6-氟-5-苯并咪唑-2-硫醇 | 142313-30-2

• 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: 6-氟-5-苯并咪唑-2-硫醇
• 中文别名: 6-氯-5-氟苯咪唑-2-硫；6-氯-5-氟苯并咪唑-2-硫醇
• 英文名称: 5-chloro-6-fluoro-2-mercaptobenzimidazole
• 英文别名: 5-chloro-6-fluoro-1H-benzoimidazole-2-thiol；5-chloro-6-fluoro-1,3-dihydrobenzimidazole-2-thione
• CAS: 142313-30-2
• 化学式: C₇H₄ClFN₂S
• mdl: MFCD00052490
• 分子量: 202.64
• InChiKey: DQXCFZSRGLNXKW-UHFFFAOYSA-N

物化性质

• 熔点：
  298-301 °C
• 沸点：
  294.0±50.0 °C(Predicted)
• 密度：
  1.7875 (rough estimate)
• 溶解度：
  26.5 [ug/mL]
• 稳定性/保质期：

  如果遵照规格使用和储存，则不会分解，没有已知危险反应。请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S24/25,S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P310+P330,P405
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H315,H319
• 储存条件：
  请将贮藏器保持密封，并存放在阴凉、干燥处。同时，确保工作间有良好的通风或排气装置。

SDS

Name:	6-Chloro-5-Fluorobenzimidazole-2-Thiol Material Safety Data Sheet
Synonym:	None Known
CAS:	142313-30-2

Section 1 - Chemical Product MSDS Name:6-Chloro-5-Fluorobenzimidazole-2-Thiol Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
142313-30-2	6-Chloro-5-Fluorobenzimidazole-2-Thiol	ca. 100	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. 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:
Wash thoroughly after handling. Use with adequate ventilation.
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.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 142313-30-2: 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: 298 - 301 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: C7H4ClFN2S
Molecular Weight: 202.64

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Amines, oxidizing agents, alcohols, water.
Hazardous Decomposition Products:
Hydrogen chloride, hydrogen cyanide, sulfur dioxide, carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen fluoride gas, sulfuric acid, nitric acid.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 142313-30-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Chloro-5-Fluorobenzimidazole-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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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# 142313-30-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 142313-30-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 142313-30-2 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-氯-1-甲基-4-硝基咪唑 、 6-氟-5-苯并咪唑-2-硫醇 在 sodium hydroxide 作用下， 反应 1.0h， 以51%的产率得到6-chloro-5-fluoro-2-(3-methyl-5-nitro-imidazol-4-yl)sulfanyl-1H-benzimidazole
  参考文献：
  名称：

  Rational Design of Novel Immunosuppressive Drugs:  Analogues of Azathioprine Lacking the 6-Mercaptopurine Substituent Retain or Have Enhanced Immunosuppressive Effects

  摘要：

  Clinical use of the immunosuppressive drug azathioprine is limited by potentially serious toxic effects related to depression of bone marrow function. The immunosuppressive and toxic properties of azathioprine are regarded as being properties of the cytotoxicity of its metabolite, 6-mercaptopurine (6-MP). However, azathioprine has an immunosuppressive effect additional to that attributable to 6-MP alone, and we propose that this is associated with an action of the methylnitroimidazolyl substituent. This suggests a route to the rational design of nontoxic immunosuppressants by replacing the 6-MP component of azathioprine with nontoxic thiols. We have synthesized and tested in vitro 24 such analogues, with two being further tested in vivo. In the human mixed lymphocyte reaction, virtually all compounds showed some degree of activity, 10 compounds being more active than azathioprine. In vivo, two compounds were more effective than azathioprine at prolonging graft survival in mice. In an oral toxicity study in male CD1 mice at doses equivalent to those at which azathioprine caused severe bone marrow depression both analogues had no toxic effects. Our results show that the immunosuppressive effects and bone marrow toxicity of azathioprine are not a consequence of release of 6-MP alone, and with appropriate modification can be separated, an approach which may lead to less toxic immunosuppressive drugs.

