3-甲酸基噻吩-2-硼酸 | 17303-83-2

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲酸基噻吩-2-硼酸
• 中文别名: 3-甲酰基噻吩-2-硼酸；3-甲醛基噻吩-2-硼酸；3-甲酰噻吩-2-硼酸
• 英文名称: 3-formylthiophene-2-boronic acid
• 英文别名: 3-formyl-2-thiopheneboronic acid；(3-formylthiophen-2-yl)boronic acid；3-formyl-2-thienyl boronic acid
• CAS: 17303-83-2
• 化学式: C₅H₅BO₃S
• mdl: MFCD01075679
• 分子量: 155.97
• InChiKey: HYXMHAHVUFTVFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  330 °C (dec.) (lit.)
• 沸点：
  381.2±52.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下稳定，应避免与氧化物和空气接触。 注：原文中部分格式标签已被简化以适应Markdown格式。

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36
• 危险品运输编号：
  NONH for all modes of transport
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  常温下应密闭避光保存，并保持通风和干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Formylthiophene-2-boronic acid
Synonyms: (3-Formyl-2-thienyl)boronic acid; 3-Formyl-2-thiopheneboronic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Formylthiophene-2-boronic acid
CAS number: 17303-83-2

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, under −20◦C.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H5BO3S
Molecular weight: 156.0

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-甲酸基噻吩-2-硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 204.0h， 生成 4-(3'-(hydroxymethyl)-5''-(3,4,5-tris(dodecyloxy)phenyl)-[2,2':5',2''-terthiophen]-5-yl)phthalonitril
  参考文献：
  名称：

  寡噻吩系酞菁的液晶点击程序-自组装，对准和光电流

  摘要：

  已经成功制备了一系列具有酞菁供体核，寡噻吩触角和富勒烯受体的星形液晶（LC）。这种分层的自组装导致了最近发现的Click程序促进了纳米级分离的螺旋形施主-受主-天线LC系统的发展。该模型系统揭示了能量转换，电荷产生和传输的所有光物理前提。可以通过棒涂生产150 nm的均匀非晶薄膜。退火不仅通过点击程序诱导了色谱柱的形成，而且使非澄清样品在夹心几何结构（ITO和Ag / MoO 3）。微观研究和光电流测量已证实了这一点，在退火步骤之后，光电流增加了300倍。

  DOI：

  10.1039/d1tc00710f

文献信息

• Preparation and use of ortho-sulfonamido aryl hydroxamic acids as matrix
  申请人：American Cyanamid Company

  公开号：US05929097A1

  公开（公告）日：1999-07-27

  The present invention relates to the discovery of novel, low molecular weight, non-peptide inhibitors of matrix metalloproteinases (e.g. gelatinases, stromelysins and collagenases) and TNF-.alpha. converting enzyme (TACE, tumor necrosis factor-.alpha. converting enzyme) which are useful for the treatment of diseases in which these enzymes are implicated such as arthritis, tumor growth and metastasis, angiogenesis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, proteinuria, aneurysmal aortic disease, degenerative cartilage loss following traumatic joint injury, demyelinating diseases of the nervous system, graft rejection, cachexia, anorexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease, HIV infection, age related macular degeneration, diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, ocular inflammation, keratoconus, Sjogren's syndrome, myopia, ocular tumors, ocular angiogenesis/neovascularization. The TACE and MMP inhibiting ortho-sulfonamido aryl hydroxamic acids of the present invention are represented by the formula ##STR1## where the hydroxamic acid moiety and the sulfonamido moiety are bonded to adjacent carbons on group A.

