1-苯基吡咯烷 | 4096-21-3

• 物质功能分类: 香精与香料 - 合成香料 - 内酯和含氧杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-苯基吡咯烷
• 中文别名: 1-苯基吡咯啉；N-苯基四氢吡咯
• 英文名称: N-phenylpyrrolidine
• 英文别名: 1-phenylpyrrolidine；N-phenylpyrolidine；N-phenyltetrahydropyrrole；NPP
• CAS: 4096-21-3
• 化学式: C₁₀H₁₃N
• mdl: MFCD00015897
• 分子量: 147.22
• InChiKey: VDQQJMHXZCMNMU-UHFFFAOYSA-N

物化性质

• 熔点：
  11°C
• 沸点：
  133-134°C 19mm
• 密度：
  1.0180
• 闪点：
  133-134°C/19mm
• 稳定性/保质期：
  在常温常压下，这是一种稳定的油状液体。它的沸点为119-120℃（1.6kPa）和81℃（0.06kPa）。相对密度为1.0260（25/4℃），折光率为1.5813，并且可以溶于乙醚。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S28,S36/37
• 危险类别码：
  R21/22
• 危险品运输编号：
  2810
• 海关编码：
  2933990090
• 包装等级：
  III
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H312
• 储存条件：
  请将产品存放在避光、通风干燥的地方，并密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Phenylpyrrolidine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H311: Toxic in contact with skin
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P361: Remove/Take off immediately all contaminated clothing
P312: Call a POISON CENTER or doctor/physician if you feel unwell
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 1-Phenylpyrrolidine
CAS number: 4096-21-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H13N
Molecular weight: 147.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：

• 呈油状液体。
• 沸点在1.6 kPa时为119-120℃，而在0.06 kPa时为81℃。
• 相对密度为1.0260（25/4℃）。
• 折光率为1.5813。
• 溶于乙醚。

用途： 该物质是驱肠虫药驱晓净的中间体。

生产方法： 由1,4-二溴丁烷与苯胺环合而得。具体步骤如下：将碳酸钠配制成水溶液，加入二溴丁烷和苯胺。搅拌并加热至90℃，保温反应6小时后冷却静置分层，取油层用水洗至pH为7，再用无水硫酸钠脱除水分即得N-苯基吡咯烷。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  1-(4-碘苯基)吡咯烷	1-(4-iodophenyl)pyrrolidine	87350-76-3	C10H12IN	273.116
  ——	1-(4-fluorophenyl)pyrrolidine	4280-34-6	C10H12FN	165.21
  1-(3-氟苯基)吡咯烷	1-(3-fluorophenyl)pyrrolidine	139909-17-4	C10H12FN	165.21
  ——	N-4-Chlorbutylanilin	42330-98-3	C10H14ClN	183.681
  ——	4-(phenylamino)butan-1-ol	6517-80-2	C10H15NO	165.235
  N,N-双(2-溴乙基)苯胺	N,N-bis(2-bromoethyl)aniline	2045-19-4	C10H13Br2N	307.028
  N,N-二烯丙苯胺	N,N-diallylaniline	6247-00-3	C12H15N	173.258
  1-苯基-2-吡咯烷酮	1-phenylpyrrolidin-2-one	4641-57-0	C10H11NO	161.203
  1-(2-氟苯基)吡咯烷	1-(2-fluorophenyl)pyrrolidine	758691-88-2	C10H12FN	165.21
  ——	N-(3-butenyl)aniline	29369-71-9	C10H13N	147.22
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1-(4-碘苯基)吡咯烷	1-(4-iodophenyl)pyrrolidine	87350-76-3	C10H12IN	273.116
  N-对溴苯吡咯烷	1-(4-bromo-phenyl)-pyrrolidine	22090-26-2	C10H12BrN	226.116
  4-吡咯烷苯硫酚	4-Pyrrolidinothiophenol	106365-88-2	C10H13NS	179.286
  ——	1-(4-nitrosophenyl)pyrrolidine	52695-15-5	C10H12N2O	176.218
  4-(1-吡咯啉基)苯甲醛	4-(pyrrolidin-1-yl)benzaldehyde	51980-54-2	C11H13NO	175.23
  ——	1-(4-isothiocyanatophenyl)pyrrolidine	51317-64-7	C11H12N2S	204.296
  ——	N-butyl-N-phenylformamide	35082-00-9	C11H15NO	177.246
  ——	4,4'-di(pyrrolidin-1-yl)-1,1'-biphenyl	959276-94-9	C20H24N2	292.424
  ——	1-([1,1'-biphenyl]-4-yl)pyrrolidine	265991-28-4	C16H17N	223.318
  1-[4-[(4-吡咯烷-1-基苯基)甲基]苯基]吡咯烷	Bis(4-pyrrolidinophenyl)methane	53926-61-7	C21H26N2	306.451

