1-(4-甲氧基苯)-1'-环丙腈 | 16728-00-0

• 物质功能分类: 有机原料
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(4-甲氧基苯)-1'-环丙腈
• 中文别名: 1-(4-甲氧基苯基)环丙甲腈；1-(4-甲氧基苯基)-1-环丙胺甲腈；1-(4-甲氧基苯)-1-环丙腈；1-(4-甲氧苯基)-1-环丙烷甲腈
• 英文名称: 1-(4-methoxyphenyl)cyclopropane-1-carbonitrile
• 英文别名: 1-(4-methoxyphenyl)cyclopropanecarbonitrile；1-(4-methoxyphenyl)-1-cyanocyclopropane；4-(1-Cyanocyclopropyl)anisole；1-(p-Methoxy-phenyl)-cyclopropyl-carbonitril；1-(p-Methoxyphenyl)cyclopropancarbonitril
• CAS: 16728-00-0
• 化学式: C₁₁H₁₁NO
• mdl: MFCD00019212
• 分子量: 173.214
• InChiKey: OIQRGAQXQLASRC-UHFFFAOYSA-N

物化性质

• 沸点：
  315.3±35.0 °C(Predicted)
• 密度：
  1.08
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

SDS

Name:	1-(4-METHOXYPHENYL)-1-CYCLOPROPANE- CARBONITRILE Material Safety Data Sheet
Synonym:
CAS:	16728-00-0

Section 1 - Chemical Product MSDS Name:1-(4-METHOXYPHENYL)-1-CYCLOPROPANE- CARBONITRILE Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16728-00-0	1-(4-METHOXYPHENYL)-1-CYCLOPROPANE-		240-786-4

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
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. 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.

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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. Clean up spills immediately, observing precautions in the Protective Equipment section.

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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. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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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. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 16728-00-0: Personal Protective Equipment Eyes: Not available.
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: Not available.
Color: Not available.
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0840g/cm3
Molecular Formula: C11H11NO
Molecular Weight: 173.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16728-00-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(4-METHOXYPHENYL)-1-CYCLOPROPANE- CARBONITRILE - 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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 16728-00-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16728-00-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16728-00-0 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：

  1-(4-甲氧基苯)-1'-环丙腈 在 硫酸 、 lithium hydroxide 作用下， 以 水 为溶剂， 反应 36.0h， 生成 1-(4-甲氧基苯基)-环丙烷甲酸甲酯
  参考文献：
  名称：

  Lewis碱性硫族化物催化剂对环丙基二酯的亲电溴化反应

  摘要：

  已经开发了使用三苯基膦硫化物（Ph 3 PS）或二苯基硒化物（Ph 2 Se）作为路易斯碱性硫族化物催化剂的环丙基甲基二酯的高效且区域选择性的亲电子溴化反应。据观察，博士3 PS利于形成抗非对映体，并产生多功能γ内酯。有趣的是，当使用Ph 2 Se作为催化剂时，非对映选择性被逆转，其中偏爱合成产物而不是反产物。

  DOI：

  10.1002/adsc.201800886
• 作为产物：
  描述：

  1-(4-甲氧基苯)-1-环丙羧酸 在 氯化亚砜 、 palladium diacetate 、 Selectfluor 、 乙腈 作用下， 以 四氢呋喃 为溶剂， 反应 19.08h， 生成 1-(4-甲氧基苯)-1'-环丙腈
  参考文献：
  名称：

  钯催化伯酰胺脱水形成腈的开发和利用。

  摘要：

  在Selectfluor的存在下，钯（II）催化剂可将伯酰胺高效且化学选择性地转化为腈。酰胺可以连接到芳环，杂芳环或脂族侧链上，并且该反应可耐受空间体积和电子修饰。含有三个谷氨酰胺基团的肽醇的脱水为每个谷氨酰胺残基提供了构效关系。因此，这种脱水可以通过合成突变与谷氨酰胺的丙氨酸扫描相似。

  DOI：

  10.1021/acs.orglett.8b02422

文献信息

• Lewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of Cyclopropylmethyl Amide
  作者：Ying-Chieh Wong、Zhihai Ke、Ying-Yeung Yeung

  DOI：10.1021/acs.orglett.5b02557

  日期：2015.10.16

  A Lewis basic sulfide catalyzed electrophilic bromocyclization of cyclopropylmethyl amide has been developed. The catalytic protocol is applicable to both 1,1- and 1,2-substituted cyclopropylmethyl amides, giving oxazolines and oxazines in good yields and excellent diastereoselectivity.

