4-硝基硫氰酸苄酯 | 13287-49-5

• 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-硝基硫氰酸苄酯
• 中文别名: 4-硝基苄基硫氰酸酯
• 英文名称: 4-Nitro-benzylthiocyanat
• 英文别名: 4-nitrobenzyl thiocyanate；p-nitrobenzyl thiocyanate；(4-nitrophenyl)methyl thiocyanate
• CAS: 13287-49-5
• 化学式: C₈H₆N₂O₂S
• mdl: MFCD00024784
• 分子量: 194.214
• InChiKey: NUMYTLIHYKESKM-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S36/37
• 危险类别码：
  R20/22,R32
• 海关编码：
  2930909090
• 危险品运输编号：
  UN 2811

SDS

Name:	4-Nitro-Benzylthiocyanate 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	13287-49-5

Section 1 - Chemical Product MSDS Name:4-Nitro-Benzylthiocyanate 99% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13287-49-5	4-Nitro-Benzylthiocyanate	99	236-299-1

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. May cause conjunctivitis, ulceration and turbidity of the cornea.
Skin:
May cause skin irritation. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material.
Ingestion:
May cause irritation of the digestive tract. May cause liver and kidney damage. 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. Exposure produces central nervous system depression. In rare instances, exposure may cause sensitization, resulting in inflammation of the mucous membranes and in eczematous eruptions.
Chronic:
May cause liver and kidney damage. Effects may be delayed. May cause lung damage. Repeated or prolonged exposure may cause allergic reactions in sensitive individuals. Inhalation of product may aggravate existing chronic repiratory problems such as asthma, emphysema or bronchitis.

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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. Do NOT allow victim to rub eyes or keep eyes closed.
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:
For ingestion, the stomach sould be intubated, aspirated, and lavaged with a slurry of activated charcoal--protect the airway from aspiration of gastric contents.

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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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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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. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Discard contaminated shoes.
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# 13287-49-5: Personal Protective Equipment Eyes: Wear chemical splash goggles. 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 minimize contact with skin.
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: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 84.00 - 86.00 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: C8H6N2O2S
Molecular Weight: 194.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrocarbons.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13287-49-5: XL1615000 LD50/LC50:
Not available.
Carcinogenicity:
4-Nitro-Benzylthiocyanate - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 13287-49-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13287-49-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13287-49-5 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：

  4-硝基硫氰酸苄酯 在 偶氮二异丁腈 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以32%的产率得到4-硝基甲苯
  参考文献：
  名称：

  Bowman, W. Russell; Crosby, David; Westlake, Paul J., Journal of the Chemical Society. Perkin transactions II, 1991, # 1, p. 73 - 80

  摘要：

  DOI：
• 作为产物：
  描述：

  硫氰酸苄酯 生成 4-硝基硫氰酸苄酯
  参考文献：
  名称：

  Henry, Chemische Berichte, 1869, vol. 2, p. 637

  摘要：

  DOI：

文献信息

• 2-Chloro-1-methylpyridinium iodide, an efficient reagent for the conversion of alcohols into alkyl thiocyanates both under solvent and solvent-free conditions
  作者：Babak Mokhtari、Roya Azadi、Edris Mardani

  DOI：10.1016/j.tetlet.2011.11.050

  日期：2012.2

  reagent for the simple phosphine-free conversion of alcohols into the corresponding alkyl thiocyanates is described. This transformation can be achieved either in acetonitrile or under solvent-free conditions and the products obtained in good to excellent yields. The solvent-free procedure described here is the first report on the solvent-free thiocyanation of alcohols.

  描述了Mukaiyama试剂在将醇简单地无膦转化为相应的烷基硫氰酸酯中的新应用。该转化可以在乙腈中或在无溶剂条件下完成，所获得的产物收率良好至优异。本文所述的无溶剂程序是有关醇类无溶剂硫氰化的首次报道。
• β-Cyclodextrin Immobilized onto Dowex Resin: A Unique Microvessel and Heterogeneous Catalyst in Nucleophilic Substitution Reactions
  作者：Ali Reza Kiasat、Nasrollah Zarinderakht、Soheil Sayyahi

  DOI：10.1002/cjoc.201280003

  日期：2012.3

  The catalytic activity of β‐cyclodextrin immobilized on Dowex resin as an efficient solid‐liquid phase transfer catalyst was developed for the synthesis of alkyl thiocyanates and phenacyl derivatives in water. The nucleophilic substitution reactions were performed under mild reaction condition and gave the products in excellent yields. Furthermore, the catalyst could be recycled by facile separation

