5,6-二氯苯并咪唑-2-硫醇 | 19462-98-7

• 物质功能分类: 化学试剂 - 有机试剂 - 硫醇盐
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 5,6-二氯苯并咪唑-2-硫醇
• 中文别名: 5,6-二氯苯咪唑-2-硫；5,6-二氯-2-巯基苯并咪唑
• 英文名称: 5,6-dichloro-1H-benzimidazole-2-thiol
• 英文别名: 5,6-dichloro-2-mercapto benzimidazole；5,6-dichloro-1H-benzo[d]imidazole-2-thiol；5,6-dichloro-1,3-dihydrobenzimidazole-2-thione
• CAS: 19462-98-7
• 化学式: C₇H₄Cl₂N₂S
• 分子量: 219.094
• InChiKey: AFDOMGKBKBKUHB-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C
• 沸点：
  329.8±52.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品标志：
  Xn
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温下应密闭避光保存，并保持通风和干燥。

SDS

Name:	5 6-Dichloro-1H-benzo[d]imidazole-2-thiol 95+% Material Safety Data Sheet
Synonym:
CAS:	19462-98-7

Section 1 - Chemical Product MSDS Name:5 6-Dichloro-1H-benzo[d]imidazole-2-thiol 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
19462-98-7	5,6-Dichloro-1H-benzo[d]imidazole-2-th	95+%	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.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
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:
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# 19462-98-7: 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: tan
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: > 320 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: C7H4Cl2N2S
Molecular Weight: 219

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acid chlorides.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, 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# 19462-98-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5,6-Dichloro-1H-benzo[d]imidazole-2-thiol - 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 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# 19462-98-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 19462-98-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 19462-98-7 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：

  5,6-二氯苯并咪唑-2-硫醇 在 sodium hydroxide 、 双氧水 作用下， 生成 5,6-dichlorobenzimidazole-2-sulfonic acid
  参考文献：
  名称：

  Benzimidazoles as NMDA Glycine-Site Antagonists: Study on the Structural Requirements in 2-Position of the Ligand

  摘要：

  A series of different substituted benzimidazole derivatives has been synthesized and evaluated for the ability to displace [3H]MDL-105,519 to rat cortical membranes. Two benzimidazole-2-carboxylic acids 9 b and 9 c, in this substitution pattern not yet described as glycine antagonists, showed IC50 values of 0.89 microM (9 b) and 38.0 microM (9 c). Replacement of the carboxylate function in 2-position by a sulfonic acid moiety appreciably increased solubility, but decreased the affinity giving evidence for the strong need of the carboxylate group within the ligand. Further structure-activity studies using benzimidazole-2-one derivatives with an acetic acid moiety adjacent to a ring nitrogen revealed new insights into the importance of amide functionalities within the heterocycle for the affinity of antagonist glycine-site ligands.

  DOI：

  10.1002/(sici)1521-4184(20005)333:5<123::aid-ardp123>3.0.co;2-5
• 作为产物：
  描述：

  邻二氯苯 在 镍 氢氧化钾 、 硫酸 、 三氧化硫 、 氢气 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 34.5h， 生成 5,6-二氯苯并咪唑-2-硫醇
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 2-Mercapto-5,6-dichlorobenzimidazole-β-D-ribofuranonucleoside Derivatives

  摘要：

  2-Mercapto-5,6-dichlorobenzimidazole beta-D-ribofuranonucleoside derivatives 8-10 have been synthesized and their antiviral properties examined. According to the glycosylation procedure used, the beta-D-N-1 isomer (and the N,N-bis-riboside) or the beta D-S-2-isomer have been obtained. All the prepared compounds were tested for their activity against a variety of RNA and DNA viruses, but they did not show significant antiviral activity.

  DOI：

  10.1080/15257779408013253

文献信息

• Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazoles <i>via</i> a sulfinyl radical
  作者：Mei Fu、Xiaochen Ji、Yongtong Li、Guo-Jun Deng、Huawen Huang

  DOI：10.1039/d0gc02269a

  日期：——

  A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to

  发现温和的不含过渡金属的无毒需氧光氧化还原系统可实现2-巯基苯并咪唑的高效脱硫。这种可行的催化系统包括低催化剂含量的Rose Bengal作为光敏剂，以及廉价的无毒NaCl（催化量）作为添加剂，并与氧气气氛相结合。该方案提供了重要的替代途径，可以以通常的高收率获得各种苯并咪唑和氘代苯并咪唑产品，并且对各种合成和药学上有用的功能具有良好的耐受性。机理研究表明，单电子转移和能量转移都可能在初始步骤发生，并且亚硫酰基自由基中间体参与了关键的脱硫过程。
• Metal‐Free Synthesis of Imidazo[2,1‐ <i>b</i> ]thiazoles from Thioimidazoles and Ketones Mediated by Selectfluor
  作者：Jinwu Zhao、Qiannan Xiao、Jiaxi Chen、Jingxiu Xu

