1,4-戊二烯-3-醇 | 922-65-6

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 无环烃
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,4-戊二烯-3-醇
• 中文别名: 二乙烯基甲醇
• 英文名称: divinylcarbinol
• 英文别名: 1,4-pentadien-3-ol；penta-1,4-dien-3-ol；1,4-pentadiene-3-ol；pentan-1,4-dien-3-ol；3-hydroxy-1,4-pentadiene
• CAS: 922-65-6
• 化学式: C₅H₈O
• mdl: MFCD00008633
• 分子量: 84.1179
• InChiKey: ICMWSAALRSINTC-UHFFFAOYSA-N

物化性质

• 沸点：
  115-116 °C (lit.)
• 密度：
  0.865 g/mL at 25 °C (lit.)
• 闪点：
  86 °F
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• 稳定性/保质期：
  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

毒理性

• 副作用

神经毒素 - 急性溶剂综合征

Neurotoxin - Acute solvent syndrome

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险等级：
  3.2
• 危险品标志：
  Xn
• 危险类别码：
  R22,R10
• WGK Germany：
  3
• 海关编码：
  29052990
• 危险品运输编号：
  UN 1987 3/PG 3
• 包装等级：
  III
• 危险类别：
  3.2
• 危险性防范说明：
  P210,P233,P240,P241,P242,P243,P264,P270,P273,P280,P301+P312+P330,P303+P361+P353,P370+P378,P403+P235,P501
• 危险性描述：
  H225,H302,H401,H412
• 储存条件：
  存储条件：2-8℃，避光，通风干燥处，密封保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,4-Pentadien-3-ol
CAS-No. : 922-65-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Flammable liquids (Category 3)
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Flammable. Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H226 Flammable liquid and vapour.
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Contains .?. May produce an allergic reaction.
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R10 Flammable.
R22 Harmful if swallowed.
S-phrase(s) none
Sensitising components:
Hydroquinone
May produce an allergic reaction.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Mixtures
Synonyms : Divinyl carbinol
Formula : C5H8O
Molecular Weight : 84,12 g/mol
Component Classification Concentration
Penta-1,4-dien-3-ol
CAS-No. 922-65-6 Flam. Liq. 3; Acute Tox. 4; 50 - 100 %
EC-No. 213-080-9 H226, H302
Xn, R10 - R22
Hydroquinone
CAS-No. 123-31-9 Acute Tox. 4; Skin Irrit. 2; Eye 0,1 - 1 %
EC-No. 204-617-8 Dam. 1; Skin Sens. 1; Muta. 2;
Index-No. 604-005-00-4 Carc. 2; Aquatic Acute 1;
H302, H315, H317, H318,
H341, H351, H400
Xn, N, Carc.Cat.3, Mut.Cat.3,
R22 - R40 - R41 - R43 - R68 -
R50
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13).
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, Flame retardant antistatic protective clothing, The type
of protective equipment must be selected according to the concentration and amount of the
dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: clear, liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 60 - 61 °C at 107 hPa
boiling range
g) Flash point 32 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,867 g/cm3
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Contains the following stabiliser(s):
Hydroquinone (0,4 %)
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong bases, Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
no data available
Skin corrosion/irritation
no data available
no data available
Serious eye damage/eye irritation
no data available
no data available
Respiratory or skin sensitization
no data available
no data available
Germ cell mutagenicity
no data available
no data available
Carcinogenicity
IARC: 3 - Group 3: Not classifiable as to its carcinogenicity to humans (Hydroquinone)
Reproductive toxicity
no data available
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin
May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
Toxic to aquatic life.
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 1987 IMDG: 1987 IATA: 1987
UN proper shipping name
ADR/RID: ALCOHOLS, N.O.S. (Penta-1,4-dien-3-ol)
IMDG: ALCOHOLS, N.O.S. (Penta-1,4-dien-3-ol)
IATA: Alcohols, n.o.s. (Penta-1,4-dien-3-ol)
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: no IMDG Marine Pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Text of H-code(s) and R-phrase(s) mentioned in Section 3
Acute Tox. Acute toxicity
Aquatic Acute Acute aquatic toxicity
Carc. Carcinogenicity
Eye Dam. Serious eye damage
Flam. Liq. Flammable liquids
H226 Flammable liquid and vapour.
H302 Harmful if swallowed.
H315 Causes skin irritation.
H317 May cause an allergic skin reaction.
H318 Causes serious eye damage.
H341 Suspected of causing genetic defects.
H351 Suspected of causing cancer.
H400 Very toxic to aquatic life.
Muta. Germ cell mutagenicity
Skin Irrit. Skin irritation
Skin Sens. Skin sensitization
N Dangerous for the environment
R10 Flammable.
R22 Harmful if swallowed.
R40 Limited evidence of a carcinogenic effect.
R41 Risk of serious damage to eyes.
Xn Harmful
R43 May cause sensitization by skin contact.
R50 Very toxic to aquatic organisms.
R68 Possible risk of irreversible effects.
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