  固定在Dowex树脂上的β-环糊精作为一种有效的固液相转移催化剂，具有催化活性，可用于在水中合成烷基硫氰酸酯和苯甲酰基衍生物。亲核取代反应在温和的反应条件下进行，并以优异的产率获得了产物。此外，可以通过容易的分离来回收催化剂，而不会损失任何活性。
• A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers
  作者：Nasser Iranpoor、Habib Firouzabadi、Roya Azadi

  DOI：10.1016/j.tetlet.2006.05.145

  日期：2006.7

  A new diphenylphosphinite ionic liquid (IL-OPPh2) is introduced. This ionic liquid is used as both a reagent and a solvent to convert alcohols and trimethylsilyl and tetrahydropyranyl (THP) ethers into their corresponding alkyl bromides, thiocyanates or isothiocyanates in the presence of Br2 and SCN− at 80 °C. In this ionic liquid, bromination and thiocyanation of alcohols occurs highly selectively

  介绍了一种新型的二苯基次膦酸酯离子液体（IL-OPPh 2）。这种离子液体用作两者的试剂和转换醇和三甲基甲硅烷和四氢吡喃基（THP）溶剂醚类为它们相应的烷基溴化物，硫氰酸盐或异硫氰酸盐在溴的存在下2和SCN -在80℃下。在这种离子液体中，在三甲基甲硅烷基和THP-醚的存在下以及在不同类别的醇之间，醇的溴化和硫氰化反应会高度选择性地发生。该离子液体的使用使得所需的产物易于从次膦酸酯副产物中分离出来。
• Tetrazole regioisomers in the development of nitro group-containing antitubercular agents
  作者：Galina Karabanovich、Jaroslav Roh、Ondřej Soukup、Ivona Pávková、Markéta Pasdiorová、Vojtěch Tambor、Jiřina Stolaříková、Marcela Vejsová、Kateřina Vávrová、Věra Klimešová、Alexandr Hrabálek

  DOI：10.1039/c4md00301b

  日期：——

  Tetrazole derivatives containing nitro substituents have been identified as promising antitubercular agents. In this study, the antitubercular potency, selectivity and toxicity of tetrazole 1,5- and 2,5-regioisomers were examined. We prepared a series of 1- and 2-alkyl-5-benzylsulfanyl-2H-tetrazoles and their selenium analogs with various nitro group substitutions. These 1,5- and 2,5-regioisomers were

  含有硝基取代基的四唑衍生物已被确认为有希望的抗结核药。在这项研究中，抗结核药的抗结核效力，选择性和毒性四唑检查了1，5-和2，5-区域异构体。我们制备了一系列的1-和2-烷基-5-苄基硫烷基-2 H-四唑及其衍生物硒具有各种硝基取代基的类似物。分离并使用1 H和/或13 C NMR明确鉴定这些1,5-和2,5-区域异构体。在制备的化合物中，1-和2-烷基-5-[（3,5-二硝基苄基）硫烷基] -2 H-四唑衍生物及其衍生物硒生物甾体显示出最高的抗分枝杆菌活性，对结核分枝杆菌CNCTC My 331/88的最小抑制浓度（MIC）值约为1μM（0.37–0.46μgmL -1）。与1-烷基异构体相比，2-烷基区域异构体始终表现出较高的抗分枝杆菌活性和对哺乳动物细胞系的体外毒性。与1-烷基异构体相反，2-烷基区域异构体的抗分枝杆菌活性受烷基取代基类型的影响较小。此外，3,5-二硝基苄基部分本身不
• Potent anti-proliferative activities of organochalcogenocyanates towards breast cancer
  作者：Kaustav Banerjee、Ganesan Padmavathi、Debojit Bhattacherjee、Suchismita Saha、Ajaikumar B. Kunnumakkara、Krishna P. Bhabak

  DOI：10.1039/c8ob01891j

  日期：——

  The synthesis of benzylic and mesitylenic organochalcogenocyanates has been described and the compounds have been studied for their anti-proliferative activities in breast cancer cells (MDA-MB-231, MCF-7 and T-47D).

  苯基和间甲苯基有机硫、硒、碲氰酸盐的合成已经被描述，并且这些化合物已经被研究其在乳腺癌细胞（MDA-MB-231、MCF-7和T-47D）中的抗增殖活性。

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