3-(5-硝基-2-呋喃基)丙烯醛 | 1874-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 3-(5-硝基-2-呋喃基)丙烯醛
• 中文别名: 5-硝基呋喃-2-丙烯醛
• 英文名称: 5-nitrofurylacrolein
• 英文别名: 5-nitro-2-furanacrolein；3-(5-Nitrofuran-2-yl)prop-2-enal
• CAS: 1874-22-2
• 化学式: C₇H₅NO₄
• 分子量: 167.121
• InChiKey: DXWCZMGIIFEEPU-UHFFFAOYSA-N

物化性质

• 熔点：
  117°C
• 沸点：
  295.67°C (rough estimate)
• 密度：
  1.5216 (rough estimate)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 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：
  76
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22,R20/21,R36/37/38
• 海关编码：
  2932190090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501,P201,P202,P281,P308+P313,P405
• 危险性描述：
  H315,H319,H335,H341,H361
• 储存条件：
  保持贮藏器密封，并将其存放在阴凉、干燥处。确保工作区间有良好的通风或排气装置。

SDS

Name:	5-Nitro-2-furanacrolein tech 92% Material Safety Data Sheet
Synonym:	3-[(5-Nitro)-2-furanyl]-2-propenal; 5-Nitrofuran-2-acrylaldehyde; 2-Furanacrolein, 5-nitro-; 2-Propenal, 3-(5-nitro-2-furanyl)
CAS:	1874-22-2

Section 1 - Chemical Product MSDS Name:5-Nitro-2-furanacrolein tech 92% Material Safety Data Sheet
Synonym:3-[(5-Nitro)-2-furanyl]-2-propenal; 5-Nitrofuran-2-acrylaldehyde; 2-Furanacrolein, 5-nitro-; 2-Propenal, 3-(5-nitro-2-furanyl)

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1874-22-2	5-Nitro-2-furanacrolein, tech.	92	217-499-8

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.
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.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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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 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:
Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Use with adequate ventilation.
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# 1874-22-2: 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: Powder
Color: orange-brown
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 109.00 - 114.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C7H5NO4
Molecular Weight: 167.12

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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, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
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# 1874-22-2: LT8530780 LD50/LC50:
Not available.
Carcinogenicity:
5-Nitro-2-furanacrolein, tech. - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 1874-22-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1874-22-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1874-22-2 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： β-(5-硝基-2-呋喃基)丙烯醛主要用于合成硝呋肼（Nifurzide）、Furaginum、硝呋马佐（Nifurmade）和硝呋立宗（Nifurizone）。

用途简介： 暂无内容

用途： β-(5-硝基-2-呋喃基)丙烯醛主要用于合成硝呋肼（Nifurzide）、Furaginum、硝呋马佐（Nifurmade）和硝呋立宗（Nifurizone）。

反应信息

• 作为反应物：
  描述：

  3-(5-硝基-2-呋喃基)丙烯醛 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 3-(5-硝基-2-呋喃基)-2-丙烯-1-醇
  参考文献：
  名称：

  Sasaki, Pharmaceutical Bulletin, 1953, vol. 1, p. 343,345

  摘要：

  DOI：

文献信息

• Organocatalytic enantioselective synthesis of 2,3-dihydropyridazines
  作者：Maitane Fernández、Jose L. Vicario、Efraím Reyes、Luisa Carrillo、Dolores Badía

  DOI：10.1039/c2cc17370k

  日期：——

  We have developed an efficient procedure for the easy and straightforward preparation of functionalized dihydropyridazines as highly enantiopure materials by reaction of pyruvaldehyde 2-tosyl hydrazone with a variety of α,β-unsaturated aldehydes using a chiral secondary amine as catalyst. The overall process consists of a cascade reaction involving an initial aza-Michael reaction, in which the stereocentre is installed, followed by an intramolecular aldol reaction/dehydration step.

  我们开发了一种高效的方法，通过使用手性二级胺作为催化剂，将丙酮醛2-托磺酰肼与多种α,β-不饱和醛反应，简单而直接地制备功能化的二氢吡嗪，得到高度对映体纯的材料。整个过程包括一个级联反应，涉及初始的氮杂迈克尔反应，在这一过程中形成了立体中心，然后是一个分子内的醛醇反应/脱水步骤。
• FURYL AND THIENYL TRIAZOLE DERIVATIVES AND THERAPEUTIC USES THEREOF
  申请人：DENTISTRY OF NEW JERSEY UNIVERSITY OF MEDICINE AND

  公开号：US20140243381A1

  公开（公告）日：2014-08-28

  Nitric oxide biosynthesis-inhibiting anti-inflammatory and anti-microbial compounds of Formula (3) and Formula (4) wherein R1 and R2 are independently selected from optionally substituted thienyl, optionally substituted furyl, optionally substituted —CH═CH-thienyl and optionally substituted provided that R2 is substituted with as nitro group Treatment methods utilizing the compounds, and methods of synthesis of the compounds are also disclosed.

