2-氨基-2,3-二甲基丁腈 | 13893-53-3

• 物质功能分类: 化学农药原药 - 除草剂 - 除草剂中间体
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氨基-2,3-二甲基丁腈
• 英文名称: 2-amino-2,3-dimethylbutyronitrile
• 英文别名: 2-amino-2,3-dimethylbutanenitrile
• CAS: 13893-53-3
• 化学式: C₆H₁₂N₂
• mdl: MFCD00661864
• 分子量: 112.175
• InChiKey: CAOHBROWLMCZRP-UHFFFAOYSA-N

物化性质

• 沸点：
  43 °C
• 密度：
  0.896±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇（少许）
• LogP：
  0.7 at 23℃ and pH6.1-10.5
• 解离常数：
  5 at 25℃
• 物理描述：
  Liquid

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-2,3-dimethylbutyronitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-2,3-dimethylbutyronitrile
CAS number: 13893-53-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H12N2
Molecular weight: 112.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

2-氨基-2,3-二甲基丁腈被青生红球菌用于生物合成2-氨基-2,3-二甲基丁酰胺，它是合成强效咪唑啉除草剂的重要中间体。此外，它还用于制备新的手性配体。

化学性质

该物质为无色液体，呈碱性，沸点85～87℃/0.94 kPa，折射率25(D) 1.4333，微溶于水，可与乙醚、乙醇等有机溶剂互溶。

用途

2-氨基-2,3-二甲基丁腈是合成咪草酸、咪唑烟酸、咪唑乙烟酸、咪唑喹啉酸和甲氧咪草烟等多种咪唑啉酮类除草剂的中间体。

生产方法

其制备方法是在反应瓶中加入氰化钠、水及浓氨水，室温下搅拌至氰化钠完全溶解，再加入NH4Cl和相转移催化剂苄基三乙基氯化铵，在搅拌下滴加甲基异丙基酮，控制滴加速度以保持液温不超过30℃。滴加完毕后，继续室温搅拌4～6小时，分层静置，分出有机相。水相用二氯甲烷萃取2次，合并有机相并用无水硫酸钠干燥。有机相经过滤，滤液常压蒸馏回收二氯甲烷，并蒸去少量未反应的甲基异丙基酮。减压蒸馏收集85～87℃/0.94 kPa馏分得到成品。

反应信息

• 作为反应物：
  描述：

  2-氨基-2,3-二甲基丁腈 在 ammonium hydroxide 、 双氧水 作用下， 生成 2-氨基-2,3-二甲基丁酰胺
  参考文献：
  名称：

  Preparation, 1H and 13C NMR Spectra of Substituted 2-Benzoylaminocarboxamides

  摘要：

  一种基于咪唑啉酮的新型除草剂自1983年起由美国赛诺美公司推出，商业名称为Arsenal、Pursuit、Scepter、Assert等。这些化合物能够消灭双子叶杂草，对哺乳动物和鱼类几乎无毒（LD₅₀ 大鼠 - 500 毫克/千克，LD₅₀ 鳟鱼 - 300 毫克/千克），根据AMES试验结果，这些化合物不具有致突变性。本研究的目的是合成取代的2-苯甲酰氨基羧酰胺，作为制备咪唑啉酮和潜在生物活性物质的起始原料（式 I - III）。

  DOI：

  10.1135/cccc19950150
• 作为产物：
  描述：

  L-酒石酸 在 氨 作用下， 以 水 为溶剂， 生成 2-氨基-2,3-二甲基丁腈
  参考文献：
  名称：

  Process for the resolution of certain racemic amino nitriles

  摘要：

  这项发明是关于通过它们各自的酒石酸盐对某些取代的混合氨基腈进行选择性和同时的分离-消旋-分离的过程。该发明还涉及由上述氨基腈制备的某些已分离（旋光活性）氨基酰胺，以及由此制备的具有除草作用的取代氧代咪唑啉基烟酸和3-喹啉羧酸。

  公开号：

  US04683324A1

文献信息

• Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures
  作者：Saidul Islam、Dejan-Krešimir Bučar、Matthew W. Powner

  DOI：10.1038/nchem.2703

  日期：2017.6

  permits ribonucleotide synthesis, even from complex sugar mixtures. Remarkably, aminal formation also overcomes the thermodynamically favoured isomerization of glyceraldehyde into dihydroxyacetone because only the aminal of glyceraldehyde separates from the equilibrating mixture. Finally, we show that aminal formation provides a novel pathway to amino acids that avoids the synthesis of the non-proteinogenic

