3-氯-2-甲基苯基硼酸 | 313545-20-9

• 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: 3-氯-2-甲基苯基硼酸
• 中文别名: (3-氯-2-甲基)苯硼酸
• 英文名称: (3-chloro-2-methylphenyl)boronic acid
• 英文别名: 3-Chloro-2-methylphenylboronic acid
• CAS: 313545-20-9
• 化学式: C₇H₈BClO₂
• mdl: MFCD04115641
• 分子量: 170.403
• InChiKey: BJPNVVXTUYMJPN-UHFFFAOYSA-N

物化性质

• 熔点：
  142-146
• 沸点：
  325.3±52.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT, KEEP COLD
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-Chloro-2-methylphenylboronic acid
Product Name:
Synonyms:

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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
Wear protective gloves/protective clothing/eye protection/face protection
P280:
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.
3-Chloro-2-methylphenylboronic acid
Ingredient name:
CAS number: 313545-20-9

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H8BClO2
Molecular weight: 170.4

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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, hydrogen chloride.

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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

用途

3-氯-2-甲基苯基硼酸又称(3-氯-2-甲基)苯硼酸或2-甲基-3-氯苯硼酸。它是一种白色固体粉末，广泛用作化工中间体，特别是在医药和精细化工产品的合成中。

制备

1. 缩醛制备：在氮气保护下，将40g 3-氯-2-甲基苯甲醛、25g乙二醇及250ml甲苯加入到1000mL三口烧瓶中。加热回流分水，反应结束后使用质量浓度为30%的碳酸钾溶液洗涤、干燥并脱溶。精馏后得到40g纯品缩乙二醇，收率为82%。

2. 锂化：同样在氮气保护下，将上述制得的苯甲醛缩乙二醇加入到1000mL三口烧瓶中，并加入400ml四氢呋喃。冷却至-80℃，滴加正丁基锂96ml，确保温度保持在-80℃，保温反应直至得到苯基锂化物中间体。

3. 硼化：将制得的苯基锂化物冷却到-80℃，分批加入60g液体硼酸三丁酯。滴加完毕后继续保温反应并控制温度为-80℃。反应结束后向体系中加入10%盐酸进行搅拌，调节pH值至1～2，静置分层、萃取合并有机层，干燥脱溶后再补加水旋干脱溶，得到粗品3-氯-2-甲基苯基硼酸26.4g，收率为80%。

4. 纯化：将26.4g 3-醛基-4-甲基苯硼酸粗品加入到500ml锥形瓶中，用乙酸乙酯热熔后加入100ml石油醚冷却结晶。经离心分离得到纯净的3-氯-2-甲基苯基硼酸产品23.07g，收率为70%。

反应信息

• 作为反应物：
  描述：

  3-氯-2-甲基苯基硼酸 在 吡啶 、 copper diacetate 、 肼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  生成3,8-取代的1,2,4-三唑并吡啶类化合物作为人11β-羟类固醇脱氢酶1型（11β-HSD-1）的有效抑制剂

  摘要：

  修改了一系列11β-HSD-1的吡啶基酰胺/磺酰胺抑制剂，以加入新的1,2,4-三唑并吡啶支架。优化TZP核心3和8位上的取代基，特别着重于增强代谢稳定性，导致鉴定出化合物38作为该酶的有效且代谢稳定的抑制剂。

  DOI：

  10.1016/j.bmcl.2011.05.101
• 作为产物：
  描述：

  硼酸三异丙酯 、 2-溴-6-氯甲苯 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 hexanes 、 水 为溶剂， 反应 0.75h， 以61%的产率得到3-氯-2-甲基苯基硼酸
  参考文献：
  名称：

  [EN] DUAL NK1/NK3 ANTAGONISTS FOR TREATING SCHIZOPHRENIA
  [FR] ANTAGONISTES DOUBLES DES RECEPTEURS NK1/NK3 POUR TRAITER LA SCHIZOPHRENIE

