3-氨基丁烯酰胺 | 15846-25-0

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 中文名称: 3-氨基丁烯酰胺
• 中文别名: (Z)-3-氨基丁-2-烯酰胺
• 英文名称: 3-Aminocrotonsaeureamid
• 英文别名: β-aminocrotonamide；3-aminocrotonamide；2-Butenamide, 3-amino-；3-aminobut-2-enamide
• CAS: 15846-25-0
• 化学式: C₄H₈N₂O
• 分子量: 100.12
• InChiKey: UAUSQEVPWPGBHG-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  278.5±32.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924199090

SDS

Name:	3-Aminocrotonamide Tech. 85% Material Safety Data Sheet
Synonym:	None known
CAS:	15846-25-0

Section 1 - Chemical Product MSDS Name:3-Aminocrotonamide Tech. 85% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15846-25-0	3-Aminocrotonamide	95	239-956-0

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
Causes eye irritation. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Do NOT allow victim to rub eyes or keep eyes closed.
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:
Never give anything by mouth to an unconscious person. Get medical aid. 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. 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.
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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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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# 15846-25-0: 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: Crystalline powder
Color: yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 100.00 - 102.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H8N2O
Molecular Weight: 100.12

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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, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15846-25-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Aminocrotonamide - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 15846-25-0: No information available.
Canada
CAS# 15846-25-0 is listed on Canada's NDSL List.
CAS# 15846-25-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15846-25-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-氨基丁烯酰胺 在 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、100.0 kPa 条件下， 以97.8%的产率得到3-氨基丁酰胺
  参考文献：
  名称：

  一种γ-氨基丁酰胺的制备方法

  摘要：

  本发明公开了一种γ‑氨基丁酰胺的制备方法，其特征在于，该方法包括如下步骤：S1、在惰性气氛下，将γ‑丁内酯和氨气投入反应釜中，在催化剂作用下进行封闭反应；S2、反应后，除去所述催化剂，获得中间产物；S3、将所述中间产物真空蒸馏，获得γ‑氨基丁酰胺。本发明提供了一种制备γ‑氨基丁酰胺的新方法，该方法显著提高了γ‑氨基丁酰胺产物的收率，本发明方法的产物总收率可以达到94％以上。本发明方法中所用的原料简单易得，制备过程简单，反应条件温和、易于控制，本发明的反应原料利用率高。

  公开号：

  CN117105803A
• 作为产物：
  描述：

  乙酰乙酸甲酯 在 ammonium hydroxide 作用下， 以84.8%的产率得到3-氨基丁烯酰胺
  参考文献：
  名称：

  一种γ-氨基丁酰胺的制备方法

  摘要：

  本发明公开了一种γ‑氨基丁酰胺的制备方法，其特征在于，该方法包括如下步骤：S1、在惰性气氛下，将γ‑丁内酯和氨气投入反应釜中，在催化剂作用下进行封闭反应；S2、反应后，除去所述催化剂，获得中间产物；S3、将所述中间产物真空蒸馏，获得γ‑氨基丁酰胺。本发明提供了一种制备γ‑氨基丁酰胺的新方法，该方法显著提高了γ‑氨基丁酰胺产物的收率，本发明方法的产物总收率可以达到94％以上。本发明方法中所用的原料简单易得，制备过程简单，反应条件温和、易于控制，本发明的反应原料利用率高。

  公开号：

  CN117105803A

文献信息

• Unfused heterobicycles as amplifiers of phleomycin. V. A range of pyridinylpyrimidines with strongly basic side chains
  作者：DJ Brown、WB Cowden

  DOI：10.1071/ch9821203

  日期：——

  The condensation of 3-aminocrotonamide with ethyl pyridine-2-carboxylate or a related ester gave 6-methylpyrimidin-4(3H)-ones, each bearing at its 2-position a pyridin-2'-yl, pyridin-3'-yl, pyridin- 4'-yl, furan-2'-yl, furan-3'-yl, thien-2'-yl or pyrazin-2'-yl substituent. Of these, the pyridinyl derivatives (1a), (2a) and (3a) were converted into their 4-chloro analogues and thence by nucleophilic displacement into the corresponding β-dimethylaminoethylthio, β-dimethylaminoethylamino, β-dimethylaminoethoxy and γ-dimethylaminopropylamino derivatives. The activities of these compounds as amplifiers of phleomycin against Escherichia coli are reported.