  益生元合成生物氨基酸和核苷酸的主要问题是避免伴随合成不希望的或不相关的副产物。另外，多步路径需要能够使反应物顺序添加和纯化中间体的机制，这与合理的地球化学情况一致。在这里，我们表明2-氨基噻唑与二碳糖和三碳糖（分别为甘醇醛和甘油醛）选择性反应，从而导致它们的积累和纯化为稳定的结晶类缩醛胺。这允许甚至从复杂的糖混合物中合成核糖核苷酸。值得注意的是 氨醛的形成还克服了甘油醛热力学上有利于异构化为二羟基丙酮的异构化问题，因为只有甘油醛的氨醛才从平衡混合物中分离出来。最后，我们表明氨基形成为氨基酸提供了一种新颖的途径，从而避免了非蛋白质生成的α，α-二取代类似物的合成。控制益生元混合物中蛋白质氨基酸和核糖核苷酸装配的常见物理化学机制表明，这些必需的代谢物类别具有统一的化学起源。
• Substituent Effect on Acidity of Substituted 2-(4-Nitrobenzoylamino)alkanamides in Methanol-Dimethyl Sulfoxide Mixtures
  作者：Petr Mitaš、Miloš Sedlák、Jaromír Kaválek

  DOI：10.1135/cccc19980085

  日期：——

  The dissociation constants of substituted 2-(4-nitrobenzoylamino)alkanamides, N-[2-(4-nitrobenzoylamino)alkanoyl]pyrrolidines, and N-alkyl-4-nitrobenzamides have been measured spectrophotometrically in 60 and 80% v/v DMSO. The pK_A values of these N-acids are discussed from the point of view of substituents at the acetamide α-carbon atom.

  已发送中文翻译结果。如果您有任何其他问题或需要进一步帮助，请随时告诉我。谢谢！
• Ruthenium‐Catalyzed Deaminative Hydrogenation of Amino Nitriles: Direct Access to 1,2‐Amino Alcohols
  作者：Pilar Calleja、Martin Ernst、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1002/chem.201900531

  日期：2019.7.17

  approach for the efficient and highly selective synthesis of 1,2‐amino alcohols by direct reductive hydrolysis of N‐formyl‐protected α‐amino nitriles is reported. The commercially available RuHCl(CO)(PPh3)3 complex was found to be a suitable catalyst for this operationally simple protocol, in which no stoichiometric amounts of undesired metal waste are generated. The deaminative hydrogenation is performed

  报道了一种通过N-甲酰基保护的α-氨基腈直接还原水解来高效，高选择性合成1,2-氨基醇的新方法。发现可商购获得的RuHCl（CO）（PPh 3）3络合物对于该操作简单的方案是合适的催化剂，其中不产生化学计量的不希望的金属废物。脱氨氢化反应在55 bar H 2下进行，使用1,4-二恶烷/水的6：1混合物作为溶剂。另外，在非常相似的条件下由氰基酮制备羟甲基醇。
• [EN] PROCESS FOR PRODUCING SUBSTITUTED AMINO ALCOHOLS<br/>[FR] PROCÉDÉ DE PRODUCTION D'AMINO-ALCOOLS SUBSTITUÉS
  申请人：BASF SE

  公开号：WO2020094454A1

  公开（公告）日：2020-05-14

  The present invention relates to a process for producing a compound of the formula (I) comprising at least the process step: a) reacting a compound of the formula (II) with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.

  本发明涉及一种制备式(I)化合物的方法，至少包括以下步骤：a) 在至少一种均相过渡金属催化剂TMC 1存在下，将式(II)化合物与氢气和水反应。
• [EN] PROCESS FOR THE RACEMISATION OF ENANTIOMERICALLY ENRICHED ALPHA-AMINO NITRILES<br/>[FR] METHODE DE RACEMISATION D'ALPHA-AMINONITRILES ENRICHIS D'ENANTIOMERES
  申请人：DSM IP ASSETS BV

  公开号：WO2004046088A1

  公开（公告）日：2004-06-03

  Process for the racemisation of an enantiomerically enriched α-amino nitrile characterized in that the enantiomerically enriched α-amino nitrile is contacted with a lewis acid catalyst. Preferably an aprotic solvent is used. The lewis acid catalyst preferably comprises a metal chosen from main group elements IA-IVA of the Periodic Table (CAS version), the transition metals and the lanthanides, in particular Al, Ti, Zr, or lanthanides. The catalsyt for example has the general structure MnXpSqLr, and preferably is chosen from the group of aluminum alkoxides, aluminum alkyls, lanthanide alkoxydes and lanthanocenes. The racemisation may be performed in combination with a resolution process, for instance in combination with an enzymatic or a crystallization induced resolution process, preferably in situ, for instance in situ in a crystallization induced asymmetric transformation process.

  对富集对映体的α-氨基腈进行消旋的过程特点在于将富集对映体的α-氨基腈与路易斯酸催化剂接触。最好使用无水溶剂。路易斯酸催化剂最好包括从周期表（CAS版本）的主族元素IA-IVA、过渡金属和镧系元素中选择的金属，特别是铝、钛、锆或镧系元素。例如，催化剂具有一般结构MnXpSqLr，最好从铝烷氧化物、铝烷基、镧系烷氧化物和镧系烷基中选择。消旋可以与分离过程结合进行，例如与酶法或结晶诱导的分离过程结合，最好是原位的，例如在结晶诱导的不对称转化过程中原位进行。