2-硝基-Alpha,Alpha,Alpha-三氟甲苯 | 384-22-5

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟甲苯系列
• 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-硝基-Alpha,Alpha,Alpha-三氟甲苯
• 中文别名: 邻硝基三氟甲苯；2-硝基三氟甲基苯；2-硝基三氟甲苯；邻三氟甲基硝基苯
• 英文名称: 2-nitrobenzotrifluoride
• 英文别名: 1-nitro-2-(trifluoromethyl)benzene；2-(trifluoromethyl)nitrobenzene；o-nitro(trifluoro)toluene；2-Nitro-α,α,α-trifluorotoluene
• CAS: 384-22-5
• 化学式: C₇H₄F₃NO₂
• mdl: MFCD00007145
• 分子量: 191.109
• InChiKey: NDZJSUCUYPZXPR-UHFFFAOYSA-N

物化性质

• 熔点：
  32°C
• 沸点：
  216°C
• 密度：
  1.3910 (estimate)
• 闪点：
  95°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  2-nitro-alpha,alpha,alpha-trifluorotoluene appears as yellow crystals. Insoluble in water. (NTP, 1992)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  5

ADMET

毒理性

• 副作用

高铁血红蛋白血症 - 血液中高铁血红蛋白含量增加；该化合物被归类为次要毒性效应。

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn,Xi,T
• 安全说明：
  S24/25,S26,S36/37/39
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2904909090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 2306

SDS

Name:	2-Nitro-alpha alpha alpha-trifluoro- toluene 99% Material Safety Data Sheet
Synonym:	2-Nitrobenzotrifluorid
CAS:	384-22-5

Section 1 - Chemical Product MSDS Name:2-Nitro-alpha alpha alpha-trifluoro- toluene 99% Material Safety Data Sheet
Synonym:2-Nitrobenzotrifluorid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
384-22-5	2-Nitro-_,_,_-trifluorotoluene, 99%		206-855-8

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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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.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
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.
Notes to Physician:

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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:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up, then place into a suitable container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Not available.
Storage:
Not available.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 384-22-5: United States OSHA: 2.5 mg/m3 TWA (as F) (listed under Fluorides Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 104.0 - 105.0 deg C @ 20.00mm
Freezing/Melting Point: 31.00 - 32.00 deg C
Autoignition Temperature: Not available.
Flash Point: 95 deg C ( 203.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H4F3NO2
Molecular Weight: 191.11

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Strong oxidizing agents - strong bases - strong reducing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 384-22-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Nitro-_,_,_-trifluorotoluene, 99% - 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: NITROBENZOTRIFLUORIDES
Hazard Class: 6.1
UN Number: 2306
Packing Group: II
IMO
Shipping Name: NITROBENZOTRIFLUORIDES, LIQUID or SOLID
Hazard Class: 6.1
UN Number: 2306
Packing Group: II
RID/ADR
Shipping Name: NITROBENZOTRIFLUORIDES
Hazard Class: 6.1
UN Number: 2306
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
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# 384-22-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 384-22-5 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 384-22-5 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：

  2-硝基-Alpha,Alpha,Alpha-三氟甲苯 在 氨 、 sodium amide 作用下， 生成 2-硝基苯甲腈
  参考文献：
  名称：

  Studies on organic fluorine compounds. XVII. Reaction of benzotrifluoride derivatives with sodium amide.

  摘要：

  苯并三氟甲基化合物的钠胺反应被研究。邻硝基和对氨基苯并三氟甲基化合物分别生成了相应的苯甲腈。间硝基苯并三氟甲基化合物生成了3,3'-双（三氟甲基）偶氮苯和对间-双（三氟甲基）苯并[c]-喹啉5-氧化物。对硝基苯并三氟甲基化合物生成了对硝基苯甲腈、2,2'-二硝基-5,5'-双（三氟甲基）联苯和4,4'-二氰基偶氮苯。针对每种产物，提出了反应机理。

  DOI：

  10.1248/cpb.23.636
• 作为产物：
  描述：

  [Ru(η⁵-1-nitro-2-trifluoromethylcyclohexadienyl)(η⁵-cyclopentadiene)] 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氘代乙腈 为溶剂， 反应 24.0h， 以100%的产率得到2-硝基-Alpha,Alpha,Alpha-三氟甲苯
  参考文献：
  名称：

  电子缺陷芳烃的亲核三氟甲基化

  摘要：

  提出了芳烃的新型三氟甲基化，其在温和的反应条件下进行，并且具有用于药物和农用化学品的后期功能化的潜力。该新反应允许通过C‒H活化途径将硝基芳烃区域选择性地转化为1,2-三氟甲基化的硝基芳烃。此外，还提出了硝基芳烃向三氟甲基芳烃的取代。

  DOI：

  10.1039/c7cc05415g
• 作为试剂：
  描述：

  一氧化碳 、 正丁胺 在 selenium 2-硝基-Alpha,Alpha,Alpha-三氟甲苯 作用下， 以 邻二氯苯 为溶剂， 78.0 ℃ 、101.32 kPa 条件下， 生成 N,N-二正丁基尿素
  参考文献：
  名称：

  Manov-Yuvenskii, V. I., Russian Journal of Physical Chemistry, 1995, vol. 69, # 5, p. 715 - 720

  摘要：

  DOI：

文献信息

• [EN] ANTHELMINTIC AGENTS AND THEIR USE<br/>[FR] AGENTS ANTHELMINTIQUES ET LEUR UTILISATION
  申请人：INTERVET INT BV

  公开号：WO2010115688A1

  公开（公告）日：2010-10-14

  This invention is directed to compounds and salts that are generally useful as anthelmintic agents or as intermediates in processes for making anthelmintic agents. This invention also is directed to processes for making the compounds and salts, pharmaceutical compositions and kits comprising the compounds and salts, uses of the compounds and salts to make medicaments, and treatments comprising the administration of the compounds and salts to animals in need of the treatments.

