2,6-二氯肉桂酸 | 5345-89-1

• 物质功能分类: 香精与香料 - 合成香料 - 芳香肉桂酸、酯及衍生物
• 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: 2,6-二氯肉桂酸
• 中文别名: 2,6-二氯肉桂酸,主要为反式；2,6-二氯苯乙烯酸
• 英文名称: 3-(2,6-dichlorophenyl)prop-2-enoic acid
• CAS: 5345-89-1
• 化学式: C₉H₆Cl₂O₂
• mdl: MFCD00004374
• 分子量: 217.051
• InChiKey: OIPVGRCXMFBNAN-UHFFFAOYSA-N

物化性质

• 熔点：
  192-196 °C
• 沸点：
  355.8±27.0 °C(Predicted)
• 密度：
  1.3115 (estimate)
• 稳定性/保质期：
  常温常压下稳定，是一种白色结晶体，不溶于水但溶于乙醇、乙酸乙酯等有机溶剂。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S37
• 危险类别码：
  R37/38
• 海关编码：
  2916399090
• RTECS号：
  UD3333800
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  避光、阴凉干燥处，密封保存。

SDS

Name:	2 6-Dichlorocinnamic Acid 99% Predominantly Trans Material Safety Data Sheet
Synonym:	3-(2,6-Dichlorophenyl)-2-Propenoic Acid
CAS:	5345-89-1

Section 1 - Chemical Product MSDS Name:2 6-Dichlorocinnamic Acid 99% Predominantly Trans Material Safety Data Sheet
Synonym:3-(2,6-Dichlorophenyl)-2-Propenoic Acid

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5345-89-1	2,6-dichlorocinnamic Acid	99	226-301-9

Hazard Symbols: XI
Risk Phrases: 37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

---

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
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:
Treat symptomatically and supportively.

---

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.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. 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.

---

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# 5345-89-1: 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:
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: light beige
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 194.00 - 196.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H6Cl2O2
Molecular Weight: 217.05

---

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, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5345-89-1: UD3333800 LD50/LC50:
Not available.
Carcinogenicity:
2,6-dichlorocinnamic Acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 37/38 Irritating to respiratory system and skin.
Safety Phrases:
S 28 After contact with skin, wash immediately
with...
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# 5345-89-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5345-89-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5345-89-1 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法： 2,4-二氯肉桂酸是一种有机合成中间体。

用途简介：（这部分内容为空，暂无具体信息）

反应信息

• 作为反应物：
  描述：

  2,6-二氯肉桂酸 在 碘苯二乙酸 、 四乙基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以82%的产率得到2-(2-bromovinyl)-1,3-dichlorobenzene
  参考文献：
  名称：

  用二乙酰氧基碘苯将α，β-不饱和羧酸脱羧溴化的新系统。

  摘要：

  讨论了在室温下使用二乙酰氧基碘苯（IBD）与四乙基溴化铵（TEAB）结合的简单温和的方法，将多种α，β-不饱和羧酸转化为相应的溴代烯烃。该系统的优点是反应时间短，易于后处理并具有优异的收率。

  DOI：

  10.1248/cpb.57.1243
• 作为产物：
  描述：

  丙二酸 、 2,6-二氯苯甲醛 在 哌啶 、 吡啶 作用下， 反应 6.0h， 生成 2,6-二氯肉桂酸
  参考文献：
  名称：

  银促进 α,β-不饱和羧酸的脱羧二氟亚甲基化合成烯丙基二氟化物

  摘要：

  一种具有良好官能团耐受性和广泛底物范围的有效方法可以通过银促进的芳基或烷基取代的α,β-不饱和羧酸与苯并-1,3 的脱羧偕二氟亚甲基化反应来提供具有独特E立体选择性的烯丙基二氟化物-二唑二氟甲基溴在温和的反应条件下。

  DOI：

  10.1002/asia.202200448

文献信息

• Transition-metal-free synthesis of vinyl sulfones via tandem cross-decarboxylative/coupling reactions of sodium sulfinates and cinnamic acids
  作者：Yanli Xu、Xiaodong Tang、Weigao Hu、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c4gc00542b

  日期：——

  A transition-metal-free synthesis of vinyl sulfones, utilizing sodium sulfinates and cinnamic acids through tandem cross-decarboxylative/coupling reactions, has been developed.

