3-苯甲酰基吡啶 | 5424-19-1

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-苯甲酰基吡啶
• 中文别名: 苯基-3-吡啶基甲酮；3-苯甲酰吡啶
• 英文名称: 3-Benzoylpyridine
• 英文别名: phenyl(pyridin-3-yl)methanone
• CAS: 5424-19-1
• 化学式: C₁₂H₉NO
• mdl: MFCD00006394
• 分子量: 183.21
• InChiKey: RYMBAPVTUHZCNF-UHFFFAOYSA-N

物化性质

• 熔点：
  36-40 °C(lit.)
• 沸点：
  307 °C(lit.)
• 密度：
  1.1261 (rough estimate)
• 闪点：
  302 °F
• 溶解度：
  溶于甲醇
• LogP：
  1.880
• 稳定性/保质期：

  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 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：
  2933399090
• 危险品运输编号：
  25kgs
• RTECS号：
  OB6401000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温、避光、存放在阴凉干燥处并密封保存。

SDS

Name:	3-Benzoylpyridine 97% Material Safety Data Sheet
Synonym:	Phenyl-3-pyridyl ketone; Ketone, phenyl 3-pyridyl; Methanone, phenyl-3-pyridinyl-; Pyridine, 3-benzoyl-; 3-Pyridyl phenyl keton
CAS:	5424-19-1

Section 1 - Chemical Product MSDS Name:3-Benzoylpyridine 97% Material Safety Data Sheet
Synonym:Phenyl-3-pyridyl ketone; Ketone, phenyl 3-pyridyl; Methanone, phenyl-3-pyridinyl-; Pyridine, 3-benzoyl-; 3-Pyridyl phenyl keton

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5424-19-1	3-Benzoylpyridine	97	226-561-3

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.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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.
Chronic:
No information found.

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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.
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.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. 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. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation.
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# 5424-19-1: 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:
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: Chunks
Color: white to pale yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 307 deg C @ 760.00mmHg
Freezing/Melting Point: 36.00 - 40.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: 150 deg C ( 302.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C12H9NO
Molecular Weight: 183.21

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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, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, chloride fumes.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5424-19-1: OB6401000 LD50/LC50:
Not available.
Carcinogenicity:
3-Benzoylpyridine - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 5424-19-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5424-19-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5424-19-1 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

3-苯甲酰基吡啶是somane解毒剂HGG-12的分解产物。

反应信息

• 作为反应物：
  描述：

  3-苯甲酰基吡啶 在 三氯化铝 、 溴 作用下， 反应 4.0h， 以30%的产率得到3-(3-溴苯甲酰基)吡啶
  参考文献：
  名称：

  与齐美啶有关的吡啶基烯丙基胺的合成及其对神经元单胺摄取的抑制作用。

  摘要：

  抗抑郁药齐美碱[6，（Z）-3-（4-溴苯基）-N，N-二甲基-3-（3-吡啶基）烯丙胺]的类似物是神经元5-羟色胺再摄取的选择性抑制剂，其合成方法如下：为了获得具有顺式构型（相对于吡啶基和烯丙胺）的化合物的几种途径。两种方法利用适当取代的苯甲酰基吡啶作为起始原料。在另外两个途径中，将6中的溴直接置换（CN）或通过相应的硫代衍生物转化为H，Cl，I，Me，SiMe3和SMe。通过UV，1H NMR和镧系元素引起的1H NMR位移确定构型。通过测量小鼠脑切片（体外和体内）中的[3H]去甲肾上腺素和5-羟基[14C]色胺的积累，将这些化合物评估为摄取抑制剂。在顺式系列中，对位取代有利于5-羟基色胺活性，而邻位取代有利于NA活性。对5-羟色胺的体外作用对对位取代基的变化不敏感，而仅用Cl，Br（6）和I观察到明显的体内作用。

  DOI：

  10.1021/jm00144a025
• 作为产物：
  描述：

  3-氟吡啶 在 氧气 、 sodium hydride 作用下， 反应 5.58h， 生成 3-苯甲酰基吡啶
  参考文献：
  名称：

  Ohba, Setsuya; Sakamoto, Takao; Yamanaka, Hiroshi, Heterocycles, 1990, vol. 31, # 7, p. 1301 - 1308

