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3-甲基-5-(4,4,5,5-四甲基[1,3,2]二噁硼烷-2-基)苯甲腈 | 1220219-59-9

中文名称
3-甲基-5-(4,4,5,5-四甲基[1,3,2]二噁硼烷-2-基)苯甲腈
中文别名
3-甲基-5-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)苄腈;3-甲基-5-氰基-苯硼酸频哪醇酯
英文名称
3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
英文别名
——
3-甲基-5-(4,4,5,5-四甲基[1,3,2]二噁硼烷-2-基)苯甲腈化学式
CAS
1220219-59-9
化学式
C14H18BNO2
mdl
——
分子量
243.113
InChiKey
ICOWRQHPEDTPCR-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    369.2±35.0 °C(Predicted)
  • 密度:
    1.05±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.17
  • 重原子数:
    18
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    42.2
  • 氢给体数:
    0
  • 氢受体数:
    3

安全信息

  • 海关编码:
    2934999090
  • 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

SDS:57ee7bdaaae245e06c931687e9ddb3eb
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Material Safety Data Sheet

Section 1. Identification of the substance
Product Name: 3-Cyano-5-methylphenylboronic acid pinacol ester
Synonyms: 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

Section 3. Composition/information on ingredients.
Ingredient name: 3-Cyano-5-methylphenylboronic acid pinacol ester
CAS number: 1220219-59-9

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.

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.

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.

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.
Store in closed vessels, refrigerated.
Storage:

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.

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C14H18BNO2
Molecular weight: 243.1

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

Section 11. Toxicological information
No data.

Section 12. Ecological information
No data.

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.

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

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.


SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    3-甲基-5-(4,4,5,5-四甲基[1,3,2]二噁硼烷-2-基)苯甲腈 在 copper diacetate 、 三乙胺 、 sodium nitrite 作用下, 以 乙腈 为溶剂, 反应 12.0h, 以0.073 g的产率得到3-甲基-5-硝基苯腈
    参考文献:
    名称:
    带有芳基化的芳烃的邻位/对位导向基团的亚硝化
    摘要:
    在本文中,我们报道了荟萃芳烃的-nitration轴承邻/对位用铱催化的C-H硼化反应之后是新开发的铜(II)粗频哪醇的芳基硼酸酯入的催化的变换引导组(多个)以一锅的方式对应的硝基芳烃。该协议允许的合成元-nitrated芳烃是乏味来制备或使用现有的方法需要多步合成。该反应可耐受多种邻位/对位导向基团,例如-F,-Cl,-Br,-CH 3,-Et,-i Pr -OCH 3和-OCF 3。它还提供对π电子缺陷杂环的硝基衍生物(例如吡啶和喹啉衍生物)的区域选择性访问。该方法的应用在复杂分子的后期修饰中以及在以克级制备到FDA批准的药物Nilotinib途中的中间体中得到了证明。最后,我们证明了通过该策略获得的硝基产物也可以通过Baran的胺化方案直接转化为苯胺或受阻胺。
    DOI:
    10.1002/chem.201901633
  • 作为产物:
    描述:
    3,5-二甲基苯硼酸频哪醇酯亚硝酸特丁酯N-羟基邻苯二甲酰亚胺 、 palladium diacetate 作用下, 以 乙腈 为溶剂, 反应 24.0h, 以80%的产率得到3-甲基-5-(4,4,5,5-四甲基[1,3,2]二噁硼烷-2-基)苯甲腈
    参考文献:
    名称:
    钯(II)催化将甲基芳烃直接转化为芳族腈
    摘要:
    从甲基到腈:使用Pd(OAc)2和N-羟基邻苯二甲酰亚胺(NHPI)作为催化剂,亚硝酸叔丁酯作为氮源,开发了一种温和的氨氧化方法,该方法将甲基芳烃直接转化为芳族腈。氧化剂。
    DOI:
    10.1002/anie.201305731
  • 作为试剂:
    描述:
    间甲基苯腈联硼酸频那醇酯 、 在 Bis(1,5-cyclooctadiene)dimethoxydiiridium 3-甲基-5-(4,4,5,5-四甲基[1,3,2]二噁硼烷-2-基)苯甲腈 、 4,4′-di-tert-butyl-2,2′-dipyridyl 、 乙醚2-甲基戊烷 作用下, 以 甲基叔丁基醚 为溶剂, 以yielded the title compound (2.34 g, 9.63 mmol) as a white solid的产率得到3-甲基-5-(4,4,5,5-四甲基[1,3,2]二噁硼烷-2-基)苯甲腈
    参考文献:
    名称:
    4-(3-CYANOPHENYL)-6-PYRIDINYLPYRIMIDINE MGLU5 MODULATORS
    摘要:
    本文披露了一种新的化合物,其化学式为其中R1、R2、R3、R4和n的定义在此,以及它们在治疗、预防、改善、控制或减少与调节mGlu5受体功能相关的炎症、神经或精神障碍的风险方面的用途。
    公开号:
    US20160145236A1
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文献信息

