2-甲砜基苯硼酸 | 330804-03-0

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲砜基苯硼酸
• 中文别名: 2-(甲磺酰基)苯硼酸；2-(甲基磺酰基)苯基硼酸；2-(甲基磺酰基)苯硼酸；B-[2-(甲基磺酰基)苯基]-硼酸
• 英文名称: (2-(methylsulfonyl)phenyl)boronic acid
• 英文别名: (2-methanesulfonylphenyl)boronic acid；2-(Methylsulfonyl)phenylboronic acid；(2-methylsulfonylphenyl)boronic acid
• CAS: 330804-03-0
• 化学式: C₇H₉BO₄S
• mdl: MFCD02179472
• 分子量: 200.023
• InChiKey: MSQFFCRGQPVQRS-UHFFFAOYSA-N

物化性质

• 熔点：
  78-84°C
• 沸点：
  469.2±51.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methylsulfonylphenylboronic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Methylsulfonylphenylboronic acid
CAS number: 330804-03-0

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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.

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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: C7H9BO4S
Molecular weight: 200.0

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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

制备方法与用途

应用

2-甲砜基苯硼酸是一种重要的有机合成中间体，可通过 Suzuki 芳基偶联反应合成多烯烃、苯乙烯和联苯的衍生物，进而应用于众多天然产物及有机材料的合成中。

制备

首先，在成盐釜中加入1800公斤水、700公斤砜磺酰氯、450公斤碳酸氢钠和330公斤亚硫酸钠。在常压下进行成盐反应，反应温度控制在60℃，保温时间4小时。反应产生的二氧化碳气体及少量水分将被排出。待反应完成后，在40-50℃趁热过滤，母液用真空抽入甲基化釜中，滤渣另行处理。

接着，将母液进一步加热至70℃并在0.5公斤/厘米³压力下通入一氯甲烷158公斤，保温冷却结晶。当结晶母液冷却到40℃后，放料过滤，滤饼经离心机离心，过滤后的母液和离心母液集中蒸馏处理。水汽经冷凝器冷凝后套用，产生的废盐另行处理。

湿品再经干燥器干燥后即得甲砜基苯，其含量在99%以上，产率约为70%。将甲砜基苯溴化得到邻溴甲砜基苯。

合成2-甲砜基苯硼酸

在反应瓶中加入0.05摩尔（0.1当量）的邻溴甲砜基苯、0.55摩尔（1.1当量）镁屑和数粒单质碘，然后加入300毫升四氢呋喃（THF），搅拌后升温至回流引发格氏反应。在回流状态下继续滴加间溴甲苯0.45摩尔（0.9当量）。滴加完毕后，在回流条件下保温反应直至完成。

降温至-60℃，开始滴加硼酸三甲酯1.0摩尔（2.0当量），滴加完毕后保温反应直到原料完全反应。升温，加入水并滴加盐酸进行水解，调节pH值至1-2，保温反应。反应时间到后，旋转蒸发，抽干，打浆纯化，烘干即得白色固体2-甲砜基苯硼酸0.44摩尔，水分含量为0.05%，纯度98.64%，产率为88.0%。

反应信息

• 作为反应物：
  描述：

  2-甲砜基苯硼酸 在 四(三苯基膦)钯 、 四丁基溴化铵 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.5h， 生成 methyl 2-[3-(3-cyanophenyl)-5-[[4-(2-methylsulfonylphenyl)phenyl]carbamoyl]-4H-1,2-oxazol-5-yl]acetate
  参考文献：
  名称：

  Design and Synthesis of Isoxazoline Derivatives as Factor Xa Inhibitors. 1

  摘要：

  Thrombosis is a major cause of mortality in the industrialized world. Therefore, the prevention of blood coagulation has become a major target for new therapeutic agents. One attractive approach is the inhibition of factor Xa (FXa), the enzyme directly responsible for protbrombin activation. We report a series of novel biaryl-substituted isoxazoline derivatives in which the biaryl moiety was designed to interact with the S-4 aryl-binding domain of the FXa active site. Several of the compounds herein have low nanomolar affinity for FXa, have good in vitro selectivity for FXa, and show potent antithrombotic efficacy in vivo, The three most potent compounds (33, 35, and 37) have inhibition constants for human FXa of 3.9, 2.3, and 0.83 nM, respectively, and ID50's ranging from 0.15 to 0.26 mu mol/kg/h in the rabbit arterio-venous thrombosis model.

  DOI：

  10.1021/jm980405i

文献信息

• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20150259357A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , R 2 , R 3 , R 3 ′, L, W, and V are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention

  本发明涉及式（I）的化合物，或其形式，其中环A，R1，R2，R3，R3'，L，W和V如本文所定义，可用作FLAP调节剂。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• Synthesis and structure activity relationship of the first class of LXR inverse agonists
  作者：Bahaa Elgendy、Kristine Griffett、Lamees Hegazy、Paolo Di Fruscia、Kirby Sample、Emmalie Schoepke、Theodore M. Kamenecka、Thomas P. Burris

  DOI：10.1016/j.bioorg.2021.105540

  日期：2022.2

  anticancer activity of SR9243 (7) and this suggests that new inverse agonists have great potential as anticancer agents. We identified compounds with distinct selectivity toward both LXR isoforms, which can be excellent tools to study the pharmacology of both isoforms. We employed molecular dynamic (MD) simulations to better understand the molecular mechanism underlying inverse agonist activity and to