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-苯甲酰基吡啶 、 (5-carboxypentyl)triphenylphosphonium bromide 在 3-苯甲酰基吡啶 作用下， 生成 7-苯基-7-(3-吡啶基)-6-庚烯酸 、 7-phenyl-7-(3-pyridyl)-6-heptenic acid
  参考文献：
  名称：

  J. Med. Chem. 1985, 28, 287-294

  摘要：

  DOI：

文献信息

• General Method for the Suzuki–Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature
  作者：Peng Lei、Guangrong Meng、Yun Ling、Jie An、Steven P. Nolan、Michal Szostak

  DOI：10.1021/acs.orglett.7b03191

  日期：2017.12.15

  temperature Suzuki–Miyaura cross-coupling of commonly encountered primary benzamides is reported. A combination of site-selective N,N-di-Boc-activation (tert-butoxycarbonyl activation) of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd(NHC)(cin)Cl] (NHC = N-heterocyclic carbene; cin = cinnamyl) provides a highly effective route to biaryl ketones from primary

  据报道，室温下，通常遇到的主要苯甲酰胺的Suzuki-Miyaura交叉偶联是一种通用的，高度选择性的方法。酰胺氮的位点选择性N，N -di-Boc活化（叔丁氧基羰基活化）与稳定的空气和水分稳定的，定义明确的和高反应性的[Pd（NHC）（cin）Cl ]（NHC = N-杂环卡宾； cin =肉桂基）提供了一种从伯酰胺高收率制备联芳基酮的高效途径。酰胺酰基交叉偶联首次获得了> 1000的TON。
• Highly enantioselective carbonyl reduction with borane catalyzed by chiral spiroborate esters derived from chiral beta-aminoalcohols
  申请人：Ortiz-Marciales Margarita

  公开号：US20080200672A1

  公开（公告）日：2008-08-21

  Novel spiroborate esters derived from non-recemic 1,2-amino alcohols were examined as chiral catalyst in the borane reduction of acetophenone and other aromatic ketones at room temperature. The optically active alcohols were obtained in excellent chemical yields and up to 99% ee with less than 10% catalyst.

  从非手性1,2-氨基醇衍生的新型螺环硼酸酯作为手性催化剂在室温下用于苯乙酮和其他芳香酮的硼氢化还原反应。光学活性醇以极高的化学产率获得，ee值高达99%，催化剂用量不到10%。
• Heterocyclic substituted isoxazolidines and their use as fungicides
  申请人：Dow Agrosciences LLC

  公开号：US06313147B1

  公开（公告）日：2001-11-06

  Compounds with fungicidal properties having formula X is CH or nitrogen; R is (C1-C12)alkyl, halo(C1-C12)alkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, (C1-C12)alkoxy(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C3-C7)cycloalkyl(C1-C4)alkyl, aralkyl, aryloxy(C1-C4)alkyl or heterocyclic; R1 is aryl, heterocyclic or C(R6R7R8). R2 and R3 are each selected from hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C1-C12)alkoxy, halo(C1-C12)alkoxy, (C3-C7)cycloalkyl, (C3-C7)cycloalkyl(C1-C4)alkyl, aryl, aralkyl, heterocyclic; cyano, and (C1-C4)alkoxycarbonyl; R4 and R5 are each selected from hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C3-C7)cycloalkyl(C1-C4)alkyl, aryl, aryloxy(C1-C4)alkyl, aralkyl, heterocyclic, cyano, and (C1-C4)alkoxycarbonyl such that R4 and R5 are not both hydrogen; R6, R7, and R8 are each selected from hydrogen, (C1-C12)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C1-C12)alkoxy(C1-C12)alkyl, (C3-C7)cycloalkyl, (C3-C7)cycloalkyl(C1-C4)alkyl, aryl, aralkyl, and heterocyclic(C1-C4)alkyl.

