1-甲基-1H-咪唑-4-甲腈 | 66121-69-5

• 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-甲腈
• 英文名称: 1-methyl-1H-imidazole-4-carbonitrile
• 英文别名: 1-methylimidazole-4-carbonitrile；4-cyano-1-methylimidazole；1-methyl-4-cyanoimidazole
• CAS: 66121-69-5
• 化学式: C₅H₅N₃
• 分子量: 107.115
• InChiKey: LAKVILSENFFPRR-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  314.1±15.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥环境中存放。

SDS

Name:	1-Methyl-1H-imidazole-4-carbonitrile Material Safety Data Sheet
Synonym:	None Known
CAS:	66121-69-5

Section 1 - Chemical Product MSDS Name:1-Methyl-1H-imidazole-4-carbonitrile Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
66121-69-5	1-Methyl-1H-imidazole-4-carbonitrile	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin. May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration.
Chronic:
Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes.

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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:
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. Wash mouth out with 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 water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 66121-69-5: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 64 - 66 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H5N3
Molecular Weight: 107.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 66121-69-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Methyl-1H-imidazole-4-carbonitrile - 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 SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
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.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 66121-69-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 66121-69-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 66121-69-5 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

反应信息

• 作为反应物：
  描述：

  1-甲基-1H-咪唑-4-甲腈 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 盐酸羟胺 、 palladium diacetate 、 2-氯-1,3-二甲基氯化咪唑啉 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 pivalic anhydride 、 sodium hydroxide 、 sodium t-butanolate 、 N,N'-二甲基乙二胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~100.0 ℃ 、122.02 kPa 条件下， 反应 68.5h， 生成 N,N-二环丙基-4-[(1,5-二甲基-1H-吡唑-3-基)氨基]-6-乙基-1,6-二氢-1-甲基-咪唑并[4,5-d]吡咯并[2,3-b]吡啶-7-甲酰胺
  参考文献：
  名称：

  Ni-Catalyzed C–H Functionalization in the Formation of a Complex Heterocycle: Synthesis of the Potent JAK2 Inhibitor BMS-911543

  摘要：

  BMS-911543 is a complex pyrrolopyridine investigated as a potential treatment for myeloproliferative disorders. The development of a short and efficient synthesis of this molecule is described. During the course of our studies, a Ni-mediated C-N bond formation was invented, which enabled the rapid construction of the highly substituted 2-aminopyridine core. The synthesis of this complex, nitrogen-rich heterocycle was accomplished in only eight steps starting from readily available materials.

  DOI：

  10.1021/acs.joc.5b00572
• 作为产物：
  描述：

  ethyl 4-cyano-1-methyl-1H-imidazole-5-carboxylate 在 四乙基氢氧化铵 作用下， 以 水 为溶剂， 反应 0.58h， 生成 1-甲基-1H-咪唑-4-甲腈
  参考文献：
  名称：

  Synthesis and assignments of regioisomeric cyanoimidazole esters

  摘要：

  Regioassignments of ethyl cyanoimidazolecarboxylates have been performed by the nuclear Overhauser effect(NOE) studies on the regioisomeric monocyanoimidazdes obtained by the hydrolysis of the esters followed by decarboxylation. Alternately, regioassignment could also be carried out by comparing the chemical shifts of the N-methyl groups.

  DOI：

  10.1016/s0040-4020(01)86980-5

文献信息

• Regiochemistry of N-substitution of some 4(5)-substituted imidazoles under solvent-free conditions
  作者：Larisa Oresmaa、Helena Taberman、Matti Haukka、Pirjo Vainiotalo、Paula Aulaskari

  DOI：10.1002/jhet.5570440632

  日期：2007.11

  Imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole were N-benzylated and N-methylated using benzyl chloride and methyl iodide on zinc oxide (ZnO), alumina, and KF/alumina under basic conditions without solvent. Triethylamine (Et3N) or potassium carbonate was added as base in the reactions on ZnO and alumina. Imidazole-4(5)-carboxaldehyde was also benzylated on silica and carbon nanotubes. The effect

