(1-苄基-2-磺酰基-1H-咪唑-5-基)甲醇 | 98412-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: (1-苄基-2-磺酰基-1H-咪唑-5-基)甲醇
• 中文别名: 1-(苄基)-5-羟甲基-3H-咪唑-2-硫酮
• 英文名称: (1-benzyl-2-mercapto-1H-imidazol-5-yl)methanol
• 英文别名: 1-benzyl-2-mercapto-5-hydroxymethyl-imidazole；3-benzyl-4-(hydroxymethyl)-1H-imidazole-2-thione
• CAS: 98412-23-8
• 化学式: C₁₁H₁₂N₂OS
• mdl: MFCD02179523
• 分子量: 220.295
• InChiKey: IIQWCVZBUKMFBS-UHFFFAOYSA-N

物化性质

• 熔点：
  238 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933290090
• 安全说明：
  S24/25

SDS

Name:	(1-Benzyl-2-sulfanyl-1H-imidazol-5-yl)methanol 97% Material Safety Data Sheet
Synonym:
CAS:	98412-23-8

Section 1 - Chemical Product MSDS Name:(1-Benzyl-2-sulfanyl-1H-imidazol-5-yl)methanol 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
98412-23-8	(1-Benzyl-2-sulfanyl-1H-imidazol-5-yl)	97	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
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.
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.
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# 98412-23-8: 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: Powder
Color: white
Odor: odorless - slight odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 238 - 240 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: C11H12N2OS
Molecular Weight: 220.3

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 98412-23-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1-Benzyl-2-sulfanyl-1H-imidazol-5-yl)methanol - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 98412-23-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 98412-23-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 98412-23-8 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-苄基-2-磺酰基-1H-咪唑-5-基)甲醇 在 manganese(IV) oxide 、 sodium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.17h， 生成 1-苄基-2-甲基磺酰-咪唑-5-甲醛
  参考文献：
  名称：

  新型咪唑基苯甲酰胺和异羟肟酸衍生物作为有效组蛋白脱乙酰酶抑制剂和抗癌剂的设计、合成和生物学评价

  摘要：

  设计并合成了带有苯甲酰胺或异羟肟酸基团（作为锌结合基团）的新型咪唑作为 HDAC 抑制剂。针对三种类型的癌细胞（包括 HCT-116、A549、PC3 和正常细胞系 (CHO)）评估了化合物的细胞毒性。研究了这些化合物对泛 HDAC 同工酶（包括 HDAC 1、2、3 和 6）的抑制活性，并评估了最有效的泛 HDAC 抑制剂对 HDAC1 的活性。大多数化合物对癌细胞表现出显着的细胞毒性，但对正常 CHO 细胞系没有表现出显着的细胞毒性。化合物7d对所有测试的癌细胞都显示出有希望的抗增殖活性，比其他化合物更强。该化合物对 HCT-116 细胞系表现出显着的细胞毒性。化合物7c、6a、7b在 HCT-116 细胞系中显示出强的泛 HDAC 抑制活性，几乎与恩替司他相同。化合物7d和7c强烈抑制HDAC1，IC 50值分别为0.56 μM和0.77 μM，与Entinostat (IC 50 =

  DOI：

  10.1016/j.molstruc.2023.136951
• 作为产物：
  描述：

  异丙醚 、 dihydroxyacetone dimer 、 benzylamine hydrochloride 在 溶剂黄146 作用下， 以 水 、 异丙醇 为溶剂， 以92.6%的产率得到(1-苄基-2-磺酰基-1H-咪唑-5-基)甲醇
  参考文献：
  名称：

  Process for preparing a 1-substituted 5-hydroxymethyl imidazole

  摘要：

  一种制备式I所示1-取代的5-羟甲基咪唑的方法：，其中R代表烷基、羟烷基、烯丙基或取代或未取代的芳甲基或二芳甲基，该方法包括以下步骤：在过渡金属催化剂和氧化剂的存在下，于溶剂中反应式II所示1-取代的2-巯基-5-羟甲基咪唑：，其中R如上定义。

  公开号：

  US06630593B1

文献信息

• Design, synthesis and biological evaluation of novel imidazole-chalcone derivatives as potential anticancer agents and tubulin polymerization inhibitors
  作者：Sara Rahimzadeh Oskuei、Salimeh Mirzaei、Mohammad Reza Jafari-Nik、Farzin Hadizadeh、Farhad Eisvand、Fatemeh Mosaffa、Razieh Ghodsi

  DOI：10.1016/j.bioorg.2021.104904

  日期：2021.7

  Novel imidazole-chalcone derivatives were designed and synthesized as tubulin polymerization inhibitors and anticancer agents. The antiproliferative activity of the imidazole-chalcone was assessed on some human cancer cell lines including A549 (adenocarcinoma human alveolar basal epithelial cells), MCF-7 (human breast cancer cells), MCF-7/MX (mitoxantrone resistant human breast cancer cells), and HEPG2

