甲基环氧丙醇 | 86884-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 甲基环氧丙醇
• 中文别名: 2-甲基-2,3-环氧基-1-丙醇；2-甲基环氧丙醇
• 英文名称: (R)-2-methylglycidol
• 英文别名: (R)-(2-methyloxiran-2-yl)methanol；(2R)-(-)-2-methyl-2,3-epoxy-1-propanol；[(2R)-2-methyloxiran-2-yl]methanol
• CAS: 86884-89-1
• 化学式: C₄H₈O₂
• 分子量: 88.1063
• InChiKey: AAVHHYWBSVSPPN-SCSAIBSYSA-N

物化性质

• 沸点：
  107°C (estimate)
• 密度：
  1.1000

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2910900090
• 储存条件：
  温度：20°C，环境气体：惰性气体

SDS

Name:	(R)-2-Methyl glycidol Material Safety Data Sheet
Synonym:	None
CAS:	86884-89-1

Section 1 - Chemical Product MSDS Name:(R)-2-Methyl glycidol Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
86884-89-1	(R)-2-Methyl glycidol	100	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause cyanosis of the extremities. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. Aspiration may lead to pulmonary edema. May cause systemic effects. Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Combustible liquid.
Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Do NOT get water inside containers.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not allow contact with water. Discard contaminated shoes. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Keep from contact with moist air and steam.
Storage:
Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Deep freeze (below -20C). Storage under a nitrogen blanket has been recommended. Store protected from moisture.

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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# 86884-89-1: 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: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 107 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: 415 deg C ( 779.00 deg F)
Flash Point: 62 deg C ( 143.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.1000g/cm3
Molecular Formula: C4H8O2
Molecular Weight: 88.11

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, moisture, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Moisture, acids, bases, strong 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# 86884-89-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-2-Methyl glycidol - 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: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 25 Avoid contact with eyes.
S 28 After contact with skin, wash immediately
with...
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 86884-89-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 86884-89-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 86884-89-1 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

用途：用于生产甲基甘油和树脂，也可应用于医药、农药以及助剂的制造。

反应信息

• 作为反应物：
  描述：

  甲基环氧丙醇 在 戴斯-马丁氧化剂 作用下， 以 乙二醇甲醚 为溶剂， 生成 (S)-2-hydroxy-2-methyl-3-azidopropanal
  参考文献：
  名称：

  Process of producing 8A- and 9A-azalide antibiotics

  摘要：

  披露了一种生产8a-和9a-氮杂环化合物的方法，包括将8a-氮杂或9a-氮杂氮杂环东部片段或其衍生物与以下化合物的反应：X--A'--Y，其中X和Y是适当的反应基团，A'是形成氮杂环西部的片段或化合物，然后将此中间体环化以形成目标8a-或9a-氮杂环化合物。可以根据此过程合成I、II和III型公式化合物以及其他氮杂环化合物。

  公开号：

  US05332807A1
• 作为产物：
  描述：

  2-甲基-2-丙烯-1-醇 在 titanium(IV) isopropylate 、 过氧化氢异丙苯 、 D-(-)-酒石酸二异丙酯 作用下， 以 二氯甲烷 为溶剂， 以79 %的产率得到甲基环氧丙醇
  参考文献：
  名称：

  硫代羧酸A及其衍生物的合成及生物活性

  摘要：

  青霉属代谢物硫代羧酸 A ( 1a ) 和三个相近的类似物分 14 个步骤合成。立体异构元素是通过立体选择性 Sharpless 环氧化、( E )-二溴化物的选择性还原和 Suzuki 交叉偶联来安装的。以 6% 的总收率获得硫代羧酸 A ( 1a )。合成产物和天然分离物在它们的特定旋转和对大肠杆菌和金黄色葡萄球菌的抗菌活性方面有显着差异。这种模块化合成路线应该足够灵活，以允许合成其他天然和非天然的 3-甲氧基羰基二氢呋喃-4-用于生物学研究。

  DOI：

  10.1021/acs.jnatprod.2c00870

文献信息

• Mapping the substrate selectivity of new hydrolases using colorimetric screening: lipases from Bacillus thermocatenulatus and Ophiostoma piliferum, esterases from Pseudomonas fluorescens and Streptomyces diastatochromogenes
  作者：Andrew Man Fai Liu、Neil A Somers、Romas J Kazlauskas、Terry S Brush、Frank Zocher、Markus M Enzelberger、Uwe T Bornscheuer、Geoff P Horsman、Alessandra Mezzetti、Claudia Schmidt-Dannert、Rolf D Schmid

