4-溴甲基-2,1,3-苯并噻重氮 | 16405-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 中文名称: 4-溴甲基-2,1,3-苯并噻重氮
• 中文别名: 4-(溴甲基)-2,1,3-苯并噻二唑
• 英文名称: 4-(bromomethyl)benzo[c][1,2,5]thiadiazole
• 英文别名: 4-(bromomethyl)-2,1,3-benzothiadiazole；4-bromomethyl-2,1,3-benzothiadiazole；4-bromomethyl-benzo[1,2,5]thiadiazole；4-bromomethyl-benzo[1,2,5]thiadiazol；4-bromomethyl-benzo[2,1,3]thiadiazole；4-Brommethyl-benz-<2,1,3>-thiadiazol
• CAS: 16405-99-5
• 化学式: C₇H₅BrN₂S
• mdl: MFCD00457946
• 分子量: 229.1
• InChiKey: QKHNCECWIKLSSV-UHFFFAOYSA-N

物化性质

• 熔点：
  89 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R34
• 海关编码：
  2934999090
• 危险品运输编号：
  UN 3261

SDS

Name:	4-(Bromomethyl)-2 1 3-benzothiadiazole 97% Material Safety Data Sheet
Synonym:
CAS:	16405-99-5

Section 1 - Chemical Product MSDS Name:4-(Bromomethyl)-2 1 3-benzothiadiazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16405-99-5	4-(Bromomethyl)-2,1,3-benzothiadiazole	97%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 16405-99-5: 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: 84 - 86 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: C7H5BrN2S
Molecular Weight: 229

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16405-99-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(Bromomethyl)-2,1,3-benzothiadiazole - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
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.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 16405-99-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16405-99-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16405-99-5 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：

  4-溴甲基-2,1,3-苯并噻重氮 在 盐酸 、 硝酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 (7-nitro-benzo[1,2,5]thiadiazol-4-yl)-acetic acid
  参考文献：
  名称：

  Pesin,V.G. et al., Journal of general chemistry of the USSR, 1964, vol. 34, p. 1270 - 1273

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氨基甲苯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 氢溴酸 作用下， 以 四氯乙烯 为溶剂， 反应 15.0h， 生成 4-溴甲基-2,1,3-苯并噻重氮
  参考文献：
  名称：

  通过引入4-烷氧基噻唑作为供体单元，使D–A型功能染料具有惊人的特性

  摘要：

  在这项研究中，我们报告了新型供体-受体分子的合成。这些新染料包括苯并[ c ] [1,2,5]噻二唑和带有一个或两个4-烷氧基噻唑作为供体部分的侧基，它们在没有Pd催化的交叉偶联反应的情况下被引入。光学和电化学性质通过吸收，发射光谱和循环伏安法测量进行了研究。我们通过实验发现从HOMO到LUMO的令人惊讶的小带隙分别为2.4 eV和2 eV，这也使用DFT计算进行了研究。

  DOI：

  10.1016/j.tet.2016.04.046
• 作为试剂：
  描述：

  4-甲基-2,1,3-苯并噻二唑 、 N-溴代丁二酰亚胺(NBS) 、 ethyl acetate n-hexane 、 在 ice water 、 丁二酰亚胺 、 disodium;dioxido-oxo-sulfanylidene-λ6-sulfane 、 Brine 、 Sodium sulfate-III 、 4-溴甲基-2,1,3-苯并噻重氮 作用下， 以 四氯化碳 为溶剂， 反应 8.0h， 生成 4-溴甲基-2,1,3-苯并噻重氮
  参考文献：
  名称：

  Cyclic bis-benzimidazole ligands and metal complexes thereof

  摘要：

  通过将(2-氨基苯基)-苯并咪唑-4-甲醛乙二醇缩醛或(2-硝基苯基)-苯并咪唑-4-苯甲醛与酸接触，可在金属或金属盐的存在下形成以下公式的环状双苯并咪唑配体。其中R1和R2可以相同或不同，并选自H、具有1至10个碳原子的烷基、苄基、取代的2-乙基苯基、羰基、苯基取代基、甲磺酰基和烷基磺酸盐基；R3和R4可以相同或不同，并选自H、甲基和乙基；R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17和R18可以相同或不同，并选自H、具有1至10个碳原子的烷基、氟、氯、溴、碘、硝基、氨基、羧酸盐、酯和苯基。

  公开号：

  US06376664B1

文献信息

• Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide⋅⋅⋅Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket
  作者：Maude Giroud、Jakov Ivkovic、Mara Martignoni、Marianne Fleuti、Nils Trapp、Wolfgang Haap、Andreas Kuglstatter、Jörg Benz、Bernd Kuhn、Tanja Schirmeister、François Diederich

  DOI：10.1002/cmdc.201600563

  日期：2017.2.3

  We report an extensive “heteroarene scan” of triazine nitrile ligands of the cysteine protease human cathepsin L (hCatL) to investigate π‐stacking on the peptide amide bond Gly67–Gly68 at the entrance of the S3 pocket. This heteroarene⋅⋅⋅peptide bond stacking was supported by a co‐crystal structure of an imidazopyridine ligand with hCatL. Inhibitory constants (Ki) are strongly influenced by the diverse

