肉桂基氯 | 21087-29-6

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 肉桂基氯
• 中文别名: 3-氯-1-苯基-1-丙烯
• 英文名称: Cinnamyl chloride
• 英文别名: trans-3-phenylprop-2-enyl chloride；(E)-(3-chloroprop-1-en-1-yl)benzene；(E)-cinnamyl chloride；[(E)-3-chloroprop-1-enyl]benzene
• CAS: 21087-29-6
• 化学式: C₉H₉Cl
• 分子量: 152.623
• InChiKey: IWTYTFSSTWXZFU-QPJJXVBHSA-N

物化性质

• 熔点：
  −19 °C(lit.)
• 沸点：
  108 °C12 mm Hg(lit.)
• 密度：
  1.096 g/mL at 25 °C(lit.)
• 闪点：
  175 °F
• 保留指数：
  1262
• 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)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。 Lacrimator (Lachrymator) - 刺激眼睛并引起流泪的物质。 Toxic Pneumonitis - 由于吸入金属烟雾或有毒气体和蒸气引起的肺部炎症。

Dermatotoxin - Skin burns. Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears. Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

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

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。 Lacrimator (Lachrymator) - 刺激眼睛并引起流泪的物质。 Toxic Pneumonitis - 由于吸入金属烟雾或有毒气体和蒸气引起的肺部炎症。

Dermatotoxin - Skin burns. Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears. Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

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

毒理性

• 毒性数据

LC50 (大鼠) = 29毫克/立方米/4小时

LC50 (rat) = 29 mg/m3/4hr

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

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：
  2942000000
• 危险品运输编号：
  UN 1760 8/PG 2
• 包装等级：
  II
• 危险类别：
  8,6.1
• 危险性防范说明：
  P210,P260,P264,P270,P271,P280,P284,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P320,P363,P370+P378,P403+P233,P403+P235,P405,P501
• 危险性描述：
  H227,H302,H314,H330,H334
• 储存条件：
  存放在0至6°C的阴凉干燥处。

SDS

Name:	Cinnamyl Chloride 95% Trans Material Safety Data Sheet
Synonym:	3-Chloro-1-Phenyl-1-Propene; (3-Chloro-1-Propenyl)Benzen
CAS:	21087-29-6

Section 1 - Chemical Product MSDS Name:Cinnamyl Chloride 95% Trans Material Safety Data Sheet
Synonym:3-Chloro-1-Phenyl-1-Propene; (3-Chloro-1-Propenyl)Benzen

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
21087-29-6	Cinnamyl Chloride	95	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
Causes eye irritation. Lachrymator (substance which increases the flow of tears).
Skin:
Causes skin irritation.
Ingestion:
Causes 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.
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 immediately.
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 immediately. 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. Combustible liquid.
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:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. 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 general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 21087-29-6: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 120 - 126 deg C @ 15.00mm Hg
Freezing/Melting Point: 7 deg C
Autoignition Temperature: Not available.
Flash Point: 79 deg C ( 174.20 deg F)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water: acetone, formic acid, benzene, ethyl eth
Specific Gravity/Density: 1.0800g/cm3
Molecular Formula: C9H9Cl
Molecular Weight: 152.62

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, 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.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 21087-29-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cinnamyl Chloride - Not listed by ACGIH, IARC, or NTP.

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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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
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# 21087-29-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 21087-29-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 21087-29-6 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

肉桂基氯是一种常见的医药中间体，广泛应用于合成诸如桂利嗪、盐酸氟桂利琴等钙拮抗剂类药物，同时也作为一种香料使用。临床上，它常用于预防和治疗偏头痛及由前庭功能障碍引起的眩晕、耳鸣等症状。

