2-萘甲腈 | 613-46-7

• 物质功能分类: 化学试剂 - 有机试剂 - 双环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-萘甲腈
• 中文别名: 2-氰基萘；萘-2-甲腈；2-氰基萘,萘-2-甲腈；萘-2-腈；2-萘腈
• 英文名称: 2-Cyanonaphthalene
• 英文别名: 2-naphthalenecarbonitrile；2-naphthonitrile；naphthalene-2-carbonitrile
• CAS: 613-46-7
• 化学式: C₁₁H₇N
• mdl: MFCD00016807
• 分子量: 153.183
• InChiKey: AZKDTTQQTKDXLH-UHFFFAOYSA-N

物化性质

• 熔点：
  63-68 °C
• 沸点：
  156-158°C 12mm
• 密度：
  1.0755
• 闪点：
  156-158°C/12mm
• 溶解度：
  溶于苯、甲醇
• 保留指数：
  1497.4;1529;261.3;261.5;255.6;260.88
• 稳定性/保质期：
  - 在常温常压下，它不会分解。 - 它存在于烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  Xn,T,N
• 安全说明：
  S26,S36/37,S36/37/39,S39,S45,S61
• 危险类别码：
  R20/21/22,R37/38,R51/53,R25,R41
• WGK Germany：
  3
• 海关编码：
  29269090
• 危险品运输编号：
  3276
• 危险类别：
  6.1
• RTECS号：
  QL5976350
• 包装等级：
  III
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  贮存： 将密器密封，并储存在密封的主藏器中。应将其置于阴凉、干燥的地方。

SDS

Name:	2-Naphthonitrile 97% Material Safety Data Sheet
Synonym:	2-Naphthalenecarbonitrile; beta-Cyanonaphthalene
CAS:	613-46-7

Section 1 - Chemical Product MSDS Name:2-Naphthonitrile 97% Material Safety Data Sheet
Synonym:2-Naphthalenecarbonitrile; beta-Cyanonaphthalene

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
613-46-7	2-Naphthonitrile	97.0	210-344-5

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.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
The toxicological properties of this substance have not been fully investigated. Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration.
Chronic:
Chronic exposure to cyanide solutions may lead to the development of a "cyanide" rash, characterized by itching, and by macular, papular, and vesicular eruptions, and may be accompanied by secondary infections. Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
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. Do NOT use mouth-to-mouth resuscitation.
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 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Avoid contact with skin and eyes. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. 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# 613-46-7: Personal Protective Equipment Eyes: Wear chemical splash goggles.
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: Crystalline powder
Color: off-white to light beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 63-68 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:
Molecular Formula: C11H7N
Molecular Weight: 153.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 613-46-7: QL5976350 LD50/LC50:
Not available.
Carcinogenicity:
2-Naphthonitrile - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 613-46-7: No information available.
Canada
CAS# 613-46-7 is listed on Canada's NDSL List.
CAS# 613-46-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 613-46-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

2-萘甲腈是合成一种具有适中介电各向异性的优良液晶材料的重要中间体。此外，许多天然产物和临床药物中都含有氰基团，例如抗肿瘤药Letrozole、β抑制剂Bucindolol、激酶抑制剂Neratinib、心血管药cromakalim、抗HIV药Etravirine、抗痛风药Febuxostat、抗抑郁药Citalopram以及糖尿病药物alogliptin等。

应用领域

2-萘甲腈作为有机化学中优良的反应中间体，已被广泛应用于生物学、医药、农药及功能材料等领域中。

制备

2-萘甲腈的制备如下：

在充满氮气的手套箱中，向具有封口塞的小瓶中依次加入NiCl₂·6H₂O (5.9 mg, 0.025 mmol)，dppf (16.6 mg, 0.03 mmol)，Zn (6.5 mg, 0.1 mmol)，Zn(CN)₂ (47.0 mg, 0.4 mmol)，DMAP (91.6 mg, 0.75 mmol)，2-萘甲磺酸酯 (0.5 mmol)，CH₃CN (5 mL)。盖好盖子后移出手套箱，直接置于50℃油浴中加热反应8小时。冷却至室温后，经TLC检测并硅胶过滤、乙酸乙酯洗涤、浓缩和柱层析纯化（使用石油醚/乙酸乙酯 = 35:1作为淋洗剂），最终得到白色固体2-萘甲腈71.6 mg，收率93%。经¹HNMR测定纯度大于98%。

反应信息

• 作为反应物：
  描述：

  2-萘甲腈 在 甲基锂 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 19.58h， 生成 1-(3,4-dihydroquinolin-1(2H)-yl)-2-naphthonitrile
  参考文献：
  名称：

  芳烷基硫醚的亲核胺化和醚化

  摘要：

  报道了能够合成二芳基苯胺衍生物的无过渡金属的方案。该方法可以进一步用于制备芳基烷基醚。由于反应条件温和，因此可以耐受多种硫醚，苯胺和醇类。通过进行克级反应（20 mmol），然后将腈基转化为可合成使用的醛，酮和羧酸，证明了我们方法的优势。

  DOI：

  10.1021/acs.orglett.8b01758
• 作为产物：
  描述：

  N,N-二甲基-2-萘甲酰胺 在 二异丁基氢化铝 、 氨 、 碘 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 1.5h， 以90%的产率得到2-萘甲腈
  参考文献：
  名称：

