2,6-二氟苯甲酰异氰酸酯 | 60731-73-9

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 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: 2,6-二氟苯甲酰异氰酸酯
• 中文别名: 2,6-二氟苯基异氰酸脂；2,6-二氟苯甲酰基异氰酸酯
• 英文名称: 2,6-difluorobenzoyl isocyanate
• CAS: 60731-73-9
• 化学式: C₈H₃F₂NO₂
• 分子量: 183.114
• InChiKey: ZRJSABISRHPRSB-UHFFFAOYSA-N

物化性质

• 熔点：
  140-143.3 °C
• 沸点：
  66 °C (0.2 mmHg)
• 密度：
  1.4723 (estimate)
• 稳定性/保质期：
  本品为油状液体，遇水分解，溶于甲苯、二甲苯等溶剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2929109000
• 储存条件：
  存放于0-6°C阴凉干燥处

SDS

Name:	2 6-Difluorobenzoyl Isocyanate Material Safety Data Sheet
Synonym:	None
CAS:	60731-73-9

Section 1 - Chemical Product MSDS Name:2 6-Difluorobenzoyl Isocyanate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
60731-73-9	2,6-Difluorobenzoyl isocyanate	>80	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.Heat sensitive.
Potential Health Effects
Eye:
Causes eye irritation. Lachrymator (substance which increases the flow of tears).
Skin:
Causes skin irritation. Harmful if absorbed through the skin. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material. Organic isocyanates can cause local irritation and allergic reactions.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May cause liver and kidney damage.
Inhalation:
Causes respiratory tract irritation. Exposure produces central nervous system depression. At high concentrations, isocyanates affect mucous membranes of the respiratory tract and may lead to fatal pulmonary edema. Exposure to low and often even unmeasurable isocyanate concentration results in sensitization. Can produce delayed pulmonary edema. 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: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. 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. Treat symptomatically and supportively.
Antidote: Always have a cyanide antidote kit on hand when working with cyanide compounds. Get medical advice to use.

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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. Dusts at sufficient concentrations can form explosive mixtures with air. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Will react with water to form toxic and corrosive fumes. Contact with water can cause violent liberation of heat and splattering of the material. Contact with metals may evolve flammable hydrogen gas.
Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Do NOT get water inside containers. For large fires, use water spray, fog or alcohol-resistant foam. For small fires, use carbon dioxide, dry chemical, dry sand, or alcohol-resistant foam. Most foams will react with the material and release corrosive/toxic gases. 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:
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 contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse. Discard contaminated shoes.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Deep freeze (below -20C).

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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# 60731-73-9: 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 or liquid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 66 deg C @ .20mm Hg
Freezing/Melting Point: 28.4 deg C (dec)
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 28.4 deg C
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H3F2NO2
Molecular Weight: 183.11

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 60731-73-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,6-Difluorobenzoyl isocyanate - 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: ISOCYANATES, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2206
Packing Group: III
IMO
Shipping Name: ISOCYANATES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 2206
Packing Group: III
RID/ADR
Shipping Name: ISOCYANATES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 2206
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
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 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 60731-73-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 60731-73-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 60731-73-9 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

制备方法与用途

化学性质

本品为油状液体，遇水分解，并能溶解于甲苯、二甲苯等溶剂中。

用途

2,6-二氟苯甲酰基异氰酸酯是合成苯甲酰脲类杀虫剂的重要中间体，可用于制备多种此类杀虫剂品种，包括氟铃脲、除虫脲、氟啶脲、氟虫脲、啶蜱脲、氟酰脲、虱螨脲、氟苯脲和氟螨脲等。

生产方法

2,6-二氟苯甲酰胺与草酰氯反应生成相应的异氰酸酯。具体操作为将2,6-二氟苯甲酰胺及溶剂加入搪瓷反应釜中，搅拌下滴加草酰氯；待定量的草酰氯滴加完毕后，升温脱去溶剂，即可得到2,6-二氟苯甲酰基异氰酸酯。

反应信息

• 作为反应物：
  描述：

  2,6-二氟苯甲酰异氰酸酯 在 potassium carbonate 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 生成 4-(3-(2,6-difluorobenzoyl)ureido)phenyl(4-(trifluoromethyl)phenyl)carbamate
  参考文献：
  名称：

