4-乙酰胺基-3-硝基苯甲酸 | 1539-06-6

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 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: 4-乙酰胺基-3-硝基苯甲酸
• 中文别名: 4-乙酰氨基-3-硝基苯甲酸
• 英文名称: 3-nitro-4-acetamidobenzoic acid
• 英文别名: 4-acetamido-3-nitrobenzoic acid；4-(acetylamino)-3-nitrobenzoic acid
• CAS: 1539-06-6
• 化学式: C₉H₈N₂O₅
• 分子量: 224.173
• InChiKey: BRQIMWBIZLRLSV-UHFFFAOYSA-N

物化性质

• 熔点：
  220-224 °C (lit.)
• 沸点：
  365.56°C (rough estimate)
• 密度：
  1.4656 (rough estimate)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知危险反应，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 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：
  112
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280
• 危险性描述：
  H317
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉、干燥处。同时，确保工作环境有良好的通风或排气设施。

SDS

Name:	4-Acetamide-3-Nitrobenzoic Acid Material Safety Data Sheet
Synonym:	None Known
CAS:	1539-06-6

Section 1 - Chemical Product MSDS Name:4-Acetamide-3-Nitrobenzoic Acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1539-06-6	4-Acetamide-3-Nitrobenzoic Acid	ca. 100	216-265-2

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

---

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. 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. 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 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. 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:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 1539-06-6: 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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 210-212 deg C
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: C9H8N2O5
Molecular Weight: 224.17

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents, strong bases.
Hazardous Decomposition Products:
Hydrogen cyanide, carbon monoxide, oxides of nitrogen, carbon dioxide, nitric acid.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1539-06-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Acetamide-3-Nitrobenzoic 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 1539-06-6: No information available.
Canada
CAS# 1539-06-6 is listed on Canada's NDSL List.
CAS# 1539-06-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1539-06-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-乙酰胺基-3-硝基苯甲酸 在 乙醇 、 硫酸 作用下， 生成 4-氨基-3-硝基苯甲酸乙酯
  参考文献：
  名称：

  DE151725

  摘要：

  公开号：
• 作为产物：
  描述：

  对乙酰氨基苯甲酸 在 硫酸 、 硝酸 作用下， 反应 0.67h， 以84%的产率得到4-乙酰胺基-3-硝基苯甲酸
  参考文献：
  名称：

  具有杀锥虫活性的苯甲酸衍生物：转唾液酸酶的酶促分析和分子对接研究

  摘要：

  恰加斯病或美洲锥虫病仍然是发展中国家的一个重要公共卫生问题。在过去十年中，转唾液酸酶已成为新型抗恰加斯药物的药理学靶点。在这项工作中，目的是设计和发现一系列新的苯甲酸衍生物作为转唾液酸酶 (TS) 抑制剂和抗锥虫药。三种化合物（14、18 和 19）共享一个对氨基苯甲酸部分在两种菌株中显示出比市售药物硝呋莫司和苯硝唑更有效的锥虫杀灭活性：50% 的群体 (LC50) 的裂解浓度 <0.15 µM在 NINOA 菌株上，LC50 < 0.22 µM 在 INC-5 菌株上。此外，化合物 18 显示出对转唾液酸酶的中等抑制 (47%) 和类似于 DANA 的结合模型（模式 A）。

  DOI：

  10.3390/molecules22111863

文献信息

• Structure-Based Inhibitors of Influenza Virus Sialidase. A Benzoic Acid Lead with Novel Interaction
  作者：Sangeeta Singh、Marek J. Jedrzejas、Gillian M. Air、Ming Luo、W. Graeme Laver、Wayne J. Brouillette

  DOI：10.1021/jm00017a005

  日期：1995.8

  for infection of the virus. The catalytic site is highly conserved among all known influenza variants, suggesting that this protein is a suitable target for drug intervention. The most potent known inhibitors are analogs of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (Neu5Ac2en), particularly the 4-guanidino derivative (4-guanidino-Neu5Ac2en). We utilized the benzene ring of 4-(N-acetylamino)benzoic

  流感病毒唾液酸酶是一种表面酶，对于感染病毒至关重要。在所有已知的流感变体中，催化位点均高度保守，表明该蛋白是药物干预的合适靶标。最有效的已知抑制剂是2-脱氧-2，3-二氢-N-乙酰神经氨酸（Neu5Ac2en），特别是4-胍基衍生物（4-胍基-Neu5Ac2en）的类似物。我们利用4-（N-乙酰氨基）苯甲酸的苯环作为环状模板替代Neu5Ac2en的二氢吡喃环。在这项研究中，准备了几种3-（N-酰基氨基）衍生物作为Neu5Ac2en甘油侧链的潜在替代物，并且发现其中一些与唾液酸酶的相同结合亚位相互作用。更重要的意义是观察到，迄今为止确定的最有效的流感唾液酸酶苯甲酸抑制剂（IC50 = 10 microM）3-胍基苯甲酸衍生物（相当于4-胍基-Neu5Ac2en的4-胍基）。与胍基结合子位点相反，唾液酸酶上的甘油结合子位点。因此，该苯甲酸衍生物提供了一种新化合物，该化合物以新颖的方式与流感唾液酸酶的催化​​位点相互作用。
• The reduction of aromatic nitro groups on solid supports using sodium hydrosulfite (Na2S2O4)
  作者：Randall A Scheuerman、David Tumelty

