α-氯代肉桂醛 | 18365-42-9

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪醛（含缩醛，半缩醛）
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: α-氯代肉桂醛
• 中文别名: alpha-氯代肉桂醛；a-氯代肉桂醛；Alpha-氯代肉桂醛
• 英文名称: α-chloro-cinnamaldehyde
• 英文别名: 2-chlorocinnamaldehyde；2-Chloro-3-phenylprop-2-enal
• CAS: 18365-42-9
• 化学式: C₉H₇ClO
• mdl: MFCD00077440
• 分子量: 166.607
• InChiKey: SARRRAKOHPKFBW-UHFFFAOYSA-N

物化性质

• 熔点：
  20-22 °C(lit.)
• 沸点：
  107-108 °C3 mm Hg(lit.)
• 密度：
  1.1466 (rough estimate)
• 闪点：
  >230 °F
• 稳定性/保质期：

  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2913000090
• 危险品运输编号：
  UN 2810
• RTECS号：
  GD6489990
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	Alpha-Chlorocinnamaldehyde 95% Material Safety Data Sheet
Synonym:	2-Chloro-3-Phenyl-2-Propenal
CAS:	18365-42-9

Section 1 - Chemical Product MSDS Name:Alpha-Chlorocinnamaldehyde 95% Material Safety Data Sheet
Synonym:2-Chloro-3-Phenyl-2-Propenal

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
18365-42-9	Alpha-Chlorocinnamaldehyde	95	242-237-4

Hazard Symbols: T
Risk Phrases: 23/24 33

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation and in contact with skin. Danger of cumulative effects.The toxicological properties of this material have not been fully investigated.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
May cause eye irritation. Lachrymator (substance which increases the flow of tears).
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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. Do NOT allow victim to rub eyes or keep eyes closed.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:

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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. 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:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. 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:
Avoid runoff into storm sewers and ditches which lead to waterways.
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Remove all sources of ignition. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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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# 18365-42-9: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid above room te
Color: brown to orange
Odor: aldehyde-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 132.0 - 133.0 deg C
Freezing/Melting Point: 32.00 - 33.00 deg C
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H7ClO
Molecular Weight: 166.61

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, ignition sources, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Hydrogen chloride, 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# 18365-42-9: GD6489990 LD50/LC50:
Not available.
Carcinogenicity:
Alpha-Chlorocinnamaldehyde - 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: T
Risk Phrases:
R 23/24 Toxic by inhalation and in contact with
skin.
R 33 Danger of cumulative effects.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 18365-42-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 18365-42-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 18365-42-9 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

制备方法：由肉桂醛与氯加成，再在碳酸钠存在下脱去HCl而得。

合成制备方法：同样是由肉桂醛与氯加成，在碳酸钠存在下脱去HCl而得到目标产物。

用途简介：本品是一种用于医药领域的中间体。

用途：暂无具体用途说明。

反应信息

• 作为反应物：
  描述：

  α-氯代肉桂醛 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.67h， 生成 4-chloro-5-phenyl-2,4-pentadienoic acid
  参考文献：
  名称：

  WO2006/52916

  摘要：

  公开号：
• 作为产物：
  描述：

  肉桂醛 在 吡啶 、 苯基氯化硒 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以100%的产率得到α-氯代肉桂醛
  参考文献：
  名称：

  A convenient preparation of 2-haloenones from enones using phenylselenium halides

  摘要：

  DOI：

  10.1016/s0040-4039(01)81890-6

文献信息

• Reaction of cinnamaldehyde and derivatives with Raney Ni–Al alloy and Al powder in water. Reduction or oxido-reduction?
  作者：Alina-Marieta Simion、Takashi Arimura、Cristian Simion

  DOI：10.1016/j.crci.2012.11.022

  日期：2013.5

  Résumé A series of experiments dealing with the reduction of cinnamaldehyde and parent compounds was carried out in completely aqueous media in order to assess the character of this process. We wish to show that the treatment of these substrates in water with Raney catalysts is an oxido-reductive process.