  一种不含过渡金属的乙烯磺酰合成方法已经开发出来，它利用了亚硫酸钠和肉桂酸通过串联的脱羧/偶联反应。

• Iodine-mediated synthesis of (E)-vinyl sulfones from sodium sulfinates and cinnamic acids in aqueous medium
  作者：Jian Gao、Junyi Lai、Gaoqing Yuan

  DOI：10.1039/c5ra10896a

  日期：——

  With water as the reaction medium, a green and efficient method has been developed for the synthesis of (E)-vinyl sulfones via I2-mediated decarboxylative cross-coupling reactions of sodium sulfinates with cinnamic acids. This synthetic route could effectively avoid the use of toxic organic solvents and transition metal catalysts, and the target products could be obtained with moderate to excellent

  以水为反应介质，已经开发了一种绿色有效的方法，用于通过亚磺酸钠与肉桂酸的I 2介导的脱羧交叉偶联反应合成（E）-乙烯基砜。该合成路线可有效避免使用有毒的有机溶剂和过渡金属催化剂，在绿色和温和的条件下，可以以中等至极好的收率获得目标产物。
• Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis
  作者：Pan Xu、Ablimit Abdukader、Kaidong Hu、Yixiang Cheng、Chengjian Zhu

  DOI：10.1039/c3cc48598f

  日期：——

  A visible-light-induced decarboxylative trifluoromethylation of alpha,beta-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed. The corresponding trifluoromethylated alkenes were obtained in moderate to high yields with excellent functional group tolerance at ambient temperature. Preliminary mechanistic analyses suggest a radical-type mechanism.

  公开了使用Togni试剂作为CF 3源的可见光诱导的α，β-不饱和羧酸的脱羧三氟甲基化。以中等至高产率获得了相应的三氟甲基化烯烃，其在环境温度下具有优异的官能团耐受性。初步的机械分析表明是一种激进型机制。
• Visible-Light-Mediated Oxidative Decarboxylative Coupling of Cinnamic Acid Derivatives with Tetrahydrofuran
  作者：Zheng Liu、Leifeng Wang、Dong Liu、Zhigang Wang

  DOI：10.1055/s-0035-1560661

  日期：——

  A visible-light-mediated protocol for direct oxidative decarboxylative coupling of various cinnamic acid derivatives with tetrahydrofuran was developed, leading to simple preparations of a range of vinyltetrahydrofurans under operationally mild and convenient conditions.

  开发了一种可见光介导的各种肉桂酸衍生物与四氢呋喃直接氧化脱羧偶联的方案，从而在操作温和方便的条件下简单地制备了一系列乙烯基四氢呋喃。
• Electrochemical Synthesis Strategy for C_vinyl-CF₃ Compounds through Decarboxylative Trifluoromethylation
  作者：Huanliang Hong、Yibiao Li、Lu Chen、Bin Li、Zhongzhi Zhu、Xiuwen Chen、Ling Chen、Yubing Huang

  DOI：10.1021/acs.joc.9b00766

  日期：2019.5.3

  An efficient decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids using the Langlois reagent as a trifluoromethyl precursor has been achieved by an electro-oxidative strategy. Under catalyst-free and external oxidant-free electrolysis conditions, a series of Cvinyl-CF3 compounds are obtained with a high regioselectivity in good yields. The successful trapping of the CF3 radical

  通过电氧化策略，已经使用Langlois试剂作为三氟甲基前体，对α，β-不饱和羧酸进行了有效的脱羧三氟甲基化。在无催化剂和无外部氧化剂的电解条件下，以高产率获得了具有高区域选择性的一系列C乙烯基-CF 3化合物。清除剂成功捕获CF 3自由基已证实该系统涉及自由基过程。