  本发明涉及新发现的低分子量、非肽类基质金属蛋白酶（例如明胶酶、溶基质素和胶原酶）和肿瘤坏死因子α转化酶（TACE，肿瘤坏死因子α转化酶）的抑制剂，这些抑制剂用于治疗与这些酶相关的疾病，如关节炎、肿瘤生长和转移、血管生成、组织溃疡、异常伤口愈合、牙周病、骨病、蛋白尿、动脉瘤性主动脉疾病、关节创伤后的退行性软骨损失、神经系统脱髓鞘疾病、移植物排斥、恶病质、厌食、炎症、发热、胰岛素抵抗、感染性休克、充血性心力衰竭、中枢神经系统炎症性疾病、炎症性肠病、HIV感染、与年龄相关的黄斑变性、糖尿病视网膜病变、增生性玻璃体视网膜病变、早产儿视网膜病变、眼内炎症、圆锥角膜、干燥综合症、近视、眼内肿瘤、眼内血管生成/新生血管。本发明的TACE和MMP抑制的邻磺酰胺基芳基羟肟酸由下式表示：##STR1##，其中羟肟酸基团和磺酰胺基团通过相邻的碳原子与A组连接。
• Aryl thiophene derivatives as PDE IV inhibitors
  申请人：Merck & Co., Inc.

  公开号：US06034089A1

  公开（公告）日：2000-03-07

  The invention encompasses the novel compound of Formula I useful in the treatment of diseases, including asthma, by raising the level of cyclic adenosine-3',5'-monophosphate (cAMP) through the inhibition of phosphodiesterase IV (PDE IV). ##STR1## The invention also encompasses certain pharmaceutical compositions and methods for treatment of diseases by inhibition of PDE IV, resulting in an elevation of cAMP, comprising the use of compounds of Formula I.

  该发明涵盖了一种新型化合物，其化学式为I，可用于治疗包括哮喘在内的疾病，通过通过抑制磷酸二酯酶IV（PDE IV）提高环状腺苷-3'，5'-单磷酸（cAMP）的水平。 该发明还涵盖了通过抑制PDE IV治疗疾病的某些药物组合物和方法，导致cAMP升高，包括使用化合物I的用途。
• [EN] THIOPHEN-2-YL-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES AND THE USE THEREOF AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS<br/>[FR] DÉRIVÉS D'ACIDE THIOPHÈNE-2-YL-PYRIDINE-2-YL -1H-PYRAZOLE-4-CARBOXYLIQUE ET LEUR UTILISATION COMME ACTIVATEURS DE LA GUANYLATE CYCLASE SOLUBLE
  申请人：NOVARTIS AG

  公开号：WO2016001876A1

  公开（公告）日：2016-01-07

  The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了化合物(I)或其药学上可接受的盐；制造本发明化合物的方法及其治疗用途。本发明还提供了药理活性剂的组合和药物组成。
• Synthesis of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide
  作者：Keita Hyodo、Hikaru Nonobe、Shuhei Nishinaga、Yasushi Nishihara

  DOI：10.1016/j.tetlet.2014.05.035

  日期：2014.7

  Phenanthro[1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki–Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki–Miyaura coupling of the brominated

  苯并[1,2- b：8,7- b ']二噻吩（PDT）是通过2-噻吩硼或-锌化合物与1,4-二溴苯的Suzuki-Miyaura或Negishi交联制备的，然后用路易斯酸制备催化环氧化物的区域选择性环芳构化。铃木-Miyaura通过引入线性烷基将溴化PDT与烷基硼烷偶联，也可以高收率合成一系列2,9-二烷基化菲咯啉[1,2- b：8,7- b ']二噻吩（PDT）衍生物。取代基。
• Rhodium(II)-Catalyzed Cyclization of Bis(N-tosylhydrazone)s: An Efficient Approach towards Polycyclic Aromatic Compounds
  作者：Ying Xia、Zhenxing Liu、Qing Xiao、Peiyuan Qu、Rui Ge、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201201374

  日期：2012.6.4

  Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki–Miyaura cross‐coupling and a [Rh2(OAc)4]‐catalyzed carbene reaction using easily available bis(N‐tosylhydrazone)s as intermediates (see scheme; Ts=4‐toluenesulfonyl).

  在PAC之前：通过将Suzuki–Miyaura交叉偶联和[Rh 2（OAc）4 ]催化的卡宾反应结合使用，可轻松获得多环芳族化合物（PAC），方法是使用双（N-甲苯磺酰hydr）作为中间体（参见方案； Ts = 4-甲苯磺酰基）。