2-(甲基硫代)-6-硝基-1,3-苯并噻唑 | 3621-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(甲基硫代)-6-硝基-1,3-苯并噻唑
• 英文名称: 2-methylthio-6-nitrobenzothiazole
• 英文别名: 2-(methylthio)-6-nitrobenzo[d]thiazole；2-(Methylthio)-6-nitro-1,3-benzothiazole；2-methylsulfanyl-6-nitro-1,3-benzothiazole
• CAS: 3621-99-6
• 化学式: C₈H₆N₂O₂S₂
• mdl: MFCD00085141
• 分子量: 226.28
• InChiKey: UGURRSVQWLYDOY-UHFFFAOYSA-N

物化性质

• 熔点：
  134 °C
• 沸点：
  395.4±34.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 安全说明：
  S26,S37/39

SDS

Name:	2-(Methylthio)-6-nitro-1 3-benzothiazole 97% Material Safety Data Sheet
Synonym:
CAS:	3621-99-6

Section 1 - Chemical Product MSDS Name:2-(Methylthio)-6-nitro-1 3-benzothiazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3621-99-6	2-(Methylthio)-6-nitro-1,3-benzothiazo	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes 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:
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:
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# 3621-99-6: 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: white - pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 134 - 136 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: C8H6N2O2S2
Molecular Weight: 226

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Reducing agents, 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# 3621-99-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(Methylthio)-6-nitro-1,3-benzothiazole - 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: XI
Risk Phrases:
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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 3621-99-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3621-99-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3621-99-6 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-(甲基硫代)-6-硝基-1,3-苯并噻唑 在 盐酸 、 sodium hydroxide 、 potassium permanganate 、 铁粉 、 potassium carbonate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 6-amino-3-methyl-2(3H)-benzothiazolone
  参考文献：
  名称：

  Synthetic chemotherapeutic agents. IV. Synthesis of 3-substituted thiazolo(5,4-f)quinoline derivatives.

  摘要：

  研究并证明了通过噻唰盐合成3,6-二取代-2,9-二氧-2,3,6,9-四氢噻唑并[5,4-f]喹啉-8-羧酸的方法是切实可行的。噻唑盐与各种亲核试剂的反应得到了几种新衍生物。还进行了苯并噻唑-2-酮和苯并噻唑-2-硫酮衍生物的Gould-Jacobs反应。

  DOI：

  10.1248/cpb.24.1050
• 作为产物：
  描述：

  2-甲硫基苯并噻唑 在 硫酸 、 硝酸 作用下， 反应 1.0h， 以75%的产率得到2-(甲基硫代)-6-硝基-1,3-苯并噻唑
  参考文献：
  名称：

  设计，合成和生物学评估新型不对称杂志作为群体感应抑制剂†

  摘要：

  使用群体感应抑制剂靶向群体感应信号为已知抗生素的应用开辟了新途径。在这种情况下，合成了二十五个不对称嗪并作为群体感应抑制剂进行了评估。采用有效的一锅法，将3-甲基-2-（甲硫基）苯并[ d ]噻唑-3-盐，水合肼和取代的醛直接连接，得到所设计的化合物。初步测试了合成的化合物抑制紫薇色杆菌中基于CviR受体的QS信号的潜力。生物测定筛选结果表明，两种化合物对CviR受体均表现出强效的QS抑制活性，在200μM时显示出对紫丁香素的抑制作用（> 50％）。此外，使用铜绿假单胞菌的PlasB-gfp（ASV）生物监测菌株检查推定的阳性命中物抑制LasR受体基QS的潜力。发现这些化合物以剂量依赖性方式抑制QS介导的GFP信号。两种活性化合物在浓度为50μM时也表现出生物膜清除率。进行了对接研究，以检验其与铜绿假单胞菌LasR蛋白结合的潜力。

  DOI：

  10.1039/c5ra12925g

文献信息

• 2-[1H-Benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides as kinase inhibitors
  申请人：Aurrecoechea Natalia

  公开号：US20100081653A1

  公开（公告）日：2010-04-01

  2-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamides and their salts are kinase inhibitors, useful in the treatment of cancer.

  2-[1H-苯并咪唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺和2-[苯并噻唑-2(3H)-基]-2-(嘧啶-2-基)乙酰胺及其盐是激酶抑制剂，在癌症治疗中有用。
• Divergent S- and C-Difluoromethylation of 2-Substituted Benzothiazoles
  作者：Xiu Wang、Wenchao Ye、Taige Kong、Chenlu Wang、Chuanfa Ni、Jinbo Hu

  DOI：10.1021/acs.orglett.1c03267

  日期：2021.11.5

  Two unprecedented and complementary synthetic strategies for S- and C-difluoromethylation of 2-substituted benzothiazoles have been developed by taking advantage of the remarkably different reactivity of CF2H– and 2-PySO2CF2– nucleophiles. A variety of structurally diverse difluoromethyl 2-isocyanophenyl sulfides and 2-difluoromethylated benzothiazoles were synthesized with these two new synthetic

