o-nitrobenzaltosylhydrazone | 58809-90-8

• 物质功能分类: 化学试剂 - 有机试剂 - 腙
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: o-nitrobenzaltosylhydrazone
• 英文别名: N'-(2-nitrobenzylidene)tosylhydrazide；2-nitrobenzaldehyde tosylhydrazone；N’-(2-nitrobenzylidene)-4-methylbenzenesulfonohydrazide；Fluorenon-tosylhydrazon；4-methyl-N'-(2-nitrobenzylidene)-benzenesulfonohydrazide；toluene-4-sulfonic acid-(2-nitro-benzylidenehydrazide)；Toluol-4-sulfonsaeure-(2-nitro-benzylidenhydrazid)；4-methyl-N-[(Z)-(2-nitrophenyl)methylideneamino]benzenesulfonamide；4-methyl-N-[(2-nitrophenyl)methylideneamino]benzenesulfonamide
• CAS: 58809-90-8
• 化学式: C₁₄H₁₃N₃O₄S
• 分子量: 319.341
• InChiKey: OOOLPNHDHGDYPS-UHFFFAOYSA-N

物化性质

• 熔点：
  153-156 °C
• 密度：
  1.3759 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2935009090
• 储存条件：
  密封保存于2-8℃阴凉干燥处

SDS

Name:	2-Nitrobenzaldehyde Tosylhydrazone 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	58809-90-8

Section 1 - Chemical Product MSDS Name:2-Nitrobenzaldehyde Tosylhydrazone 99% Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
58809-90-8	2-Nitrobenzaldehyde Tosylhydrazone	99%	unlisted

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.

---

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 immediately.
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:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively.

---

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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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.

---

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. Keep container tightly closed.
Avoid ingestion and inhalation. Use with adequate ventilation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 58809-90-8: 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:
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 156 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: C14H13N3O4S
Molecular Weight: 319.32

---

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:
Oxidizing agents, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 58809-90-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Nitrobenzaldehyde Tosylhydrazone - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

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# 58809-90-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 58809-90-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 58809-90-8 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  o-nitrobenzaltosylhydrazone 在 poly(diselanediyl-1,2-phenylene) 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以96%的产率得到邻硝基苯甲酸
  参考文献：
  名称：

  ONE-POT OXIDATION OF AZOMETHINE COMPOUNDS INTO ARENECARBOXYLIC ACIDS

  摘要：

  Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.

  DOI：

  10.1081/scc-100105891
• 作为产物：
  描述：

  邻硝基苯甲醇 在 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 o-nitrobenzaltosylhydrazone
  参考文献：
  名称：

  一种苯并氮杂䓬桥环衍生物及其制备方法

  摘要：

  本发明涉及药物化学技术领域，公开了一种苯并氮杂桥环衍生物及其制备方法，该衍生物的制备方法包括以下步骤：将底物(1.0eq)、硫取代的苯丙醛(1.5eq)、碱DABCO(0.2eq)和干燥乙腈(2.0mL)加入反应试管中，混合物在常温下反应24小时，反应完成后浓缩纯化得到半缩醛产物3。然后半缩醛产物、氯仿(0.5mL)、H2O(100μL)加入到反应试管中，并于60℃下搅拌72h。反应通过薄层色谱监测完成，然后通过柱层析直接纯化反应混合物，得到相应的目标产物。该制备方法操作简便、反应温和、收率高。本发明提供的衍生物具有良好的抗菌活性，具有广阔的市场应用前景。

  公开号：

  CN116514809A

文献信息

• Direct Activation of Unmodified Morita–Baylis–Hillman Alcohols through Phosphine Catalysis for Rapid Construction of Three-Dimensional Heterocyclic Compounds
  作者：Leijie Zhou、Chunhao Yuan、Yuan Zeng、Qijun Wang、Chang Wang、Min Liu、Wei Wang、Yongjun Wu、Bing Zheng、Hongchao Guo

  DOI：10.1021/acs.orglett.9b01783

  日期：2019.6.21

  The phosphine-catalyzed tandem annulation reaction of Morita–Baylis–Hillman (MBH) alcohols with azomethine imines has been achieved for the synthesis of biologically important (epoxymethano)-pyrazolo[5,1-b]quinazoline derivatives. A variety of MBH alcohols and azomethine imines were well-tolerated under the mild reaction conditions, providing novel 3D heterocyclic compounds in high yields with excellent

  Morita–Baylis–Hillman（MBH）醇与偶氮甲亚胺的膦催化串联环化反应已实现，用于合成生物学上重要的（环氧甲氧基）-吡唑并[5,1- b ]喹唑啉衍生物。在温和的反应条件下，多种MBH醇和甲亚胺亚胺具有良好的耐受性，从而以高收率提供了具有出色的非对映选择性的新型3D杂环化合物。这是首次实现了未改性的MBH醇作为新的氧杂合成子的直接活化。
• A chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction through a kinetic resolution of MBH alcohols: highly enantioselective synthesis of three-dimensional heterocyclic compounds
  作者：Leijie Zhou、Yuan Zeng、Xing Gao、Qijun Wang、Chang Wang、Bo Wang、Wei Wang、Yongjun Wu、Bing Zheng、Hongchao Guo

  DOI：10.1039/c9cc05483a

  日期：——

  dearomative tandem annulation reaction of unmodified Morita–Baylis–Hillman alcohols with azomethine imines has been achieved through a kinetic resolution of MBH alcohols under mild conditions, giving pharmaceutically interesting functionalized hetero-bicyclo[3.3.1]nonane derivatives in good to excellent yields with excellent enantioselectivities.