  具有杀真菌性质的化合物的化学式为X是CH或氮；R是(C1-C12)烷基，卤代(C1-C12)烷基，(C2-C8)烯基，卤代(C2-C8)烯基，(C2-C8)炔基，卤代(C2-C8)炔基，(C1-C12)烷氧基(C1-C12)烷基，(C3-C7)环烷基，卤代(C3-C7)环烷基，(C3-C7)环烷基(C1-C4)烷基，芳基烷基，芳基氧基(C1-C4)烷基或杂环；R1是芳基，杂环或C(R6R7R8)。R2和R3分别选自氢，(C1-C12)烷基，卤代(C1-C12)烷基，(C1-C12)烷氧基，卤代(C1-C12)烷氧基，(C3-C7)环烷基，(C3-C7)环烷基(C1-C4)烷基，芳基，芳基烷基，杂环；氰基和(C1-C4)烷氧羰基；R4和R5分别选自氢，(C1-C12)烷基，卤代(C1-C12)烷基，(C2-C8)烯基，卤代(C2-C8)烯基，(C2-C8)炔基，卤代(C2-C8)炔基，(C3-C7)环烷基，卤代(C3-C7)环烷基，(C3-C7)环烷基(C1-C4)烷基，芳基，芳基氧基(C1-C4)烷基，芳基烷基，杂环，氰基和(C1-C4)烷氧羰基，使得R4和R5不同时为氢；R6、R7和R8分别选自氢，(C1-C12)烷基，(C2-C8)烯基，(C2-C8)炔基，(C1-C12)烷氧基(C1-C12)烷基，(C3-C7)环烷基，(C3-C7)环烷基(C1-C4)烷基，芳基，芳基烷基和杂环(C1-C4)烷基。
• Palladium-Catalyzed Synthesis of Diaryl Ketones from Aldehydes and (Hetero)Aryl Halides via C–H Bond Activation
  作者：Takayuki Wakaki、Takaya Togo、Daisuke Yoshidome、Yoichiro Kuninobu、Motomu Kanai

  DOI：10.1021/acscatal.8b00440

  日期：2018.4.6

  We developed a palladium-catalyzed C–H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support

  我们开发了钯催化的CH转化，可从醛和（杂）芳基卤化物合成酮。吡啶甲酰胺配体的使用是实现转化的关键。使用该反应，即使以克为单位，杂芳基酮以及二芳基酮也以良好至优异的产率合成。密度泛函理论（DFT）计算的结果支持C–H键激活途径。
• FLUOROALKYLATING AGENT
  申请人：IHARA CHEMICAL INDUSTRY CO., LTD.

  公开号：US20170197920A1

  公开（公告）日：2017-07-13

  Problem to be Solved It is intended to provide an industrially preferable fluoroalkylating agent and use thereof. Solution The present invention provides a fluoroalkylating agent represented by the general formula (1) wherein R 1 is a C1 to C8 fluoroalkyl group; R 2 and R 3 are each independently a C1 to C12 alkyl group or the like; Y 1 to Y 4 are each independently a hydrogen atom, a halogen atom, or the like; and X − is a monovalent anion. A compound of the general formula (3): R 4 —S—R 1 having an introduced C1 to C8 fluoroalkyl group is easily obtained by reacting a compound of the general formula (2): R 4 —S—Z wherein R 4 is a hydrocarbon group or the like; and Z is a leaving group, with the compound of the general formula (1).

  要解决的问题 旨在提供一种工业上可取的氟烷基化剂及其使用方法。 解决方案 本发明提供了一种由通式（1）表示的氟烷基化剂，其中R 1 是C1到C8的氟烷基团；R 2 和R 3 分别独立地是C1到C12的烷基团或类似物；Y 1 到Y 4 分别独立地是氢原子、卤素原子或类似物；X − 是一价阴离子。 通式（3）的化合物：R 4 —S—R 1 ，其中引入了C1到C8的氟烷基团，可通过将通式（2）的化合物：R 4 —S—Z（其中R 4 是烃基团或类似物；Z是离去基团）与通式（1）的化合物反应而轻松获得。

表征谱图