1-甲基-1H-咪唑-4,5-二甲腈 | 19485-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-1H-咪唑-4,5-二甲腈
• 中文别名: 4,5-二氰基-1-甲基-1H-咪唑；1-甲基咪唑-4,5-二甲腈
• 英文名称: 1-methyl-4,5-dicyanoimidazole
• 英文别名: 1-methyl-1H-imidazole-4,5-dicarbonitrile；4,5-dicyano-1-methylimidazole；1-Methyl-4,5-dicyanoimidazol；1-methylimidazole-4,5-dicarbonitrile
• CAS: 19485-35-9
• 化学式: C₆H₄N₄
• mdl: MFCD01567299
• 分子量: 132.125
• InChiKey: SUOVGHDPXJUFME-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85
• 沸点：
  148-150/0.5mm
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下稳定，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xn,Xi
• 危险类别码：
  R25
• 危险品运输编号：
  3439
• 海关编码：
  2933290090
• 包装等级：
  III
• 危险类别：
  6.1
• 安全说明：
  S20,S26,S36/37,S45,S60,S9
• 危险性防范说明：
  P261,P280,P305+P351+P338,P304+P340,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H331,H335
• 储存条件：
  常温密闭避光，通风干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,5-Dicyano-1-methyl-1H-imidazole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H331: Toxic if inhaled
H302: Harmful if swallowed
H312: Harmful in contact with skin
Causes skin irritation
H315:
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 4,5-Dicyano-1-methyl-1H-imidazole
CAS number: 19485-35-9

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H6N4
Molecular weight: 132.1

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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
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (4,5-Dicyano-1-methyl-1H-imidazole)

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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

反应信息

• 作为反应物：
  描述：

  1-甲基-1H-咪唑-4,5-二甲腈 在 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 4,5-bis(hydroxymethyl)-1-methyl-1H-imidazole
  参考文献：
  名称：

  yl鎓环化的N-杂环卡宾。

  摘要：

  通过氢化物从相关的环庚三烯化合物中提取氢化物，可以得到阳离子对苯二甲酰基咪唑基亚烷基ITrop +的衍生物。光谱，结构和理论数据表明，ITrop +作为苯并咪唑基亚胺的阳离子亲和性，具有高度还原的σ供体和强的π受体特性。

  DOI：

  10.1039/d0cc04482b
• 作为产物：
  描述：

  2-溴-1-甲基-1H-咪唑-4,5-二甲腈 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以48%的产率得到1-甲基-1H-咪唑-4,5-二甲腈
  参考文献：
  名称：

  Apen, Paul G.; Rasmussen, Paul G., Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1091 - 1095

  摘要：

  DOI：

文献信息

• [EN] ANTICANCER COMBINATION THERAPY WITH N-(1-ACRYLOYL-AZETIDIN-3-YL)-2-((1H-INDAZOL-3-YL)AMINO)METHYL)-1H-IMIDAZOLE-5-CARBOXAMIDE INHIBITOR OF KRAS-G12C<br/>[FR] POLYTHÉRAPIE ANTICANCÉREUSE AVEC UN INHIBITEUR DE N-(1-ACRYLOYL-AZÉTIDIN-3-YL)-2-((1H-INDAZOL-3-YL) AMINO) MÉTHYL)-1 H-IMIDAZOLE-5-CARBOXAMIDE DE KRAS-G12C
  申请人：TAIHO PHARMACEUTICAL CO LTD

  公开号：WO2021215545A1

  公开（公告）日：2021-10-28

  A method of treating cancer comprises administering: (a) a therapeutically effective amount of a compound of Formula (I) or a pharmaceutically acceptable salt thereof; and (b) a therapeutically effective amount of an additional anti-cancer agent, to a subject in need of such treatment, the compound of Formula (I) being: where X, R1, R2, ring A, L1, L2, L3, and R5 are as defined in this disclosure.

  治疗癌症的方法包括向需要此类治疗的受试者施用：(a) 公式(I)的化合物或其药用可接受的盐的治疗有效量；和(b) 另一种抗癌药物的治疗有效量，其中公式(I)的化合物为：其中X、R1、R2、环A、L1、L2、L3和R5的定义如本公开说明书中所定义。
• Convenient Synthesis of Methyl 1-Methyl-2,4-dibromo-5-imidazolecarboxylate
  作者：John F. O'Connell、Jonathan Parquette、William E. Yelle、Wilhelm Wang、Henry Rapoport

  DOI：10.1055/s-1988-27702

  日期：——

  Three syntheses of methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8) are presented. One proceeds from sarcosine via ring closure, bromination, and desulfurization. The second uses N-methylimidazole, polybromination, and selective halogen-metal interchange. The third and most efficient and preparatively useful route begins with diaminomaleonitrile (13). Ring closure with triethyl orthoformate followed by methylation and hydrolysis affords 1-methyl-4,5-imidazoledicarboxylic acid (16). Regioselective decarboxylation followed by esterification yields methyl 1-methyl-5-imidazolecarboxylate (18). Subsequent dibromination gives the completely substituted imidazole 8. The primary purification in this sequence is fractional sublimation of 18 after the esterification step. An overall yield of 26% is achieved from diaminomaleonitrile (13) to methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8), which is a key intermediate for the synthesis of tricyclic imidazo cooked food mutagens.