反应信息

• 作为反应物：
  描述：

  1-苯基吡咯烷 在 盐酸 、 sodium nitrite 作用下， 生成 1-(4-nitrosophenyl)pyrrolidine
  参考文献：
  名称：

  Reppe et al., Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,145

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯基-4-甲氧基苯甲酰胺 在 三(乙酰丙酮酸)钌(III) 、 ytterbium(III) triflate hydrate 、 氢气 、 1,1,1-三(二苯基膦甲基)乙烷 作用下， 以 四氢呋喃 为溶剂， 150.0 ℃ 、500.01 kPa 条件下， 反应 30.0h， 生成 1-苯基吡咯烷
  参考文献：
  名称：

  实现仲酰胺和叔酰胺向胺的一般钌催化氢化†

  摘要：

  使用 [Ru(acac) 3 ]、1,1,1-三(二苯基膦甲基)乙烷 (Triphos) 和 Yb组合生成的原位催化剂，在温和条件下将多种仲酰胺和叔酰胺氢化成相应的胺（OTf）3。与之前的报道相比，金属三氟甲磺酸盐的存在可以减轻反应条件，从而提高所需胺的产率和选择性。两次放大实验的优异分离产率证实了反应方案的可行性。对照实验表明，在酰胺羰基最初还原后，反应通过醇与中间体半缩醛胺塌陷产生的胺进行还原胺化来进行。

  DOI：

  10.1039/c5sc04671h
• 作为试剂：
  描述：

  3-甲基二苯胺 、 三(4-碘苯)胺 在 copper(I) bromide 氢氧化钾 、 1-苯基吡咯烷 作用下， 以 萜品油烯 为溶剂， 反应 6.0h， 以84.7%的产率得到4,4',4''-三(N-3-甲基苯基-N-苯基氨基)三苯胺
  参考文献：
  名称：

  JP2005/350416

  摘要：

  公开号：

文献信息

• Dye–polyoxometalate coordination polymer as a photo-driven electron pump for photocatalytic radical coupling reactions
  作者：Zheng Ming、Tiexin Zhang、Wenming Tian、Jianing Li、Zhenhui Liu、Renhai Liu、Zhongmin Liu、Chunying Duan

  DOI：10.1039/d1cc04209b

  日期：——

  To alleviate diffusion-limited photoinduced electron transfer (PET) in solution, a triphenylamine-derived dye and a Keggin polyoxometalate-type electron relay were coupled into a coordination polymer to photoinduce long-lived charge-separation pairs with enough reductive/oxidative potential to pump multiple electrons unidirectionally from external electron donors to acceptors, thus furnishing photocatalytic

  为了减轻溶液中扩散受限的光致电子转移 (PET)，将三苯胺衍生的染料和 Keggin 多金属氧酸盐型电子继电器耦合到配位聚合物中，以光诱导长寿命的电荷分离对，并具有足够的还原/氧化电位来泵浦多个电子单向从外部电子供体到受体，从而提供光催化自由基偶联，以提供增值的 α-氨基 C-H 芳基化产物。
• Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis of<i>N</i>-Substituted Cyclic Amines
  作者：Michael C. Venuti、Oswald Ort

  DOI：10.1055/s-1988-27777

  日期：——

  Borane-methyl sulfide (BMS) reduction of variously N-substituted succinamic and glutaramic esters affords the corresponding N-substituted pyrrolidines and piperidines in high yields. The limitations, mainly caused by steric hinderance around the amine nitrogen, and putative intermediates involved in this conversion, as detected by incomplete reaction and/or synthesis followed by BMS reduction, indicate that cyclization and amide reduction successfully compete with ester reduction to afford the N-substituted cyclized amines.

