5-氯-1-苯并噻吩-3-甲醛 | 16296-68-7

• 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: 5-氯-1-苯并噻吩-3-甲醛
• 英文名称: 5-chloro-1-benzothiophene-3-carbaldehyde
• CAS: 16296-68-7
• 化学式: C₉H₅ClOS
• mdl: MFCD02677690
• 分子量: 196.657
• InChiKey: JDEWSTAKAXZTOX-UHFFFAOYSA-N

物化性质

• 熔点：
  109 °C
• 沸点：
  338.8±22.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 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

• 危险品标志：
  Xi
• 危险类别码：
  R22,R36
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

SDS

Name:	5-Chloro-1-benzothiophene-3-carbaldehyde Material Safety Data Sheet
Synonym:
CAS:	16296-68-7

Section 1 - Chemical Product MSDS Name: 5-Chloro-1-benzothiophene-3-carbaldehyde Material Safety Data Sheet
Synonym:

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16296-68-7	5-Chloro-1-benzothiophene-3-carbaldehy	TECH	unlisted

+++++
Hazard Symbols: XN

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Harmful if swallowed. Irritating to eyes, respiratory system and skin. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May cause respiratory tract irritation.
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:

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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:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 16296-68-7: 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: 119 - 121 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: C9H5ClOS
Molecular Weight: 196.66

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing materials, strong oxidizing agents, acids (mineral, non-oxidizing, e.g. hydrochloric acid, hydrofluoric acid, muriatic acid, phosphoric acid), acids (mineral, oxidizing, e.g. chromic acid, hypochlorous acid, nitric acid, sulfuric acid), acids (organic, e.g. acetic acid, benzoic acid, formic acid, methanoic acid, oxalic acid), caustics (e.g. ammonia, ammonium hydroxide, calcium hydroxide, potassium hydroxide, sodium hydroxide), metals (alkali and alkaline, e.g. cesium, potassium, sodium), metals and metal compounds (toxic, e.g. beryllium, lead acetate, nickel carbonyl, tetraethyl lead), nitrides (e.g. potassium nitride, sodium nitride), peroxides and hydroperoxides (organic, e.g. acetyl peroxide, benzoyl peroxide, butyl peroxide, methyl ethyl ketone peroxide), oxidizing agents (strong, e.g. bromine, hydrogen peroxide, nitrogen dioxide, potassium nitrate), reducing agents (strong, e.g. aluminum carbide, chlorosilane, hydrogen phosphide, lithium hydride), water reactive substance.
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# 16296-68-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Chloro-1-benzothiophene-3-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 Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

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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. 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# 16296-68-7: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 16296-68-7 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 16296-68-7 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 10/08/2004 Revision #0 Date: Original. The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-氯-1-苯并噻吩-3-甲醛 在 sodium carbonate 作用下， 以 四氯化碳 为溶剂， 以22.2 g (55%)的产率得到5-氯苯并[B]噻吩-3-羧酸
  参考文献：
  名称：

  Anti-inflammatory and analgesic benzothiophene and benzafuran

  摘要：

  式(I)的化合物：其中：Ar是苯基，可以在o-，m-或p-位置被C.sub.1-4烷基，C.sub.1-4烷氧基，三氟甲基，溴，氯或氟取代，吡啶基，可以选择性地由C.sub.1-4烷基，2-呋喃基或2-噻吩基N-取代，或者可以选择性地在3-，4-或5-位置被甲基，氯或溴取代，或3-呋喃基或3-噻吩基取代；X是氧，硫，亚硫氧或砜，Y是亚甲基，R.sub.1和R.sub.3是氢或C.sub.1-4烷基，R.sub.2是氢，C.sub.1-4烷基，氟，氯或溴，或者X是亚甲基，Y是氧，R.sub.1和R.sub.3都是氢，R.sub.2是氢，氟，氯或溴；R.sub.4是氢或C.sub.1-4烷基，或其盐，具有镇痛和/或抗炎活性。

  公开号：

  US04548948A1
• 作为产物：
  描述：

  (4-氯苯基硫)丙-2-酮 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 potassium iodide 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 64.0h， 生成 5-氯-1-苯并噻吩-3-甲醛
  参考文献：
  名称：

  [EN] TARGETED RADIOPHARMACEUTICALS FOR THE DIAGNOSIS AND TREATMENT OF PROSTATE CANCER
  [FR] PRODUITS RADIOPHARMACEUTIQUES CIBLÉS POUR LE DIAGNOSTIC ET LE TRAITEMENT DU CANCER DE LA PROSTATE

  摘要：

  通用式(I)的化合物：其中：n为1、2或3；R1、R2、R3和R4独立地代表OH或Q；Q代表从群组中选择的组织靶向基团，或其立体异构体、水合物、溶剂合物、盐或其混合物，制备所述化合物的方法，用于制备所述化合物的中间化合物，包含所述化合物的药物组合物和组合物，以及用于制造用于治疗或预防疾病的药物组合物的所述化合物的用途，特别是软组织疾病的治疗或预防，作为唯一药剂或与其他活性成分结合使用。

  公开号：

  WO2021013978A1

文献信息

• Synthesis, Testing and Structure-Activity Studies on a Library of 5-HT4 Ligands
  作者：Amir Hanna-Elias、David T. Manallack、Alla Levit、William Nguyen、Fadi Ayad、Glen Perera、Marina Shapiro、Helen R. Irving、Ian M. Coupar、Magdy N. Iskander

  DOI：10.2174/157340610793563965

  日期：2010.11.1

  Several indole derivatives and analogues comprising a range of related structural classes were designed, synthesized and tested as ligands for the 5-HT4 receptor. Within each series, binding experiments showed compounds with good affinity demonstrating high percentage displacement values at 1 µM. The most potent of these (20) had a pKi of 8.54 demonstrating very good affinity. These indole analogues were combined with 55 ligands that were previously produced in our laboratory to explore the structure-activity relationships of these 5-HT4 ligands. A CoMFA (Comparative Molecular Field Analysis) analysis was used to extend an earlier simple pharmacophore to suggest two new molecular features beyond the primary amino binding site. The pharmacophore confirmed that a newly described tetrahydroquinoline analogue was able to match the basic requirements of the model and the pharmacology of this molecule is provided in more detail.

