肉桂酸烯丙酯 | 1866-31-5

• 物质功能分类: 香精与香料 - 合成香料 - 羧酸及酯类香料
• 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: 肉桂酸烯丙酯
• 中文别名: 3-苯基-2-丙烯酸-2-丙烯基酯；3-苯基丙烯酸烯丙酯；桂酸烯丙酯；桂皮酸丙烯酯；肉桂酸丙烯酯
• 英文名称: allyl cinnamate
• 英文别名: Prop-2-enyl 3-phenylprop-2-enoate
• CAS: 1866-31-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: KCMITHMNVLRGJU-UHFFFAOYSA-N

物化性质

• 沸点：
  150-152 °C15 mm Hg(lit.)
• 密度：
  1.053 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 溶解度：
  Insoluble in water, soluble in alcohol and oils, almost insoluble in Propylene glycol.
• LogP：
  2.93
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2916399090
• RTECS号：
  GD8050000
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  请将贮藏器保持密封，并存放在阴凉干燥处。同时，确保工作环境有良好的通风或排气设施。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Allyl cinnamate
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 1866-31-5
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
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : Allyl 3-phenylacrylate
Formula : C12H12O2
Molecular Weight : 188,22 g/mol
CAS-No. : 1866-31-5
EC-No. : 217-477-8
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Allyl cinnamate
CAS-No. 1866-31-5 Acute Tox. 4; H302 <= 100 %
EC-No. 217-477-8
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Allyl cinnamate
CAS-No. 1866-31-5 Xn, R22 <= 100 %
EC-No. 217-477-8
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
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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. 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
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
For precautions see section 2.2.
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)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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, 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).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: 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 150 - 152 °C at 20 hPa - lit.
boiling range
g) Flash point 113 °C - closed cup
h) Evapouration 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 1,053 g/cm3 at 25 °C
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
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents, Strong bases
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 1.520 mg/kg
LD50 Dermal - rabbit - > 5.000 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
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
Additional Information
RTECS: GD8050000
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

毒性

• GRAS (FEMA)。
• LD₅₀ 为 1520 mg/kg（大鼠，经口）。

使用限量

• FEMA (mg/kg): 软饮料 1.0；冷饮 1.4；糖果 1.8；焙烤食品 2.6。
• FDA 规定为适度为限 (FDA §172.515)。

化学性质

• 无色至淡黄色微粘液体，具有桃子和杏子般的甜香气。沸点在 150～152℃（2000Pa）之间。
• 不溶于水，可溶于乙醇，并且易溶于乙醚。

用途

• GB 2760—1996 规定其为允许使用的食用香料。主要用于配制浆果、葡萄和桃子等水果型香精，并用于焙烤制品及糖果中。

生产方法

• 由桂酸和烯丙醇在浓硫酸存在下进行酯化而成。

类别与特性

• 有毒物品。
• 毒性分级：中毒。
• 急性毒性：口服 - 大鼠 LD₅₀: 1520 毫克/公斤。
• 刺激数据：
  • 皮肤 - 人，20 毫克/48 小时 中度刺激。
• 可燃性危险特性：易燃；燃烧产生刺激烟雾。
• 储运特性：需存放在通风良好、低温干燥的库房内，并与食品原料分开存放。
• 灭火剂：干粉、泡沫、砂土、二氧化碳，以及雾状水。

反应信息

• 作为反应物：
  描述：

  肉桂酸烯丙酯 在 sodium tetrahydroborate 、 盐酸 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以87%的产率得到肉桂酸
  参考文献：
  名称：

  利用 DMSO 中的 NaBH4 轻松且化学选择性地裂解烯丙基羧酸酯

  摘要：

  摘要 使用廉价的硼氢化钠试剂在二甲基亚砜 (DMSO) 中观察到了一种新的烯丙基羧酸酯脱保护方法。脂肪族和芳香族烯丙基羧酸酯顺利脱保护。烯丙酯基团可以比苯酚更好地选择性脱保护。

  DOI：

  10.1080/00397910902963694
• 作为产物：
  描述：

  1,3-dichloro-2-propyl cinnamate 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 48.0h， 以98%的产率得到肉桂酸烯丙酯
  参考文献：
  名称：

  串联的Finkelstein重排消除反应：烯丙基酯的直接合成路线

  摘要：

  烯丙基酯可以通过NaI诱导的2-氯-1-（氯甲基）乙基酯的Finkelstein重排消除反应获得。碘化钠可以在还原当量以下使用还原剂作为硫代硫酸钠使用。使用大多数已研究的各种酯均可获得高收率。所描述的方法避免了使用烯丙醇作为试剂。2-氯-1-（氯甲基）乙酯是由甘油制成的，甘油是生物柴油工业的主要副产品。还证实了碘作为水解烯丙基酯的试剂的有效性。

  DOI：

  10.1016/j.tet.2009.04.042

文献信息

• Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol
  作者：Thomas Vielhaber、Christoph Topf

  DOI：10.1016/j.apcata.2021.118280

  日期：2021.8

  glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated CCbonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields

  我们传达了一种用户友好且无需手套箱的催化协议，用于酮和酯和腈的共轭 C C键的锰催化氢化。相应的催化剂很容易由特权 [Mn(CO) 5 Br] 前体和廉价的 2-吡啶甲胺原位组装。催化转化在t- BuOK存在下进行，从而以良好至极好的收率获得相应的氢化产物。所描述的系统提供了对仲醇和饱和酯的快速和原子效率的访问，避免了使用氧敏感和昂贵的基于膦的配体。
• [EN] BIODEGRADABLE SOLVENTS FOR THE CHEMICAL INDUSTRY<br/>[FR] SOLVANTS BIODÉGRADABLES POUR L'INDUSTRIE CHIMIQUE
  申请人：UNIV DUBLIN CITY