  利用 CF 2 H和 2 - PySO 2 CF 2亲核试剂的显着不同反应性，开发了两种前所未有的互补合成策略，用于 2-取代的苯并噻唑的 S-和 C-二氟甲基化。用这两种新的合成方案合成了多种结构多样的二氟甲基 2-异氰基苯硫醚和 2-二氟甲基苯并噻唑。
• Exploration of Benzothiazole Rhodacyanines as Allosteric Inhibitors of Protein–Protein Interactions with Heat Shock Protein 70 (Hsp70)
  作者：Hao Shao、Xiaokai Li、Michael A. Moses、Luke A. Gilbert、Chakrapani Kalyanaraman、Zapporah T. Young、Margarita Chernova、Sara N. Journey、Jonathan S. Weissman、Byron Hann、Matthew P. Jacobson、Len Neckers、Jason E. Gestwicki

  DOI：10.1021/acs.jmedchem.8b00583

  日期：2018.7.26

  Cancer cells rely on the chaperone heat shock protein 70 (Hsp70) for survival and proliferation. Recently, benzothiazole rhodacyanines have been shown to bind an allosteric site on Hsp70, interrupting its binding to nucleotide-exchange factors (NEFs) and promoting cell death in breast cancer cell lines. However, proof-of-concept molecules, such as JG-98, have relatively modest potency (EC50 ≈ 0.7–0

  癌细胞依靠伴侣热休克蛋白 70 (HSP70) 来生存和增殖。最近，苯并噻唑罗丹青素已被证明与 HSP70 上的变构位点结合，中断其与核苷酸交换因子 (NEF) 的结合并促进乳腺癌细胞系中的细胞死亡。然而，概念验证分子，如 JG-98，具有相对适中的效力（EC 50 ≈ 0.7–0.4 μM），并且在动物中迅速代谢。在这里，我们通过~300 种类似物的基于结构和特性的设计探索了这个化学系列，表明最有效的 EC 50提高了 10 倍以上值（~0.05 至 0.03 μM）对抗两种乳腺癌细胞。生物标志物和全基因组 CRISPRi 筛选证实 HSP70 家族的成员是细胞靶点。基于这些结果，发现 JG-231 可减少 MDA-MB-231 异种移植模型（4 mg/kg，腹腔注射）中的肿瘤负荷。总之，这些研究支持 HSP70 可能是抗癌治疗的有希望的靶点的假设。
• Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis
  作者：Jian Rong、Ling Deng、Ping Tan、Chuanfa Ni、Yucheng Gu、Jinbo Hu

  DOI：10.1002/anie.201510533

  日期：2016.2.18

  visible‐light photoredox catalysis. A wide range of readily available mono‐, di‐, and trifluoromethyl heteroaryl sulfones can thus be used as efficient radical fluoroalkylation reagents under mild conditions. This method not only describes a new synthetic application of fluorinated sulfones, but also provides a new route to fluoroalkyl radicals.

  可见光光氧化还原催化作用使异氰酸酯与氟化砜发生自由基氟烷基化。因此，在温和的条件下，可以使用各种容易获得的单，二和三氟甲基杂芳基砜作为有效的自由基氟代烷基化试剂。该方法不仅描述了氟化砜的新合成应用，而且为氟代烷基自由基的制备提供了新途径。
• Tunable Heteroaromatic Sulfones Enhance in-Cell Cysteine Profiling
  作者：Hashim F. Motiwala、Yu-Hsuan Kuo、Brittany L. Stinger、Bruce A. Palfey、Brent R. Martin

  DOI：10.1021/jacs.9b08831

  日期：2020.1.29

  offer advantages over existing cysteine alkylation reagents, including accelerated reaction rates, improved stability, and robust ionization for mass spectrometry applications. Overall, heteroaromatic sulfones provide modular tunability, shifted chromatographic elution times, and superior in-cell cysteine profiling for in-depth proteome-wide analysis and covalent ligand discovery.

  杂芳族砜通过亲核芳香取代与半胱氨酸反应，为半胱氨酸缀合提供机械选择性和不可逆支架。在这里，我们评估了具有不同氧化态、杂原子取代和一系列给电子和吸电子取代基的杂芳族硫化物库。与传统的半胱氨酸偶联试剂相比，选择取代对反应性和稳定性产生了深远的影响，将反应速率提高了 > 3 个数量级。研究结果建立了一系列可合成的可跨多个可调中心可调的亲电支架。新的亲电子试剂及其相应的炔烃偶联物直接在培养的细胞中进行分析，在几分钟内以亚毫摩尔浓度实现硫醇饱和。将脱硫生物素功能化探针直接添加到培养细胞中简化了富集和洗脱，从而能够在标准分析时间的一小部分内通过质谱发现在其天然细胞环境中标记的 >3000 个反应性和/或可接近的硫醇。令人惊讶的是，在重复实验中，只有 1/2 的注释半胱氨酸被碘乙酰胺-脱硫生物素和甲基磺酰基苯并噻唑-脱硫生物素鉴定，证明了质谱分析的互补检测。与现有的半胱氨酸烷基化试剂相比，这些探针具有优