  DOI：10.1016/s0040-4039(00)00959-x

  日期：2000.8

  An improved method for reducing aromatic nitro compounds on solid-phase supports using sodium hydrosulfite is presented. Conditions have been optimized to enable the use of this reagent for reductions on both polyethyleneglycol-polystyrene (PEG) resins and traditional polystyrene (PS) resins.

  提出了一种使用亚硫酸氢钠还原固相载体上芳族硝基化合物的改进方法。已对条件进行了优化，以使该试剂可用于还原聚乙二醇-聚苯乙烯（PEG）树脂和传统聚苯乙烯（PS）树脂。
• Anthelmintic 5(6)-benzene ring substituted benzimidazole-2-carbamates
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04139626A1

  公开（公告）日：1979-02-13

  Benzene ring substituted benzimidazole-2-carbamate derivatives represented by the formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; ##STR2## is a 5, 6, 7 or 8 membered heterocyclic ring containing 1 to 2 hetero atoms; the ##STR3## substitution being at the 5(6)-position; and the pharmaceutically acceptable salts thereof. The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.

  苯环取代的苯并咪唑-2-氨基甲酸酯衍生物，其由以下公式表示：##STR1## 其中R是具有1至4个碳原子的低级烷基；##STR2## 是一个包含1至2个杂原子的5、6、7或8成员杂环；##STR3## 取代位于5(6)-位置；以及药用可接受的盐。这些化合物作为农药特别有用，尤其是作为驱虫剂和抗真菌剂。
• Benzimidazole compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06352985B1

  公开（公告）日：2002-03-05

  A benzimidazole compound represented by the formula (I): wherein R3 is a carboxyl group, a esterified carboxyl group, an amidated carboxyl group, an amino group, an amido group, or a sulfonyl group, or their pharmaceutically acceptable salts. Because of their blood sugar-depressing effect or PDE5 inhibitory effect, these compounds or salts thereof are useful as medicines for treating impaired glucose tolerance, diabetes, diabetic complications, syndrome of insulin resistance, hyperlipidemia, atherosclerosis, cardiovascular disorders, hyperglycemia, or hypertension; or stenocardia, hypertension, pulmonary hypertension, congestive heart failure, glomerulopathy, tubulointerstitial disorders, renal failure, atherosclerosis, angiostenosis, distal angiopathy, cerebral apoplexy, chronic reversible obstructions, allergic rhinitis, urticaria, glaucoma, diseases characterized by enteromotility disorders, impotence, diabetic complications, nephritis, cancerous cachexia, or restenosis after PTCA.

  一种由公式（I）表示的苯并咪唑化合物：其中R3是一个羧基、酯化羧基、酰胺化羧基、氨基、酰胺基或磺酰基，或其药学上可接受的盐。由于它们具有降低血糖作用或PDE5抑制作用，这些化合物或其盐可用作治疗糖耐量受损、糖尿病、糖尿病并发症、胰岛素抵抗综合征、高脂血症、动脉粥样硬化、心血管疾病、高血糖或高血压的药物；或心绞痛、高血压、肺动脉高压、充血性心力衰竭、肾小球病、肾小管间质疾病、肾功能衰竭、动脉粥样硬化、血管狭窄、远端血管病、脑卒中、慢性可逆性梗阻、过敏性鼻炎、荨麻疹、青光眼、以肠蠕动障碍为特征的疾病、阳痿、糖尿病并发症、肾炎、癌性消瘦或PTCA后再狭窄的药物。
• Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04154846A1

  公开（公告）日：1979-05-15

  Benzimidazole carbamate derivatives are provided having the structure ##STR1## wherein R is lower alkyl, lower alkenylalkyl, lower alkynylalkyl, phenyl, substituted phenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl or phenylalkyl, R.sup.1 is lower alkyl, phenylalkyl or di-lower alkylaminoalkyl, Z is a single bond or a straight or branched chain alkylene group, and n is 0, 1 or 2. These compounds are useful as anthelmintic agents administered orally or parenterally.

  提供了具有结构##STR1##的苯并咪唑羰基衍生物，其中R是较低的烷基、较低的烯烃基烷基、较低的炔烃基烷基、苯基、取代苯基、环烷基、环烯烃基、环烷基烷基、环烯烃基烷基或苯基烷基，R.sup.1是较低的烷基、苯基烷基或二较低烷基氨基烷基，Z是单键或直链或支链烷基基团，n为0、1或2。这些化合物可作为口服或静脉注射的驱虫剂。