  将 3-aminocrotonamide 与吡啶-2-羧酸乙酯或相关酯类缩合后得到 6-甲基嘧啶-4(3H)-酮，每个酮的 2-位上都含有吡啶-2'-基、吡啶-3'-基、吡啶-4'-基、呋喃-2'-基 2'-基、吡啶-3'-基、吡啶-4'-基、呋喃-2'-基、呋喃-3'-基、噻吩-2'-基或吡嗪-2'-基。 或吡嗪-2'-基取代基。其中，吡啶基衍生物 (1a)、(2a) 和 (3a) (3a) 转化为它们的 4-氯类似物，然后通过亲核 置换成相应的 β-二甲氨基乙硫基、β-二甲氨基乙氨基、 β-二甲氨基乙氧基和 γ-二甲氨基丙基氨基衍生物。这些 报告了这些化合物作为夫来霉素的放大剂对大肠杆菌的活性。
• Unfused heterobicycles as amplifiers of phleomycin. VI. Some thienyl- and thiazolyl-pyrimidines with strongly basic side chains
  作者：DJ Brown、WB Cowden、L Strekowski

  DOI：10.1071/ch9821209

  日期：——

  2-Chloro-4-(thien-2'-yl)pyrimidine (2a) and its thiazol-2'-yl analogue (2d) are prepared by condensation of 2-chloropyrimidine with thien-2-yl- and thiazol-2-yl-lithium, followed by oxidation of the dihydro intermediates. 4-Chloro-6-methyl-2-(thien-2'-yl)pyrimidine (3b),its 2-(2',4'-dimethylthiazol-5'-yl) analogue (3f) and the 2-(2'-methylthiazol-4'-yl) analogue (4b) are made from the corresponding pyrimidinones, which are available by primary synthesis. Each chloro compound is converted by nucleophilic displacement into its β-dimethylaminoethylamino and β-dimethylaminoethylthio derivatives, for which activities as amplifiers of phleomycin are reported and discussed.

  2-氯-4-(噻吩-2'-基)嘧啶(2a)及其噻唑-2'-基类似物(2d)的制备方法是 通过 2-氯嘧啶与噻吩-2'-基和噻唑-2'-基锂缩合，然后通过噻唑-2'-基类似物 噻唑-2'-基锂缩合，然后氧化二氢 中间体。4-氯-6-甲基-2-(噻吩-2'-基)嘧啶 (3b)、其 2-（2',4'-二甲基噻唑-5'-基）类似物（3f）和 2-(2'-甲基噻唑-4'-基)类似物(4b)由相应的嘧啶酮类化合物制成，这些化合物可通过初级合成获得。 每个氯代化合物通过亲核置换转化为其 β-二甲基氨基乙基氨基 和 β-二甲氨基乙硫基 衍生物，并报告和讨论了这些衍生物作为新霉素扩增剂的活性。 讨论。
• 一种3-氨基丁酰胺类化合物的制备方法
  申请人：浙江工业大学

  公开号：CN107501120B

  公开（公告）日：2019-10-18

  本发明公开了一种3‑氨基丁酰胺类化合物的制备方法，所述方法为：以式(I)所示化合物为原料，在氨水中，于20～70℃下反应完全后，得式(II)所示化合物；将式(II)所示化合物加入溶剂中，以雷尼镍为催化剂，在30～50℃、0.1MPa～1.5MPa的条件下进行还原加氢反应，得式(III)所示化合物；本发明反应工艺条件简单，反应条件温和，是常规的氨解反应(现有氨解反应需要高压设备，且耗能较高)和加氢还原反应，且氨解反应的氨解母液可直接循环套用，操作简便。所得产物收率和纯度都较高，总收率在77％以上，纯度在98％以上。本发明方法是适用于工业产业化的3‑氨基丁酰胺类化合物的制备方法，对环境友好。
• Studies on ketene and its derivatives. LXXVI. Reactions of acetoacetamide and .BETA.-aminocrotonamide with .BETA.-diketone, .BETA.-ketoaldehyde and related compounds.
  作者：TETSUZO KATO、MASAKI NODA