  基于磺酰脲类受体结合位点二分模型的新型含氨基甲酸酯基苯甲酰脲类药物的设计、合成及杀虫评价

  摘要：

  背景：苯甲酰脲类是最常用的几丁质合成抑制剂。但是，苯甲酰脲类杀虫剂的确切靶位点尚未确定。目的：研究是否可以设计合成具有二分体模型的苯甲酰苯基脲类类似物作为活性提高的新型杀虫剂。方法：基于磺酰脲类受体结合位点和商品化除虫脲的二分模型，通过关键中间体2,6-二氟-N-((4-羟苯基)氨甲酰基)苯甲酰胺设计合成了一系列含有氨基甲酸酯基团的新型苯甲酰脲类化合物。 (2). 目标化合物的结构经1H NMR和高分辨率质谱(HRMS)确证。结果：生物测定结果表明，这些目标化合物对东方粘虫 (Mythimna Separata Walker)、小菜蛾 (Plutella xylostella) 和蚊子 (Culex pipiens pallens) 等广谱昆虫具有良好的杀幼虫活性。含有 N,N-二异丙基 (3g) 的化合物对东方粘虫表现出最高的杀虫活性（10 mg kg-1 时为 40%），与除虫脲相当。

  DOI：

  10.2174/1570180819666220512182621
• 作为产物：
  描述：

  1,3-二氟苯 在 硫酸 、 盐酸羟胺 、 氨 、 对甲苯磺酸 、 臭氧 、 sodium amide 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 38.75h， 生成 2,6-二氟苯甲酰异氰酸酯
  参考文献：
  名称：

  Odinokov; Ishmuratov; Kukovinets, Russian Journal of Organic Chemistry, 1998, vol. 34, # 2, p. 202 - 204

  摘要：

  DOI：
• 作为试剂：
  描述：

  N-(4-methylphenylaminothio)phthalimide 、 2,3-二甲基-1,3-丁二烯 在 2,6-二氟苯甲酰异氰酸酯 、 三乙胺 作用下， 生成 2-(p-tolyl)-4,5-dimethyl-3,6-dihydro-2H-1,2-thiazine
  参考文献：
  名称：

  Bryce, Martin R.; Heaton, Julie N.; Taylor, Paul C., Journal of the Chemical Society. Perkin transactions I, 1994, # 14, p. 1935 - 1944

  摘要：

  DOI：

文献信息

• Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide
  作者：Peng Lei、Yan Xu、Juan Du、Xin-Ling Yang、Hui-Zhu Yuan、Gao-Fei Xu、Yun Ling

  DOI：10.1016/j.bmcl.2016.03.085

  日期：2016.5

  excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against

  为了寻找具有高生物活性的新的铅化合物，采用连接活性亚结构法设计了一系列N-取代的苯甲酰基-1,2,3,4-四氢喹啉基-1-羧酰胺。由取代的苯甲酸按四个步骤合成目标化合物，并通过1 H NMR，IR光谱和元素分析确定其结构。体外生物测定结果表明，某些目标化合物表现出优异的杀真菌活性，且取代基的位置在杀真菌活性中起重要作用。特别是，化合物5n对两种测试真菌Valsa mali和Sclerotionia sclerotiorum的杀真菌活性比市售杀真菌剂氟苯尼更好。，其EC 50值分别为3.44和2.63 mg / L。而且它还显示出良好的针对核盘菌的体内杀真菌活性，其EC 50值为29.52 mg / L。
• Convenient One-Pot Two-Step Synthesis of Symmetrical and Unsymmetrical Diacyl Ureas, Acyl Urea/Carbamate/Thiocarbamate Derivatives, and Related Compounds
  作者：Jozef Stec、Anolan Hernandez、Gregory Grooms、Abir El-Alfy

  DOI：10.1055/s-0036-1588724

  日期：——

  chemist’s toolbox. A wide range of chemicals such as amides, hydrazides, amines, alcohols, carbazate, and sulfonate were reacted with acyl isocyanates generated by the reaction of primary amides with oxalyl chloride to give symmetrical and unsymmetrical diacyl urea derivatives, acyl ureas/carbamates/thiocarbamates, and related compounds. This method provides means for convenient one-pot, two-step synthesis

  献给Richard J. Whitby教授 抽象的 使各种化学物质（例如酰胺，酰肼，胺，醇，氨基甲酸酯和磺酸盐）与由伯酰胺与草酰氯反应生成的酰基异氰酸酯反应，生成对称和不对称的二酰基脲衍生物，酰基脲/氨基甲酸酯/硫代氨基甲酸酯，及相关化合物。该方法提供了从廉价的和可商购的起始试剂方便地一锅，两步合成带有脲，氨基甲酸酯和其他官能团的化合物的方法。预期本报告中提出的结果将扩展药物化学家的工具箱。 使各种化学物质（例如酰胺，酰肼，胺，醇，氨基甲酸酯和磺酸盐）与由伯酰胺与草酰氯反应生成的酰基异氰酸酯反应，生成对称和不对称的二酰基脲衍生物，酰基脲/氨基甲酸酯/硫代氨基甲酸酯，及相关化合物。该方法提供了从廉价的和可商购的起始试剂方便地一锅，两步合成带有脲，氨基甲酸酯和其他官能团的化合物的方法。预期本报告中提出的结果将扩展药物化学家的工具箱。
• Accessing Difluoromethylated and Trifluoromethylated <i>cis</i> ‐Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization
  作者：Xue Zhang、Liang Ling、Meiming Luo、Xiaoming Zeng