  设计、合成并测试了几种吲哚衍生物及其类似物，这些化合物属于一系列相关的结构类别，作为 5-HT4 受体的配体。在每个系列中，结合实验显示具有良好亲和力的化合物在 1 µM 浓度下表现出高百分比的置换值。其中最有效的化合物（20）的 pKi 值为 8.54，显示出非常好的亲和力。这些吲哚类似物与之前在我们实验室合成的 55 种配体相结合，以探索这些 5-HT4 配体的结构-活性关系。通过比较分子场分析（CoMFA），从早期简单的药效团模型延伸出两个新的分子特征，超越了主要的氨基结合位点。该药效团确认了一种新描述的四氢喹啉类似物能够匹配模型的基本要求，并且该分子的药理学特性有更详细的说明。
• NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS
  申请人：Oncostellae, S.L.

  公开号：EP3480201A1

  公开（公告）日：2019-05-08

  The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.

  本发明涉及一种新型的二氢吡啶衍生物，其化学式为(I)：作为选择的核受体调节剂，所述核受体包括雄激素受体和糖皮质激素受体，以及其制备方法，包括所述化合物的制药组合物和利用所述化合物制造用于治疗可以通过调节雄激素受体和/或糖皮质激素受体改善的病理情况或疾病的药物，所述病理情况或疾病包括癌症、转移性癌症、良性前列腺增生、多囊卵巢综合征（PCOS）、脱发、多毛症、痤疮、性腺功能减退、肌肉消耗性疾病、虚弱、库欣综合征、抗精神病药物诱导的体重增加、肥胖、创伤后应激障碍和酗酒。
• Robenidine Analogues as Gram-Positive Antibacterial Agents
  作者：Rebecca J. Abraham、Andrew J. Stevens、Kelly A. Young、Cecilia Russell、Anastasia Qvist、Manouchehr Khazandi、Hui San Wong、Sam Abraham、Abiodun D. Ogunniyi、Stephen W. Page、Ryan O’Handley、Adam McCluskey、Darren J. Trott

  DOI：10.1021/acs.jmedchem.5b01797

  日期：2016.3.10

  also accommodated a CH2OH moiety (75; 2,2′-bis[1-(4-chlorophenyl)-2-hydroxyethylidene]carbonimidic dihydrazide). Analogues 1, 27 (2,2′-bis[4-(1,1-dimethylethyl)phenyl]methylene}carbonimidic dihydrazide), and 69 (2,2′-bis[1-(4-chlorophenyl)ethylidene]carbonimidic dihydrazide hydrochloride) were active against 24 clinical MRSA and MSSA isolates. No dose-limiting cytotoxicity at ≥2× MIC or hemolysis at

  Robenidine 1（2,2'-双[（4-氯苯基）亚甲基]羰基二酰肼）具有抗MRSA和VRE的活性，MIC分别为8.1和4.7μM。SAR显示4-F（8），3-F（9），3-CH 3（22）和4-C（CH 3）3（27）（23.7–71μM）和用3-Cl（3），4-CH 3（21）和4-CH（CH 3）2（26）（8.1-13.0μM）。亚胺碳烷基化确定了一个甲基/乙基结合口袋，该口袋也可以容纳CH 2 OH部分（75; 2,2'-双[1-（4-氯苯基）-2-羟基亚乙基]亚氨基二酰肼。类似物1，27（2,2'-双[4-（1,1-二甲基乙基）苯基]亚甲基}肼carbonimidic）和69（2,2'-双[1-（4-氯苯基）亚乙基] carbonimidic盐酸二酰肼）对24种临床MRSA和MSSA分离物具有活性。在≥2xMIC时未观察到剂量限制的细胞毒性，在≥8xMIC时未观察到溶血。
• HETEROCYCLIC COMPOUNDS AS ANTIBIOTIC POTENTIATORS
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：US20160168140A1

  公开（公告）日：2016-06-16

  The invention relates to heterocyclic compounds and their use as antibiotics and/or as antibiotic potentiators. The compounds may act as colistin potentiators and SOS inhibitors.

  这项发明涉及杂环化合物及其作为抗生素和/或抗生素增效剂的用途。这些化合物可能作为科利斯汀增效剂和SOS抑制剂起作用。
• HETEROCYCLIC COMPOUNDS AS POSITIVE MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR 2 (MGLU2 receptor)
  申请人：GENESTE Herve

  公开号：US20080300260A1

  公开（公告）日：2008-12-04

  The present invention relates to heterocyclic compounds which are positive modulators of metabotropic glutamate receptor. The present invention also relates to the use of these compounds for preparing a pharmaceutical composition and to a method of treating a medical disorder, selected from neurological and psychiatric disorders associated with glutamate dysfunction.

  本发明涉及异环化合物，这些化合物是代谢型谷氨酸受体的阳性调节剂。本发明还涉及使用这些化合物制备药物组合物以及治疗神经系统和精神疾病的方法，这些疾病与谷氨酸功能障碍有关。