3.4-dimethoxy-2-nitrocinnamic acid | 20567-38-8

• 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
• 英文名称: 3.4-dimethoxy-2-nitrocinnamic acid
• 英文别名: 2-Nitro-4.5-dimethoxy-zimtsaeure；4,5-Dimethoxy-o-nitrozimtsaeure；3-(4,5-Dimethoxy-2-nitrophenyl)prop-2-enoic acid
• CAS: 20567-38-8
• 化学式: C₁₁H₁₁NO₆
• 分子量: 253.211
• InChiKey: BZIRMMAJZSOLEW-UHFFFAOYSA-N

物化性质

• 熔点：
  293 °C (dec.)(lit.)
• 沸点：
  483℃
• 密度：
  1.369
• 闪点：
  246℃
• 稳定性/保质期：
  避免接触强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  将物品存放在紧密封装的容器中，并储存在阴凉、干燥的地方。

SDS

Name:	4 5-Dimethoxy-2-Nitrocinnamic Acid 97% Material Safety Data Sheet
Synonym:	3-(4,5-Dimethoxy-2-Nitrophenyl)acrylic Acid
CAS:	20567-38-8

Section 1 - Chemical Product MSDS Name:4 5-Dimethoxy-2-Nitrocinnamic Acid 97% Material Safety Data Sheet
Synonym:3-(4,5-Dimethoxy-2-Nitrophenyl)acrylic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
20567-38-8	4,5-Dimethoxy-2-Nitrocinnamic Acid	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
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.
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. Wash mouth out with 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.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
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.

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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.

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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# 20567-38-8: 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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: > 270 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: C11H11NO6
Molecular Weight: 253.21

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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, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, 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# 20567-38-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4,5-Dimethoxy-2-Nitrocinnamic Acid - 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: Not available.
Risk Phrases:
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# 20567-38-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 20567-38-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 20567-38-8 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

反应信息

• 作为反应物：
  描述：

  3.4-dimethoxy-2-nitrocinnamic acid 在 ammonium formate on silica gel 、 锌 作用下， 以 二氧化碳 为溶剂， 50.0 ℃ 、12.0 MPa 条件下， 以75%的产率得到6,7-dimethoxy-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  使用锌粉和甲酸铵通过邻硝基芳酸的还原环化合成吲哚酮和喹诺酮

  摘要：

  在超临界流体二氧化碳 (scCO2) 介质下使用 Zn 和 HCO2NH4 开发了一种用于从邻硝基芳酸合成吲哚酮和喹诺酮衍生物的新方案。该过程包括将硝基还原为氨基，然后原位环化。

  DOI：

  10.3184/030823408x320647
• 作为产物：
  描述：

  丙二酸 、 6-硝基藜芦醛 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.37h， 以94%的产率得到3.4-dimethoxy-2-nitrocinnamic acid
  参考文献：
  名称：

  A Simple and Straightforward Synthesis of Cinnamic acids and Ylidene Malononitriles via Knoevenagel Condensation Employing DABCO as Catalyst

  摘要：

  通过在催化量的 DABCO 存在下芳族醛与丙二酸和丙二腈的 Knoevenagel 缩合，开发了一种合成取代肉桂酸和亚基丙二腈的有效方法。该方法具有反应条件温和、收率优异、反应时间短、无需进一步纯化等优点。

  DOI：

  10.14233/ajchem.2017.20575

文献信息

• An efficient route to xanthine based A2A adenosine receptor antagonists and functional derivatives
  作者：Paul LaBeaume、Ma Dong、Michail Sitkovsky、Elizabeth V. Jones、Rhiannon Thomas、Sara Sadler、Amy E. Kallmerten、Graham B. Jones

  DOI：10.1039/c003382k

  日期：——

  A one-pot route to 8-substituted xanthines has been developed from 5,6-diaminouracils and carboxaldehydes. Yields are good and the process applicable to a range of substrates including a family of A2A adenosine receptor antagonists. A new route to the KW-6002 family of antagonists is presented including a pro-drug variant, and application to related image contrast agents developed.

  已开发出一条从5,6-二氨基尿嘧啶和羰基化合物出发，制备8-取代黄嘌呤的一锅法路线。该方法产率高，适用于多种底物，包括一组A2A腺苷受体拮抗剂。本文介绍了一条制备KW-6002拮抗剂家族的新路线，包括一种前药变体，并应用于开发相关造影剂。
• (3-羟基)丙酸基苯胺衍生物及其制备方法
  申请人：河南省科学院化学研究所有限公司

  公开号：CN104628588B

  公开（公告）日：2016-08-24

  本发明公开了一类具有如下结构式的(3‑羟基)丙酸基苯胺衍生物及其制备方法，属于有机化学合成领域。其合成通过丙烯酸基硝基苯及其取代衍生物与水合肼反应实现。R为H，被C1‑5烷氧基单取代或多取代，C1‑5烷氧基二取代时烷氧基成环或卤素单取代等。该新型氨基酸衍生物含有羟基，属于多官能团氨基酸。能增加齐墩果酸的水溶性。此外，其合成方法比较简单，步骤简短、安全环保、适于规模化工业化生产。
• Therapeutic agent for Parkinson's disease
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05484920A1

