4-溴-2,1,3-苯并噻二唑 | 22034-13-5

• 物质功能分类: 医药中间体 - 杂环化合物
• 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-2,1,3-苯并噻二唑
• 英文名称: 4-Bromo-benzo[1,2,5]thiadiazole
• 英文别名: 4-bromobenzo[c][1,2,5]thiadiazole；4-bromo-2,1,3-benzothiadiazole；4-bromobenzothiadiazole
• CAS: 22034-13-5
• 化学式: C₆H₃BrN₂S
• mdl: MFCD00614355
• 分子量: 215.073
• InChiKey: KYKBVPGDKGABHY-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  272.2±13.0 °C(Predicted)
• 密度：
  1.859±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• WGK Germany：
  3
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 安全说明：
  S26,S37/39
• 储存条件：
  2-8°C，干燥密封

SDS

Name:	4-Bromo-2 1 3-benzothiadiazole 97% Material Safety Data Sheet
Synonym:
CAS:	22034-13-5

Section 1 - Chemical Product MSDS Name:4-Bromo-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#
22034-13-5	4-Bromo-2,1,3-benzothiadiazole	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# 22034-13-5: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 83 - 85 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: C6H3BrN2S
Molecular Weight: 215.07

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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.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 22034-13-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Bromo-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
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# 22034-13-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 22034-13-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 22034-13-5 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

制备方法与用途

4-溴-2,1,3-苯并噻二唑是一种杂环有机物，常被用作医药中间体。

反应信息

• 作为反应物：
  描述：

  4-溴-2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 4-bromo-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  [EN] BRIDGED, BICYCLIC HETEROCYCLIC OR SPIRO BICYCLIC HETEROCYCLIC DERIVATIVES OF PYRAZOLO[1,5-A]PYRIMIDINES, METHODS FOR PREPARATION AND USES THEREOF
  [FR] DÉRIVÉS HÉTÉROCYCLIQUES BICYCLIQUES PONTÉS OU HÉTÉROCYCLIQUES BICYCLIQUES SPIRO DE PYRAZOLO[1,5-A]PYRIMIDINES, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2009108838A8
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 氢溴酸 、 溴 作用下， 反应 3.0h， 以65%的产率得到4-溴-2,1,3-苯并噻二唑
  参考文献：
  名称：

  增强光敏性的策略：聚合和供体-受体偶数-奇效应

  摘要：

  具有供体-受体（D-A）结构的有机光敏剂（PS）设计中的一个特殊挑战是，它基于试验和错误而不是特定的规则。现在，通过提出两种提高光敏效率的有效策略来应对这些挑战：聚合促进的光敏和D-A奇偶效应。已发现共轭聚合物表现出更高的1 O 2发电效率要比它们的小分子同行高。此外，具有AD结构的PS与具有AD结构的PS相比，具有更高的光敏效率。理论计算表明，通过这些策略可以提高系统间穿越（ISC）的效率。体外和体内实验均表明，所得材料可在图像引导的光动力抗癌治疗中用作光敏剂。这些准则适用于其他聚合物和小分子，以导致新PS的发展。

  DOI：

  10.1002/anie.201810326

文献信息

• 페나진계 화합물 및 이를 포함하는 유기발광소자
  申请人：LT Materials Co.,Ltd. 엘티소재주식회사(120060104982) Corp. No ▼ 110111-3251082BRN ▼104-81-94599

  公开号：KR101612903B1

  公开（公告）日：2016-04-19

  본 발명은 페나진계 화합물 및 이를 포함하는 유기발광소자에 관한 것이다.

  本发明涉及苯并氮杂化合物及其包含的有机发光二极管。
• 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
• Indolylbenzothiadiazoles with varying substituents on the indole ring: a systematic study on the self-recovering mechanochromic luminescence
  作者：Suguru Ito、Tomohiro Taguchi、Takeshi Yamada、Takashi Ubukata、Yoshitaka Yamaguchi、Masatoshi Asami

  DOI：10.1039/c7ra01006k

  日期：——

  exposure to mechanical stimuli. Remarkably, the fluorescence spectra after mechanical stimulus (grinding) were in good agreement with those of the molten fluorophores. Based on powder X-ray diffraction and DSC analyses of crystalline and amorphous samples, we propose an amorphization of the crystalline fluorophores to be responsible for the change of emission color in response to mechanical stimuli. Accordingly