  DOI：10.1002/ejoc.202000815

  日期：2020.8.31

  Promoted by Selectfluor, imidazo[2,1‐b]thiazoles could be prepared from thioimidazoles and ketones. This metal‐free protocol was applicable to various ketones, including strong electron‐withdrawing substituted aryl ketones and alkyl ketones. Moreover, this procedure featured simple operation and easy work‐up.

  在Selectfluor的促进下，可以从硫代咪唑和酮制备咪唑并[2,1- b ]噻唑。该无金属方案适用于各种酮，包括强吸电子取代的芳基酮和烷基酮。此外，该程序具有操作简单，易于维护的特点。
• Synthesis and Antimycobacterial and Antiprotozoal Activities of Some Novel Nitrobenzylated Heterocycles
  作者：Agata Górska、Lidia Chomicz、Justyna Żebrowska、Przemysław Myjak、Ewa Augustynowicz-Kopeć、Zofia Zwolska、Janusz Piekarczyk、Henryk Rebandel、Zygmunt Kazimierczuk

  DOI：10.1515/znb-2006-0120

  日期：2006.1.1

  A series of N-, S-, and O-mononitro- and dinitrobenzyl derivatives of heterocycles was synthesized by alkylation of heterocyclic bases with the respective nitrobenzyl chlorides. Of the newly synthesized compounds, dinitrobenzylsulfanyl derivatives of 1-methyl-2-mercaptoimidazole (2c) and of 5-nitro- and 5,6-dichloro-2-mercaptobenzimidazole (8b and 8c, and 8e and 8f, respectively) showed considerable antimycobacterial activity. On a molar basis, nine of the novel compounds showed also a considerably higher antiprotozoal efficacy than metronidazole that reduced T. hominis viability to 73.5% at 8 μg/ml.

  一系列N-、S-和O-单硝基和二硝基苯基杂环衍生物通过用相应的硝基苯基氯化物烷基化杂环碱合成。在新合成的化合物中，1-甲基-2-巯基咪唑（2c）和5-硝基-和5,6-二氯-2-巯基苯并咪唑（8b和8c，以及8e和8f，分别）的二硝基苯基硫醚衍生物显示出相当大的抗分枝杆菌活性。按摩尔计算，九种新化合物的抗原虫效力也比甲硝唑高得多，将T. hominis的存活率降低到8 μg/ml时的73.5%。
• DMSO/H ₂ O ₂ Promoted Regioselective Synthesis of Benzoimidazo[2,1‐b]thiazoles from 2‐Mercaptobenzimidazoles and Ketones in Water
  作者：Jingxiu Xu、Renjin Deng、Jiaxi Chen、Xiaodong Tang、Jinwu Zhao

  DOI：10.1002/adsc.201900909

  日期：2019.11.19

  We report a green and regioselective process for the construction of benzoimidazo[2,1‐b]thiazole skeletons in water using DMSO/H2O2 as an oxidant. The experimental data lend support to a mechanism in which the transformation is initiated by oxidizing methylene of ketone into carbon radical under the oxidation of DMSO/H2O2. This operationally simple and metal‐free procedure could facilitate a diverse

  我们报告了使用DMSO / H 2 O 2作为氧化剂在水中构建苯并咪唑并[2,1-b]噻唑骨架的绿色和区域选择性过程。实验数据为通过在DMSO / H 2 O 2的氧化下将酮的亚甲基氧化为碳自由基而引发转化的机理提供了支持。这种操作简单且无金属的方法可以促进苯并咪唑并[2,1-b]噻唑衍生物的多样化收集。
• An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water
  作者：Xing Liu、Min Liu、Wan Xu、Meng-Tian Zeng、Hui Zhu、Cai-Zhu Chang、Zhi-Bing Dong

  DOI：10.1039/c7gc02311a

  日期：——

  An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope

  一种有效而实用的方法，是通过将2-氨基硫酚，2-氨基酚和1,2-苯二胺与四甲基秋兰姆二硫化物环化，一步一步合成苯并噻唑-2-硫醇，苯并恶唑-2-硫醇和苯并咪唑啉-2-硫酮（描述了在水中的TMTD。该方法的特点包括无金属/配体，优异的产率，较短的反应时间和广泛的底物范围。该方法提供了一些潜在的生物活性化合物的简便的制备方法。