对羟基亚苄基丙酮 | 3160-35-8

• 物质功能分类: 香精与香料 - 合成香料 - 酮类香料
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 对羟基亚苄基丙酮
• 中文别名: 4-亚羟苄基丙酮；4-羟基苯亚甲基丙酮；4-(对羟基苯基)-3-丁烯-2-酮；4-羟基亚苄基丙酮
• 英文名称: 4-(4'-hydroxyphenyl)but-3-en-2-one
• 英文别名: 4-(4-hydroxyphenyl)-3-buten-2-one；4-hydroxybenzylideneacetone；4-(hydroxyphenyl)-3-buten-2-one；4-hydroxybenzalacetone；1-(4-hydroxyphenyl)but-1-en-3-one；p-hydroxybenzylideneacetone；p-hydroxybenzalacetone；4-(4-hydroxyphenyl)but-3-en-2-one
• CAS: 3160-35-8
• 化学式: C₁₀H₁₀O₂
• mdl: MFCD00016490
• 分子量: 162.188
• InChiKey: OCNIKEFATSKIBE-UHFFFAOYSA-N

物化性质

• 熔点：
  108-111°C
• 沸点：
  318.1±17.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)
• 溶解度：
  最易溶于水性溶剂。
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• TSCA：
  Yes
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存于阴凉干燥处

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-(4-Hydroxyphenyl)but-3-en-2-one
CAS-No. : 3160-35-8
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
Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C10H10O2
Molecular Weight : 162,19 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
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
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
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
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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: solid
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 no data available
boiling range
g) Flash point no data available
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 no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition 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
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
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
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
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 May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
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
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
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: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
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
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：用于有机合成的中间体

反应信息

• 作为反应物：
  描述：

  对羟基亚苄基丙酮 在 palladium on activated charcoal 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 5-hydroxy-1-(4-hydroxyphenyl)dodecan-3-one
  参考文献：
  名称：

  6-和8-姜油类似物作为抗生物膜剂的结构-活性关系。

  摘要：

  铜绿假单胞菌是免疫功能低下患者慢性感染的病原体。仲裁感应电路的中断是一种有吸引力的策略，用于治疗与铜绿假单胞菌感染相关的疾病。在这项研究中，我们设计和合成了一系列针对LasR的姜醇类似物，LasR是铜绿假单胞菌群体感应网络的主要调节剂。结构-活性关系研究表明，头部的氢键相互作用，中部的立体化学和旋转刚度以及尾部的最佳烷基链长度是增强LasR结合亲和力和抑制作用的重要因素。生物膜形成的过程。最有效的化合物41，类似物为（与已知的LasR拮抗剂（S）-6-姜油醇相比，R）-8-姜油醇旋转受限，显示出更强的LasR结合亲和力和生物膜形成抑制作用。这种新的LasR拮抗剂可以用作开发抗生物膜药物以治疗铜绿假单胞菌感染的早期先导化合物。

  DOI：

  10.1021/acs.jmedchem.7b01426
• 作为产物：
  描述：

  覆盆子酮 在 eugenol oxidase from Rhodococcus jostii RHA₁ 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以48%的产率得到对羟基亚苄基丙酮
  参考文献：
  名称：

  何氏红球菌RHA1丁香酚氧化酶的生物催化性质和结构分析：多功能氧化生物催化剂。

  摘要：

  氧化酶的选择性：约氏红球菌（Rhodococcus jostii） RHA1的丁香酚氧化酶是一种强大的生物催化剂，可用于多种氧化反应，包括脱氢反应以及消旋外消旋仲醇的动力学拆分。晶体结构提供了对这种氧化生物催化剂的选择性的了解。

  DOI：

  10.1002/cbic.201600148

文献信息

• Chemoselective transfer hydrogenation of α,β-unsaturated carbonyls catalyzed by a reusable supported Pd nanoparticles on biomass-derived carbon
  作者：Tao Song、Yanan Duan、Yong Yang

  DOI：10.1016/j.catcom.2018.11.017

  日期：2019.2

  We herein report highly chemoselective transfer hydrogenation of α,β-unsaturated carbonyl compounds to saturated carbonyls with formic acid as a hydrogen donor over a stable and recyclable heterogeneous Pd nanoparticles (NPs) on N,O-dual doped hierarchical porous biomass-derived carbon. The synergistic effect between Pd NPs and incorporated heteroatoms on carbon plays a critical role on promoting the

