4-溴甲基肉桂酸甲酯 | 946-99-6

• 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: 4-溴甲基肉桂酸甲酯
• 中文别名: 对溴甲基肉桂酸甲酯；4-(溴甲基)肉桂酸甲酯
• 英文名称: methyl 3-(4-bromomethyl)cinnamate
• 英文别名: methyl p-bromomethylcinnamate；methyl 4-bromomethyl cinnamate；2-Propenoic acid, 3-[4-(bromomethyl)phenyl]-, methyl ester；methyl 3-[4-(bromomethyl)phenyl]prop-2-enoate
• CAS: 946-99-6
• 化学式: C₁₁H₁₁BrO₂
• mdl: MFCD02684186
• 分子量: 255.111
• InChiKey: ZSRCGGBALFGALF-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  333.9±22.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、DMSO、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 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：
  Xi
• 海关编码：
  2916399090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P264,P270,P271,P280,P303+P361+P353,P304+P340,P305+P351+P338,P310,P330,P331,P363,P403+P233,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H314

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-(4-bromomethyl)cinnamate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 3-(4-bromomethyl)cinnamate
CAS number: 946-99-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H11BrO2
Molecular weight: 255.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

甲基(4-溴甲基)桂酸酯用于合成对位、间位和邻位双(2-氯乙基)氨基甲基桂酸盐及其酯，这些化合物用作抑制剂。

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
  ——	methyl 3-(4-methylphenyl)acrylate	7560-43-2	C11H12O2	176.215
  对甲基肉桂酸	4-methylcinnamic acid	1866-39-3	C10H10O2	162.188

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-甲酰基肉桂酸甲酯	methyl 4-formylcinnamate	7560-50-1	C11H10O3	190.199
  ——	methyl p-chloromethylcinnamate	87087-40-9	C11H11ClO2	210.66
  ——	methyl p-cyanomethylcinnamate	87087-45-4	C12H11NO2	201.225

反应信息

• 作为反应物：
  描述：

  4-溴甲基肉桂酸甲酯 在 calcium hydride 、 silver nitrate 作用下， 以 乙醚 为溶剂， 反应 200.0h， 以80%的产率得到methyl p-nitromethylcinnamate
  参考文献：
  名称：

  13 C核磁共振波谱法测定感应效应

  摘要：

  已经制备了一系列间-和对-XCH 2-取代的肉桂酸甲酯，并且已经在乙醇中确定了α-和β-侧链碳的13 C nmr化学位移。在大多数情况下，取代基诱导的化学位移的大小与X基团的感应取代基常数成正比。C–H超共轭在从取代基到更远距离的感应效应的传递中似乎起着重要作用。乙烯基碳在对位系列中，但是在其他三种情况下，中继似乎主要是通过直接场效应实现的。

  DOI：

  10.1039/p29830000843
• 作为产物：
  描述：

  methyl 3-(4-methylphenyl)acrylate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 4-溴甲基肉桂酸甲酯
  参考文献：
  名称：

  β-Carboline和N -hydroxycinnamamide杂种作为抗药性肝细胞癌的抗癌药

  摘要：

  为了努力开发可以克服耐药性（导致癌症死亡的首要原因）的抗癌剂，我们开发了一系列新型的β-咔啉和N-羟基肉桂酰胺作为组蛋白脱乙酰基酶（HDAC）抑制剂。大多数杂种13a-p对四种人类癌细胞均表现出很强的抗增殖作用，且低微摩尔IC 50值。13p系列最有效的化合物显示出高HDAC1 / 6抑制作用，并且还提高了组蛋白H3，H4和α-微管蛋白的乙酰化水平。重要的是，13p对药物敏感的HepG2和Bel7402细胞以及耐药的Bel7402 / 5FU细胞表现出很高的抗癌能力。混合13p通过调节这些Bel7402 / 5FU细胞中凋亡相关蛋白的表达，触发了明显的凋亡。最后，13p通过在Bel7402 / 5FU细胞中增加LC3-II的表达以及p62和LC3-I的表达的退化而诱导了大量的自噬通量活性。总体而言，13p是一种新型的β-咔啉/ N-羟基肉桂酰胺杂化物，具有显着的抗癌效力，值得进一步评估其对耐药性肝细胞癌的治疗。

  DOI：

  10.1016/j.ejmech.2019.02.054

文献信息

• Design, synthesis, and preliminary bioactivity evaluation of <i>N</i> -benzylpyrimidin-2-amine derivatives as novel histone deacetylase inhibitor
  作者：Yi Zhou、Yanyan Dun、Huansheng Fu、Lei Wang、Xiaole Pan、Xinying Yang、Hao Fang

  DOI：10.1111/cbdd.13019

  日期：2017.11

  Histone deacetylase inhibitors have been identified for the treatment of cancer. Lately, we designed and synthesized a series of substituted N-benzylpyrimidin-2-amine derivatives as potent HDAC inhibitors. Target compounds 6a, 6d, 8a, 8c, and 8f not only exhibited almost equally enzymatic inhibitory activity with SAHA, but showed better antiproliferative activities.