  DOI：10.1002/anie.201907457

  日期：2019.11.18

  Reported here is a straightforward process in which a cyclic (alkyl)(amino)carbene/Rh catalyst system facilitates the preferential addition of hydrogen to the substitution sites of difluoromethylated and trifluoromethylated arenes and heteroarenes, leading to dearomative reduction. This strategy enables the diastereoselective synthesis of cis-difluoromethylated and cis-trifluoromethylated cycloalkanes

  此处报道的是一种简单的方法，其中环状（烷基）（氨基）卡宾/ Rh催化剂体系有助于将氢优先添加到二氟甲基化和三氟甲基化的芳烃和杂芳烃的取代位上，从而导致脱芳族还原反应。该策略使非对映选择性合成顺式-二氟甲基化和顺式-三氟甲基化的环烷烃和饱和的杂环，甚至允许形成具有定义的赤道取向的二-和三氟甲基的全顺式多-三氟甲基化的环状产物。氘标记研究表明，氢优先攻击平面芳烃的取代位，从而导致脱芳香化作用，可能以异质Rh为反应性物种，
• Synthesis and Bioactivity of N-Benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] Semicarbazide Derivatives
  作者：Zining Cui、Yun Ling、Baoju Li、Yongqiang Li、Changhui Rui、Jingrong Cui、Yanxia Shi、Xinling Yang

  DOI：10.3390/molecules15064267

  日期：——

  novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates

  为了寻找具有良好活性的新型几丁质合成抑制剂（CSIs），选择典型的CSIs类苯甲酰苯脲作为先导化合物，通过将苯甲酰苯脲的脲键转化为氨基脲基团并改变其结构，设计了15种含有呋喃部分的新型衍生物。苯胺部分变成糠酰基。标题化合物由取代苯甲酰异氰酸酯与5-(取代苯基)-2-呋喃酰肼反应合成，结构经IR、1H-NMR、元素分析和单晶X射线衍射分析(化合物E2 ）。生物测定结果表明，标题化合物表现出良好的杀虫活性，尤其是对小菜蛾（Plutella xylostella L.），但杀真菌活性较低。令人鼓舞的是，标题化合物对人早幼粒细胞白血病细胞系（HL-60）具有明显的抗癌活性，部分标题化合物对人肝癌细胞系（Bel-7402）、人胃癌细胞系（BGC-823）也有活性, 和人鼻咽癌细胞系 (KB)。结果表明，先导化合物中的连接对生物活性和光谱很重要。尿素键的修饰是发现新农药和候选药物的有效策略。结果表明，
• Synthesis and Fungicidal Activity of Aryl Carbamic Acid-5-aryl-2-furanmethyl Ester
  作者：Ying Li、Bao-Ju Li、Yun Ling、Hong-Jian Miao、Yan-Xia Shi、Xin-Ling Yang

  DOI：10.1021/jf9043277

  日期：2010.3.10

  Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters

  甲壳素是昆虫表皮和真菌细胞壁的主要结构成分，但在植物和脊椎动物中却不存在，被认为是害虫防治剂的安全和选择性目标。几丁质合成抑制剂（CSIs）众所周知是昆虫生长调节剂（IGR），但在农业中却很少被用作杀真菌剂。为了找到具有良好活性的新型CSI，选择典型的CSI苯甲酰苯基脲作为先导化合物，并通过将苯甲酰基苯基脲的脲键转化为氨基甲酸酯设计了26种新型的芳基氨基甲酸-5-芳基-2-呋喃甲酯。并将苯胺部分变成呋喃甲基。合成了标题化合物，并通过IR，1确认了其结构1 H NMR和元素分析。进行了初步的杀虫和杀真菌生物测定。结果表明，标题化合物对淡色库蚊和小菜蛾没有杀虫作用，但大多数化合物对棒杆菌，黄瓜枯草芽孢杆菌，灰葡萄孢菌和尖孢镰刀菌均表现出良好的杀菌活性。特别是，化合物V-4，V-6，V-7和V-8对四种菌株的活性比商业化杀菌剂更好。形态学结果表明该化合物V-21干扰了C. cassiicola的