对氨基苯乙腈 | 3544-25-0

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 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: 对氨基苯乙腈
• 中文别名: 4-氨基苯乙腈；4-氨基苯基乙腈；對胺苯乙腈；4-氨基苄氰
• 英文名称: p-aminophenylacetonitrile
• 英文别名: 4-amino-benzeneacetonitrile；2-(4-aminophenyl)acetonitrile；4-aminobenzyl cyanide；4-aminophenylacetonitrile
• CAS: 3544-25-0
• 化学式: C₈H₈N₂
• mdl: MFCD00007912
• 分子量: 132.165
• InChiKey: YCWRFIYBUQBHJI-UHFFFAOYSA-N

物化性质

• 熔点：
  45-48 °C(lit.)
• 沸点：
  312 °C(lit.)
• 密度：
  1.4747 (rough estimate)
• 闪点：
  >230 °F
• 溶解度：
  溶于甲醇
• 暴露限值：
  NIOSH: IDLH 25 mg/m3
• 稳定性/保质期：
  常温常压下稳定，为白色或淡黄色结晶。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 安全说明：
  S36,S36/37
• 危险品运输编号：
  3276
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险类别：
  6.1
• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 包装等级：
  III
• 危险性防范说明：
  P501,P261,P270,P271,P264,P280,P361+P364,P301+P310+P330,P302+P352+P312,P304+P340+P311,P403+P233,P405
• 危险性描述：
  H301,H311,H331
• 储存条件：
  常温下应存于避光、通风且干燥的地方，并密封保存。

SDS

Name:	4-Aminobenzyl cyanide 99% Material Safety Data Sheet
Synonym:	4-Aminophenylacetonitrile; 4-Aminobenzyl cyanide
CAS:	3544-25-0

Section 1 - Chemical Product MSDS Name:4-Aminobenzyl cyanide 99% Material Safety Data Sheet
Synonym:4-Aminophenylacetonitrile; 4-Aminobenzyl cyanide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3544-25-0	4-Aminobenzyl cyanide	99	222-587-4

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
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. 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, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. 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:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. Combustion generates toxic fumes. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
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. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Use only with adequate ventilation. Avoid breathing dust.
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# 3544-25-0: United States OSHA: 5 mg/m3 TWA (listed under Cyanide anion).
Germany: (listed as cyanide anion): Skin absorber Netherlands: (listed as cyanide anion): 5 mg/m3 MAC (as CN) 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:
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: yellow to brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 312 deg C @ 760 mm Hg
Freezing/Melting Point: 44-48 deg C
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: slightly soluble
Specific Gravity/Density:
Molecular Formula: C8H8N2
Molecular Weight: 132.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong reducing agents, strong acids, and strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, cyanides.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3544-25-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Aminobenzyl cyanide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Bacteria: Phytobacterium phosphoreum: EC50 = 0.36-0.40 mg/L; 5,15,30 minutes; Microtox test; 15 degrees C

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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
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: Nitriles, Toxic, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: Nitriles, Toxic, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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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# 3544-25-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3544-25-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3544-25-0 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

制备方法与用途

用途广泛，用于制备丁二酸、戊二醇、四氢呋喃和吡喃等化合物。此外，它也用作涂料、树脂和油脂的溶剂，在印染工业中用作润滑剂和分散剂。在医药领域，它是中间体，还可作为药品的脱色剂和脱臭剂。同时，它还被用作增塑剂、除草剂和杀虫剂等有机合成的原料。

反应信息

• 作为反应物：
  描述：

  对氨基苯乙腈 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 肼 作用下， 以 N,N-二甲基甲酰胺-d7 、 乙腈 为溶剂， 反应 28.0h， 生成 米拉贝隆
  参考文献：
  名称：

  Mirabegron合成新方法的研究

  摘要：

  Mirabegron是一种肌肉松弛药，用于治疗膀胱过度活动症。现有的米拉贝隆合成方法生产的中间产物4-（2-（（苯乙基氨基）乙基）苯胺，使最终产品的纯化过程复杂化。在这项研究中，我们设计了一种低成本的原料用于米拉贝隆的新合成路线，并以99.6％的纯度和61％的总收率生产米拉贝隆。特别是，这种新的合成路线没有产生副产物4-（2-（苯乙氨基）乙基）苯胺，这大大简化了产物纯化过程。