  摘要：

  使用一般式化合物，其中取代基如权利要求1中所述，或其药用活性酸盐，用于制备治疗精神分裂症的药物。

  公开号：

  WO2005002577A1

文献信息

• [EN] SUBSTITUTED PYRAZOLE AND PYRROLE COMPOUNDS AND METHODS FOR USING THEM FOR INHIBITION OF INITIATION OF TRANSLATION AND TREATMENT OF DISEASES AND DISORDERS RELATING THERETO<br/>[FR] COMPOSÉS PYRAZOLE ET PYRROLE SUBSTITUÉS ET PROCÉDÉS D'UTILISATION DE CES DERNIERS POUR L'INHIBITION DE L'INITIATION DE LA TRADUCTION ET LE TRAITEMENT DE MALADIES ET DE TROUBLES ASSOCIÉS À CETTE DERNIÈRE
  申请人：BANTAM PHARMACEUTICAL LLC

  公开号：WO2016196644A1

  公开（公告）日：2016-12-08

  Disclosed are pyrazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure (I) and pharmaceutically acceptable salts and /V-oxides thereof, wherein X1, X2, Z1, Z2, the ring system denoted by "a", R1, A1A, L1B, A1B, L1A, L2, Q, L3, R3, A4A, L4B, A4B, L4A, R4, L5, and R5 are as described herein. In certain embodiments, compounds disclosed herein disrupt the elF4E/eiF4G interaction, and can be used to treat hyperproliferative disorder, a neurological disease or disorder, or autism.

  揭示了吡唑化合物，以及其药物组合物和使用方法。其中一种实施例是具有结构（I）及其药用可接受的盐和/或氧化物，其中X1、X2、Z1、Z2、由“a”表示的环系统、R1、A1A、L1B、A1B、L1A、L2、Q、L3、R3、A4A、L4B、A4B、L4A、R4、L5和R5如本文所述。在某些实施例中，本文所披露的化合物破坏elF4E/eiF4G相互作用，并可用于治疗过度增殖性疾病、神经系统疾病或障碍，或自闭症。
• [EN] NEW THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS DE THIÉNOPYRIMIDINE, PROCÉDÉ POUR LEUR PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2015097123A1

  公开（公告）日：2015-07-02

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description.

  式（I）的化合物：其中R1、R2、R3、R4、R5、R6、R7、R12、X、A和n的定义如描述中所述。
• [EN] NEW BICYCLIC DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS BICYCLIQUES, LEUR PROCÉDÉ DE PRÉPARATION, ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2016207217A1

  公开（公告）日：2016-12-29

  Compounds of formula (I); wherein R1, R2, R3, R4, R5, R6, R7, R8, R14, W, A and n are as defined in the description. Medicaments.

  式(I)的化合物；其中R1、R2、R3、R4、R5、R6、R7、R8、R14、W、A和n的定义如描述所示。药物。
• Intermolecular Reductive C–N Cross Coupling of Nitroarenes and Boronic Acids by P^III/P^V═O Catalysis
  作者：Trevor V. Nykaza、Julian C. Cooper、Gen Li、Nolwenn Mahieu、Antonio Ramirez、Michael R. Luzung、Alexander T. Radosevich

  DOI：10.1021/jacs.8b10769

  日期：2018.11.14

  intermolecular C-N coupling is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane) and a terminal hydrosilane reductant (phenylsilane) to drive reductive intermolecular coupling of nitro(hetero)arenes with boronic acids. Applications to the construction of both Csp2-N (from arylboronic acids) and Csp3-N bonds (from alkylboronic acids) are demonstrated;

  报道了一种通过分子间 CN 偶联合成芳基和杂芳基胺的主要基团催化方法。该方法采用基于小环有机磷的催化剂（1,2,2,3,4,4-六甲基膦烷）和末端氢硅烷还原剂（苯基硅烷）来驱动硝基（杂）芳烃与硼酸的还原性分子间偶联。展示了在构建 Csp2-N（来自芳基硼酸）和 Csp3-N 键（来自烷基硼酸）中的应用；该反应在 Csp3-N 键形成方面是立体有择的。该方法构成了一条从现成的构件到有价值的含氮产品的新途径，与现有催化 CN 偶联方法在范围和化学选择性方面具有互补性。
• [EN] MTH1 INHIBITORS FOR TREATMENT OF CANCER<br/>[FR] INHIBITEURS MTH1 POUR LE TRAITEMENT DU CANCER
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2015187088A1

  公开（公告）日：2015-12-10

  A compound of formula I, (I) or a pharmaceutically-acceptable salt thereof. The compound is useful in the treatment of cancer.

  公式I的化合物(I)或其药用可接受的盐。该化合物在治疗癌症中很有用。