1-苯并噻吩-5-甲醛 | 10133-30-9

• 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-苯并噻吩-5-甲醛
• 中文别名: 苯并[B]噻吩-5-甲醛
• 英文名称: benzo[b]thiophene-5-carbaldehyde
• 英文别名: 1-benzothiophene-5-carbaldehyde；benzo[b]thiophene-5-carboxaldehyde
• CAS: 10133-30-9
• 化学式: C₉H₆OS
• mdl: MFCD05663673
• 分子量: 162.212
• InChiKey: QHHRWAPVYHRAJA-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  303.2±15.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  存储条件：2-8℃，需使用惰性气体保护。

SDS

Name:	1-Benzothiophene-5-carbaldehyde Material Safety Data Sheet
Synonym:	None know
CAS:	10133-30-9

Section 1 - Chemical Product MSDS Name:1-Benzothiophene-5-carbaldehyde Material Safety Data Sheet
Synonym:None know

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10133-30-9	1-Benzothiophene-5-carbaldehyde	95+%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
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.
Ingestion:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. Avoid generating dusty conditions.

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Section 7 - HANDLING and STORAGE
Handling:
Use with adequate ventilation. Minimize dust generation and accumulation. 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# 10133-30-9: 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: 56 - 57 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: C9H6OS
Molecular Weight: 162.21

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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:
Strong oxidizing agents, reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 10133-30-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Benzothiophene-5-carbaldehyde - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
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.
WGK (Water Danger/Protection)
CAS# 10133-30-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10133-30-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10133-30-9 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-苯并噻吩-5-甲醛 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 benzo[b]thiophene-5-carbaldehyde oxime
  参考文献：
  名称：

  [EN] SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS
  [FR] COMPOSÉS SPIRO-OXADIAZOLINE EN TANT QU'AGONISTES DES RÉCEPTEURS DE L'ACÉTYLCHOLINE Α-7 NICOTINIQUE

  摘要：

  本发明涉及新型螺环-噁二唑啉化合物，适用作a7-nAChR的激动剂或部分激动剂，以及这些化合物和组合物的制备方法、药物组合物，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物。具体而言，涉及向需要的患者（例如患有认知缺陷和/或希望增强认知功能的患者）施用螺环-噁二唑啉cx7-nAChR激动剂或部分激动剂的方法，以使其获益。

  公开号：

  WO2015066371A1
• 作为产物：
  描述：

  5-溴苯并[b]噻吩 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-苯并噻吩-5-甲醛
  参考文献：
  名称：

  GAMMA-DIKETONES AS WNT/BETA -CATENIN SIGNALING PATHWAY ACTIVATORS

  摘要：

  本公开提供了激活Wnt/β-连环蛋白信号通路并因此治疗或预防与信号转导相关的疾病的γ-二酮或其类似物；这些疾病包括骨质疏松症和骨关节病；骨发育不全、骨缺陷、骨折、牙周病、耳硬化症、伤口愈合、颅颌面缺陷、溶骨性骨病、创伤性脑损伤或脊柱损伤、与中枢神经系统分化和发育相关的脑萎缩/神经系统疾病，包括帕金森病、中风、缺血性脑疾病、癫痫、阿尔茨海默病、抑郁症、躁郁症、精神分裂症；耳部疾病如耳蜗毛细胞丧失；眼部疾病如老年性黄斑变性、糖尿病性黄斑水肿或视网膜色素变性以及与干细胞分化和生长相关的疾病，如脱发、造血相关疾病和组织再生相关疾病。

  公开号：

  US20140243349A1

文献信息

• Studies on Cognitive Enhancing Agents. III. Antiamnestic and Antihypoxic Activities of a Series of l-Bicycloaryl-2-(.OMEGA.-aminoalkoxy)ethanols.
  作者：Satoshi ONO、Tetsuo YAMAFUJI、Hisaaki CHAKI、Hajime MORITA、Yozo TODO、Naomi OKADA、Mutsuko MAEKAWA、Kazunori KITAMURA、Masaru TAI、Hirokazu NARITA

  DOI：10.1248/cpb.43.1492

  日期：——

  2-(2-Aminoethoxy)-1-hydroxyethyl derivatives of bicyclic arenes) naphthalene, thianaphthene, benzofuran, and indole) were prepared and screened for antiamnestic (AA) and antihypoxic (AH) activities which were evaluated by measuring the reversing potency in electroconvulsion-induced amnesia and the protective effect against hypoxia, respectively, in mice. Compound 3o, 1-(benzo[b]thiophen-5-yl)-2-(2-diethylaminoethoxy)ethanol, showed the best AA and AH activity profile, being superior to our prototype compound, 2-(2-dimethylaminoethoxy)-1-phenylethanol (1). Elongation of the ethylene linkage in the side chain of 3o to 3- and 4-carbon moiethies brought about a significant decrease in AH activity. Compound 3o was further investigated for its protective effect against Co2-induced memory impairment and for acute toxicity in mice. It is ten-fold more potent than tacrine in the amnesia-reversal assay and is considerably less toxic than tacrine.