  我们报道了半胱氨酸蛋白酶人组织蛋白酶L（hCatL）的三嗪腈配体的广泛的“杂芳烃扫描”，以研究S3口袋入口处的肽酰胺键Gly67–Gly68上的π堆积。杂芳基·····肽键的堆叠由咪唑并吡啶配体与hCatL的共晶体结构支持。抑制常数（ķ我）受到杂环的多样性和与S3口袋局部环境的特定相互作用的强烈影响。结合亲和力变化三个数量级。与烃类似物相比，所有杂芳族配体均具有增强的结合力。从杂芳烃和肽键的局部偶极矩的方向预测的能量贡献无法得到证实。分子间的C-S⋅⋅⋅O= C相互作用（硫族元素键）与Asn66的主链C = O增强了苯并噻吩基（K i = 4 n m）和苯并噻唑基（K i = 17 n m）配体的结合。 S3口袋。还测试了配体的相关酶罗德沙星。
• Synthesis and Electronic and Photophysical Properties of [2.2]- and [3.3]Paracyclophane-Based Donor–Donor′–Acceptor Triads
  作者：Takaaki Miyazaki、Masahiko Shibahara、Jun-ichi Fujishige、Motonori Watanabe、Kenta Goto、Teruo Shinmyozu

  DOI：10.1021/jo5020273

  日期：2014.12.5

  n]PCP(D′)-NI(A) (4, 5), and 10-methyl-10H-phenothiazine (Me-PTZ, D)-[2.2]PCP-2,1,3-benzothiadiazole (BTD, A) 6, were synthesized for the elucidation of their photophysical properties. The absorption spectra and electrochemical properties indicated that the chromophores (D, D′, and A) do not interact with each other in the ground state. Cz-(CH2)3-[2.2]PCP-(CH2)3-NI 1 and Cz-(CH2)3-[3.3]PCP-(CH2)3-NI 2 show an

  三种类型的供体（d）端供体'（d'）的-受体（A）三单元组1 - 6具有不同的d-A的组合，咔唑（CZ，d） - [ Ñ。Ñ ] PCP（d'） - 1,8-萘二甲酰亚胺（NI，A）（1 - 3），10 ħ -吩噻嗪（PTZ，d） - [ Ñ。Ñ ] PCP（d'） - NI（A）（4，5），和10-甲基10 ħ -吩噻嗪（ME-PTZ，d） - [2.2] PCP -2,1,3-苯并噻二唑（BTD， A）6合成，以阐明其光物理性质。吸收光谱和电化学性质表明，发色团（D，D'和A）在基态下不相互作用。CZ-（CH 2）3- [2.2] PCP-（CH 2）3 -NI 1和CZ-（CH 2）3- [3.3] PCP-（CH 2）3 -NI 2显示PCP之间的激基复合物发射和环部分中的NI部分和该带的强度在2中比在1中要高得多，而CZ-（CH 2）2- [2.2] PCP-（CH 2）2 -NI
• <i>Retracted</i> : Microwave Assisted Synthesis of Trifluoro Substituted 2-Aminobenzimidazole Derivatives <i>via</i> Iodoacetic Acid Mediated One-pot Condensation
  作者：R. Sriram、R. Sapthagiri、L. Ilavarasan、A. Ravi

  DOI：10.1002/jhet.2841

  日期：2017.7

  Microwave‐assisted efficient one‐pot syntheses of trifluoro substituted 2‐aminobenzimidazole derivative were synthesized using iodoacetic acid mediated cyclodesulfurization of thioureas. This method eliminates need to handle preformed substituted thioureas, requires lesser reaction time and temperature, is facile, and also gives higher yields of the target molecules.

  微波辅助高效的一锅合成三氟取代的2-氨基苯并咪唑衍生物是使用碘乙酸介导的硫脲的环脱硫反应而合成的。该方法消除了处理预先形成的取代的硫脲的需要，需要更少的反应时间和温度，容易，并且还提供了更高的目标分子产率。
• SUBSTITUTED HETEROCYCLIC COMPOUNDS
  申请人：ZHUO Jincong

  公开号：US20100240671A1

  公开（公告）日：2010-09-23

  The present invention relates to substituted heterocyclic compounds of Formula I or XI: or pharmaceutically acceptable salts or N-oxides or quaternary ammonium salts thereof wherein constituent members are provided hereinwith, as well as their compositions and methods of use, which are histamine II4 receptor inhibitors useful in the treatment of histamine II4 receptor-associated conditions or diseases or disorders including, for example, inflammatory diseases or disorders, pruritus, and pain.

  本发明涉及式I或XI的取代杂环化合物： 或其药用可接受的盐或N-氧化物或季铵盐，其中所述成员在此提供，并且它们的组合物和使用方法，这些方法是组胺H24受体抑制剂，用于治疗组胺H24受体相关的疾病或疾病，包括例如炎症性疾病或疾病，瘙痒和疼痛。
• [EN] BENZIMIDAZOLE DERIVATIVES USEFUL AS POTASSIUM CHANNEL INHIBITORS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE UTILES COMME INHIBITEURS DE CANAL POTASSIQUE
  申请人：ACESION PHARMA APS

  公开号：WO2019038315A1

  公开（公告）日：2019-02-28

  The present invention relates to compounds of the general formula (I). The compounds of formula I are potassium channel inhibitors useful for treatment of a cardiac disease, disorder or condition in a mammal.

  本发明涉及具有通用公式(I)的化合物。公式I的化合物是钾通道抑制剂，用于治疗哺乳动物的心脏疾病、失调或状况。