  氮氧化物生物合成抑制抗炎和抗微生物化合物的公式（3）和公式（4），其中R1和R2分别选自可选择取代噻吩基、可选择取代呋喃基、可选择取代-CH═CH-噻吩基和可选择取代，前提是R2被取代为硝基。还公开了利用这些化合物的治疗方法，以及合成这些化合物的方法。
• Derivatives of 1,2,4-triazole imines acting as dual iNOS and tumor cell growth inhibitors
  作者：Christophe Guillon、Anna M. Vetrano、Jaya Saxena、Angela Hunter、Geraldine Verderone、Thomas M. Finetti、Jeffrey Wisnoski、Peter W. DeMatteo、Robert D. Rapp、Ned D. Heindel、Laurie B. Joseph、Diane E. Heck、Jeffrey D. Laskin

  DOI：10.1016/j.bioorg.2020.104128

  日期：2020.10

  4-(R2-imino)-3-mercapto-5-(R1)-4H-1,2,4-triazoles derivatives were synthesized, characterized and evaluated for their ability to inhibit nitric oxide (NO) production in PAM212 mouse keratinocytes, which led to the discovery and the subsequent evaluation of their growth inhibitory cytotoxic potency toward that same mouse cell line together with a number of human cells lines (PC3, HT-29 and HeLa). Some limited

  合成了一组 4-(R 2 -imino)-3-mercapto-5-(R 1 )-4 H -1,2,4-triazoles 衍生物，表征并评估了它们抑制一氧化氮 (NO) 的能力PAM212 小鼠角质形成细胞中的产生，这导致发现并随后评估了它们对同一小鼠细胞系以及许多人类细胞系（PC3、HT-29 和 HeLa）的生长抑制细胞毒效力。可以为 NO 产生抑制效力和生长抑制细胞毒性建立一些有限的 SAR。值得注意的是，设计为呋喃妥因模拟物的化合物是最有效的抗肿瘤剂。
• Synthesis and properties of macroheterocyclic azomethines based on 4-aminobenzo-15-crown-5
  作者：N. Yu. Sadovskaya、V. N. Glushko、V. M. Retivov、S. K. Belus’、V. V. Grokhovskii

  DOI：10.1134/s1070363215120191

  日期：2015.12

  number of new stable azomethine crown ether derivatives have been synthesized by condensation of 4-aminobenzo-15-crown-5 with aromatic aldehydes. Complexation of the products with transition metal cations (Cu2+, Zn2+, Fe3+, Co3+, Ni3+) has been studied by spectrophotometry.

  通过将4-氨基苯并-15-冠-5与芳族醛缩合，合成了许多新的稳定的甲亚胺冠醚衍生物。通过分光光度法研究了产物与过渡金属阳离子（Cu 2 +，Zn 2 +，Fe 3+，Co 3+，Ni 3+）的络合。
• Synthesis and antimicrobial activity of some nitrofuran-containing azomethines
  作者：P. A. Pavlov、N. Yu. Basova、P. P. Pavlov

  DOI：10.1007/bf02524409

  日期：2000.6

  A strategy used fbr the synthesis of well-known nitrofuran derivatives possessing antimicrobial properties consists in the condensation of 5-nitrofurfurol or 5-nitrofurylacrolein with compounds containing primary amino groups. By using 5-nitro-2-furahydrazimide (NFH), incorporating its own C=N fragment, as the nitrofuran-containing component, we may principally change the situation and employ most

  用于合成具有抗微生物特性的众所周知的硝基呋喃衍生物的策略包括将 5-硝基呋喃或 5-硝基呋喃丙烯醛与含有伯氨基的化合物缩合。通过使用 5-硝基-2-呋喃肼 (NFH)，结合其自身的 C=N 片段，作为含硝基呋喃的成分，我们可以主要改变这种情况，并在合成中使用最多样化的醛（包括硝基呋喃基团的醛）含硝基呋喃的偶氮甲碱。在这项研究中，我们仅使用四种含硝基呋喃的醛作为含羰基组分合成了一系列新的偶氮甲碱。然而，之前有报道称这些醛类可以产生高效的抗菌制剂 [1, 2]。