  在碱性条件下，在无溶剂的情况下，使用苄基氯和甲基碘在氧化锌（ZnO），氧化铝和KF /氧化铝上对N-苄基化和N-甲基化咪唑4（5）-甲醛和4（5）-氰基咪唑。在ZnO和氧化铝上的反应中，加入三乙胺（Et 3 N）或碳酸钾作为碱。咪唑-4（5）-甲醛在二氧化硅和碳纳米管上也被苄基化。研究了碱和固体对1,4-和1,5-取代的化合物的产物分布的影响。在某些情况下，咪唑-4（5）-甲醛和4（5）-氰基咪唑的产物比率不同。在KF /氧化铝上的反应中，两种化合物都偏爱1,4-产物。Et 3的组合N和ZnO有利于1,5-产物，但是腈的作用并不那么明显。当在催化量的氯化锌以Et 3 N为碱的条件下进行醛的N-苄基化和甲基化时，产物分布与在ZnO上的反应相同。在ZnCl 2存在下，腈在ZnO上给出不同的产物比率。另外，当咪唑在KF /氧化铝上被苄基化时，产生了N-苄基咪唑和1，3-二苄基咪唑的混合物。当使用两当量的苄基氯时，仅提供后者的产物。
• Substituted thieno[2,3-d]pyrimidines as adenosine A2A receptor antagonists
  作者：Brian C. Shook、Devraj Chakravarty、J. Kent Barbay、Aihua Wang、Kristi Leonard、Vernon Alford、Mark T. Powell、Stefanie Rassnick、Robert H. Scannevin、Karen Carroll、Nathaniel Wallace、Jeffrey Crooke、Mark Ault、Lisa Lampron、Lori Westover、Kenneth Rhodes、Paul F. Jackson

  DOI：10.1016/j.bmcl.2013.02.078

  日期：2013.5

  A novel series of benzyl substituted thieno[2,3-d]pyrimidines were identified as potent A2A receptor antagonists. Several five- and six-membered heterocyclic replacements for the optimized methylfuran were explored. Select compounds effectively reverse catalepsy in mice when dosed orally.

  一系列新的苄基取代的噻吩并[2,3- d ]嘧啶类化合物被认为是有效的A 2A受体拮抗剂。探索了几种用于优化甲基呋喃的五元和六元杂环取代基。口服时，选择的化合物可有效逆转小鼠的僵直。
• SUBSTITUTED BIARYLS, PROCESS FOR THEIR MANUFACTURE AND USE THEREOF AS MEDICAMENTS
  申请人：Dahmann Georg

  公开号：US20080051578A1

  公开（公告）日：2008-02-28

  The present invention relates to compounds of general formula (I) wherein A, B, L, R 1 , R 2 , R 3a and R 3b are defined as in the specification, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及一般式(I)的化合物，其中A、B、L、R1、R2、R3a和R3b如规范中定义，其互变异构体、对映体、非对映体、其混合物及其盐，特别是其与无机或有机酸或碱形成的生理上可接受的盐，具有有价值的性质。
• [EN] PROCESS FOR THE PREPARATION OF N,N-DICYCLOPROPYL-4-(1,5-DIMETHYL-1H-PYRAZOL-3-YLAMINO)-6-ETHYL-1-METHYL-1,6-DIHYDROIMIDAZO[4,5-d]PYRROLO[2,3-b]PYRIDINE-7-CARBOXAMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DU N,N-DICYCLOPROPYL-4-(1,5-DIMÉTHYL-1H-PYRAZOL-3YLAMINO)-6-ÉTHYL-1-MÉTHYL-1,6-DIHYDROIMIDAZO[4,5-D]PYRROLO[2,3-B]PYRIDINE-7-CARBOXAMIDE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015031562A1

  公开（公告）日：2015-03-05

  The invention relates to an improved process for synthesizing N,N-dicyclopropyl-4-(1,5-dimethyl-1H-pyrazol-3-ylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide of the formula: (I) Compound (I) is currently in clinical trials for the treatment of myeloproliferative disorders, such as polycythaemia vera, thrombocythaemia and primary myelofibrosis.

  该发明涉及一种改进的合成N,N-二环丙基-4-(1,5-二甲基-1H-吡唑-3-基氨基)-6-乙基-1-甲基-1,6-二氢咪唑并[4,5-d]吡咯并[2,3-b]吡啶-7-羧酰胺的方法，该化合物的化学式为：(I) 化合物(I)目前正在临床试验中用于治疗骨髓增殖性疾病，如真性红细胞增多症、血小板增多症和原发性骨髓纤维化。
• 유기 금속 착물, 이를 이용한 유기 전계 발광 소자 및 표시 장치
  申请人：SAMSUNG ELECTRONICS CO., LTD. 삼성전자주식회사(119981042713) Corp. No ▼ 130111-0006246BRN ▼124-81-00998

  公开号：KR102046153B1

  公开（公告）日：2019-12-02

  유기 금속 착물, 이를 이용한 유기 전계 발광 소자 및 표시 장치에 관한 것으로, 하기 화학식 1로 표시되는 유기 금속 착물을 제공할 수 있다. [화학식 1] 상기 화학식 1에 대한 정의는 명세서 내에 존재한다.

  这段文字的中文翻译如下：有机金属络合物，涉及利用该有机金属络合物制备有机电致发光器件和显示器件，可提供如下化学式1所示的有机金属络合物。关于上述化学式1的定义在规范文件中存在。