  双环芳烃（萘、噻吊、苯并呋喃和吲哚）的2-(2-氨基乙氧基)-1-羟乙基衍生物被制备并筛选出具有抗遗忘（AA）和抗缺氧（AH）活性的化合物。这些活性通过测定逆转电休克诱导的遗忘和保护小鼠免受缺氧影响的效力来评估。化合物3o，1-(苯并[b]噻吩-5-基)-2-(2-二乙基氨基乙氧基)乙醇，显示出最佳的AA和AH活性特征，优于我们的原型化合物，2-(2-二甲基氨基乙氧基)-1-苯乙醇（1）。在3o的侧链中延长乙烯链接到3-和4-碳单元，显著降低了AH活性。化合物3o进一步研究了其对Co2诱导记忆障碍的保护作用和在小鼠中的急性毒性。在逆转遗忘试验中，其效力是他克林的十倍，并且毒性远低于他克林。
• Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds
  作者：Erin E. Stache、Alyssa B. Ertel、Tomislav Rovis、Abigail G. Doyle

  DOI：10.1021/acscatal.8b03592

  日期：2018.12.7

  oxygen-centered nucleophile. We show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H atom trapping to afford the deoxygenated products. Using the same method, we demonstrate access to synthetically versatile acyl radicals, which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity

  尽管醇和羧酸作为有机分子中的官能团盛行，并且有可能用作自由基前体，但C-O键仍然难以激活。我们报告了通过光氧化还原催化直接从这些普遍存在的官能团同时进入烷基和酰基自由基的合成策略。该方法利用了磷化氢自由基的独特反应性，该反应是由膦自由基阳离子和以氧为中心的亲核试剂之间的极性/ SET交叉产生的。我们显示了在末端醇被俘获以提供脱氧产物的情况下，将苄醇还原为相应的苄基所需要的反应性。使用相同的方法，我们演示了合成通用的酰基自由基的获得方法，可以将芳香族和脂肪族羧酸还原为相应的醛，并具有出色的化学选择性。该协议还通过分子内酰基自由基环化将羧酸转化为杂环和环状酮，从而一步一步形成C–O，C–N和C–C键。
• 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。
• Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction
  作者：Bedřich Formánek、Jiří Tauchman、Ivana Císařová、Jan Veselý

  DOI：10.1021/acs.joc.0c00882

  日期：2020.7.2

  derivatives containing three stereocenters were prepared via one-step synthesis in yields ranging from 88 to 96% and in enantioselectivities (enantiomeric excess (ee)) ranging from 85 to 97%, with diastereoselectivities of approximately 14/2/1. Therefore, this method provides an efficient route for the synthesis of a new class of optically active 2-spirobenzothiophenones.

  本报告描述了在金鸡纳生物碱胺存在下2-亚烷基苯并[ b ]噻吩酮衍生物与烯酮之间的有机催化级联反应。通过一步合成，制备了包含三个立体中心的螺苯并噻吩苯甲酸环己烷衍生物，其产率为88％至96％，对映选择性（对映体过量（ee））为85至97％，非对映选择性约为14/2/1。因此，该方法为合成新型的光学活性的2-螺苯并噻吩酮提供了有效的途径。
• Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes
  作者：Lisa Kötzner、Matthew J. Webber、Alberto Martínez、Claudia De Fusco、Benjamin List

  DOI：10.1002/anie.201400474

  日期：2014.5.12

  The first asymmetric organocatalytic synthesis of helicenes is reported. A novel SPINOL‐derived phosphoric acid, bearing extended π‐substituents, catalyzes the asymmetric synthesis of helicenes through an enantioselective Fischer indole reaction. A variety of azahelicenes and diazahelicenes could be obtained with good to excellent yields and enantioselectivities.

  报道了螺旋烯的首次不对称有机催化合成。一种新颖的SPINOL衍生的磷酸，带有扩展的π取代基，通过对映选择性Fischer吲哚反应催化螺旋烯的不对称合成。可以以良好或优异的产率和对映选择性获得各种氮杂庚烯酮和二氮杂戊烯酮。

表征谱图