3-（苄氨基）丙腈 | 706-03-6

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 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: 3-（苄氨基）丙腈
• 中文别名: 3-(苯甲基氨基)丙正离子基腈；3-(苯甲基氨基)丙腈；3-(苄氨基)丙腈；3-(苯甲基氨基)丙腈, 97+%
• 英文名称: 3-(benzylamino)propionitrile
• 英文别名: 3-(benzylamino)propanenitrile；3-(N-benzylamino)propionitrile
• CAS: 706-03-6
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD00001955
• 分子量: 160.219
• InChiKey: MWTGBAURSCEGSL-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  276.13°C (rough estimate)
• 密度：
  1.024 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  溶于二甲基亚砜。
• 稳定性/保质期：
  远离氧化物、酸、酸性氯化物及酸酐。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xn
• 安全说明：
  S23,S26,S37/39
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN3276
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  存放在密封容器内，并放置在阴凉、干燥处。储存地点须远离氧化剂。避免与酸或酸性物质一同存放，远离含氯酸和酸酐的区域。

SDS

Name:	3-(Benzylamino)propionitrile 97% Material Safety Data Sheet
Synonym:
CAS:	706-03-6

Section 1 - Chemical Product MSDS Name:3-(Benzylamino)propionitrile 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
706-03-6	3-(Benzylamino)propionitrile	97	211-890-7

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:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes 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:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
Prolonged or repeated skin contact may cause dermatitis. Effects may be delayed.

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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. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. 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.
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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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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. Provide ventilation.

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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. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation.
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# 706-03-6: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0240 g/cm3
Molecular Formula: C10H12N2
Molecular Weight: 160.22

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat.
Incompatibilities with Other Materials:
Acid anhydrides, acid chlorides, acids, strong oxidizing agents, carbon dioxide.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 706-03-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(Benzylamino)propionitrile - 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
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
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 23 Do not inhale gas/fumes/vapour/spray.
WGK (Water Danger/Protection)
CAS# 706-03-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 706-03-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 706-03-6 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

3-(苄胺)丙腈与1-羟甲基-5-甲基-1H-吡唑-3-羧酸乙酯在温和条件下发生aza型迈克尔反应。

反应

以3-(苄氨基)丙腈为起始试剂，合成了以下化合物：

• (3R,4S)-1-苄基-4-苯基吡咯烷-3-羧酸是合成生物活性化合物的关键手性构块。
• 1-{[苄基-(2-氰基乙基)-氨基]-甲基}-5-甲基-1H-吡唑-3-羧酸乙酯。
• (3-(苄胺)-3,5-二甲基吡唑-1-基甲基)氨基)丙腈。

反应信息

• 作为反应物：
  描述：

  3-（苄氨基）丙腈 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-乙基苄胺
  参考文献：
  名称：

  Efficient, asymmetric synthesis of (−)-isooncinotine

  摘要：

  Asymmetric synthesis of (-)-isooncinotine, a 22-membered lactam of spermidine alkaloid, starting from resolution of 2-piperidineethanol with (S)-10-camphorsulfonic acid is reported. Michael addition, amidations, and aluminum hydride reduction were applied to form the moiety of spermidine. Retro-Michael addition was observed when beta-amido- and beta-amino-propionitriles were reduced by LAH. The effects of LAH versus AlH3 were discussed. The synthesis of the skeleton of this macrolide is achieved with ring-closing metathesis of the diene prepared from acylation of the spermidine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.068
• 作为产物：
  描述：

  1-苄基-3-吡咯烷酮 在 ammonium hydroxide 、 dipotassium peroxodisulfate 、 copper(II) nitrate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以10%的产率得到3-（苄氨基）丙腈
  参考文献：
  名称：

  铜氨介导的羰基化合物的氧化

  摘要：

  NH 4 OH水溶液中的铜（II），在大多数情况下，与O 2或K 2 S 2 O 8作为辅助氧化剂一起使用时，如果有良好的碳电絮凝剂，可将酮氧化裂解为腈。对于未活化的酮，观察到的主要反应是酮亚胺的氧化偶联反应，生成嗪。

  DOI：

  10.1016/s0040-4039(00)74473-x

文献信息

• Pyrrolidine derivatives
  申请人：——

  公开号：US20020049243A1

  公开（公告）日：2002-04-25

  The present invention relates to pyrrolidine derivatives and dimeric forms and/or pharmaceutically acceptable esters, and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.

