4-氟苯基氨基甲酸叔丁酯 | 60144-53-8

• 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: 4-氟苯基氨基甲酸叔丁酯
• 英文名称: N-(tert-butoxycarbonyl)-4-fluoroaniline
• 英文别名: tert-butyl (4-fluorophenyl)carbamate；(4-fluoro-phenyl)-carbamic acid tert-butyl ester；tert-butyl N-(4-fluorophenyl)carbamate；N-boc-4-fluoroaniline；Tert-butyl 4-fluorophenylcarbamate
• CAS: 60144-53-8
• 化学式: C₁₁H₁₄FNO₂
• mdl: MFCD07127707
• 分子量: 211.236
• InChiKey: OJVWNENFSPSLRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl 4-fluorophenylcarbamate
Synonyms: N-BOC-4-fluoroaniline

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: tert-Butyl 4-fluorophenylcarbamate
CAS number: 60144-53-8

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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.
Store in closed vessels, refrigerated.
Storage:

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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
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H14FNO2
Molecular weight: 211.2

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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, hydrogen fluoride.

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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

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
  N-Boc-苯胺	tert-butyl phenylcarbamate	3422-01-3	C11H15NO2	193.246
  4-叔丁基苯基氨基甲酸叔丁酯	1,1-dimethylethyl-N-[4-(1,1-dimethylethyl)phenyl] carbamate	110969-43-2	C15H23NO2	249.353
  N-羟基-N-苯基氨基甲酸叔丁酯	N-Boc phenylhydroxylamine	58377-40-5	C11H15NO3	209.245

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  N-Boc-苯胺	tert-butyl phenylcarbamate	3422-01-3	C11H15NO2	193.246
  ——	(2-bromo-4-fluoro-phenyl)-carbamic acid tert-butyl ester	384793-18-4	C11H13BrFNO2	290.132
  ——	benzyl (4-fluorophenyl)carbamate	208341-62-2	C14H12FNO2	245.253
  N-BOC4-氟-2-甲酰基苯胺	tert-butyl N-(2-formyl-4-fluorophenyl)carbamate	844891-31-2	C12H14FNO3	239.246
  ——	N-(tert-butoxycarbonylaminophenyl)morpholine	564483-40-5	C15H22N2O3	278.351
  ——	tert-butyl 2-[(E)-2-chloroethenyl]-4-fluorophenylcarbamate	908600-91-9	C13H15ClFNO2	271.719
  [5-氟-2-({[(2-甲基-2-丙基)氧基]羰基}氨基)苯基]硼酸	(2-((tert-butoxycarbonyl)amino)-5-fluorophenyl)boronic acid	925207-17-6	C11H15BFNO4	255.054

反应信息

• 作为反应物：
  描述：

  4-氟苯基氨基甲酸叔丁酯 在 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以72%的产率得到4-氟苯胺
  参考文献：
  名称：

  用于选择性水解裂解质子离子液体催化策略叔丁氧基羰胺（Ñ -Boc）†

  摘要：

  使用质子离子液体作为有效催化剂，设计了一种简单，温和且有效的策略，用于选择性水解裂解N-叔丁氧羰基（Boc）。对于N- Boc保护的芳族，杂芳族，脂族化合物以及手性氨基酸酯和肽，脱保护反应进行得很好。在反应条件下，各种不稳定的保护基如叔丁酯，叔丁醚，苄氧羰基（Cbz），TBDMS，O- Boc和S- Boc不受影响。

  DOI：

  10.1039/c4ra13419b
• 作为产物：
  描述：

  N-Boc-苯胺 在 PIFA 、 氟化氢吡啶 作用下， 反应 0.5h， 以49%的产率得到4-氟苯基氨基甲酸叔丁酯
  参考文献：
  名称：

  Fluorine Radiolabelling Process

  摘要：

  该发明涉及一种用于制备18F标记化合物的过程，该过程包括处理以下结构的化合物（I）：其中EDG是从—OH、—OR4、—NHR5和—NR55R5中选择的电子给体基团；R1、R2、X1和X2如本文所定义；以及R3从H、X3和X4中选择，其中X3是一种可单齿解离替代基团，而X4是一种双齿可解离替代基团，它与EDG对位的环碳原子上键合（a）到所述的X1或X2，（b）到EDG的对位环碳原子；在氧化剂存在下用[18F]氟化物处理，从而产生当化合物（I）中的R3为H时，化合物（II）的18F标记化合物，其中EDG如上所定义，而R1、R2、X1和X2如本文所定义；或者从而产生当化合物（I）中的R3为所述的可单齿解离替代基团X3时，化合物（IIa），其中EDG'为O、NR5、—NR55R5或[OR4]+，而R4、R5、R55、R1、R2、X1、X2和X3如本文所定义；或者从而产生当化合物（I）中的R3为所述的双齿可解离替代基团X4时，化合物（IIc）或化合物（IId），其中EDG'为O、NR5、—NR55R5或[OR4]+，而R4、R5、R55、R1、R2、X1、X2和X4如本文所定义。