  介绍了三种合成甲基1-甲基-2,4-二溴-5-咪唑甲酸酯(8)的方法。第一种方法是通过肌氨酸的环化、溴化和脱硫步骤进行。第二种方法使用N-甲基咪唑、多溴化和选择性卤素-金属互换。第三种方法最为高效且实用，始于二氨基富马腈(13)。通过三乙基原甲酸酯进行环化，随后甲基化和水解得到1-甲基-4,5-咪唑二羧酸(16)。区域选择性脱羧后再酯化得到甲基1-甲基-5-咪唑甲酸酯(18)。后续的双溴化得到完全取代的咪唑8。在此序列中主要的纯化步骤是酯化步骤后的分馏升华。从二氨基富马腈(13)到甲基1-甲基-2,4-二溴-5-咪唑甲酸酯(8)的总收率为26%，后者是合成三环咪唑熟食诱变剂的关键中间体。
• WATER-SOLUBLE CAMPTOTHECIN DERIVATIVE, PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：Zhou Wenqiang

  公开号：US20140155336A1

  公开（公告）日：2014-06-05

  The present invention relates to a water soluble derivative of camptothecin and preparation method thereof, the derivative having a structure of formula I and being appropriate in water solubility, and having anti-cancer activity and stability of lactonic ring. The present invention also relates to a method for synthesizing the compound and medical use of the compound.

  本发明涉及一种水溶性紫杉醇衍生物及其制备方法，所述衍生物具有式I的结构，在水溶性方面适宜，并具有抗癌活性和内酯环的稳定性。本发明还涉及一种合成该化合物的方法以及该化合物的医药用途。
• CAMPTOTHECIN DERIVATIVE, AND PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION AND APPLICATION
  申请人：Zhou Wenqiang

  公开号：US20140107342A1

  公开（公告）日：2014-04-17

  The present invention relates to a camptothecin derivative having a structure as represented by Formula (II), in which X n+ is selected from H + , K + , Na + , Li + , Mg 2+ , Ca 2+ , Zn 2+ , Fe 3+ , and ammonium ion, while R 1 , R 2 , R 3 , and R 4 independently represent a hydrogen, a hydroxyl group, a nitro group, a cyano group, a halogen, a carboxyl group, an optionally substituted amino group, a silicon-containing group, a monocyclic aryloxy group, an optionally substituted C1-C6 alkoxy group, an optionally substituted C1-C6 alkylcarbonyl group, an optionally substituted C1-C6 alkyl group, or an optionally substituted C3-C6 cycloalkyl group; alternatively, R 1 and R 2 are connected via one to three other atoms to form a heterocyclic ring; and in another embodiment, R 3 and R 4 are oxygen atoms and connected via —O—(CH 2 ) n —O—, forming a ring, in which n=I or 2. The compound has great water-solubility, chemical stability, and great efficacy in treatment on cancer.

  本发明涉及一种具有如下式（II）所表示结构的紫杉醌衍生物，其中X n+ 选自H + 、K + 、Na + 、Li + 、Mg 2+ 、Ca 2+ 、Zn 2+ 、Fe 3+ 和铵离子，而R 1 、R 2 、R 3 和R 4 独立地代表氢、羟基、硝基、氰基、卤素、羧基、可选择取代的氨基、含硅基团、单环芳氧基团、可选择取代的C1-C6烷氧基团、可选择取代的C1-C6烷基羰基团、可选择取代的C1-C6烷基团，或可选择取代的C3-C6环烷基团；或者，R 1 和R 2 通过一到三个其他原子连接形成杂环环；在另一实施例中，R 3 和R 4 是氧原子，并通过—O—(CH 2 ) n —O—连接形成一个环，其中n=1或2。该化合物具有很高的水溶性、化学稳定性，并在癌症治疗中具有很高的功效。
• Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands
  作者：Maria Anastassiadou、Saı̈da Danoun、Louis Crane、Geneviève Baziard-Mouysset、Marc Payard、Daniel-Henri Caignard、Marie-Claire Rettori、Pierre Renard

  DOI：10.1016/s0968-0896(00)00280-7

  日期：2001.3

  heterocyclic-imidazoline compounds have been prepared and evaluated in vitro as imidazoline sites (I1 and I2) and alpha-adrenergic (alpha1 and alpha2) receptor ligands. Their pKi values indicate that linkage of the imidazoline moiety at the 2-position with an aromatic substituent dramatically decreases alpha-adrenergic affinity. I1 sites are more accessible by phenyl imidazolines substituted by a methyl or a methoxy

  已经制备了几种系列的2-芳基或杂环-咪唑啉化合物，并在体外评估为咪唑啉位点（I1和I2）和α-肾上腺素能（α1和α2）受体配体。它们的pKi值表明2-位咪唑啉部分与芳族取代基的连接显着降低了α-肾上腺素的亲和力。通过在邻位或间位上被甲基或甲氧基取代的苯基咪唑啉更易于接近I1位点。实际上，2-（2'-甲氧基苯基）-咪唑啉（17）是有史以来最好的I1配体之一（pKi = 8.53，I1 / I2> 3388）。另一方面，在对位中存在甲基时，I 2选择性增加。原始化合物2-（3'-氟-4'-甲苯基）-咪唑啉（31）是I2位点的新有效配体，具有高选择性（pKi = 8。