2-苯基-1H-咪唑-4-缩醛 | 68282-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基-1H-咪唑-4-缩醛
• 中文别名: 2-苯基-1H-咪唑-4-甲醛
• 英文名称: 2-phenyl-1H-imidazole-4-carbaldehyde
• 英文别名: 2-phenyl-4-formylimidazole；2-phenyl-1H-imidazole-5-carbaldehyde
• CAS: 68282-47-3
• 化学式: C₁₀H₈N₂O
• mdl: MFCD00173729
• 分子量: 172.186
• InChiKey: LFKJFIOTRHYONM-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169°C
• 沸点：
  418.9±18.0 °C(Predicted)
• 密度：
  1.248

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 危险类别码：
  R21/22
• 海关编码：
  2933290090
• 安全说明：
  S22,S36/37/39
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

SDS

Name:	2-Phenyl-1H-imidazole-4-carbaldehyde 97% Material Safety Data Sheet
Synonym:	4-Formyl-2-phenylimidazol
CAS:	68282-47-3

Section 1 - Chemical Product MSDS Name:2-Phenyl-1H-imidazole-4-carbaldehyde 97% Material Safety Data Sheet
Synonym:4-Formyl-2-phenylimidazol

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
68282-47-3	2-Phenyl-1H-imidazole-4-carbaldehyde	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. 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:

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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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 68282-47-3: Personal Protective Equipment Eyes: Not available.
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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 167 - 169 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: C10H8N2O
Molecular Weight: 172

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 68282-47-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Phenyl-1H-imidazole-4-carbaldehyde - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 21/22 Harmful in contact with skin and if
swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 68282-47-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 68282-47-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 68282-47-3 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：

  2-苯基-1H-咪唑-4-缩醛 在 ALDH₂C₄ 、 nicotinamide adenine dinucleotide 作用下， 以 aq. buffer 为溶剂， 生成 2-苯基-1H-咪唑-4-羧酸单水合物
  参考文献：
  名称：

  家族 2 和家族 10 的植物醛脱氢酶氧化咪唑和吡唑衍生的醛

  摘要：

  家族 2 的植物胞质醛脱氢酶（ALDH2，EC 1.2.1.3）是非特异性酶，参与乙醛的代谢或苯丙素的生物合成等。植物氨基醛脱氢酶（AMADH、ALDH10 家族、EC 1.2.1.19）具有广泛的特异性，在多胺降解或渗透保护剂的产生中发挥着重要作用。我们测试了咪唑和吡唑甲醛及其烷基、烯丙基、苄基、苯基、嘧啶基或噻吩基衍生物作为植物 ALDH2 和 ALDH10 酶的可能底物。咪唑是组氨酸、组胺以及某些生物碱的组成部分。它也出现在合成药物中，例如咪唑抗真菌剂。含有吡唑的生物化合物很少见（例如吡唑-1-丙氨酸和吡唑呋林抗生素），但该环经常作为许多合成药物和农药的成分被发现。目的是评估基于唑杂环的醛化合物是否被酶氧化，这将进一步支持它们作为解毒醛清除剂的预期作用。所分析的咪唑和吡唑甲醛仅被 ALDH10 缓慢转化，但被胞质玉米 ALDH2 异构体（特别是 ALDH2C1）充分氧化。在后一种情况下，各自的K

  DOI：

  10.1016/j.cbi.2019.02.008
• 作为产物：
  描述：

  苯甲醛 在 氨 、 硝酸 、 copper(II) acetate monohydrate 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 2-苯基-1H-咪唑-4-缩醛
  参考文献：
  名称：

  13C CPMAS NMR 作为克服快速互变异构效应的 2-苯基取代咪唑的完整结构描述的工具

  摘要：

  迄今为止，尚未详细研究 2-苯基咪唑甲醛的互变异构化，尽管该过程对于咪唑衍生物来说是众所周知的现象。这就是为什么我们将研究重点放在一系列 2-苯基咪唑甲醛及其母体醇上，这些醇在溶液和固态下通过详细的 1H 和 13C NMR 合成和研究。明显的问题是快速互变异构阻碍了通过常规 13C NMR 测量对化合物的完整结构描述。事实上，溶液中的 13C NMR 光谱显示出较差的分辨率，并且在大多数情况下，无法检测到来自咪唑环的信号。为了避免这个问题，我们使用 13C CP-MAS NMR 作为替代光谱方法，用于对所研究的 2-苯基咪唑系列进行明确的光谱表征。通过考虑互变异构过程和分子间相互作用，结合量子化学DFT-GIAO方法对数据进行了分析。DFT (B3LYP/6-31G(d,p)) 计算允许识别和建议气相和 DMSO 溶剂中的优选互变异构体，对于醇类是（2-苯基-1H-咪唑-4-基）甲醇及其类似物，醛类是

  DOI：

  10.3390/molecules25173770

文献信息

• Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist
  申请人：SmithKline Beecham Corporation

  公开号：US05977101A1

  公开（公告）日：1999-11-02

  Vitronectin receptor antagonists having the formula: ##STR1## which are useful for the treatment of inflammation, cancer and cardiovascular disorders, such as atherosclerosis and restenosis, and diseases wherein bone resorption is a factor, such as osteoporsis.

