1-(1-苯并噻吩-2-基)-2-溴-1-乙酮 | 97511-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 1-(1-苯并噻吩-2-基)-2-溴-1-乙酮
• 英文名称: 1-(benzo[b]thiophen-2-yl)-2-bromoethanone
• 英文别名: 2-(bromoacetyl)benzo[b]thiophene；1-(1-Benzothiophen-2-yl)-2-bromo-1-ethanone；1-(1-benzothiophen-2-yl)-2-bromoethanone
• CAS: 97511-06-3
• 化学式: C₁₀H₇BrOS
• 分子量: 255.135
• InChiKey: WVTSOGFICBVCRE-UHFFFAOYSA-N

物化性质

• 熔点：
  117.5-118.5

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 海关编码：
  2934999090

SDS

Name:	1-(1-Benzothiophen-2-yl)-2-bromo-1-ethanone Material Safety Data Sheet
Synonym:	None Known
CAS:	97511-06-3

Section 1 - Chemical Product MSDS Name:1-(1-Benzothiophen-2-yl)-2-bromo-1-ethanone Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
97511-06-3	1-(1-Benzothiophen-2-yl)-2-bromo-1-eth	97+%	unlisted

Hazard Symbols: C
Risk Phrases: 22 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Harmful if swallowed. Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

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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. Do NOT allow victim to rub eyes or keep eyes closed.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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 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. 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:
Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing.
Keep container tightly closed. Do not ingest or inhale. Use only in a chemical fume hood. Discard contaminated shoes.
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# 97511-06-3: 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: White
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 117.5 - 118.5 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: C10H7BrOS
Molecular Weight: 255.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
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# 97511-06-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(1-Benzothiophen-2-yl)-2-bromo-1-ethanone - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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 22 Harmful if swallowed.
R 34 Causes burns.
Safety Phrases:
S 22 Do not breathe dust.
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# 97511-06-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 97511-06-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 97511-06-3 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：

  1-(1-苯并噻吩-2-基)-2-溴-1-乙酮 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 生成 2-azido-1-(benzo[b]thiophen-2-yl)ethanone
  参考文献：
  名称：

  松萝酸烯胺酮偶联的1,2,3-三唑类用作抗菌剂和抗结核剂。

  摘要：

  （+）-尿酸是地衣中的二次代谢产物，具有广泛的生物学特性，例如抗肿瘤，抗微生物，抗病毒，抗炎和杀虫活性。对这些药理活性感兴趣并挖掘其潜力，我们在此介绍新的松萝酸烯胺酮偶联的1,2,3-三唑10-44作为抗分枝杆菌药的合成和生物学评估。将（+）-松香酸与炔丙基胺缩合，得到具有末端乙炔基部分的松香酸烯胺酮8。在铜催化下，它进一步与各种叠氮化物A1-A35反应，以高收率得到三唑10-44。在合成的化合物中，糖精衍生物36被证明是活性最高的类似物，在MIC值为2.5μM时可抑制结核分枝杆菌（Mtb）。类似物16和27，以及3，4-二氟苯酰基和2-酰基萘单元分别在MIC值为5.4和5.3μM时抑制Mtb。在测试的革兰氏阳性和革兰氏阴性细菌中，新衍生物对枯草芽孢杆菌具有活性，化合物18 [3-（三氟甲基）苯甲酰基]和29（N-酰基吗啉基）分别显示抑制浓度41和90.7μM，而它们对其他测试细菌菌株没有

  DOI：

  10.1021/acs.jnatprod.9b00475
• 作为产物：
  描述：

  2-乙酰基苯并噻吩 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 3.5h， 生成 1-(1-苯并噻吩-2-基)-2-溴-1-乙酮
  参考文献：
  名称：