  • Regioselective Conversion of Arenes to<i>N</i>-aryl-1,2,3-triazoles Using CH Borylation
    作者:Rajavel Srinivasan、Anthony G. Coyne、Chris Abell
    DOI:10.1002/chem.201403021
    日期:2014.9.8
    A one‐pot protocol for the synthesis of N‐aryl 1,2,3‐triazoles from arenes by an iridium‐catalyzed CH borylation/copper catalyzed azidation/click sequence is described. 1 mol % of Cu(OTf)2 was found to efficiently catalyze both the azidation and the click reaction. The applicability of this method is demonstrated by the late‐stage chemoselective installation of 1,2,3‐triazole moiety into unactivated
    的单釜协议用于合成Ñ -芳基的1,2,3-三唑芳烃通过催化的Ç  ħ化/催化的叠氮化/击序列进行说明。发现1mol%的Cu(OTf)2有效地催化了叠氮化和点击反应。1,2,3-三唑部分在化学上重要的未活化分子的后期化学选择性安装证明了该方法的适用性。
  • Meta Halogenation of 1,3-Disubstituted Arenes via Iridium-Catalyzed Arene Borylation
    作者:Jaclyn M. Murphy、Xuebin Liao、John F. Hartwig
    DOI:10.1021/ja076498n
    日期:2007.12.1
    copper(II) bromide or chloride converts arylboronic esters to the corresponding aryl halides. A variety of arenes containing alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols were converted to the corresponding 3,5-disubstituted aryl bromides and chlorides in yields ranging from 46% to 85%. In addition, 2,6-disubstituted and 3-substituted pyridines were converted
    我们报告了 1,3-二取代芳烃的间位卤化,通过使用催化的芳烃化学形成 3,5-二取代芳基化物和化物。催化的芳烃与 B2pin2 发生化反应,然后硼酸酯溴化铜 (II) 反应,将芳基硼酸酯转化为相应的芳基卤化物。各种含有烷氧基、烷基、卤素、腈、酯、酰胺和新戊酰基芳烃TIPS 保护的醇以 46% 到 85% 的产率转化为相应的 3,5-二取代芳基化物和化物。此外,2,6-二取代和3-取代吡啶分别转化为4-卤代和5-卤代吡啶
  • Microwave-assisted, Ir-catalyzed aromatic C–H borylation
    作者:Li Zeqing、Liang Zhibin、Wang Yuqiang、Yu Pei
    DOI:10.1007/s11164-012-0725-4
    日期:2013.4
    One-step conversions of 1,3-disubstituted benzenes to aryl boronates and 2,6-disubstituted pyridines to heteroaryl boronates are described. Microwave heating was used for all reactions. [(COD)Ir(μ-OMe)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine were used as catalysts, in methyl tert-butyl ether. Acceleration of the rate of reaction was remarkable compared with that of same reaction under conventional heating conditions.
    一步法将1,3-二取代苯转化为芳基硼酸盐,以及将2,6-二取代吡啶转化为杂芳基硼酸盐的反应被描述。所有反应均采用微波加热。使用[(COD)Ir(μ-OMe)]2和4,4′-二叔丁基-2,2′-联吡啶作为催化剂,溶剂为甲基叔丁基醚。与传统加热条件下的相同反应相比,反应速率的加速效果显著。
  • Sterically controlled C–H/C–H homocoupling of arenes <i>via</i> C–H borylation
    作者:Xiaocong Pei、Guan Zhou、Xuejing Li、Yuchen Xu、Resmi C. Panicker、Rajavel Srinivasan
    DOI:10.1039/c9ob00995g
    日期:——
    A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain
    描述了一种温和的一锅法方案,该方案通过顺序的Ir催化的CH硼酸酯化和Cu催化的芳烃均偶联合成对称的联芳基。所形成的联芳基的区域化学空间上受CH硼酸酯化步骤的控制。该方法还成功地扩展到了杂芳烃。通过这种方法获得的某些产品无法通过Ullmann或Suzuki耦合协议获得。最后,我们显示了一锅序列描述了CH化/ Cu催化的均偶联/ Pd催化的Suzuki偶联以获得π扩展的芳烃骨架。
  • Sterically Controlled Alkylation of Arenes through Iridium-Catalyzed CH Borylation
    作者:Daniel W. Robbins、John F. Hartwig
    DOI:10.1002/anie.201208203
    日期:2013.1.14
    one‐pot method for the site‐selective alkylation of arenes controlled by steric effects is reported. The process occurs through Ir‐catalyzed CH borylation, followed by Pd‐ or Ni‐catalyzed coupling with alkyl electrophiles. This selectivity complements that of the typical Friedel–Crafts alkylation; meta‐selective alkylation of a broad range of arenes with various electronic properties and functional
    互补化学:报道了一种通过空间效应控制芳烃的位点选择性烷基化的单锅法。发生的过程通过催化的Ç  ħ基化,随后Pd或Ni基催化的亲电子烷基偶联。这种选择性补充了典型的Friedel-Crafts烷基化反应的选择性。元的宽范围的各种电子性质和官能团的芳烃-选择性的烷基化发生在良好的产率与部位选择性高。
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同类化合物

(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S,S)-邻甲苯基-DIPAMP (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(-)-4,12-双(二苯基膦基)[2.2]对环芳烷(1,5环辛二烯)铑(I)四氟硼酸盐 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(4-叔丁基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(3-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-4,7-双(3,5-二-叔丁基苯基)膦基-7“-[(吡啶-2-基甲基)氨基]-2,2”,3,3'-四氢1,1'-螺二茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (R)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4S,4''S)-2,2''-亚环戊基双[4,5-二氢-4-(苯甲基)恶唑] (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (3aR,6aS)-5-氧代六氢环戊基[c]吡咯-2(1H)-羧酸酯 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[((1S,2S)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1S,2S,3R,5R)-2-(苄氧基)甲基-6-氧杂双环[3.1.0]己-3-醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (1-(2,6-二氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙蒿油 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫-d6 龙胆紫