  硼烷-硫化甲基（BMS）还原各种N-取代的琥珀酰胺和戊二酰胺酯，可以高产率地得到相应的N-取代吡咯烷和哌啶。这一转化过程中，由于胺氮周围的空间阻碍限制，以及通过不完全反应和/或合成后续的BMS还原检测到的假定中间体，表明环化作用和酰胺还原成功地与酯还原竞争，从而得到了N-取代的环化胺。
• The titanocene-catalyzed reduction of acetamides to tertiary amines by PhMeSiH₂
  作者：Kumaravel Selvakumar、Kesamreddy Rangareddy、John F Harrod

  DOI：10.1139/v04-063

  日期：2004.8.1

  A variety of acetamide derivatives are reduced in excellent yields to tertiary amines by PhMeSiH₂ in the presence of Cp₂TiX₂ (X = F or Me) catalysts. The reactions are very clean at 80 °C. At room temperature a secondary reaction, hydrogenolysis of the C(O)—N bond, intervenes and reduces the chemoselectivity. Nevertheless, this chemistry provides a simple methodology for the amide/alkylamine transformation using inexpensive, commercially available reagents.Key words: amides, reduction, secondary amides, methylphenylsilane, titanocene, catalysis.

  一种多样的乙酰胺衍生物在PhMeSiH₂存在下与Cp₂TiX₂（X = F或Me）催化剂反应，以优异的产率还原为三级胺。这些反应在80°C下非常干净。在室温下，发生了C(O)—N键的次级反应，氢解作用介入并降低了化学选择性。尽管如此，这种化学方法提供了一种简单的方法，利用廉价、易获得的试剂进行酰胺/烷胺转化。关键词：酰胺、还原、次级酰胺、甲基苯基硅烷、二茂钛、催化。
• Diisobutylaluminum borohydride: An efficient reagent for the reduction of tertiary amides to the corresponding amines under ambient conditions
  作者：Rachel A. Snelling、Gabriella Amberchan、Angel Resendez、Chris L. Murphy、Lauren Porter、Bakthan Singaram

  DOI：10.1016/j.tetlet.2017.09.030

  日期：2017.10

  A synthetically simple mixed metal hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], is easily generated from a 1:1 mixture of borane-dimethylsulfide (BMS) and diisobutylaluminum hydride (DIBAL). The reduction of tertiary amides using (iBu)2AlBH4 is complete within five minutes under ambient conditions and the product tertiary amines were isolated in 70–99% yields by a simple acid-base extraction

  合成简单的混合金属氢化物二异丁基硼氢化铝[（i Bu）2 AlBH 4 ]易于从硼烷-二甲基硫醚（BMS）和二异丁基氢化铝（DIBAL）的1：1混合物中生成。在环境条件下，使用（i Bu）2 AlBH 4可以在五分钟内完成叔酰胺的还原，并且可以通过简单的酸碱萃取以70-99％的产率分离出叔胺产物。本文报道的这种新方法学非常适用于将脂族和芳族叔酰胺以及内酰胺还原为相应的胺，并且产物的分离和纯化不需要柱色谱法。
• Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
  作者：Gabriella Amberchan、Rachel A. Snelling、Enrique Moya、Madison Landi、Kyle Lutz、Roxanne Gatihi、Bakthan Singaram

  DOI：10.1021/acs.joc.0c03062

  日期：2021.5.7

  from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce

  由氢化二异丁基铝（DIBAL）和硼烷二甲基硫醚（BMS）合成的二元氢化物二异丁基硼氢化铝[（i Bu）2 AlBH 4 ]在还原各种有机官能团方面显示出巨大潜力。这种独特的二元氢化物（i Bu）2 AlBH 4易于合成，通用且易于使用。醛，酮，酯和环氧化物以基本定量的收率非常快地还原为相应的醇。该二元氢化物可以在25°C下以有效方式将叔酰胺迅速还原为相应的胺。此外，腈以基本上定量的产率转化为相应的胺。这些反应在环境条件下发生，并在一个小时或更短的时间内完成。还原产物可通过简单的酸碱萃取而分离，无需使用柱色谱法。进一步的研究表明（i Bu）2 AlBH 4如一系列竞争反应所示，它具有成为选择性氢化物供体的潜力。讨论了（i Bu）2 AlBH 4，DIBAL和BMS之间的异同。

表征谱图