用途：用于不对称环氧化反应的原料。

反应信息

• 作为反应物：
  描述：

  1,4-戊二烯-3-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 216.0h， 以56%的产率得到(S)-1-[(R)-oxiran-2-yl]prop-2-enol
  参考文献：
  名称：

  澳大利亚热带雨林中的抗癌剂：螺缩醛EBC-23、24、25、72、73、75和76

  摘要：

  EBC-23、24、25、72、73、75和76是从澳大利亚热带雨林中的laubatii肉桂（月桂科）的果实中分离出来的。EBC-23（1）以9个线性步骤立体选择性合成，总产率为8％，以确认报道的相对立体化学并确定绝对立体化学。全面合成的关键是一系列的Tietze–Smith linchpin反应。发现新的螺缩醛结构基序，例如EBC-23（1），可在小鼠模型中抑制雄激素非依赖性前列腺肿瘤细胞DU145的生长，表明其具有治疗成人难治性实体瘤的潜力。

  DOI：

  10.1002/chem.200901525
• 作为产物：
  描述：

  1,4-戊二烯 生成 1,4-戊二烯-3-醇
  参考文献：
  名称：

  Di Maio,G. et al., Gazzetta Chimica Italiana, 1973, vol. 103, p. 477 - 482

  摘要：

  DOI：

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2018137593A1

  公开（公告）日：2018-08-02

  Provided are novel compounds that inhibit LRRK2 kinase activity, processes for their preparation, compositions containing them and their use in the treatment of or prevention of diseases associated with or characterized by LRRK2 kinase activity, for example Parkinson's disease, Alzheimer's disease and amyotrophic lateral sclerosis (ALS).

  提供了抑制LRRK2激酶活性的新化合物，以及它们的制备方法、含有它们的组合物以及它们在治疗或预防与LRRK2激酶活性相关或以其为特征的疾病中的用途，例如帕金森病、阿尔茨海默病和肌萎缩侧索硬化症（ALS）。
• The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide
  作者：Syed Tasadaque A. Shah、Patrick J. Guiry

  DOI：10.1039/b803949f

  日期：——

  An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities

  据报道，通过在甲醇中使用催化量的三甲基甲硅烷基溴化物（TMSBr），可以高效，化学选择性地裂解甲硅烷基醚（伯，仲和芳族化合物）。在芳基甲硅烷基醚的存在下，可以高收率化学选择裂解多种烷基甲硅烷基醚，例如TBS，TIPS和TBDPS。还使用催化量的TMSBr实现甲硅烷基酯的脱保护。
• Highly Stereoselective Intramolecular Hydroamination/Cyclization of Conjugated Aminodienes Catalyzed by Organolanthanides
  作者：Sukwon Hong、Tobin J. Marks

  DOI：10.1021/ja020226x

  日期：2002.7.1

  Efficient intramolecular hydroamination/cyclization of primary and secondary conjugated aminodienes can be effected by using organolanthanide precatalysts of the type Cp'2LnCH(TMS)2 (Cp' = eta5-Me5C5; Ln = La, Sm, Y; TMS = SiMe3) and CGCSmN(TMS)2 (CGC = Me2Si(eta5-Me4C5)(tBuN)). The transformation proceeds cleanly (>/= 90% conversion) at 25-60 degrees C with good rates and high regioselectivities,