  DOI：10.1248/cpb.24.303

  日期：——

  Reactions of acetoacetamide (I) and β-aminocrotonamide (II) with 1, 3-dioxo and related compounds were investigated. Namely, the reaction of I with 2, 4-pentanedione (III), 4-methoxy-3-pentene-2-one (VIII), 2-formylcyclohexanone (IV), 4-hydroxy-3-butene-2-one (Va), ethyl 2-ethoxymethyleneacetoacetate (Vb), and 3-ethoxymethylene-2, 4-pentanedione (Vc) afforded 3-acetyl-4, 6-dimethyl-2 (1H)-pyridone (IX), 3-acetyl-5, 6, 7, 8-tetrahydro-2-quinolone (X), 3-acetyl-6-methyl-2 (1H)-pyridone (XIa), ethyl 5-acetyl-6-methyl-2 (1H)-pyridone-3-carboxylate (XIb), and 3, 5-diacetyl-6-methyl-2 (1H)-pyridone (XIc), respectively. On the other hand, the reaction of II with III, 4-amino-3-penten-2-one (VI), 4, 4-dimethoxy-2-butanone (VII), and IV resulted in the formation of 2, 4, 6-trimethyl-3-pyridinecarboxamide (XII), 2, 6-dimethyl-3-pyridinecarboxamide (XV), and 2-methyl-5, 6, 7, 8-tetrahydro-3-quinolinecarboxamide (XIV), respectively. In the case of the reaction of II with Vb, ethyl 5-carbamoyl-2, 6-dimethyl-3-pyridinecarboxylate (XVIIa), ethyl 2-[(2-carbamoyl-1-methylvinylamino) methylene] acetoacetate (XVIIIa) were obtained. Similarly, II reacted with Vc to give 5-acetyl-2, 6-dimethyl-3-pyridinecarboxamide (XVIIb) and 3-[(2-carbamoyl-1-methylvinylamino) methylene]-2, 4-pentanedione (XVIIIb).

  研究了乙酰乙酰胺（I）和 β-氨基巴豆酰胺（II）与 1，3-二氧代及相关化合物的反应。即 I 与 2，4-戊二酮 (III)、4-甲氧基-3-戊烯-2-酮 (VIII)、2-甲酰基环己酮 (IV)、4-羟基-3-丁烯-2-酮 (Va)、2-乙氧基亚甲基乙酰乙酸乙酯 (Vb) 和 3-乙氧基亚甲基-2，4-戊二酮 (Vc) 反应，得到 3-乙酰基-4、6-二甲基-2(1H)-吡啶酮（IX）、3-乙酰基-5，6，7，8-四氢-2-喹啉酮（X）、3-乙酰基-6-甲基-2(1H)-吡啶酮（XIa）、5-乙酰基-6-甲基-2(1H)-吡啶酮-3-羧酸乙酯（XIb）和 3，5-二乙酰基-6-甲基-2(1H)-吡啶酮（XIc）。另一方面，II 与 III、4-氨基-3-戊烯-2-酮 (VI)、4, 4-二甲氧基-2-丁酮 (VII) 和 IV 反应，分别生成 2, 4, 6-三甲基-3-吡啶甲酰胺 (XII)、2, 6-二甲基-3-吡啶甲酰胺 (XV) 和 2-甲基-5, 6, 7, 8-四氢-3-喹啉甲酰胺 (XIV)。在 II 与 Vb 的反应中，得到了 5-氨基甲酰基-2，6-二甲基-3-吡啶甲酸乙酯（XVIIa）和 2-[（2-氨基甲酰基-1-甲基乙烯氨基）亚甲基]乙酰乙酸乙酯（XVIIIa）。同样，II 与 Vc 反应生成 5-乙酰基-2，6-二甲基-3-吡啶甲酰胺（XVIIb）和 3-[（2-氨基甲酰基-1-甲基乙烯氨基）亚甲基]-2，4-戊二酮（XVIIIb）。
• Synthesis and Characterization of New Boron Compounds Using Reaction of Diazonium Tetraphenylborate with Enaminoamides
  作者：Markéta Svobodová、Jan Svoboda、Bing-Han Li、Valerio Bertolasi、Luboš Socha、Miloš Sedlák、Lukáš Marek

  DOI：10.3390/molecules27020367

  日期：——

  prepared by reaction of polarized ethylenes, such as β-enaminoamides, with 4-methylbenzenediazonium tetraphenylborates. The reaction conditions (stirring in CH2Cl2 at room temperature (Method A) or stirring with CH3COONa in CH2Cl2 at room temperature (Method B) or refluxing in the CH2Cl2/toluene mixture (Method C)) controlled the formation and relative content of these compounds in the reaction mixtures

  通过极化乙烯（例如 β-烯氨基酰胺）与 4-甲基苯重氮四苯基硼酸盐反应制备了一系列恶氮硼烷、二氮杂硼烷、三氮杂硼烷和三氮杂硼烷。反应条件（在室温下在 CH2Cl2 中搅拌（方法 A）或在室温下与 中的 CH3COONa 一起搅拌（方法 B）或在 /甲苯混合物中回流（方法 C））控制这些化合物的形成和相对含量一到三种产物的反应混合物。在 250 °C 时，取代的 oxazaborines 逐渐重排为 diazaborinones。制备的化合物通过 1H NMR、13C NMR、IR 和 UV-Vis 光谱、HRMS 或微量分析进行表征。单个化合物的结构通过 11B NMR、15N NMR、1D NOESY 和 X 射线分析确认。