  （芳基烷基）咪唑类抗惊厥药的结构活性关系：(芴基烷基）咪唑类与萘啶酮和苯并咪唑的比较。

  摘要：

  （芳烷基）咪唑类是最近发现的并且在结构上不同的一类抗癫痫药。此类的两个独立发现的代表：地摩尔（α-[4-（2-苯基乙基）苯基] -1H-咪唑-1-乙醇）和萘啶酮（2-（1H-咪唑-1-基）-1-（2 -萘基萘酮）正在接受临床评估。我们的结构活性关系（SAR）研究表明，除了萘啶酮和苯并萘酚的萘基和苯乙基苯基芳基部分之外，芴基，苯并[b]噻吩基和苯并呋喃基芳基分别提供了几种高活性的（芳烷基）咪唑抗惊厥剂。这些结构上不同的芳基部分和可比较的抗惊厥活性使这一类抗惊厥药效基团是分子的烷基咪唑部分这一假设得到了证实，亲脂性芳基部分具有能够穿透血脑屏障的能力。我们将SAR研究的重点放在了（芴基烷基）咪唑系列上。该系列的代表性化合物是1-（9H-芴-2-基）-2-（1H-咪唑-1-基）乙酮。这种药物在抑制小鼠最大电击惊厥方面的功效是萘啶酮的两倍（分别为po ED50分别为25和56 mg / kg），而在

  DOI：

  10.1021/jm00159a004

文献信息

• Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
  申请人：Molino F. Bruce

  公开号：US20060052378A1

  公开（公告）日：2006-03-09

  The compounds of the present invention are represented by the chemical structure found in Formula (I): wherein: the carbon atom designated * is in the R or S configuration; and X is a fused bicyclic carbocycle or heterocycle selected from the group consisting of benzofuranyl, benzo[b]thiophenyl, benzoisothiazolyl, benzoisoxazolyl, indazolyl, indolyl, isoindolyl, indolizinyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, imidazo[1,2-a]pyridinyl, pyrazolo[1,5-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[2,3-b]pyridinyl, thieno[3,2-b]pyridinyl, 1H-pyrrolo[2,3-b]pyridinyl, indenyl, indanyl, dihydrobenzocycloheptenyl, tetrahydrobenzocycloheptenyl, dihydrobenzothiophenyl, dihydrobenzofuranyl, indolinyl, naphthyl, tetrahydronaphthyl, quinolinyl, isoquinolinyl, 4H-quinolizinyl, 9aH-quinolizinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, benzo[1,2,3]triazinyl, benzo[1,2,4]triazinyl, 2H-chromenyl, 4H-chromenyl, and a fused bicyclic carbocycle or fused bicyclic heterocycle optionally substituted with substituents (1 to 4 in number) as defined in R 14 ; with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 14 defined herein.

  本发明的化合物由以下式中的化学结构表示（I）： 其中： 指定为*的碳原子处于R或S构型；X是从苯并呋喃基、苯并噻吩基、苯并异噻唑基、苯并异噁唑基、吲哚基、吲哚基、异吲哚基、吲哚啉基、苯并咪唑基、苯并噁唑基、苯并噻唑基、苯并三唑基、咪唑并[1,2-a]吡啶基、吡唑并[1,5-a]吡啶基、[1,2,4]三唑并[4,3-a]吡啶基、噻吩并[2,3-b]吡啶基、噻吩并[3,2-b]吡啶基、1H-吡咯并[2,3-b]吡啶基、茚基、茚基、二氢苯并环庚烯基、四氢苯并环庚烯基、二氢苯并噻吩基、二氢苯并呋喃基、吲啉基、萘基、四氢萘基、喹啉基、异喹啉基、4H-喹啉基、9aH-喹啉基、喹唑啉基、喜啉基、邻苯二嗪基、喹啉基、苯并[1,2,3]三嗪基、苯并[1,2,4]三嗪基、2H-香豆素基、4H-香豆素基或者是一个可选地用取代基（1至4个）取代的螺联苯环或螺联杂环的螺联双环碳环或螺联双环杂环； 其中R1、R2、R3、R4、R5、R6、R7、R8和R14在此处定义。
• Pd(0)-Catalyzed Intramolecular “Ylide-Ullmann-Type” Cyclization of Carbonyl-Stabilized Phosphonium Ylides and Access to Phosphachromones by Exocyclic P–C Cleavage
  作者：Shuangshuang Xu、Haiyang Huang、Zeen Yan、Qiang Xiao