  设计并合成了新型咪唑-查尔酮衍生物作为微管蛋白聚合抑制剂和抗癌剂。咪唑查尔酮的抗增殖活性在一些人类癌细胞系上进行了评估，包括 A549（腺癌人类肺泡基底上皮细胞）、MCF-7（人类乳腺癌细胞）、MCF-7/MX（米托蒽醌抗性人类乳腺癌细胞）和 HEPG2（人肝细胞癌细胞）。一般来说，与其他三种细胞系相比，咪唑-查尔酮衍生物对 A549 癌细胞表现出更大的细胞毒性，其中化合物 9j' 和 9g 显示出显着的细胞毒性，IC 50对所有四种人类癌细胞的值范围为 7.05 到 63.43 μM。用 9g 和 9j' 处理的 A549 癌细胞的流式细胞术分析显示，这些化合物在低浓度下诱导细胞周期停滞在 G2/M 期，并在较高浓度下增加凋亡细胞（亚 G1 期细胞）的数量。它们还抑制了类似于考布他汀 A-4 (CA-4) 的微管蛋白聚合。A549 癌细胞中的膜联蛋白 V 结合染色分析显示化合物 9j'
• AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP2725024A1

  公开（公告）日：2014-04-30

  The present invention relates to the filed of pharmarcutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) amd a preparation method thereof, a pharmarcutical composition with the compounds as active components, and a use of the azole compounds and the pharmarcutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as deinfed in the specifictaion.

  本发明涉及药物化学领域，特别是一种由一般式（I）、（II）或（III）表示的新型类唑化合物，以及其制备方法，以这些化合物为活性成分的药物组合物，以及在制备用于治疗与Lp-PLA2酶活性相关疾病的药物中使用这些唑化合物和药物组合物的用途，其中每个取代基如规范中所定义。
• Syntheses of substituted 2-(2-alkylthio-1-benzyl-5-imidazolyl)-1,3,4-oxadiazoles
  作者：F. Hadizadeh、F. I. Tafti

  DOI：10.1002/jhet.5570390434

  日期：2002.7

  Starting from the readily available benzylamine hydrochloride a series of 2-(2-alkylthio-1-benzyl-5imida-zolyl)-1,3,4-oxadiazoles were prepared.

  从容易得到的苄胺盐酸盐开始，制备了一系列2-（2-烷硫基-1-苄基-5亚胺基-唑基）-1,3,4-恶二唑。
• Preparation of a clinically investigated ras farnesyl transferase inhibitor
  作者：Peter E. Maligres、Marjorie S. Waters、Steven A. Weissman、J. Christopher McWilliams、Stephanie Lewis、Jennifer Cowen、Robert A. Reamer、R. P. Volante、Paul J. Reider、David Askin

  DOI：10.1002/jhet.5570400206

  日期：2003.3

  The 1,5-disubstituted imidazole system was regioselectively assembled via an improved Marckwald imidazole synthesis. A new imidazole dethionation procedure has been developed to convert the Marckwald mercaptoim-idazole product to the desired imidazole. This methodology was found to be tolerant of a variety of functional groups providing good to excellent yields of 1,5-disubstituted imidazoles. A new

  ras法呢基蛋白转移酶抑制剂1的合成以多千克为单位进行了描述。反合成分析表明，氯甲基咪唑2和哌嗪酮3是可行的前体。1，5-二取代的咪唑系统是通过改进的Marckwald咪唑合成进行区域选择性组装的。已经开发了一种新的咪唑脱硫方法，以将Marckwald巯基咪唑-咪唑产品转化为所需的咪唑。发现该方法耐受各种官能团，从而提供良好至极好的1，5-二取代的咪唑收率。开发了一种新的Mitsunobu环化策略以制备芳基哌嗪酮片段3。
• Sustainable Synthesis of Thioimidazoles via Carbohydrate-Based Multicomponent Reactions
  作者：Marcus Baumann、Ian R. Baxendale

  DOI：10.1021/ol502845h

  日期：2014.12.5

  The synthesis of diversely functionalized thioimidazoles through a modern variant of the Marckwald reaction is presented. This new protocol utilizes unprotected carbohydrates as well as simple amine salts as sustainable and biorenewable starting materials. Importantly it was discovered that a bifurcated reaction pathway results from using aldoses and ketoses respectively, yielding distinct reaction

  提出了通过现代的Marckwald反应变体合成功能多样的硫代咪唑。该新方案利用未保护的碳水化合物以及简单的胺盐作为可持续的和生物可再生的原料。重要的是，发现分叉的反应途径分别由使用醛糖和酮糖产生，以高度选择性的方式产生不同的反应产物。

表征谱图