds—I
  作者：Klaus Bruns、Jens Conrad、Alois Steigel

  DOI：10.1016/0040-4020(79)88015-1

  日期：1979.1

  the 3-methyl and 3-ethyl derivatives by fractional distillation. On the basis of 1H NMR spectroscopy, the nature of the isomerism is shown to be of cis, trans type and an unambiguous cofigurational assignment of the isomers has been achieved. Although the diastereomers are of similar topography, they have distinctly different olfactory properties.

  由丁二烯和2，3-二甲基丁二烯与丙烯醛的Diels-Alder加合物制备了几种2，4-二氧杂螺环[5.5]十一烷基-8-烯。与某些被认为是纯化合物的3-取代衍生物的文献报道相反，表明这些螺环化合物通常以两种非对映异构体的1：1混合物形式获得。在3-甲基和3-乙基衍生物的情况下，通过分馏分离出异构体。在1 H NMR光谱的基础上，该异构体的性质显示为顺式，反式，并且已实现了该异构体的明确配位分配。尽管非对映异构体具有相似的形貌，但它们具有明显不同的嗅觉特性。
• A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO
  作者：Marco Frigerio、Marco Santagostino

  DOI：10.1016/0040-4039(94)80038-3

  日期：1994.10

  o-Iodoxybenzoic acid (IBX) smoothly oxidizes primary and secondary alcohols to aldehydes and ketones, respectively. 1,2-Diols are converted to α-ketols or α-diketones without any oxidative cleavage of the glycol CC bond. IBX oxidations are easily conducted in DMSO solution at room temperature, with yields ranging from good to quantitative.

  邻碘氧苯甲酸（IBX）分别将伯醇和仲醇平滑氧化为醛和酮。1,2-二醇可转化为α-酮醇或α-二酮，而乙二醇CC键没有任何氧化裂解。IBX氧化很容易在室温下的DMSO溶液中进行，收率范围从良好到定量。
• Epoxidation by sodium chlorite with aldehyde-promoted chlorine dioxide formation
  作者：Ashok Jangam、David E. Richardson

  DOI：10.1016/j.tetlet.2010.09.102

  日期：2010.12

  An improved method is described for selective room temperature epoxidation of alkenes by sodium chlorite in a solvent mixture of ethanol, acetonitrile, and water buffered at pH 7. In addition, the use of aldehydes as promoters in chlorite oxidations is described for the first time. The amount of sodium chlorite, the solvent mixture, and the addition of formaldehyde as a practical promoter were optimized

  描述了一种改进的方法，用于在乙醇，乙腈和pH值为7的水混合的溶剂混合物中，用亚氯酸钠对烯烃进行选择性的室温环氧化。此外，首次描述了在绿泥石氧化中使用醛作为促进剂。优化了亚氯酸钠的量，溶剂混合物以及作为实用促进剂的甲醛的添加。在优化研究中，将苯乙烯用作测试底物，并通过使用各种亲核和亲电底物评估了该方法的一般性。用苯乙烯获得高达89％的收率，其他亲核烯烃很容易转化为环氧化物。
• Substituted Pyrrolidine-2-Carboxamides
  申请人：Ding Qingjie

  公开号：US20100075948A1

  公开（公告）日：2010-03-25

  There are provided compounds of the formula wherein X, Y, R 1 , R 2 , R 3 , R 3 , R 4 , R 5 , R 6 and R 7 are as described herein and enantiomers and pharmaceutically acceptable salts and esters thereof. The compounds are useful as anticancer agents.

  提供了以下式的化合物 其中X、Y、R1、R2、R3、R3、R4、R5、R6和R7如本文所述，以及其对映体和药用可接受的盐和酯。这些化合物可用作抗癌药物。
• Facile Synthesis of Aryl- and Alkyl-bis(trifluoromethylsulfonyl)methanes
  作者：Aiko Hasegawa、Takuo Ishikawa、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1246/bcsj.78.1401

  日期：2005.8

  Various arylbis(trifluoromethylsulfonyl)methanes (1) have been synthesized by reacting the corresponding benzylic halides with sodium trifluoromethanesulfinate and then with triflic anhydride. In addition, when the aryl group of 1 is a pentafluorophenyl group, the nucleophilic para-substitution of the aryl group with alkyllithiums and sodium alkoxides occurs. This reaction is useful for the design of new Brønsted acids.

  通过将相应的苄基卤化物与三氟甲烷亚硫酸钠反应，然后再与三氟甲磺酸酐反应，合成了多种芳香基双(三氟甲磺酰)甲烷 (1)。此外，当1中的芳基是五氟苯基时，芳基的亲核性对位取代反应可以通过烷基锂和烷氧化钠实现。这一反应对于设计新型布朗斯特酸具有实用价值。

表征谱图