  DOI：

  10.1021/jm960132w
• 作为产物：
  描述：

  二硫化碳 、 4-氯-5-氟邻苯二胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 6-氟-5-苯并咪唑-2-硫醇
  参考文献：
  名称：

  含有苯并咪唑的新型截短侧耳素衍生物作为有效抗 MRSA 药物的设计、合成和生物学评价

  摘要：

  本研究设计、合成了一系列含有苯并咪唑的截短侧耳素衍生物，并评价了其对耐甲氧西林金黄色葡萄球菌（MRSA）的抗菌活性。通过肉汤稀释法测定了合成衍生物对四种金黄色葡萄球菌菌株（MRSA ATCC 43300、金黄色葡萄球菌ATCC 29213、金黄色葡萄球菌144 和金黄色葡萄球菌AD3）的体外抗菌活性。在这些衍生物中，化合物58对MRSA（最低抑菌浓度[MIC] = 0.0625 μg/mL）表现出优于泰妙菌素（MIC = 0.5 μg/mL）的体外抗菌作用。与泰妙菌素相比，化合物58对MRSA具有更快的杀菌动力学和更长的抗生素后作用时间。同时，在8 μg/mL浓度下，化合物58对RAW 264.7细胞没有表现出明显的细胞毒作用。此外，在减少小鼠大腿感染模型中的 MRSA 负荷方面，化合物58 (-2.04 log 10 CFU/mL) 表现出比泰妙菌素 (-1.02 log 10 CFU/mL)

  DOI：

  10.1002/ddr.22095

文献信息

• 2-Substituted benzimidazole piperidines analogs as selective melanin concentrating hormone receptor antagonists for the treatment of obesity and related disorders
  申请人：Burnett A. Duane

  公开号：US20050054628A1

  公开（公告）日：2005-03-10

  The present invention discloses compounds of formula I wherein Ar, Y, m, n, R 1 and R 4 are herein defined, said compounds being novel antagonists for melanin-concentrating hormone (MCH), as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such MCH antagonists as well as methods of using them to treat obesity, metabolic disorders, eating disorders such as hyperphagia, and diabetes.

  本发明公开了以下式I的化合物 其中Ar、Y、m、n、R1和R4在此有定义，所述化合物是新型黑素浓缩激素（MCH）拮抗剂，以及制备这种化合物的方法。在另一实施例中，本发明公开了包含这种MCH拮抗剂的药物组合物，以及使用它们治疗肥胖、代谢紊乱、食欲紊乱（如过度进食）和糖尿病的方法。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2005030704A1

  公开（公告）日：2005-04-07

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和症状的组合物和方法。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DÉSACÉTYLASE
  申请人：METHYLGENE INC

  公开号：WO2005092899A1

  公开（公告）日：2005-10-06

  The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.

  这项发明涉及一系列对抑制组蛋白去乙酰化酶（HDAC）酶活性有用的化合物。该发明还提供了一种利用这些化合物抑制细胞中组蛋白去乙酰化酶的方法，以及一种利用这些HDAC抑制剂治疗细胞增殖性疾病和病况的方法。此外，该发明提供了包含这些HDAC抑制化合物和药用可接受载体的药物组合物。
• Intermolecular Regio- and Stereoselective Sulfenoamination of Alkenes with Thioimidazoles
  作者：Nur-E Alom、Yesmin Akter Rina、Wei Li

  DOI：10.1021/acs.orglett.7b03128

  日期：2017.11.17

  An intermolecular sulfenoamination reaction utilizing a stable sulfur precursor with a broad range of alkene structures is described. More importantly, these reactions proceed in a highly regio- and stereoselective manner to afford interesting heterocyclic motifs ready for biological studies. In addition, a highly regiodivergent approach to access the opposite regioisomers for styrene derivatives was

  描述了利用具有宽范围烯烃结构的稳定硫前体的分子间磺酰胺化反应。更重要的是，这些反应以高度区域选择性和立体选择性的方式进行，从而提供了有趣的杂环基序，可用于生物学研究。此外，还开发了一种高度区域发散的方法来获得苯乙烯衍生物的相反区域异构体。
• [EN] ANTI-NEOPLASTIC COMPOUNDS, COMPOSITIONS AND METHODS<br/>[FR] COMPOSÉS ANTINÉOPLASIQUES, COMPOSITIONS ET PROCÉDÉS
  申请人：PROGENRA INC

  公开号：WO2010114881A1

  公开（公告）日：2010-10-07

  Disclosed are novel compounds which are useful as therapeutics, especially in anti-neoplastic therapy and in other therapeutic regimes where cysteine protease inhibition is implicated.

  公开的是新型化合物，这些化合物在治疗上具有用途，特别是在抗肿瘤治疗和其他涉及半胱氨酸蛋白酶抑制的治疗方案中。