  在这种交流中，通过温和条件下MBH醇的动力学拆分，实现了未修饰的Morita-Baylis-Hillman醇与偶氮甲亚胺的手性方酸酰胺催化的不对称脱芳香性串联环化反应，得到了药学上有意义的官能化杂双环[3.3.1] ]壬烷衍生物，具有良好的至优异的产率和优异的对映选择性。
• One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines
  作者：Qiang Sha、Yun-Yang Wei

  DOI：10.1039/c3ob40745d

  日期：——

  A new, convenient and efficient transition metal-free synthesis of S-alkyl dithiocarbamates through one-pot reaction of N-tosylhydrazones, carbon disulfide and amines is reported. Tosylhydrazones derived from various aromatic and aliphatic ketones or aldehydes were tested and gave dithiocarbamates in good to excellent yields. The tosylhydrazones can be generated in situ without isolation, which provides

  据报道，通过N-甲苯磺酰基hydr，二硫化碳和胺的一锅反应，一种新的，方便且有效的无过渡金属的S-烷基二硫代氨基甲酸酯的合成方法。对衍生自各种芳族和脂族酮或醛的甲苯磺酰hydr进行了测试，并以良好或优异的收率得到了二硫代氨基甲酸酯。甲苯磺酰hydr可以原位生成而无需分离，这提供了一种更简单的一锅法，可在羰基化合物，二硫化碳和胺存在下，通过羰基化合物，二硫化碳和胺的反应来合成二硫代氨基甲酸酯。4-甲基苯磺酰肼。
• A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triazepines
  作者：Yunlei Hou、Ping Gong、Xinyue Wang、Zefei Li、Chang Feng、Qi Zhen、Mingzhang Guo、Yaning Yao、Xinyu Zou、Pengfei Wang

  DOI：10.1055/a-1585-4490

  日期：2021.12

  The base-induced formal [4+3] cycloaddition reaction of C,N-cyclic azomethine imines with aza-ortho-quinone methides, generated in situ, is reported. This protocol provided an efficient method for the synthesis of biologically important 1,2,4-triazepine derivatives, with a wide substrate scope and excellent functional-group tolerance, and it gives moderate to excellent yields under mild conditions

  报告了碱诱导的正式 [4+3] 环加成反应，C,N-环状偶氮甲亚胺与氮杂邻醌甲基化物，原位生成。该协议为合成具有生物学意义的 1,2,4-三氮杂衍生物提供了一种有效的方法，具有广泛的底物范围和优异的官能团耐受性，并且在温和条件下可提供中等至优异的产率。在通过 MTT 分析筛选癌细胞系 HCT-116、H2228 和 A2780 时，几种衍生物表现出对 A2780 细胞系的体外抗肿瘤活性。
• Studies on tRNA and related compounds. XXXVII. Synthesis and physical properties of 2'- or 3'-O-(o-nitrobenzyl)nucleosides: the use of o-nitrophenyldiazomethane as a synthetic reagent.
  作者：EIKO OHTSUKA、TOSHIAKI WAKABAYASHI、SHOJI TANAKA、TOSHIKI TANAKA、KAZUYUKI OSHIE、AKIRA HASEGAWA、MORIO IKEHARA

  DOI：10.1248/cpb.29.318

  日期：——

  2'-and 3'-O-(o-Nitrobenzyl) derivatives of uridine, cytidine, adenosine and guanosine were synthesized by treatment of uridine, N-benzoylcytidine, N-benzoyladenosine and N-isobutyrylguanosine, respectively, with o-nitrophenyldiazomethane followed by isolation and deblocking. 3'-O-(o-Nitrobenzyl) guanosine is a novel compound. By using N-acylated nucleosides, separation of the 2'-and 3'-substituted isomers on silica gel became feasible and these compounds were useful intermediates for the synthesis of oligoribonucleotides. Some physical properties of these compounds were studied by ultraviolet, nuclear magnetic resonance, circular dichroism and the 2'-substituted isomers were found to have more stacked structures than the 3'-isomers.

  通过将尿苷、N-苯甲酰胞苷、N-苯甲酰腺苷和N-异丁酰鸟苷分别与邻硝基苯基二氮甲烷处理，然后进行分离和去阻断，合成了尿苷、胞苷、腺苷和鸟苷的2'-和3'-O-(邻硝基苯甲基)衍生物。3'-O-(邻硝基苯甲基)鸟苷是一种新型化合物。通过使用N-酰化核苷，使在硅胶上分离2'-和3'-取代异构体成为可能，这些化合物是合成寡核糖核苷酸的有用中间体。通过紫外线、核磁共振、圆二色性等方法研究了这些化合物的一些物理性质，发现2'-取代异构体比3'-异构体具有更紧密的堆积结构。