  简历 实验工作在一系列完全水介质中进行，涉及肉桂醛及其母体化合物的还原，以评估该过程的特性。我们希望展示在这些底物的水溶液中使用Raney催化剂的处理是一种氧化还原过程。
• Synthesis of Naphthoxazoles by Photocyclization of 4-/5-(Phenylethenyl)oxazoles
  作者：Ivana Šagud、Marija Šindler-Kulyk、Irena Škorić、Vanja Kelava、Željko Marinić

  DOI：10.1002/ejoc.201800737

  日期：2018.7.6

  The biological activity of naphtho[1,2‐d]oxazoles and heterobenz[1,2‐d]oxazoles prompted us to investigate the photochemical synthesis of substituted naphtho[1,2‐d/2,1‐d]oxazoles. The required p‐ and o‐phenyl‐substituted 5‐arylethenyloxazoles were prepared by the Van Leusen reaction. The substituted 4‐(aryl/heteroarylethenyl)oxazoles were prepared by the Wittig reaction.

  萘并[1,2- d ]恶唑和杂苯并[1,2- d ]恶唑的生物活性促使我们研究取代的萘并[1,2- d / 2,1- d ]恶唑的光化学合成。所需的对-和邻-苯基取代的5-芳基乙烯基恶唑是通过Van Leusen反应制备的。取代的4-（芳基/杂芳基乙烯基）恶唑是通过Wittig反应制备的。
• Multicomponent Reactions for the Synthesis of Complex Piperidine Scaffolds
  作者：Wei Zhu、Marisa Mena、Eric Jnoff、Na Sun、Patrick Pasau、Léon Ghosez

  DOI：10.1002/anie.200806065

  日期：2009.7.27

  Creating diversity: Multicomponent reactions for the synthesis of complex piperidine scaffolds lead to high levels of skeletal, functional, and stereochemical diversity in an efficient way (see scheme, X=OR, NR2). Connecting the acid chloride component to the dienophile generates polycyclic piperidine scaffolds by an intramolecular Diels–Alder reaction of the in situ generated azadienes.

  创造多样性：用于合成复杂哌啶支架的多组分反应以有效的方式导致高水平的骨骼，功能和立体化学多样性（参见方案，X = OR，NR 2）。通过原位生成的氮杂二烯的分子内Diels-Alder反应，将酰氯成分与亲二烯体相连，生成多环哌啶骨架。
• A New Synthetic Approach to α-Chlorocinnamaldehydes
  作者：Valentine Nenajdenko、Alexander Reznichenko、Olesya Lenkova、Alexey Shastin、Elizabeth Balenkova

  DOI：10.1055/s-2004-837303

  日期：——

  A new simple and efficient transformation of aromatic aldehydes into α-chlorocinnamaldehydes is described. Catalytic olefination reaction of hydrazones of aromatic aldehydes with 2-trichloromethyl-1,3-dioxolane gives ethylene acetals of target alkenes in moderate to good yields. The reaction proceeds stereoselectively to form preferably Z-isomers.

  报道了一种将芳香醛转化为α-氯肉桂醛的新型简单高效转化方法。催化炔丙化反应，利用芳香醛的踪与2-三氯甲基-1,3-二恶烷反应，以中等至良好产率得到目标烯烃的乙烯缩醛。该反应立体选择性地进行，优先形成Z-异构体。
• One-Pot Reactions for Modular Synthesis of Polysubstituted and Fused Pyridines
  作者：Zhidong Song、Xin Huang、Wenbin Yi、Wei Zhang

  DOI：10.1021/acs.orglett.6b02883

  日期：2016.11.4

  3-dicarbonyl-initiated one-pot Michael addition/[5 + 1] annulation/dehydrofluorinative aromatization reaction sequence is introduced for regioselective synthesis of di-, tri-, tetra-, and pentasubstituted pyridines as well as fused pyridines. This simple and modular synthesis is performed using readily available starting materials and under transition-metal catalyst-free conditions.

  引入2-氟-1,3-二羰基引发的一锅迈克尔加成反应/ [5 +1]环化/脱氟化氢芳构化反应顺序，用于区域选择性合成二，三，四和五取代的吡啶以及吡啶。使用容易获得的原料并在无过渡金属的条件下进行这种简单而模块化的合成。