  自恢复的机械变色发光体在暴露于机械刺激后，能够在室温下自动恢复其原始颜色。尽管最近对机械变色发光体进行了广泛的研究，但是由于缺乏对自我恢复的机械变色发光体的系统研究，具有特定的自恢复行为的机械变色荧光体的产生仍然是一项艰巨的任务。在此，描述了一系列具有不同固态发射颜色和恢复时间的自恢复机械变色荧光团。将不同的取代基引入4-（1 H-吲哚-2-基）-2,1,3-苯并噻二唑提供了对荧光团的机械致变色发光性质的控制。X射线衍射分析表明，在这些染料的结晶状态下，苯并噻二唑环没有堆积或没有分子间堆积，这表明暴露于机械刺激下晶体结构的相对不稳定性。值得注意的是，机械刺激（研磨）后的荧光光谱与熔融荧光团的荧光光谱非常吻合。基于粉末X射线衍射和结晶样品和无定形样品的DSC分析，我们提出了结晶荧光团的非晶化，负责响应于机械刺激而改变发射颜色。因此，
• Structural Design Principle of Small-Molecule Organic Semiconductors for Metal-Free, Visible-Light-Promoted Photocatalysis
  作者：Lei Wang、Wei Huang、Run Li、Dominik Gehrig、Paul W. M. Blom、Katharina Landfester、Kai A. I. Zhang

  DOI：10.1002/anie.201603789

  日期：2016.8.8

  on the structural design principle of small‐molecule organic semiconductors as metal‐free, pure organic and visible light‐active photocatalysts. Two series of electron‐donor and acceptor‐type organic semiconductor molecules were synthesized to meet crucial requirements, such as 1) absorption range in the visible region, 2) sufficient photoredox potential, and 3) long lifetime of photogenerated excitons

  在此，我们报告了小分子有机半导体作为无金属，纯有机和可见光活性光催化剂的结构设计原理。合成了两个系列的电子给体和受体型有机半导体分子以满足关键要求，例如1）可见光区域的吸收范围，2）足够的光氧化还原电势和3）光生激子的寿命长。在富含丙二酸酯衍生物的富电子杂芳族化合物的分子间CH官能化中证明了光催化活性。描述了光诱导电子在有机光催化剂，底物和牺牲剂之间传输的机理。凭借其可调的吸收范围和定义的能带结构，
• Functionalization of boron-doped diamond with a push–pull chromophore <i>via</i> Sonogashira and CuAAC chemistry
  作者：Jorne Raymakers、Hana Krysova、Anna Artemenko、Jan Čermák、Shannon S. Nicley、Pieter Verstappen、Sam Gielen、Alexander Kromka、Ken Haenen、Ladislav Kavan、Wouter Maes、Bohuslav Rezek

  DOI：10.1039/c8ra07545j

  日期：——

  dye-sensitized solar cells. Herein, we demonstrate the application of boron-doped nanocrystalline diamond (B:NCD) thin films, covalently functionalized with a dithienopyrrole–benzothiadiazole push–pull chromophore, as alternative photocathodes. First, a primary functional handle is introduced on H-terminated diamond via electrochemical diazonium grafting. Afterwards, Sonogashira cross-coupling and Cu(I) catalyzed

  提高 p 型光电极的性能是串联染料敏化太阳能电池领域取得重大进展的关键挑战。在此，我们展示了硼掺杂纳米晶金刚石（B：NCD）薄膜的应用，该薄膜与二噻吩并吡咯-苯并噻二唑推挽发色团共价功能化，作为替代光电阴极。首先，通过电化学重氮接枝在 H 端金刚石上引入主要功能手柄。之后，Sonogashira 交叉耦合和 Cu( I) 催化叠氮化物-炔烃环加成 (CuAAC) 反应用于连接发色团，从而能够比较表面官能化程度和在金刚石-染料界面处使用的连接剂的重要性。X 射线光电子能谱表明，与 Sonogashira 交叉偶联相比，通过CuAAC 进行的表面功能化导致发色团覆盖率略高。然而，通过光电化学和开尔文探针测量获得的光电流和光电压在通过Sonogashira 交叉耦合功能化的光阴极上大约大三倍。通过表面功能化因此，Sonogashira 交叉耦合被认为是开发基于金刚石的混合光伏的优先方法。