用途：有机化工、药物合成

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甲基苯乙烯	1-propenylbenzene	873-66-5	C9H10	118.178
  顺-β-甲基苯乙烯	cis-1-phenyl-1-propylene	766-90-5	C9H10	118.178
  3-苯基丙-2-烯-1-醇	(2E)-3-phenyl-2-propen-1-ol	4407-36-7	C9H10O	134.178
  (Z)-肉桂醇	(Z)-cinnamyl alcohol	4510-34-3	C9H10O	134.178
  肉桂醇	3-Phenylpropenol	104-54-1	C9H10O	134.178
  ——	trans-cinnamyl iodide	82859-39-0	C9H9I	244.075
  反式肉桂醛	(E)-3-phenylpropenal	14371-10-9	C9H8O	132.162
  苯乙烯	styrene	100-42-5	C8H8	104.152
  ——	(E)-N,N-dimethyl-3-phenylprop-2-en-1-amine	42817-44-7	C11H15N	161.247
  ——	(E)-trimethyl(3-phenylallyl)silane	40595-34-4	C12H18Si	190.36
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  甲基苯乙烯	1-propenylbenzene	873-66-5	C9H10	118.178
  顺-β-甲基苯乙烯	cis-1-phenyl-1-propylene	766-90-5	C9H10	118.178
  1-丙烯基苯	1-phenylpropene	637-50-3	C9H10	118.178
  1-苯-1,3-丁二烯	(E)-1-Phenyl-1,3-butadiene	16939-57-4	C10H10	130.189
  肉桂基胺	(E)-cinnamylamine	4360-51-4	C9H11N	133.193
  肉桂醇	3-Phenylpropenol	104-54-1	C9H10O	134.178
  3-苯基丙-2-烯-1-醇	(2E)-3-phenyl-2-propen-1-ol	4407-36-7	C9H10O	134.178
  反式-1-苯基-1-丁烯	(E)-1-phenyl-1-butene	1005-64-7	C10H12	132.205
  ——	1-phenylbut-1-ene	824-90-8	C10H12	132.205
  ——	trans-cinnamyl iodide	82859-39-0	C9H9I	244.075

反应信息

• 作为反应物：
  描述：

  肉桂基氯 在 sodium periodate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 以84%的产率得到反式肉桂醛
  参考文献：
  名称：

  NaIO 4 –DMF：一种用于将有机卤化物氧化为羰基化合物的新型试剂

  摘要：

  NaIO 4 –DMF在温和的条件下（150°C / 40–60分钟）将各种伯卤和仲卤化物氧化为相应的醛和酮，收率很高（70–90％）。

  DOI：

  10.1016/s0040-4039(02)02885-x
• 作为产物：
  描述：

  烯丙苯 在 苯基氯化硒 N-氯代丁二酰亚胺 、 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以66%的产率得到肉桂基氯
  参考文献：
  名称：

  Selective Selenocatalytic Allylic Chlorination

  摘要：

  [GRAPHICS]Ene-chlorination of olefins by N-chlorosuccinimide is catalyzed by phenylselenenyl chloride. This reaction demonstrates the catalytic conversion of C-H bonds into more reactive C-Cl bonds.

  DOI：

  10.1021/ol036525o
• 作为试剂：
  描述：

  烯丙基三丁基锡 、 苯甲醛 在 tris-(dibenzylideneacetone)dipalladium(0) 肉桂基氯 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以94%的产率得到1-苯基-3-丁烯-1-醇
  参考文献：
  名称：

  The Fate of Bis(η3-allyl)palladium Complexes in the Presence of Aldehydes (or Imines) and Allylic Chlorides: Stille Coupling versus Allylation of Aldehydes (or Imines)

  摘要：

  The mere presence or absence of PPh3 suffices to control the reactivity of bis(η3 -allyl)palladium complexes. In the absence of PPh3 they undergo chemoselective allylic addition to aldehydes or imines, even in the presence of allylic chlorides, whereas in the presence of PPh3 the Stille coupling reaction takes place chemoselectively, even when aldehydes or imines are also present.

  DOI：

  10.1002/1521-3773(20010903)40:17<3208::aid-anie3208>3.0.co;2-u

文献信息

• <i>cis</i>-Specific Hydrofluorination of Alkenylarenes under Palladium Catalysis through an Ionic Pathway
  作者：Enrico Emer、Lukas Pfeifer、John M. Brown、Véronique Gouverneur

  DOI：10.1002/anie.201310056

  日期：2014.4.14

  paper describes the hydrofluorination of alkenes through sequential H− and F+ addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed.