  已经鉴定出组蛋白脱乙酰基酶抑制剂可用于治疗癌症。最近，我们设计并合成了一系列取代的N-苄基嘧啶-2-胺衍生物作为有效的HDAC抑制剂。目标化合物6a，6d，8a，8c和8f不仅表现出与SAHA几乎相同的酶抑制活性，而且表现出更好的抗增殖活性。
• Dual NAMPT/HDAC Inhibitors as a New Strategy for Multitargeting Antitumor Drug Discovery
  作者：Wei Chen、Guoqiang Dong、Ying Wu、Wannian Zhang、Chaoyu Miao、Chunquan Sheng

  DOI：10.1021/acsmedchemlett.7b00414

  日期：2018.1.11

  thiazolocarboxamide inhibitors were highly active for both targets. In particular, compound 7f (NAMPT IC50 = 15 nM, HDAC1 IC50 = 2 nM) showed potent in vivo antitumor efficacy in the HCT116 xenograft model. The study offers a new strategy for multitarget antitumor drug discovery by simultaneously acting on cancer metabolism and epigenetics.

  通过药效基团融合方法设计了新型双重烟酰胺磷酸核糖基转移酶（NAMPT）和组蛋白脱乙酰基酶（HDAC）抑制剂。噻唑甲酰胺抑制剂对两个靶均具有高活性。特别地，化合物7f（NAMPT IC 50 = 15 nM，HDAC1 IC 50 = 2 nM）在HCT116异种移植模型中显示出强大的体内抗肿瘤功效。该研究通过同时作用于癌症的新陈代谢和表观遗传学，为发现多靶点抗肿瘤药物提供了新的策略。
• Pd(NHC)-catalyzed alkylsulfonylation of boronic acids: a general and efficient approach for sulfone synthesis
  作者：Haibo Zhu、Yajing Shen、Qinyue Deng、Jinjin Chen、Tao Tu

  DOI：10.1039/c7cc05851a

  日期：——

  Robust N-heterocyclic carbene palladium complexes are highly efficient catalysts for direct alkylsulfonylation of (hetero)aryl- or alkenyl-boronic acids with potassium metabisulfite and (hetero)alkyl-halides. Among them, acenaphthoimidazolylidene palladium(II) complexes exhibited the highest activities, and up to quantitative yields were obtained for diverse structurally distinct sulfones under very

  健壮的N-杂环卡宾钯络合物是高效的催化剂，可用于（杂）芳基-或烯基-硼酸与亚硫酸氢钾和（杂）烷基卤化物的直接烷基磺酰化。其中，并咪唑基亚钯钯（II）配合物表现出最高的活性，并且在非常温和的反应条件下，不同结构的砜获得了最高的定量收率。
• Water-Stable Metal–Organic Framework for Effective and Selective Cr₂O₇^2– Capture through Single-Crystal to Single-Crystal Anion Exchange
  作者：Li Ma、Jin Yang、Bing-Bing Lu、Cheng-Peng Li、Jian-Fang Ma

  DOI：10.1021/acs.inorgchem.8b01879

  日期：2018.9.17

  Cr2O72– via an anion-exchange manner. Meaningfully, the capture and separation of aqueous Cr2O72– are highly selective even in the presence of other disturbing anions. More importantly, the crystal structure of 1-Cl after anion exchange (1-Cr2O7) could be determined by single crystal X-ray diffraction, elaborating the single-crystal-to-single-crystal (SC-SC) transformation. The Cr2O72– removal process by

  从水中有效和选择性地捕获对环境有毒的Cr 2 O 7 2–对于环境保护和人类健康都是理想的，但它仍然是一个巨大的挑战。我们提出了具有大的纳米管通道（约1.4×1.4 nm 2）（1-Cl）的水稳定性阳离子金属-有机骨架（MOF ）。显着地，所得的多孔材料通过阴离子交换方式表现出快速的水相去除Cr 2 O 7 2–的能力。有意义的是，Cr 2 O 7 2–即使在存在其他干扰性阴离子的情况下也具有很高的选择性。更重要的是，阴离子交换后的1-Cl（1-Cr 2 O 7）的晶体结构可以通过单晶X射线衍射确定，详细说明单晶至单晶（SC-SC）的转变。在Cr 2 ö 7 2-通过去除工艺1-CL从而直接用Cr的晶体结构揭露2 ö 7 2- -incorporated 1铬2 ö 7。
• 奥扎格雷中间体对溴甲基肉桂酸酯的合成方法
  申请人：深圳市第二人民医院

  公开号：CN109796338B

  公开（公告）日：2022-05-06

  本发明公开了一种奥扎格雷中间体对溴甲基肉桂酸酯的合成方法，其特征在于，将对甲基肉桂酸酯溴化得到对溴甲基肉桂酸酯，所述反应过程为：1)在保护气下，将对甲基肉桂酸酯、辅助物和溶剂A混匀，控制反应温度至110～130℃，压力至4～6个大气压，搅拌1～2h后，维持反应条件，开始滴加溴化盐和冰乙酸的混合水溶液C，控制滴加时间为1～3h，滴加结束后，控制温度至140～160℃，压力至7～10个大气压，反应4～6h结束；2)将体系冷却后，倒入2～4倍体积的水中，加入溶剂B提取，分层，有机层经水洗、干燥剂干燥后，浓缩蒸除溶剂得产物。本发明合成方法选择性好、成本低、产率较高。