  公开号：

  US20130190529A1
• 作为试剂：
  描述：

  4-氟苯胺 、 三乙胺 、 二碳酸二叔丁酯 在 sodium hydroxide 、 水 、 Sodium sulfate-III 、 正庚烷 、 4-氟苯基氨基甲酸叔丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-氟苯基氨基甲酸叔丁酯
  参考文献：
  名称：

  PURINYL DERIVATIVES AND THEIR USE AS POTASSIUM CHANNEL MODULATORS

  摘要：

  本发明涉及新型嘌呤基衍生物及其作为钾通道调节剂的用途。此外，本发明还涉及制备用于治疗或缓解与钾通道活性相关的疾病或障碍的药物组合物。

  公开号：

  US20100152210A1

文献信息

• A 2,6-Bis(phenylamino)pyridinato Titanium Catalyst for the Highly Regioselective Hydroaminoalkylation of Styrenes and 1,3-Butadienes
  作者：Jaika Dörfler、Till Preuß、Alexandra Schischko、Marc Schmidtmann、Sven Doye

  DOI：10.1002/anie.201403203

  日期：2014.7.21

  hydroaminoalkylation of terminal alkenes, 1,3‐dienes, or styrenes allows a direct and highly atom efficient (100 %) synthesis of amines which can result in the formation of two regioisomers, the linear and the branched product. We present a new titanium catalyst with 2,6‐bis(phenylamino)pyridinato ligands for intermolecular hydroaminoalkylation reactions of styrenes and 1‐phenyl‐1,3‐butadienes that delivers the

  与c  C键的形成末端烯烃，1,3-二烯，或苯乙烯的催化hydroaminoalkylation允许胺的直接和高度原子效率的（100％）的合成可导致形成两种区域异构体的，直链和支链产物。我们提出了一种新型的带有2,6-双（苯基氨基）吡啶基配体的钛催化剂，用于苯乙烯和1-苯基-1,3-丁二烯的分子间加氢烷基化反应，可提供相应的线性加氢烷基化产物，具有出色的区域选择性。
• Ligand-Promoted <i>meta</i>-C–H Amination and Alkynylation
  作者：Peng Wang、Gen-Cheng Li、Pankaj Jain、Marcus E. Farmer、Jian He、Peng-Xiang Shen、Jin-Quan Yu

  DOI：10.1021/jacs.6b08942

  日期：2016.10.26

  Using a modified norbornene (methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate) as a transient mediator, meta-C-H amination and meta-C-H alkynylation of aniline and phenol substrates have been developed for the first time. Both the identification of a monoprotected 3-amino-2-hydroxypyridine/pyridone-type ligand and the use of a modified norbornene as a mediator are crucial for the realization of these

  使用改性降冰片烯（甲基双环[2.2.1]庚-2-烯-2-羧酸酯）作为瞬态介质，首次开发了苯胺和苯酚底物的间位CH胺化和间位CH炔基化。单保护的 3-氨基-2-羟基吡啶/吡啶酮型配体的鉴定和使用修饰的降冰片烯作为介体对于实现这两个前所未有的间 CH 转化至关重要。多种底物与间位 CH 胺化和间位 CH 炔化均兼容。包括吲哚、二氢吲哚和吲唑在内的杂环底物的胺化和炔基化以中等至高产率提供所需的产物。
• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。
• Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective <i>N</i>-<i>tert</i>-butyloxycarbonylation of amines
  作者：Ajit P. Ingale、Dnyaneshwar N. Garad、Dattatraya Ukale、Nitin M. Thorat、Sandeep V. Shinde

  DOI：10.1080/00397911.2021.1994998

  日期：2021.12.17

  approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride

  摘要 盐酸硫胺素促进高效和生态友好的方法已被描述的用于化学选择性Ñ -叔在环境温度下在无溶剂条件下与胺的-butyloxycarbonylation。所证明的方法已适用于各种脂肪族、芳基、杂芳基胺的N- Boc 保护。氨基的化学选择性保护发生在手性胺和氨基醇中，没有高产率的外消旋化。盐酸硫胺素稳定、经济、易处理、环保。
• Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst
  作者：Amardeep Awasthi、Anagh Mukherjee、Mandeep Singh、Garima Rathee、Kumar Vanka、Ramesh Chandra

  DOI：10.1016/j.tet.2020.131223

  日期：2020.6

  N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation

  已经描述了使用二苯基甘脲作为有机催化剂进行多种胺的化学选择性N-叔丁氧基羰基化的有效方法。第一次，使用核磁共振研究支持的密度泛函理论（DFT）计算，提出了一种可能的N-叔丁氧羰基化机理。在不形成副产物如脲，恶唑烷酮，异氰酸酯和N，N-二-Boc衍生物的情况下，形成了有机催化剂的可重复使用性和观察到所需的N-Boc保护的胺，这使本方案成为人们所希望的。