alpha-氰基异戊酸乙基酯 | 3213-49-8

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: alpha-氰基异戊酸乙基酯
• 中文别名: 异丙基氰乙酸乙酯
• 英文名称: ethyl 2-isopropylcyanoacetate
• 英文别名: ethyl 2-cyano-3-methylbutanoate；Isopropyl-cyanessigsaeure-ethylester；isopropylcyanoacetic acid ethyl ester
• CAS: 3213-49-8
• 化学式: C₈H₁₃NO₂
• mdl: MFCD02258612
• 分子量: 155.197
• InChiKey: UYXJMUDYWSXOTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  211℃ (739 Torr)
• 密度：
  0.962 g/cm3(Temp: 29.2 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Ethyl alfa-cyanoisovalerate
Synonyms: Ethyl 2-cyano-3-methylbutanoate

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Ethyl alfa-cyanoisovalerate
CAS number: 3213-49-8

---

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.

---

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.

---

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.

---

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.
Storage:

---

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.

---

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: C8H13NO2
Molecular weight: 155.2

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  alpha-氰基异戊酸乙基酯 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 3-甲基-2-亚甲基-丁酸
  参考文献：
  名称：

  Synthesis of mono- and sesquiterpenoids—IV

  摘要：

  DOI：

  10.1016/s0040-4020(01)92858-3
• 作为产物：
  描述：

  2-氰基-3-甲基丁烯酸乙酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 alpha-氰基异戊酸乙基酯
  参考文献：
  名称：

  钯催化α-氰基脂肪族羧酸盐的脱羧苯甲酰化，构建β-芳基腈

  摘要：

  发现了α-氰基脂肪族羧酸盐与苄基亲电试剂的钯催化脱羧苄基化反应。该反应表现出良好的官能团相容性，并且在相对温和的条件下进行。通过这种方法可以方便地制备各种范围的季，叔和仲β-芳基腈。

  DOI：

  10.1002/adsc.201200383

文献信息

• Synthesis of 4-amino[1] benzofuro[3,2-<i>g</i>] cinnolines
  作者：D. Ladurée、D. Florentin、M. Robba

  DOI：10.1002/jhet.5570170607

  日期：1980.9

  The synthesis of the new heterocycles, 4-amino[1]benzofuro[3,2-g]cinnolines, was accomplished by the intramolecular cyclization of the Z-configuration of cyanoarylhydrazones. The latter compounds were obtained via interaction between the diazonium salt of 3-amino-dibenzofuran and various active methylene compounds via the Japp-Klingemann reaction. The alkaline treatment of azo intermediates 4, which

  通过氰基芳基azo的Z-构型的分子内环化作用，完成了新的4-氨基[1]苯并呋喃[3,2- g ]喹啉杂环化合物的合成。后者的化合物是通过Japp-Klingemann反应通过3-氨基-二苯并呋喃的重氮盐与各种活性亚甲基化合物的相互作用而获得的。可以在缩合过程中分离出的偶氮中间体4进行碱处理，得到相应的氰基芳基hydr 5。据报道对构型和可能的异构化进行了研究。
• TERTIARY AMINE COMPOUND OR IMINE COMPOUND-POLYMER CONJUGATE AND PRODUCTION METHOD THEREFOR
  申请人：Seikagaku Corporation

  公开号：US20200138964A1

  公开（公告）日：2020-05-07

  Provided is a compound obtained by conjugating a tertiary amine compound or imine compound, which is useful as a drug, with a polymer, in which a structure D + having a quaternary ammonium salt or iminium salt formed from a tertiary amine compound or imine compound D and a polymer residue Poly having a carboxy group are bonded to each other via a structure —C(R 1 )(R 2 )OC(O)ANHC(═O)—.

  提供的是一种化合物，通过将一种三级胺化合物或亚胺化合物与聚合物共轭，用作药物，其中具有由三级胺化合物或亚胺化合物D形成的季铵盐或亚胺盐的结构D + 和具有羧基的聚合物残基Poly通过结构—C(R 1 )(R 2 )OC(O)ANHC(═O)—相互键合。
• Thiazole formation through a modified Gewald reaction
  作者：Carl J Mallia、Lukas Englert、Gary C Walter、Ian R Baxendale

  DOI：10.3762/bjoc.11.98

  日期：——

  The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the alpha-carbon to the cyano group.

  对于许多不同的底物，已经研究了通过改良的Gewald反应从腈开始合成噻唑和噻吩的方法。1,4-二噻吩-2,5-二醇用作醛前体，根据α-碳对氰基的取代作用，生成2-取代的噻唑或2-取代的氨基噻吩。
• AlCl₃ catalyzed coupling of N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon–nitrogen bond cleavage
  作者：Chen Hu、Gang Hong、Xiaofei Qian、Kwang Rim Kim、Xiaoyan Zhu、Limin Wang

  DOI：10.1039/c7ob01025g

  日期：——

  A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of the AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently

  报道了一种新的N-苄基磺酰胺与2-取代的氰基乙酸酯的交叉偶联反应，用于合成2-取代的苄基苯。在AlCl3的存在下，各种各样的N-苄基磺酰胺与2-取代的氰基乙酸酯平稳反应，以中等至极好的收率提供结构多样的苄基苯。转换可以有效地扩大到克级。该方法的实用性在具有高抗炎活性的相关生物活性剂的合成中得到进一步证明。
• Development of drug intermediates by using direct organocatalytic multi-component reactions
  作者：Dhevalapally B. Ramachary、M. Kishor、G. Babul Reddy

  DOI：10.1039/b602696f

  日期：——

  Novel, economic and environmentally friendly one-pot three-component Knoevenagel/hydrogenation (K/H) and four-component Knoevenagel/hydrogenation/alkylation (K/H/A) reactions of ketones, CH-acids, dihydropyridines and alkyl halides using proline and proline/metal carbonate catalysis, respectively, have been developed. Many of the products of these K/H and K/H/A reactions have direct applications in pharmaceutical chemistry.

  新颖、经济且环境友好的一锅法三组分Knoevenagel/氢化（K/H）和四组分Knoevenagel/氢化/烷基化（K/H/A）反应已被开发，这些反应分别使用脯氨酸和脯氨酸/金属碳酸盐作为催化剂，涉及酮类、CH-酸类、二氢吡啶类及卤代烷类物质。这些K/H和K/H/A反应的许多产物在药物化学领域具有直接应用价值。