  本发明涉及吡咯烷衍生物及其二聚体形式和/或药用可接受的酯和/或盐。这些化合物可用作金属蛋白酶抑制剂，例如锌蛋白酶，特别是锌水解酶，对治疗与血管收缩增加发生相关的疾病状态有效。
• Graphite-Supported Gold Nanoparticles as Efficient Catalyst for Aerobic Oxidation of Benzylic Amines to Imines and<i>N</i>-Substituted 1,2,3,4-Tetrahydroisoquinolines to Amides: Synthetic Applications and Mechanistic Study
  作者：Man-Ho So、Yungen Liu、Chi-Ming Ho、Chi-Ming Che

  DOI：10.1002/asia.200900261

  日期：2009.10.5

  of N‐substituted 1,2,3,4‐tetrahydroisoquinolines in the presence of aqueous NaHCO3 solution gave the corresponding amides in good yields (83–93 %) with high selectivity (up to amide/enamide=93:4) (6 examples). The same protocol can be applied to the synthesis of benzimidazoles from the reaction of o‐phenylenediamines with benzaldehydes under aerobic conditions (8 examples). By simple centrifugation

  使用氧气作为末端氧化剂对胺进行选择性氧化是绿色化学中的重要领域。在这项工作中，我们描述了使用石墨负载的金纳米颗粒（AuNPs / C）催化环状和非环状苄胺的好氧氧化为相应的亚胺，具有中等至优异的底物转化率（43-100％）和产品收率（66–99％）（19个例子）。在NaHCO 3水溶液存在下，对N-取代的1,2,3,4-四氢异喹啉进行氧化，得到的酰胺产率高（83-93％），选择性高（酰胺/酰胺= 93：4）（ 6个示例）。相同的协议可以从反应被施加到苯并咪唑的合成Ò在好氧条件下将苯二胺与苯甲醛一起使用（8个例子）。通过简单的离心，可以回收AuNPs / C并重复使用十次，以将二苄基胺氧化为N-亚苄基（苯基）甲胺，而不会显着降低催化活性和选择性。可以将协议“ AuNPs / C + O 2 ”调整为克级，通过氧化10 g 1,2,3,4-可以得到8.9 g（84％分离出的产率）3,4-二氢异
• Aza-Michael reactions in water using functionalized ionic liquids as the recyclable catalysts
  作者：X. Liu、M. Lu、G. Gu、T. Lu

  DOI：10.1007/bf03245908

  日期：2011.9

  Some recyclable SO3H-functionalized ionic liquids have been used as catalysts in water for the aza-Michael reactions of amines with α,β-unsaturated compounds to produce β-amino compounds. High yields of the products, short reaction times, mild reaction conditions, simple experimental procedure, reusable catalysts and no obvious loss of the catalytic activity make this protocol a contribution to organic

  一些可循环利用的SO 3 H-官能化的离子液体已用作水中的催化剂，用于胺与α，β-不饱和化合物的aza-Michael反应生成β-氨基化合物。产物的高产率，短的反应时间，温和的反应条件，简单的实验程序，可重复使用的催化剂以及没有明显的催化活性损失，使得该方案对有机化学有所贡献。
• <i>o</i>-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates:  Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections
  作者：K. C. Nicolaou、Casey J. N. Mathison、Tamsyn Montagnon

  DOI：10.1021/ja0400382

  日期：2004.4.28

  o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found

  发现邻碘苯甲酸 (IBX) 是一种用途广泛的高价碘 (V) 试剂，除了促进二硫缩醛和二硫缩酮的氧化裂解外，还可以有效介导胺的脱氢。通过开发相关的基于 IBX 的协议，发现大量有用的合成中间体，包括亚胺、肟、酮和芳香族 N-杂环，在特别温和的条件下很容易获得。对这些转化的进一步研究导致了对有价值的机械细节的阐明，从而得出结论，它们是通过离子而不是单电子转移 (SET) 途径进行的。
• [EN] 3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE LA 3-PHOSPHOGLYCÉRATE DÉSHYDROGÉNASE ET LEURS UTILISATIONS
  申请人：RAZE THERAPEUTICS INC

  公开号：WO2017156177A1

  公开（公告）日：2017-09-14

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。

表征谱图