  我们在此报告了在N，O-双掺杂分层多孔生物质衍生碳上稳定且可回收的异质Pd纳米颗粒（NPs）上，以甲酸为氢供体，将α，β-不饱和羰基化合物高度化学选择性转移氢化为饱和羰基的方法。Pd NP和掺入的杂原子对碳的协同作用对提高反应效率起关键作用。一系列的α，β-芳族和脂族不饱和羰基化合物被选择性还原为相应的饱和羰基化合物，分离产率高达97％，并具有对各种官能团的良好耐受性。另外，催化剂可以连续重复使用至少6次，而不会显着降低反应效率。
• Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water
  作者：Tao Song、Zhiming Ma、Yong Yang

  DOI：10.1002/cctc.201801987

  日期：2019.2.20

  selectivity for hydrogenation of C=C in α,β‐unsaturated carbonyls under mild conditions. A broad set of α,β‐aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one‐pot cascade synthesis of saturated carbonyls was realized with high activity and

  在本文中，我们报道了由竹笋中的生物质衍生的碳负载的钴纳米颗粒与水中的分子氢在水中将α，β-不饱和羰基高度化学选择性氢化为饱和羰基，这是使用非均相非贵金属催化剂的首个原型据我们所知进行这种有机转型。最佳钴纳米催化剂CoO x@ NC-800在温和条件下表现出显着的活性，对α，β-不饱和羰基中的C = C进行氢化。广泛的α，β-芳族和脂族不饱和羰基被选择性还原为相应的饱和羰基，收率高达99％，并且对各种官能团具有良好的耐受性。同时，通过酮与醛的交叉羟醛缩合，然后进行选择性加氢，实现了一种新的，直接的，高活性和高选择性的饱和羰基单锅级联反应。更重要的是，这种单罐策略适用于从容易获得的起始原料合成卢瑞瑞林A（一种多功能的生物活性和药用分子）的权宜之计，这进一步突出了该催化剂的实用性。此外，
• Diastereoselective synthesis of β-amino ketone and acid derivatives by palladium-catalyzed conjugate addition
  作者：Wubin Zhi、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1016/j.tetlet.2018.05.080

  日期：2018.7

  The first diastereoselective synthesis of β-amino ketone and β-amino acid derivatives by palladium-catalyzed conjugate addition of arylboronic acids to chiral β-enamino ketones and β-enamino esters is reported. The catalytic system employing (S)-4-(tert-butyl)oxazolidin-2-one as the chiral auxiliary in water under an air atmosphere provides β-amino ketone and β-amino acid derivatives in high yields

  报道了通过钯催化的将芳基硼酸共轭加成到手性β-烯胺酮和β-烯胺酯上的β-氨基酮和β-氨基酸衍生物的非对映选择性合成。在空气气氛下，在水中以（S）-4-（叔丁基）恶唑烷-2-酮为手性助剂的催化体系提供了高产率的β-氨基酮和β-氨基酸衍生物，具有非对映选择性。
• Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light
  作者：Kangjiang Liang、Tao Li、Na Li、Yang Zhang、Lei Shen、Zhixian Ma、Chengfeng Xia

  DOI：10.1039/c9sc06184c

  日期：——

  Disclosed herein is a photochemical Heck-type arylation of vinylphenols with non-activated aryl and heteroaryl halides under visible light irradiation. Preliminary mechanistic studies suggested that the colored vinylphenolate anions acted as a strong reducing photoactivator to directly activate (hetero)aryl halides without the need for any sacrificial reductants. The photochemically generated aryl radicals

  本文公开了在可见光照射下乙烯基酚与未活化的芳基和杂芳基卤化物的光化学Heck型芳基化。初步的机理研究表明，有色乙烯基酚酸根阴离子可作为强还原性光活化剂，直接活化（杂）芳基卤化物，而无需任何牺牲性还原剂。光化学产生的芳基与另一个乙烯基苯酚分子偶联，以区域特异性和立体选择性的方式提供Heck型芳基化产物。发达的光化学芳基化方案显示出优异的官能团耐受性，并且无需任何保护-脱保护程序即可成功应用于具有挑战性的天然产物后期修饰。
• Carbene Based Palladium-catalyzed Mizoroki-Heck Reaction
  作者：VIVEK SRIVASTAVA

  DOI：10.13005/ojc/280444

  日期：2012.12.22

  Different perhydrobenzimidazolinium chloride salts were used as a ligand for PdcatalysedMizoroki-Heck reaction. The in situ generation of carbene is the attractive feature of this catalytic system. The corresponding Mizoroki-Heck products were obtained in good yield.

  不同的过氢苯并咪唑啉氯化物盐用作Pd催化的Mizoroki-Heck反应的配体。卡宾的原位生成是该催化系统的吸引人的特征。以高收率获得了相应的Mizoroki-Heck产品。