  已经开发了路易斯碱性硫化物催化的环丙基甲基酰胺的亲电溴环化反应。该催化规程适用于1,1-和1,2-取代的环丙基甲基酰胺，从而以良好的收率和出色的非对映选择性提供了恶唑啉和恶嗪。
• [EN] DIACYLGLYCEROL ACYLTRANSFERASE 2 INHIBITORS<br/>[FR] INHIBITEURS DE DIACYLGLYCÉROL ACYLTRANSFÉRASE 2
  申请人：PFIZER

  公开号：WO2013150416A1

  公开（公告）日：2013-10-10

  Derivatives of purine, 3H-imidazo[4,5-b]pyrimidine and 1H- imidazo[4,5-d]pyrazine of Formula I that inhibit the activity of the diacylglycerol acyltransferase 2 (DGAT2) and their uses in the treatment of diseases linked thereto in animals are described herein.

  这里描述了抑制二酰基甘油酰基转移酶2（DGAT2）活性的嘌呤衍生物，即式I的3H-咪唑并[4,5-b]嘧啶和1H-咪唑并[4,5-d]吡嗪，以及它们在治疗相关动物疾病中的用途。
• Evaluation of 1,2,3‐Triazoles as Amide Bioisosteres In Cystic Fibrosis Transmembrane Conductance Regulator Modulators VX‐770 and VX‐809
  作者：Jake E. Doiron、Christina A. Le、Britton K. Ody、Jonathon B. Brace、Savannah J. Post、Nathan L. Thacker、Harrison M. Hill、Gary W. Breton、Matthew J. Mulder、Sichen Chang、Thomas M. Bridges、Liping Tang、Wei Wang、Steven M. Rowe、Stephen G. Aller、Mark Turlington

  DOI：10.1002/chem.201805919

  日期：2019.3.7

  assay could be due to the inability of VX‐770 triazole derivatives to reach the CFTR binding site. Moreover, in addition to the negative impact on biological activity, triazoles in both structural classes displayed decreased metabolic stability in human microsomes relative to the analogous amides. In contrast to the many studies that demonstrate the advantages of using the 1,2,3‐triazole, these findings

  1,2,3-三唑已成功用作多种治疗环境中的酰胺生物等排体。基于这一先例，合成了源自 VX-809 和 VX-770 的三唑类似物，它们是囊性纤维化跨膜电导调节剂 (CFTR) 的主要含酰胺调节剂，并评估了 CFTR 调节作用。与 VX-809 相比，源自 VX-809 的三唑11在细胞 TECC 测定中的 F508del-CFTR 校正中表现出显着降低的功效。令人惊讶的是，源自增效剂 VX-770 的三唑类似物在细胞 Ussing 室测定中没有显示出对 F508del、G551D 或 WT-CFTR 的增强作用。然而，膜片钳分析显示，三唑60与 VX-770 类似，可增强 WT-CFTR。60在无细胞膜片钳实验中的功效表明，细胞测定中活性的丧失可能是由于 VX-770 三唑衍生物无法到达 CFTR 结合位点。此外，除了对生物活性的负面影响之外，与类似的酰胺相比，两种结构类别的三唑在人体微粒
• Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles
  作者：Ping Fang、Tian-Sheng Mei、Bin Shuai

  DOI：10.1055/s-0039-1690872

  日期：2021.10

  A nickel-catalyzed base-promoted rearrangement of cyclo­butanone oxime esters to cyclopropanecarbonitriles was developed. The ring opening of cyclobutanone oxime esters occurs at the sterically less hindered side. A base-promoted nickelacyclobutane intermediate, formed in situ, is assumed to be involved in the formation of the product.

  开发了镍催化碱促进环丁酮肟酯重排为环丙烷甲腈的方法。环丁酮肟酯的开环发生在空间位阻较小的一侧。原位形成的碱促进的镍基环丁烷中间体被认为参与了产物的形成。
• Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp³)–H Borylation of Cyclopropanes
  作者：Yongjia Shi、Qian Gao、Senmiao Xu

  DOI：10.1021/jacs.9b04549

  日期：2019.7.10

  We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile

  我们在此报告了首次使用手性双齿硼酸配体对环丙烷甲酰胺进行 Ir 催化的对映选择性 C(sp3)-H 硼酸化。具有 α-季碳中心的多种底物可以在该反应中相容，以提供具有良好至优异对映选择性的 β-硼酸化产物。我们还证明，硼酸化产物可用作多功能前体，参与 CB 键的立体有择转化，包括合成生物活性化合物 Levomilnacipran。