  DOI：10.1021/acs.orglett.9b03948

  日期：2019.12.20

  An unprecedented palladium-catalyzed intramolecular Ullmann-type cyclization of carbonyl-stabilized phosphonium ylides with aryl bromides was successfully developed. Furthermore, a base-promoted chemoselective hydrolysis of exocyclic P-C bond of the corresponding phosphonium salts delivered various phosphachromones. Excellent selectivity and high efficiency and good functional group tolerance were

  成功开发了前所未有的钯催化羰基稳定的磷化膦与芳基溴化物的分子内Ullmann型环化反应。此外，相应phospho盐的环外PC键的碱促进的化学选择性水解递送了各种膦色酮。观察到优异的选择性和高效率以及良好的官能团耐受性。
• Dihydroimidazo[2,1-b]thiazole and dihydro-5h-thiazolo[3,2-A]pyrimidines as antidepressant agents
  申请人：——

  公开号：US20030166628A1

  公开（公告）日：2003-09-04

  The present invention relates to certain novel substituted dihydroimidazo[2,1-b]thiazole and dihydro-5H-thiazolo[3,2-a]pyrimidine compounds of Formula (I) including pharmaceutically acceptable salts thereof in which have affinity for 5-HT 1A receptors and which inhibits neuronal reuptake of 5-hydroxytryptamine and/or noradrenaline, to processes for their preparation, to pharmaceutical compositions containing them and to their use in the treatment of depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, obesity, drug addiction, drug abuse, cognitive disorders, Alzheimer's disease, obsessive-compulsive behaviour, panic attacks, social phobias, eating disorders such as bulimia, anorexia, snacking and binge eating, non-insulin dependent diabetes mellitus, hyperglycaemia, hyperlipidaemia, stress, as an aid to smoking cessation and in the treatment and/or prophylaxis of seizures, neurological disorders such as epilepsy and/or in which there is neurological damage such as stroke, brain trauma, cerebral ischaemia, head injuries and haemorrhage.

  本发明涉及某些新颖的Formula (I)中的取代二氢咪唑[2,1-b]噻唑和二氢-5H-噻唑[3,2-a]嘧啶化合物，包括其对5-HT1A受体具有亲和力并抑制5-羟色胺和/或去甲肾上腺素的神经再摄取的药用盐，以及其制备方法，含有它们的药物组合物，以及它们在治疗抑郁症、焦虑症、精神病（例如精神分裂症）、迟发性运动障碍、肥胖症、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、强迫性行为、恐慌发作、社交恐惧症、进食障碍（如暴食症、厌食症、吃零食和暴饮暴食）、非胰岛素依赖型糖尿病、高血糖、高脂血症、压力、作为戒烟辅助以及治疗和/或预防癫痫发作、癫痫等神经系统疾病以及存在神经损伤的情况（如中风、脑外伤、脑缺血、头部损伤和出血）中的用途。
• [EN] 2-PHENYLIMIDAZO[1,2-A]PYRIMIDINES AS IMAGING AGENTS<br/>[FR] 2-PHÉNYLIMIDAZO[1,2-A]PYRIMIDINES EN TANT QU'AGENTS D'IMAGERIE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014187762A1