  N，N-二取代酰胺和异丙基酯直接转化为腈

  摘要：

  通过用氢化二异丁基铝处理，然后用氨水中的分子碘处理，可以将各种N，N-二甲基酰胺，N-甲氧基-N-甲基酰胺和异丙基酯以良好至中等的收率平稳地转化为相应的腈。本反应是新颖的一锅法和实用方法，其通过分别形成半胱氨酸O -AlBu 2和半缩醛O -AlBu 2来将N，N-二取代酰胺和异丙酯转化为腈。

  DOI：

  10.1016/j.tet.2011.04.008
• 作为试剂：
  描述：

  2-氯吡啶 在 2-萘甲腈 、 tetrabutylammonium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Pyridyl-Radikal
  参考文献：
  名称：

  Enemaerke, Rasmus J.; Christensen, Torben B.; Jensen, Henrik, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2001, # 9, p. 1620 - 1630

  摘要：

  DOI：

文献信息

• Dehydrogenation of Primary Alkyl Azides to Nitriles Catalyzed by Pincer Iridium/Ruthenium Complexes
  作者：Lan Gan、Xiangqing Jia、Huaquan Fang、Guixia Liu、Zheng Huang

  DOI：10.1002/cctc.202000260

  日期：2020.7.21

  Pincer metal complexes exhibit superior catalytic activity in the dehydrogenation of plain alkanes, but find limited application in the dehydrogenation of functionalized organic molecules. Starting from easily accessible primary alkyl azides, here we report an efficient dehydrogenation of azides to nitriles using pincer iridium or ruthenium complexes as the catalysts. This method offers a route to

  夹钳金属络合物在纯链烷烃的脱氢中显示出优异的催化活性，但在功能化有机分子的脱氢中发现有限的应用。从容易获得的伯烷基叠氮化物开始，在这里我们报告了使用夹钳铱或钌络合物作为催化剂将叠氮化物有效脱氢为腈。该方法提供了一种无需氰化物即可制备腈的方法，该方法无需碳链延长，也无需使用强氧化剂。两个苄基和直链脂肪族叠氮化物可以与脱氢叔-丁基乙烯作为氢受体以中等至高产率提供腈。可以容忍各种官能团，并且对于线性烷基叠氮化物底物不会发生HC-CH键脱氢。此外，发现在不使用牺牲氢受体的情况下，夹钳式Ir催化体系可催化直接叠氮化物脱氢。
• Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
  作者：Tristan Delcaillau、Philip Boehm、Bill Morandi

  DOI：10.1021/jacs.1c00529

  日期：2021.3.17

  We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications

  我们描述了芳基腈和芳基硫醚之间的新官能团复分解。催化系统镍/dcype 对于实现这种完全可逆的转化，以良好的收率至关重要。此外，不含氰化物和硫醇的反应显示出高官能团耐受性和商业分子后期衍生化的高效率。最后，合成应用证明了它在多步合成中的多功能性和实用性。
• A mild and efficient method for the conversion of aldehydes into nitriles and thiols into disulfides using an ionic liquid oxidant
  作者：Rahman Hosseinzadeh、Hamid Golchoubian、Mahboobe Nouzarian

  DOI：10.1007/s11164-014-1562-4

  日期：2015.7

  mild and high yielding method for the conversion of various aldehydes to nitriles has been developed using an ionic liquid reagent, hexamethylene bis( N -methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), in combination with aqueous ammonia in CH3CN at room temperature. Moreover, the treatment of aromatic and aliphatic thiols with HMBMIBDCI resulted in the corresponding disulfides in solvent-free condition

  使用离子液体试剂六亚甲基双（ N- 甲基咪唑鎓）双（二氯碘酸盐）（HMBMIBDCI）并与氨水在CH 3 CN中混合，开发了一种简单，温和且高收率的方法，可将各种醛转化为腈 。室内温度。此外，用HMBMIBDCI处理芳香族和脂肪族硫醇会在室温下在无溶剂条件下产生相应的二硫化物。
• Sequential C–H activation enabled expedient delivery of polyfunctional arenes
  作者：Wensen Ouyang、Xiaoqing Cai、Xiaojian Chen、Jie Wang、Jianhang Rao、Yang Gao、Yanping Huo、Qian Chen、Xianwei Li

  DOI：10.1039/d1cc03243g

  日期：——

  Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C–H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction

  从丰富的原料中模块化构建多功能芳烃是合成化学的不懈追求，加速了药物和材料的发现。在此，使用多功能亚胺酸酯的多重 C-H 活化策略，实现了密集功能化的含硫芳烃分子库的便捷传递，从而能够简明地构建生物活性分子，如双苯萘酚。
• An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions
  作者：N. Uludag

  DOI：10.1134/s1070428020090225

  日期：2020.9

  Abstract A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes, including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding nitriles in good to excellent yields.

  摘要 已经提出了使用三氟甲磺酸酐和三乙胺将醛肟转化为腈的一种新的方便的方案。所提出的方法允许将包括芳族，杂环，脂族和脂环族醛肟在内的一系列醛肟以良好或优异的产率转化为相应的腈。

表征谱图