  DOI：10.1016/s0957-4166(01)00072-6

  日期：2001.3

  screened a general library of 29 substrates and a chiral library of 23 pairs of enantiomers. All four hydrolases catalysed the hydrolysis of unnatural substrates, but the two lipases accepted a broader range of substrates than the two esterases. As expected, the two lipases favoured more hydrophobic substrates, while the two esterases showed a preference for smaller substrates. Several moderately enantioselective

  生物化学和分子生物学的最新进展简化了新型水解酶的发现和制备。尽管这些水解酶可能解决了有机合成中的问题，但测量其选择性（尤其是对映选择性）仍然繁琐且耗时。最近，我们开发了一种比色筛选方法来测量水解酶的对映选择性。在这里，我们应用这种快速筛选方法来绘制四种新型水解酶的底物选择性图：来自嗜热芽孢杆菌的脂肪酶（DSM 730，BTL2）和丝状真菌Ophiostoma piliferum（NRRL 18917，OPL）以及来自两种细菌荧光假单胞菌（Pseudomonas fluorescens（ SIK-W1，酯酶I，PFE）和链霉菌（Tü20，SDE）。我们筛选了29种底物的通用文库和23对对映异构体的手性文库。所有四种水解酶均催化非天然底物的水解，但是与两种酯酶相比，两种脂肪酶接受的底物范围更广。不出所料，这两种脂肪酶偏爱疏水性更高的底物，而两种酯酶则偏爱较小的底物。确认了该酚醛酸酯的一些中等对映选择性反应：BTL2，丁酸酯，E
• 硝基咪唑类化合物及其制备方法和用途
  申请人：南京长澳医药科技有限公司

  公开号：CN112300192B

  公开（公告）日：2023-08-11

  本发明公开了一种新型硝基咪唑类化合物及其制备方法和用途。所述硝基咪唑类化合物具有下述通式(I)：
• On the use of epoxy alcohol-aldol rearrangement for stereoselective construction of quarternary carbon centers
  作者：Masato Shimazaki、Hisaaki Hara、Keisuke Suzuki、Gen-ichi Tsuchihashi

  DOI：10.1016/s0040-4039(01)81083-2

  日期：1987.1

  A new method for the construction of quarternary carbon centers is reported, which is based on the Lewis acid-promoted 1,2-rearrangement of β,γ-epoxy alcohols giving α,α-disubstituted aldols stereospecifically in high yields.

  报道了一种构建季碳中心的新方法，该方法基于路易斯酸促进的β，γ-环氧醇的1,2-重排，以高产率立体定向产生α，α-二取代的羟醛。
• Asymmetric synthesis of ()-(+)- and ()-(-)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolane of high enantiomeric purity
  作者：David Tanner、Peter Somfai

  DOI：10.1016/s0040-4020(01)96082-x

  日期：1986.1

  The title compounds, and ', are readily available in four steps from 2-benzyloxymethyl-2-propen-1-ol, the key step being Sharpless asymmetric epoxidation to give the chiral epoxides or '. The total chemical yield of or ' is 50%, the final products being obtained essentially optically pure. By suitable protecting group manipulation, both title enantiomers can be produced from either of the antipodal

  从2-苄氧基甲基-2-丙烯-1-醇可从四个步骤容易地获得标题化合物和'，关键步骤是Sharpless不对称环氧化以得到手性环氧化物或'。的总化学收率或'是50％，而得到的最终产物基本上光学纯的。通过适当的保护基操纵，两种标题对映异构体都可以由对映体环氧化物或β中的任何一种产生。
• SYNTHESIS OF NATURAL AND UNNATURAL FRONTALIN
  作者：Takahiro Hosokawa、Yoshiki Makabe、Toru Shinohara、Shun-Ichi Murahashi

  DOI：10.1246/cl.1985.1529

  日期：1985.10.5

  (S)-(−)- and (R)-(+)-Frontalin were synthesized, respectively, in high enantiomer excess from β-methallyl alcohol (2) by three-step procedure; (i) asymmetric epoxidation of 2, (ii) the epoxide opening with homoallylmagnesium bromide, and (iii) Pd(II)-catalyzed intramolecular acetalization.

  (S)-(-)- 和 (R)-(+)-Frontalin 分别以高对映体过量从 β-甲基烯丙醇 (2) 通过三步程序合成；(i) 2 的不对称环氧化，(ii) 用高烯丙基溴化镁打开环氧化物，以及 (iii) Pd(II) 催化的分子内缩醛化。