  公开（公告）日：2014-11-27

  The present invention relates to compounds of general formula (I) wherein R1 is phenyl, optionally substituted by one or two substituents, selected from 3H, halogen, lower alkyl, di-methyl-amino, NHC(O)-lower alkyl, C(O)O-lower alkyl, lower alkoxy, OC(3H)3, O11CH3, OCH2CH218F, lower alkoxy substituted by halogen, hydroxy, lower alkyl substituted by hydroxy, S-lower alkyl, or by a heterocyclyl group; or is benzo[d][l,3]dioxol-5-yl, 2,3-dihydrobenzo[b][l,4]dioxin-6-yl, indolin-2-one, or is heteroaryl, selected from the group consisting of thiophenyl, benzofuranyl, benzothiophenyl, pyrazinyl, or benzothiazolyl; R2 is hydrogen, lower alkyl or lower alkyl substituted by halogen; R3 is lower alkyl, C(3H)3, 11CH3, lower alkyl substituted by halogen, -(CH2)2-O-lower alkyl substituted by halogen or cycloalkyl; or R2 and R3 form together with the N-atom to which they are attach a ring containing -CH2CH2CHRCH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2-NR-CH2CH2-, -CH2CH2-O-CH2CH2-, -CH2CH2CHRCH2-, -CH2CHRCH2- or (A); R is hydrogen, halogen, lower alkyl substituted by halogen or lower alkoxy; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof. The compounds are suitable as imaging tool, which will improve diagnosis by identifying potential patients with excess of tau aggregates in the brain, which may be likely to develop Alzheimer' s disease.

  本发明涉及通式(I)的化合物，其中R1为苯基，可选择性地被一个或两个取代基取代，这些取代基选自3H、卤素、低级烷基、二甲基氨基、NHC(O)-低级烷基、C(O)O-低级烷基、低级烷氧基、OC(3H)3、O11CH3、OCH2CH218F、被卤素取代的低级烷氧基、羟基、被羟基取代的低级烷基、S-低级烷基，或被杂环基团取代；或者R1为苯并[d][1,3]二氧环戊烯-5-基、2,3-二氢苯并[b][1,4]二氧杂环己烯-6-基、茚满酮-2-基，或者为杂芳基，选自噻吩基、苯并呋喃基、苯并噻吩基、吡嗪基或苯并噻唑基；R2为氢、低级烷基或被卤素取代的低级烷基；R3为低级烷基、C(3H)3、11CH3、被卤素取代的低级烷基、-(CH2)2-O-被卤素取代的低级烷基或环烷基；或者R2和R3与其所连接的N原子一起形成含有-CH2CH2CHRCH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2-NR-CH2CH2-、-CH2CH2-O-CH2CH2-、-CH2CH2CHRCH2-、-CH2CHRCH2-或(A)的环；R为氢、卤素、被卤素取代的低级烷基或低级烷氧基；或者为药学上可接受的酸加成盐，为外消旋混合物或其相应的对映异构体和/或光学异构体。这些化合物适合作为成像工具，通过识别大脑中tau聚集体过剩的潜在患者，从而改善诊断，这些患者可能发展为阿尔茨海默病。
• Baker’s yeast-mediated synthesis of (R)- and (S)-heteroaryl-ethane-1,2-diols
  作者：Paula Veronica Podea、Csaba Paizs、Monica Ioana Toşa、Florin Dan Irimie

  DOI：10.1016/j.tetasy.2008.07.030

  日期：2008.8

  Baker’s yeast-mediated enantioselective bioreduction of 1-(heteroaryl)-2-hydroxyethanones and 2-acetoxy-1-(hetero-aryl)ethanones was used for the enantioselective synthesis of both (R)- and (S)-benzofuranyl-, benzo[b]thiophenyl- and benzo[d]thiazolyl-ethane-1,2-diols.

  贝克的酵母介导的1-（杂芳基）-2-羟基乙酮和2-乙酰氧基-1-（杂芳基）乙酮的对映选择性生物还原被用于（R）-和（S）-苯并呋喃基-苯并的对映选择性合成。[ b ]硫代苯基-和苯并[ d ]噻唑基乙烷-1,2-二醇。