  这项发明涉及一般用作驱虫剂或作为制备驱虫剂的中间体的化合物和盐。这项发明还涉及制备这些化合物和盐的方法，包括这些化合物和盐的药物组合物和试剂盒，使用这些化合物和盐制备药物，以及将这些化合物和盐用于需要治疗的动物的治疗方法。
• 一种取代硝基苯类化合物的制备方法
  申请人：联化科技股份有限公司

  公开号：CN109467509B

  公开（公告）日：2021-09-24

  本发明公开了一种取代硝基苯类化合物的制备方法。该方法包括下述步骤：溶剂中，在150℃～250℃的温度下，化合物II在碱的作用下进行如下所示的脱羧反应得到化合物I即可；所述的碱为碱金属的碳酸盐和碳酸氢盐中的一种或多种。该方法相比一些使用金属催化的脱羧方法，具有操作简单、生产成本低、后处理方便、收率高的优点，在工业化生产中更具有应用价值。
• Specific ortho orientation in the vicarious substitution of hydrogen in aromatic nitro compounds with carbanion of chloromethyl phenyl sulfone
  作者：M. Makosza、T. Glinka、A. Kinowski

  DOI：10.1016/s0040-4020(01)91141-x

  日期：1984.1

  Vicarious nucleophilic substitution of hydrogen atoms in nitroarenes with chloromethylphenyl sulfone proceeds selectively ortho to the nitro group when carried out in t-BuOK/THF base/solvent system. In the majority of 3-substituted nitrobenzene derivatives substitution occurs at the most hindered position 2. These conditions offer an efficient method of synthesis of 2,6 and 2,3-disubstituted nitrobenzene

  当在t-BuOK / THF碱/溶剂系统中进行硝基苯芳烃中的氢原子的替代亲核取代时，氯甲基苯基砜选择性地在硝基附近进行。在大多数3-取代的硝基苯衍生物中，大多数取代发生在受阻最大的位置2。这些条件提供了合成2,6和2,3-二取代的硝基苯衍生物的有效方法。
• Trifluoromethylation of Aryl and Heteroaryl Halides with Fluoroform-Derived CuCF₃: Scope, Limitations, and Mechanistic Features
  作者：Anton Lishchynskyi、Maxim A. Novikov、Eddy Martin、Eduardo C. Escudero-Adán、Petr Novák、Vladimir V. Grushin

  DOI：10.1021/jo401423h

  日期：2013.11.15

  destabilized by CuX coproduced in the reaction, the magnitude of the effect paralleling the Lewis acidity of CuX: CuCl > CuBr > CuI. While SNAr and SRN1 mechanisms are not operational, there is a well-pronounced ortho effect, i.e., the enhanced reactivity of ortho-substituted aryl halides 2-RC6H4X toward CuCF3. Intriguingly, this ortho-effect is observed for R = NO2, COOH, CHO, COOEt, COCH3, OCH3, and even

  最近在我们小组中发现的源自氟仿的CuCF 3对芳基和杂芳基卤化物表现出极高的反应活性，在没有额外配体的情况下表现最佳。各种各样的碘代芳烃在23–50°C下与“无配体” CuCF 3进行平滑的三氟甲基化反应，以几乎定量的产率得到相应的苯并三氟化物。许多低反应性的芳族溴化物也已被三氟甲基化，包括吡啶，嘧啶，吡嗪和噻唑衍生物以及带有吸电子基团和/或邻位取代基的芳基溴化物。只有最亲电子的氯代芳烃可以被三氟甲基化，例如2-氯烟酸。反应具有极高的化学选择性（没有芳烃，联芳基和C的侧链形成）2 F 5衍生物）可以以克级（最高20 mmol）高产率分离出大量的三氟甲基化产物。反应中共同产生的CuX使CuCF 3试剂不稳定，其影响程度与CuX的路易斯酸度平行：CuCl> CuBr> CuI。尽管S N Ar和S RN 1机制不起作用，但存在明显的邻位效应，即邻位取代的芳基卤化物2-RC 6 H 4 X对CuCF
• Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use
  申请人：Tegley Christopher

  公开号：US20050054670A1

  公开（公告）日：2005-03-10

  Selected compounds are effective for prophylaxis and treatment of diseases, such as angiogenesis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  所选化合物对于预防和治疗疾病，如介导血管生成的疾病，具有有效性。该发明涵盖了新颖的化合物、类似物、前药及其药用可接受的盐，用于预防和治疗涉及癌症等疾病和其他疾病或病况的药物组合物和方法。该发明还涉及制备此类化合物的方法，以及在此类方法中有用的中间体。

表征谱图