  DOI：

  10.1002/jhet.2871
• 作为产物：
  描述：

  4,4'-di(cyanomethyl)azobenzene 在 palladium on activated charcoal aminomethylpolystyrene-supported formate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以90%的产率得到对氨基苯乙腈
  参考文献：
  名称：

  Palladium-catalyzed simple and efficient hydrogenative cleavage of azo compounds using recyclable polymer-supported formate

  摘要：

  钯催化室温下使用可回收的聚合物支持的甲酸根转移氢化偶氮化合物，产生对应的胺类产物，收率极高（88%至98%）。该方法被发现在选择性上高度便利，对许多其他官能团如卤素、烯烃、腈、酮、酰胺、甲氧基和羟基具有选择性。关键词：偶氮化合物、催化转移氢化、聚合物支持的甲酸根、10% Pd-C、胺类。

  DOI：

  10.1139/v05-071

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Highly chemoselective reduction of nitroarenes over non-noble metal nickel-molybdenum oxide catalysts
  作者：Haigen Huang、Xueguang Wang、Xu Li、Chenju Chen、Xiujing Zou、Weizhong Ding、Xionggang Lu

  DOI：10.1039/c6gc03141b

  日期：——

  Chemoselective reduction of nitroarenes is an important transformation for the production of arylamines, which are the primary intermediates in the synthesis of pharmaceuticals, agrochemicals and dyes. Heterogeneous non-noble metal nickel-molybdenum...

  硝基芳烃的化学选择性还原是生产芳胺的重要转变，芳胺是合成药物，农药和染料的主要中间体。非均质非贵金属镍钼合金
• A Facile Reduction of Nitroarenes to Anilines Using FeCl₃· 6H₂O/Indium
  作者：Byung Woo Yoo、Jin Woo Choi、Sun Kyun Hwang、Dong Yoon Kim、Heung Soo Baek、Kyung Il Choi、Joong Hyup Kim

  DOI：10.1081/scc-120022471

  日期：2003.9.1

  Abstract Reduction of a variety of nitroaromatic compounds to the corresponding anilines occurs chemoselectively in high yields upon treatment with a new reduction system consisting of FeCl3 · 6H2O/indium in aqueous methanol.

  摘要 用由 FeCl3·6H2O/铟在甲醇水溶液中组成的新还原系统处理后，多种硝基芳族化合物以高产率化学选择性地还原为相应的苯胺。
• 一种芳基伯胺钌配合物、制备方法及其用途
  申请人：温州大学

  公开号：CN103804427B

  公开（公告）日：2016-04-27

  本发明涉及一种芳基伯胺钌配合物、制备方法及其用途，所述配合物在体外抗癌筛选中表现出优良的抗癌活性，其制备方法包括如下步骤：在有机溶剂中，氮气保护下，由钌卤化物或其水合物与取代苯化合物进行回流反应，得到二卤化钌二聚体；然后在有机溶剂中和氮气保护下，二卤化钌二聚体与取代苯胺化合物进行回流反应，从而得到所述芳基伯胺钌配合物。本发明还涉及所述配合物的制药用途以及包含它的药物组合物。
• [3+1+1] type cyclization of ClCF₂COONa for the assembly of imidazoles and tetrazoles <i>via in situ</i> generated isocyanides
  作者：Ya Wang、Yao Zhou、Qiuling Song

  DOI：10.1039/d0cc01919d

  日期：——

  A facile synthesis of imidazoles and tetrazoles via [3+1+1] type cyclization of ClCF2COONa is developed. A diverse array of imidazoles and tetrazoles were obtained in decent yields via isocyanide intermediates. Notably, this is the first example of the cycloaddition of in situ generated isocyanides.

  通过ClCF 2 COONa的[3 + 1 + 1]型环化，可轻松合成咪唑和四唑。通过异氰酸酯中间体以适当的产率获得了各种各样的咪唑和四唑。值得注意的是，这是就地生成的异氰酸酯环加成的第一个例子。

表征谱图