2,6-二氟二苯甲酮 | 59189-51-4

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酮
• 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: 2,6-二氟二苯甲酮
• 中文别名: 2,6-二氟苯甲酮
• 英文名称: 2,6-difluorobenzophenone
• 英文别名: (2,6-difluorophenyl)(phenyl)methanone；(2,6-difluorophenyl)-phenylmethanone
• CAS: 59189-51-4
• 化学式: C₁₃H₈F₂O
• 分子量: 218.203
• InChiKey: KTRGJHDNHIPMEY-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C (2 mmHg)
• 密度：
  1.244 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  避免接触氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2914700090

SDS

Name:	2 6-Difluorobenzophenone 97% Material Safety Data Sheet
Synonym:
CAS:	59189-51-4

Section 1 - Chemical Product MSDS Name:2 6-Difluorobenzophenone 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
59189-51-4	2,6-Difluorobenzophenone	97%	261-650-0

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. 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.
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.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 59189-51-4: Personal Protective Equipment Eyes: Not available.
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: Clear liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 120 deg C @2mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.244
Molecular Formula: C13H8F2O
Molecular Weight: 218.2

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 59189-51-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,6-Difluorobenzophenone - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
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# 59189-51-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 59189-51-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 59189-51-4 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：

  2,6-二氟二苯甲酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到(2,6-difluorophenyl)(phenyl)methanol
  参考文献：
  名称：

  EP1437344

  摘要：

  公开号：
• 作为产物：
  描述：

  2,6-二氟苯腈 、 苯磺酰肼 在 2,2'-联喹啉 、 水 、 palladium diacetate 作用下， 以 二甲基亚砜 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以77%的产率得到2,6-二氟二苯甲酮
  参考文献：
  名称：

  Pd（II）催化的腈磺酰肼与腈的脱氮和脱硫反应

  摘要：

  在温和的条件下，已成功实现了Pd（II）催化的芳基磺酰肼与腈的脱氮和脱硫加成反应。这种转变是一种新的方法，用于将芳基磺酰肼作为芳基化剂与腈加成反应，从而提供了芳基酮的另一种合成方法。报道的加成反应耐受许多常见的官能团，并且在给电子和吸电子取代基的存在下很好地起作用。值得注意的是，据报道的脱氮和脱硫方法也适用于烷基腈，这使得这种新开发的转化方法具有吸引力。

  DOI：

  10.1021/acs.joc.8b00211

文献信息

• [EN] BICYCLIC HETEROCYCLE DERIVATIVES AND USE THEREOF AS GPR119 MODULATORS<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES BICYCLIQUES ET LEUR UTILISATION EN TANT QUE MODULATEURS DE GPR119
  申请人：SCHERING CORP

  公开号：WO2009143049A1

  公开（公告）日：2009-11-26

  The present invention relates to Bicyclic Heterocycle Derivatives of formula (I), compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of GPR1 19 in a patient.

  本发明涉及公式（I）的双环杂环衍生物，包含双环杂环衍生物的组合物，以及使用双环杂环衍生物治疗或预防患者的肥胖、糖尿病、代谢紊乱、心血管疾病或与GPR119活性相关的疾病的方法。
• Palladium(II)-catalyzed addition of arylboronic acid to nitriles
  作者：Baowei Zhao、Xiyan Lu

  DOI：10.1016/j.tetlet.2006.07.074

  日期：2006.9

  The addition of arylboronic acid to nitriles catalyzed by palladium(II) species in the presence of bipyridine as the ligand was developed. The use of bipyridine is crucial for changing the properties of arylpalladium species from more electrophilic to more nucleophilic making the reaction possible.