  公开号：WO2009024607A1

  公开（公告）日：2009-02-26

  This invention relates to ionic liquid (ILs) solvents for chemical synthesis based on an alkyl - imidazolium cation core containing ionic liquids which have enhanced biodegradability and reduced toxicity relative to existing imidazolium bases ILs such as 1-butyl-3-methylimidazolium (bmmim) salts. Many of the described ILs produce a score of over 60% biodegradability over 28 days in a biodegradability test such as the Sturm Test, the Closed Bottle Test (OECD 301D) or the CO2 Headspace Test (ISO 14593). The ILs of the invention comprise an alkyl substituted imidazolium cationic core having a -C=OX- side chain in the 3-position of the imidazole ring, wherein X = O, NH, N or S and an associated counteranion characterized in that the -C=OX side chain comprises at least one ether linkage. The biodegradable and non-toxic IL may be used as green solvents for the chemical, pharmaceutical, biofuel and biomass industries. The ILs of the invention are particularly useful in hydrogenation, pericyclic and metathesis reactions.

  这项发明涉及一种基于含有烷基-咪唑啉阳离子核心的离子液体溶剂，用于化学合成，这些离子液体相对于现有如1-丁基-3-甲基咪唑啉（bmmim）盐类的咪唑啉基离子液体，具有增强的生物降解性和降低的毒性。所描述的许多离子液体在生物降解性测试中，例如Sturm测试、封闭瓶测试（OECD 301D）或CO2顶空测试（ISO 14593）中，28天内生物降解率超过60%。本发明的离子液体包括一个在咪唑啉环的3位上带有-C=OX-侧链的烷基取代咪唑啉阳离子核心，其中X=O，NH，N或S，以及一个相关的反离子，其特征在于-C=OX侧链至少包含一个醚键。这些生物降解且无毒的离子液体可作为化学、制药、生物燃料和生物质工业的绿色溶剂。特别是，本发明的离子液体在氢化、周环和复分解反应中非常有用。
• Selective hydrogenation of trans-cinnamaldehyde and hydrogenolysis-free hydrogenation of benzyl cinnamate in imidazolium ILs
  作者：Saibh Morrissey、Ian Beadham、Nicholas Gathergood

  DOI：10.1039/b815566f

  日期：——

  trans-Cinnamaldehyde is selectively hydrogenated to hydrocinnamaldehyde using a commercially available palladium catalyst in novel imidazolium ILs. The selective hydrogenation extends to benzyl cinnamate, in which the ester is protected from hydrogenolysis under similar conditions.

  使用市售的钯催化剂在新型咪唑鎓离子液体中，反式肉桂醛可以被选择性地氢化为氢化肉桂醛。这种选择性氢化过程也适用于苄基肉桂酸酯，在该反应条件下，酯基得以避免氢解作用。
• 一种苯甲酰胺邻位烯丙基化产物的制备方法及其净化提纯方法
  申请人：温州大学

  公开号：CN108129340A

  公开（公告）日：2018-06-08

  本发明公开了一种苯甲酰胺邻位烯丙基化产物的制备方法及净化提纯方法，其步骤包括：以未活化的苯甲酰胺衍生物及烯丙酯为底物，以1,2‑二氯乙烷为溶剂，在过渡金属铑催化剂、银盐氧化剂、氟化铁添加剂及膦配体作用下，在氮气气氛中，经加热反应制得粗产品，然后，对粗产品进行过滤、除溶剂，获得剩余物；对剩余物采用硅胶柱层析，经洗脱液淋洗，收集流出液；合并含有产物的流出液，对合并后的流出液进行浓缩去溶剂，然后经真空干燥得到粗产物，薄层色谱板二次分离，最终经过重结晶得目标产物。本发明具有工艺流程简单、成本低、原料简单易得、产率高的优点。
• Unique Chemoselective Hydrogenation using a Palladium Catalyst Immobilized on Ceramic
  作者：Yasunari Monguchi、Takahisa Marumoto、Tomohiro Ichikawa、Yutaka Miyake、Yoshiyuki Nagae、Michiyuki Yoshida、Yasunori Oumi、Yoshinari Sawama、Hironao Sajiki

  DOI：10.1002/cctc.201500193

  日期：2015.7.13

  specific chemoselectivity for hydrogenation that has never been achieved by other palladium‐catalyzed methods. Either aliphatic or aromatic N‐Cbz groups could be deprotected to the corresponding free‐amines, while the hydrogenolysis of benzyl esters and ethers did not proceed. Furthermore, aryl chlorides and epoxides were tolerant under the Pd/ceramic‐catalyzed hydrogenation conditions. 5 % Pd/ceramic

  开发了负载在陶瓷上的非均相钯催化剂（5％Pd /陶瓷）。该催化剂对氢化显示出特定的化学选择性，这是其他钯催化方法无法实现的。脂族或芳族N- Cbz基团都可以脱保护为相应的游离胺，而苄基酯和醚的氢解反应却没有进行。此外，芳族氯化物和环氧化物在钯/陶瓷催化的氢化条件下具有耐受性。由于在反应介质中未检测到钯浸出，因此可以重复使用5％的Pd /陶瓷，而不会降低催化剂活性。