  通过使用 Cp'2LnCH(TMS)2（Cp' = eta5-Me5C5；Ln = La、Sm、Y；TMS = SiMe3）和 CGCsmN 类型的有机镧系元素预催化剂，可以实现伯和仲共轭氨基二烯的有效分子内加氢胺化/环化(TMS)2 (CGC = Me2Si(eta5-Me4C5)(tBuN))。转化在 25-60 摄氏度下顺利进行（>/= 90% 转化率），具有良好的速率和高区域选择性，并且电子效应导致显着的速率增强。该反应的一些特征与单取代的氨基烯烃加氢胺化/环化平行，包括速率定律（[氨基二烯]中的零级），以及通过更大的镧系元素离子半径和/或更多开放的催化剂连接结构观察到的速率增强。2的合成中获得了良好到优异的非对映选择性，5-反式二取代吡咯烷（80% de）和2,6-顺式二取代哌啶（99% de）使用相应的α-甲基氨基二烯前体。2-(丙-1-烯基)哌啶与手性 C1-对称预催化剂 (
• An Efficient, Overall [4+1] Cycloadditon of 1,3-Dienes and Nitrene Precursors
  作者：Qiong Wu、Jian Hu、Xinfeng Ren、Jianrong Steve Zhou

  DOI：10.1002/chem.201101630

  日期：2011.10.4

  Intermolecular cycloadditions of conjugated dienes and nitrene precursors usually produce aziridines. A generally useful method was lacking to directly provide the [4+1] cycloadducts, 3‐pyrrolines. We have realized this transformation by using an uniquely active catalyst, copper(II) 1,1,1,5,5,5‐hexafluoroacetylacetonate ([Cu(hfacac)2]). The method is applicable to a wide array of dienes with good yields

  共轭二烯和腈前体的分子间环加成通常产生氮丙啶。缺少直接提供[4 + 1]环加合物，3-吡咯啉的通用方法。我们已经通过使用独特的活性催化剂1，（1,2,1,1,1,5,5,5,5-六氟乙酰丙酮铜（[Cu（hfacac）2 ]））实现了这种转变。该方法适用于多种具有良好产率的二烯。当使用1,4-二取代的二烯作为底物时，可以获得很好的顺式或反式选择性。有趣的是，顺式或反式优选取决于取代基的性质，而不是二烯的几何形状。机理研究表明，[4 + 1]环加成反应是通过二烯叠氮化和随后的环扩展进行的。在普通的铜催化剂中，只有[Cu（hfacac）2 ]可以有效地催化两个步骤，这说明了该催化剂的独特效率。
• Use of Allyl, 2-Tetrahydrofuryl, and 2-Tetrahydropyranyl Ethers as Useful C3-, C4-, and C5-Carbon Sources: Palladium-Catalyzed Allylation of Aldehydes
  作者：Masamichi Shimizu、Masanari Kimura、Yoshinao Tamaru

  DOI：10.1002/chem.200500450

  日期：2005.11.4

  to excellent yields with high levels of stereoselectivity. Useful C3-unit elongation, which makes the best use of an allyl ether as a protecting group and a nucleophilic allylation agent, is demonstrated. Mechanisms for the umpolung reaction (of an allyl ether into an allylic anion) and stereoselectivity associated with allylation of aldehydes are discussed.

  钯二乙基锌或钯三乙基硼烷催化促进环上的2-（烯丙氧基）四氢呋喃，2-（烯丙氧基）四氢吡喃及其羟基衍生物（核糖，葡萄糖，甘露糖，脱氧核糖，脱氧葡萄糖）的自烯丙基化。所有反应均在室温下进行，并提供多羟基产物，它们具有均烯丙基醇的结构基序，并具有良好的收率和优异的立体选择性。证明了有用的C3-单元伸长，其充分利用了烯丙基醚作为保护基和亲核烯丙基化剂。讨论了将烯丙基醚转化为烯丙基阴离子的烯丙基化反应的机理以及与醛的烯丙基化相关的立体选择性。

表征谱图