  开发了在联吡啶作为配体存在下，钯（II）催化的芳基硼酸加成腈。联吡啶的使用对于将芳族钯物种的性质从更亲电变为更亲核至关重要，从而使反应成为可能。
• Catalytic Enantioselective Borohydride Reduction of <i>Ortho</i>-Fluorinated Benzophenones
  作者：Ai Kokura、Saiko Tanaka、Taketo Ikeno、Tohru Yamada

  DOI：10.1021/ol060927p

  日期：2006.7.1

  [reaction: see text] In the presence of the optically active ketoiminatocobalt(II) complexes, the enantioselective borohydride reduction of benzophenones was successfully completed. The fluorine atom on the ortho position of the benzophenone and aryl ketones proved effective for obtaining high enantioselectivities. The combined use of modified lithium borohydride afforded the corresponding benzhydrols

  [反应：见正文]在光学活性酮亚胺钴（II）配合物的存在下，对苯甲酮的对映选择性硼氢化物还原成功完成。二苯甲酮和芳基酮邻位的氟原子被证明对获得高对映选择性是有效的。改性硼氢化锂的组合使用以高收率和高对映选择性（88-96％ee）提供了相应的苯甲醇和芳基甲醇。
• Steric and Electronic Effects Influencing β-Aryl Elimination in the Pd-catalyzed Carbon–Carbon Single Bond Activation of Triarylmethanols
  作者：James R. Bour、Jacob C. Green、Valerie J. Winton、Jeffrey B. Johnson

  DOI：10.1021/jo302592g

  日期：2013.2.15

  An analysis of the palladium-catalyzed activation of carbon–carbon single bonds within triarylmethanols has led to a greater understanding of factors influencing the β-aryl elimination process responsible for C–C bond cleavage. A series of competition reactions were utilized to determine that β-aryl elimination of aryl substituents containing ortho-substitution proceeds with significant preference

  对钯催化的三芳基甲醇中碳-碳单键活化的分析，导致人们对影响影响C-C键断裂的β-芳基消除过程的因素有了更深入的了解。利用一系列竞争反应来确定β-芳基消除含有邻位取代基的芳基取代基比未取代的苯环显着地优先进行。进一步的实验表明，与相对中性的物质相比，含有强供体或撤离取代基的底物更容易从三芳基甲醇中裂解出来。
• Biradicals from Benzoenyne−Allenes. Application in the Synthesis of 11<i>H</i>-Benzo[<i>b</i>]fluoren-11-ols, 1<i>H</i>-Cyclobut[<i>a</i>]indenes, and Related Compounds
  作者：Hongbin Li、Hai-Ren Zhang、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1021/jo0104577

  日期：2001.10.1

  New synthetic pathways to 11H-benzo[b]fluoren-11-ols, 1H-cyclobut[a]indenes, and related compounds via biradicals generated from benzoenyne-allenes were developed. Treatment of the diacetylenic propargylic alcohols 13, derived from condensation between benzophenones and the lithium acetylide of 1-(2-ethynylphenyl)-2-phenylethyne, with thionyl chloride produced the 11-chloro-11H-benzo[b]fluorene 14

  开发了通过苯并炔-丙二烯生成的双自由基合成11H-苯并[b]芴-11-醇，1H-环丁[a]茚和相关化合物的新途径。用亚硫酰氯处理二苯甲酮与1-（2-乙炔基苯基）-2-苯基乙炔的乙炔化锂之间的缩合反应得到的二炔炔丙醇13，生成11-氯-11H-苯并[b]芴14，然后水解，相应的11H-苯并[b]芴11醇15。转化涉及一系列反应，包括先生成双自由基的C2-C6环化反应（Schmittel环化反应），然后再进行分子内氯化自由基-自由基偶联形成正式的Diels-Alder加合物。有趣的是，在二炔炔炔丙醇26的情况下，由二苯并异戊二烯酮（25）获得，发生了氯化苯二炔-丙二烯中间体的分子内[2 + 2]环加成反应，仅提供了1H-环丁[a]茚烯27。反应路径的剧烈变化可归因于空间应变的出现，这是由于与氯取代基的无键相互作用沿着形成正式Diels-Alder加合物31的路径发生的。另一方面，未氯化的苯并炔