  肝 X 受体 (LXR) 是核受体家族的成员，它们在脂质和胆固醇代谢中发挥重要作用。此外，它们是几种炎症途径的关键调节剂。LXRs 的药理调节在治疗代谢疾病、神经退行性疾病和癌症方面具有巨大潜力。我们是第一组鉴定出 LXR 反向激动剂 SR9238 ( 6 ) 和 SR9243 ( 7 ) 并证明了它们在治疗肝病和癌症方面的潜在效用。在这里，我们展示了基于 SR9238 ( 6 ) 和 SR9243 ( 7 ) 的结构-活性关系 (SAR) 研究结果。这项研究确定了16、17、19和38，它们是比 SR9238 ( 6 ) 和 SR9243 ( 7 ) 更有效的反向激动剂，并抑制 DU145 细胞中脂肪酸合酶基因的表达。我们之前证明了 FASN 的抑制与 SR9243 ( 7 ) 的抗癌活性相关，这表明新的反向激动剂具有作为抗癌剂的巨大潜力。我们鉴定了对两种 LXR 异构体具有不同选择性的
• [EN] NOVEL COMPOUNDS AND THEIR USE IN THERAPY<br/>[FR] COMPOSÉS INÉDITS ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：BIOCHROMIX PHARMA AB

  公开号：WO2013009259A1

  公开（公告）日：2013-01-17

  The present invention relates to novel chemical compounds formula (I) (C)n-B-(A)m-B-(C)n (I) wherein m is 0 or 1, and n is independently 0, 1, 2 or 3, A, each B and each C are independently selected from phenylene and five-and six-membered heteroaromatic rings, and for a terminal ring B or C also from bicyclic heteroaromatic fused rings having seven to ten ring members, wherein the bond between at least two of the rings A to C may be replaced by a carbonyl group (-CO-), wherein at least two of the rings A to C are substituted with one or two groups R, and wherein each ring A to C further optionally is substituted with one or two groups R1. The compounds are useful in therapy, especially therapy of a mammal suffering from a disease involving misfolded or aggregated forms of proteins.

  本发明涉及一种新型化合物的化学式（I）（C）n-B-（A）m-B-（C）n（I），其中m为0或1，n独立地为0、1、2或3，A、每个B和每个C独立地选自苯基和五元和六元杂芳环，对于末端环B或C还可以选自具有七至十个环成员的双环杂芳融合环，其中至少两个环A到C之间的键可以被羰基（-CO-）取代，其中至少两个环A到C被一个或两个基团R取代，每个环A到C还可以选择地被一个或两个基团R1取代。这些化合物在治疗中有用，特别是在治疗患有涉及蛋白质错误折叠或聚集形式的疾病的哺乳动物的治疗中。
• [EN] NOVEL THIOPHENE COMPOUNDS AND METHOD FOR IN VIVO IMAGING<br/>[FR] NOUVEAUX COMPOSÉS DE THIOPHÈNE ET PROCÉDÉ POUR IMAGERIE IN VIVO
  申请人：BIOCHROMIX AB

  公开号：WO2013036196A1

  公开（公告）日：2013-03-14

  The present invention relates to novel labelled compounds of formula (I) (C)n-B-(A)m-B-(C)n (I) wherein m is 0 or 1, and n is independently 0, 1, 2 or 3, A, each B and each C are independently selected from phenylene and five- and six-membered heteroaromatic rings, and for a terminal ring B or C also from bicyclic heteroaromatic fused rings having seven to ten ring members, wherein the bond between at least two of the rings A to C may be replaced by a carbonyl group ( -CO- ), wherein at least two of the rings A to C are substituted with one or two groups R, and wherein each ring A to C further optionally is substituted with one or two groups R1, for use in imaging amyloid deposits and aggregated protein in living patients. The invention further relates to imaging methods using labelled or unlabelled compounds of formual I and the use of unlabelled compounds in such methods.

  本发明涉及公式（I）（C）n-B-（A）m-B-（C）n的新型标记化合物，其中m为0或1，n独立地为0、1、2或3，A、每个B和每个C独立地选自苯基和五元和六元杂芳环，对于末端环B或C还可以选自具有七至十个环成员的双环杂芳融合环，其中至少两个环A到C之间的键可以被羰基（-CO-）取代，其中至少两个环A到C被一个或两个基团R取代，每个环A到C还可以选择地被一个或两个基团R1取代，用于在活体患者中成像淀粉样沉积物和聚集蛋白。该发明还涉及使用公式I的标记或未标记化合物的成像方法，以及未标记化合物在这些方法中的使用。
• Copper-mediated aerobic (phenylsulfonyl)difluoromethylation of arylboronic acids with difluoromethyl phenyl sulfone
  作者：Xinjin Li、Jingwei Zhao、Mingyou Hu、Dingben Chen、Chuanfa Ni、Limin Wang、Jinbo Hu

  DOI：10.1039/c5cc10550a

  日期：——

  The "PhSO2CF2Cu" reagent (from PhSO2CF2H) reacts with arylboronic acids, which represents a convenient method for the introduction of the CF2 moiety into aromatics.

  “ PhSO 2 CF 2 Cu”试剂（来自PhSO 2 CF 2 H）与芳基硼酸反应，这是将CF 2部分引入芳族化合物的简便方法。