  公开（公告）日：1996-01-16

  Agents for the treatment of Parkinson's disease contain, as an active ingredient, a xanthine derivative or a pharmaceutically acceptable salt thereof. The xanthine derivative is represented by the formula: ##STR1## in which R.sup.1, R.sup.2 are R.sup.3 are independently hydrogen, lower alkyl, lower alkenyl, or lower alkynyl; and R.sup.4 represents cycloalkyl, --(CH.sub.2).sub.n --R.sup.5 (in which R.sup.5 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group; and n is an integer of 0 to 4), or ##STR2## in which Y.sup.1 and Y.sup.2 represent independently hydrogen, halogen, or lower alkyl; and Z represents substituted or unsubstituted aryl, ##STR3## in which R.sup.6 represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, or amino; and m represents an integer of 1 to 4, or a substituted or unsubstituted heterocyclic group; and X.sup.1 and X.sup.2 represent independently O or S.

  帕金森病的治疗剂含有黄嘌呤衍生物或其药学上可接受的盐作为活性成分。黄嘌呤衍生物由以下式子表示：##STR1## 其中R.sup.1、R.sup.2和R.sup.3分别表示氢、低碳基、低烯基或低炔基；而R.sup.4表示环烷基、--(CH.sub.2).sub.n --R.sup.5（其中R.sup.5表示取代或未取代的芳基或取代或未取代的杂环基；n为0到4的整数），或##STR2## 其中Y.sup.1和Y.sup.2分别表示氢、卤素或低碳基；而Z表示取代或未取代的芳基，##STR3## 其中R.sup.6表示氢、羟基、低碳基、低烷氧基、卤素、硝基或氨基；m表示1到4的整数，或取代或未取代的杂环基；而X.sup.1和X.sup.2分别表示氧或硫。
• Antidepressants
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05543415A1

  公开（公告）日：1996-08-06

  The present invention relates to an antidepressant containing as an active ingredient a xanthine derivative or a pharmaceutically acceptable salt thereof, the xanthine derivative being represented by Formula (I) : ##STR1## in which R.sup.1, R.sup.2, and R.sup.3 represent independently hydrogen, lower alkyl, lower alkenyl; R.sup.4 represents cycloalkyl, --(CH.sub.2).sub.n --R.sup.5 (in which R.sup.5 represents substituted or unsubstituted aryl or a substituted or unsubstituted heterocyclic group; and n is an integer of 0 to 4), or ##STR2## (in which Y.sup.1 and Y.sup.2 represent independently hydrogen, halogen or lower alkyl; and Z represents substituted or unsubstituted aryl, ##STR3## (in which R.sup.6 represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, or amino; and m represents an integer of 1 to 3), or a substituted or unsubstituted heterocyclic group); and X.sup.1 and X.sup.2 represent independently O or S.

  本发明涉及一种抗抑郁剂，其活性成分为黄嘌呤衍生物或其药学上可接受的盐，该黄嘌呤衍生物由式(I)表示： ##STR1## 其中R.sup.1，R.sup.2和R.sup.3分别独立表示氢，低烷基，低烯基；R.sup.4表示环烷基，--(CH.sub.2).sub.n --R.sup.5（其中R.sup.5表示取代或未取代的芳基或取代或未取代的杂环基；n为0至4的整数），或##STR2##（其中Y.sup.1和Y.sup.2分别独立表示氢，卤素或低烷基；Z表示取代或未取代的芳基，##STR3##（其中R.sup.6表示氢，羟基，低烷基，低烷氧基，卤素，硝基或氨基；m表示1至3的整数），或取代或未取代的杂环基）；X.sup.1和X.sup.2分别独立表示O或S。
• Visible-Light-Induced Metal-Free Decarboxylative Perfluoroalkylation of Aryl Acrylic Acids
  作者：Mo Yu、Kaikai Niu、Ziwen Wang、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.2c03088

  日期：2022.10.21

  for visible-light-induced perfluoroalkylation reactions of aryl acrylic acids. These reactions, which use perfluoroalkyl iodides as radical precursors and inexpensive eosin Y as a photocatalyst, proceed in a decarboxylative manner. The easy accessibility of perfluoroalkyl iodides and the broad substrate scope, mild conditions, and metal-free catalyst make this protocol applicable for the transformation

  全氟烷基化对于生物活性分子的后期修饰很重要。在这里，我们报告了一种可见光诱导的芳基丙烯酸全氟烷基化反应的方案。这些使用全氟烷基碘化物作为自由基前体和廉价的曙红 Y 作为光催化剂的反应以脱羧方式进行。全氟烷基碘化物的易获得性和广泛的底物范围、温和的条件和无金属催化剂使该协议适用于将廉价原材料转化为高价值化学品。