苯并呋喃-5-甲酸乙酯 | 17348-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 中文名称: 苯并呋喃-5-甲酸乙酯
• 中文别名: 苯并呋喃-5-羧酸乙酯；5-(乙氧基羰基)苯并[c][1,2,5]噁二唑1-氧化物
• 英文名称: 1-oxy-benzo[1,2,5]oxadiazole-5-carboxylic acid ethyl ester
• 英文别名: 5(6)-Ethoxycarbonyl-benzofuroxan；5-Ethoxycarbonyl-benzofuroxan；5-Ethoxycarbonylbenzofuroxan；Ethyl 2,1,3-benzoxadiazole-5-carboxylate 1-oxide；ethyl 1-oxido-2,1,3-benzoxadiazol-1-ium-5-carboxylate
• CAS: 17348-71-9
• 化学式: C₉H₈N₂O₄
• mdl: MFCD00276595
• 分子量: 208.174
• InChiKey: PNSWPHLJTBSRJR-UHFFFAOYSA-N

物化性质

• 熔点：
  66-67°C
• 沸点：
  335.7±34.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下稳定，应避免接触水分或潮湿环境。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2934999090

SDS

Name:	5-(Ethoxycarbonyl)-2 1 3-benzoxadiazol-1-ium-1-olate 97% Material Safety Data Sheet
Synonym:	Ethyl benzofuroxan-5-carboxylat
CAS:	17348-71-9

Section 1 - Chemical Product MSDS Name:5-(Ethoxycarbonyl)-2 1 3-benzoxadiazol-1-ium-1-olate 97% Material Safety Data Sheet
Synonym:Ethyl benzofuroxan-5-carboxylat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17348-71-9	5-(Ethoxycarbonyl)-2,1,3-benzoxadiazol	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 17348-71-9: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H8N2O4
Molecular Weight: 208

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 17348-71-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-(Ethoxycarbonyl)-2,1,3-benzoxadiazol-1-ium-1-olate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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.
WGK (Water Danger/Protection)
CAS# 17348-71-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 17348-71-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 17348-71-9 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：

  苯并呋喃-5-甲酸乙酯 在 亚磷酸三乙酯 作用下， 以 乙醇 为溶剂， 生成 苯并呋咱-5-羧酸乙酯
  参考文献：
  名称：

  潜在的抗白血病和免疫抑制药物。3.同环取代对4-硝基苯并2,1,3-恶二唑（4-硝基苯并呋喃）及其N-氧化物（4-硝基苯并呋喃）的体外药物活性的影响。

  摘要：

  DOI：

  10.1021/jm00273a012
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲酸乙酯 在 盐酸 、 sodium azide 、 sodium acetate 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 2.25h， 生成 苯并呋喃-5-甲酸乙酯
  参考文献：
  名称：

  Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

  摘要：

  Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy. Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy. The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells. Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and/or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells. Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced. Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxides have reduction potentials significantly more positive than Tirapazamine (E(pc)-0.90 V). The most potent cytotoxins to cells in culture were the 6,7,-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine. The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity. Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro. In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine. This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

  DOI：

  10.1021/jm00010a023

文献信息

• Potential antileukemic and immunosuppressive drugs. Preparation and in vitro pharmacological activity of some 2,1,3-benzoxadiazoles (benzofurazans) and their N-oxides (benzofuroxans)
  作者：P. B. Ghosh、Michael W. Whitehouse

  DOI：10.1021/jm00308a027

  日期：1968.3
• Latham,D.W.S. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 2216 - 2221
  作者：Latham,D.W.S. et al.

  DOI：——

  日期：——
• Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides
  作者：Antonio Monge、Juan A. Palop、Adela Lopez de Cerain、Virginia Senador、Francisco J. Martinez、Yolanda Sainz、Susana Narro、Estrella Garcia、Carlos de Miguel

  DOI：10.1021/jm00010a023

  日期：1995.5

  Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy. Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy. The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells. Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and/or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells. Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced. Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxides have reduction potentials significantly more positive than Tirapazamine (E(pc)-0.90 V). The most potent cytotoxins to cells in culture were the 6,7,-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine. The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity. Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro. In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine. This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.
• Potential antileukemic and immunosuppressive drugs. 3. Effects of homocyclic ring substitution on the in vitro drug activity of 4-nitrobenzo-2,1,3-oxadiazoles (4-nitrobenzofurazans) and their N-oxides (4-nitrobenzofuroxans)
  作者：P. B. Ghosh、B. Ternai、M. W. Whitehouse

  DOI：10.1021/jm00273a012

  日期：1972.3