  本文描述了通过连续的^ h烯烃的氢氟化-和F +除了在钯催化下。该反应是顺式 特异性的，因此提供了获得苄基氟化物的途径。该反应的机理涉及离子途径，并且与涉及自由基中间体的已知氢氟化反应不同。还公开了第一催化对映选择性氢氟化。
• [EN] NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS NMDA ET UTILISATIONS DE CEUX-CI
  申请人：CADENT THERAPEUTICS

  公开号：WO2018119374A1

  公开（公告）日：2018-06-28

  Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.

  本文披露了部分杂芳化合物及其在治疗神经精神障碍，例如精神分裂症和重度抑郁症中的用途方法。提供了药物组合物和制备杂芳化合物的方法。这些化合物被认为可以调节NMDA受体。
• Diphenylphosphinoyl-mediated synthesis of ketones
  作者：David J. Fox、Daniel Sejer Pedersen、Stuart Warren

  DOI：10.1039/b606873a

  日期：——

  α-Diphenylphosphinoyl ketones are selectively and sequentially alkylated at the α-position. Double lithiation and selective alkylation occurs at the less stabilised γ-position. Dephosphinoylation of the alkylation products gives ketones. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible. The method is ideally suited for the preparation of acid-sensitive ketones.

  α-二苯基膦酰基酮在α位上选择性且顺序性地进行烷基化。双锂化和选择性烷基化发生在较不稳定的γ位。脱膦酰化得到的烷基化产物是酮。单烷基化具有选择性，形成的中间体晶体高度结晶，且可以进行一步完成的方法。该方法非常适合制备酸敏感的酮。
• The reaction between acyl halides and alcohols: Alkyl halide vs. Ester formation
  作者：Paolo Strazzolini、Angelo G. Giumanini、Giancarlo Verardo

  DOI：10.1016/s0040-4020(01)80747-x

  日期：1994.4

  therefore, ester formation practically confined to a triggering role. But, in those cases where the cation is less easily formed, ester formation was favoured and, consequently, became the necessary elementary step towards alkyl halide formation. This final product, on the other hand, might be extremely slow to form in an SN2 reaction between the protonated ester function and the halide ion. In these hnstances

  在酰基卤和醇之间的反应中，热力学上有利的产物是游离羧酸和烷基卤。最初的反应通常是形成酯和HHal。当该醇非常容易被HHal质子化时产生烷基阳离子时，形成的H 2 O表现出超活性，并且与该醇成功竞争了酰基卤的制备，因此，酯的形成实际上局限于触发作用。但是，在那些阳离子不易形成的情况下，有利于酯的形成，因此成为形成卤代烷的必要的基本步骤。另一方面，最终产品在S N中的形成速度可能非常慢2质子化的酯官能团与卤离子之间的反应。因此，在这些情况下，以及在碱性溶剂竞争HHal质子的情况下，酯都是最终产物。α-羟基，α-苯基苯乙酸（2y）给出了上述虚线所示的一个显着例外，它似乎通过季中间体（E）进行了直接的氯-羟基交换，最后塌陷为α-氯- α-苯基苯乙酸（4y）。在严格相似的条件下，使用CH 2 Cl 2作为溶剂比较了不同的系统。测试了约28种不同的底物与AcCl（1a）的反应，而八种酰基卤（1）对（R
• Copper(I) and phase transfer catalysed allylic substitution by terminal alkynes
  作者：Tuyêt Jeffery

  DOI：10.1016/s0040-4039(00)99654-0

  日期：1989.1

  The Cu(I) catalysed allylic substitution of (un)substituted allyl halides by alk-1-ynes can proceed smoothly at or near room temperature under solid-liquid phase transfer conditions.

  在固-液相转移条件下，室温或接近室温，Cu（I）催化的（未）取代的烯丙基卤的烯丙基取代被烷基-1-炔平稳地进行。

表征谱图