  Vitronectin受体拮抗剂的化学式为：##STR1##，可用于治疗炎症、癌症和心血管疾病，如动脉粥样硬化和再狭窄，以及骨吸收是因素的疾病，如骨质疏松症。
• Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives: new classes of dopamine receptor subtype specific ligands
  申请人：Neurogen Corporation, Corporation of the State of Delaware

  公开号：US20030018025A1

  公开（公告）日：2003-01-23

  Disclosed are compounds of the formula: 1 wherein R 1 represents optionally substituted aryl, heteroaryl, arylalkyl, or cycloalkyl groups; X, Z, and Y are optionally substituted nitrogen or carbon atoms; R 3 and R 4 are organic or inorganic substitutents which may togther form ring structutes; m is zero, one or two; and R 5 and R 6 are are organic or inorganic substituents; and the pharmaceutically acceptable addition salts thereof, which compounds are highly selective partial agonists or antagonists at brain dopamine receptor subtypes or prodrugs thereof and are useful in the diagnosis and treatment of affective disorders such as schizophrenia and depression as well as certain movement disorders such as Parkinsonism.

  揭示了以下式的化合物： 其中R1代表可选择地取代的芳基、杂环芳基、芳基烷基或环烷基基团；X、Z和Y为可选择地取代的氮或碳原子；R3和R4为有机或无机取代基，可能共同形成环结构；m为零、一或二；R5和R6为有机或无机取代基； 以及其药学上可接受的盐， 这些化合物是高度选择性的部分激动剂或拮抗剂，作用于脑多巴胺受体亚型或其前药，并可用于诊断和治疗情感障碍，如精神分裂症和抑郁症，以及某些运动障碍，如帕金森病。
• Inhibitors of Acyl-CoA:Cholesterol <i>O</i>-Acyltransferase. 2. Identification and Structure−Activity Relationships of a Novel Series of <i>N</i>-Alkyl-<i>N</i>-(heteroaryl-substituted benzyl)-<i>N‘</i>-arylureas
  作者：Akira Tanaka、Takeshi Terasawa、Hiroyuki Hagihara、Yuri Sakuma、Noriko Ishibe、Masae Sawada、Hisashi Takasugi、Hirokazu Tanaka

  DOI：10.1021/jm9800853

  日期：1998.6.1

  tuted benzyl)-N'-arylurea and related derivatives represented by 2 and 3 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Among these novel compounds, the type 3 series was superior. A pyrazol-3-yl group on the N-benzyl group of this trisubstituted urea (i.e. 3, Ar1 =

  制备了一系列N-烷基-N-（杂芳基取代的苄基）-N'-芳基脲和相关的衍生物（用2和3表示），并对其在体外和体外抑制酰基辅酶A：胆固醇O-酰基转移酶的能力进行了评估。降低体内胆固醇喂养大鼠的血浆胆固醇水平。在这些新型化合物中，3型系列更为出色。该三取代脲的N-苄基上的吡唑-3-基（即3，Ar1 =吡唑-3-基）被鉴定为杂芳环，提供了良好的生物活性。通过优化与N-烷基（R）和N-芳基（Ar3）的组合的结果，化合物3aq（FR186054）被确定为一种新型的口服有效ACAT抑制剂，在胆固醇喂养的大鼠中表现出有效的体外ACAT抑制活性（兔子肠道微粒体IC50 = 99 nM）和出色的降胆固醇作用，而与给药方式无关（ED50 = 0.046 mg / kg，通过饮食给药，ED50 = 0. 44 mg /通过在PEG400载体中的管饲法施用1kg）。此外，一项毒理学研究表明，以10 mg / kg
• Structure−Activity Relationship Study of Prion Inhibition by 2-Aminopyridine-3,5-dicarbonitrile-Based Compounds:  Parallel Synthesis, Bioactivity, and in Vitro Pharmacokinetics
  作者：Barnaby C. H. May、Julie A. Zorn、Juanita Witkop、John Sherrill、Andrew C. Wallace、Giuseppe Legname、Stanley B. Prusiner、Fred E. Cohen

  DOI：10.1021/jm061045z

  日期：2007.1.1

  2-Aminopyridine-3,5-dicarbonitrile compounds were previously identified as mimetics of dominant-negative prion protein mutants and inhibit prion replication in cultured cells. Here, we report findings from a comprehensive structure-activity relationship study of the 6-aminopyridine-3,5-dicarbonitrile scaffold. We identify compounds with significantly improved bioactivity (approximately 40-fold) against

  2-氨基吡啶-3,5-二甲腈化合物以前被鉴定为显性负病毒蛋白突变体的模拟物，并抑制病毒在培养细胞中的复制。在这里，我们报告从6-氨基吡啶-3,5-二甲腈支架的全面的结构-活性关系研究中发现的结果。我们确定了具有明显改善的生物活性（约40倍）的抗感染性ion病毒同工型（PrPSc）复制和合适的药代动力学特征的化合物，以保证在病毒疾病的动物模型中进行评估。
• Pyrimidine, quinazoline, pteridine and triazine derivatives
  申请人：Binggeli Alfred

  公开号：US20070225271A1

  公开（公告）日：2007-09-27

  This invention is concerned with compounds of the formula wherein A, R 1 to R 5 and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.

  这项发明涉及以下式的化合物 其中A，R1至R5和G如描述和声明中所定义，并其药学上可接受的盐。该发明还涉及含有这种化合物的药物组合物，以及用于制备它们的方法和它们用于治疗和/或预防与调节SST受体亚型5相关的疾病的用途。