(1,3-dimethylimidazol-2-ylidene)borane | 1211417-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1,3-dimethylimidazol-2-ylidene)borane
• 英文别名: (1,3-dimethyl-1H-imidazol-3-ium-2-yl)trihydroborate；1,3-dimethylimidazoyl-2-ylidene borane；diMe-Imd-BH3；NHC-BH3；1,3-dimethylimidazoyl-2-ylidine borane；(1,3-Dimethylimidazol-1-ium-2-yl)boranuide；(1,3-dimethylimidazol-1-ium-2-yl)boranuide
• CAS: 1211417-77-4
• 化学式: C₅H₁₁BN₂
• 分子量: 109.967
• InChiKey: WDITXRGBBBKEET-UHFFFAOYSA-N

物化性质

• 熔点：
  134-137 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.16
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 储存条件：
  存放于惰性气体中；避免接触湿气（否则可能发生分解）。

SDS

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Section 1: Product Identification
Chemical Name: 1,3-Dimethylimidazol-2-ylidene borane, min. 97%
CAS Registry Number: 1211417-77-4
Formula: C5H11BN2
EINECS Number: none
Chemical Family: organic amine
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 1211417-77-4 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non-combustible adsorbent and
Spill and Leak Procedures:
swept up. and swept up.

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SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep in a cool, dry,
Handling and Storage:
well-ventilated area.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white pwdr.
Molecular Weight: 109.97
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: moisture sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged exposure to moisture
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, nitrogen oxides, boron oxides and organic fumes

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Not reportable under SARA 313
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1,3-dimethylimidazol-2-ylidene)borane 在 次氯酸叔丁酯 、 次氯酸 作用下， 以 aq. phosphate buffer 、 氘代乙腈 、 水 、 重水 为溶剂， 生成 1,3-dimethylimidazolium
  参考文献：
  名称：

  N-杂环碳硼烷作为活性氧的响应材料：在活细胞和组织中次氯酸的双光子成像中的应用

  摘要：

  N-杂环卡宾（NHC）硼烷经过氧化水解，生成的咪唑鎓盐对HOCl的动力学选择性优于其他活性氧（ROS），包括过氧化物和过氧亚硝酸盐。HOCl的选择性是由NHC硼烷的亲电氧化机理引起的，这与芳基硼酸与ROS的亲核氧化机理相反。NHC硼烷转化为咪唑鎓盐时伴随的极性变化可以控制发射态受激准分子的形成，从而为基于B-H键氧化的ROS荧光探针的设计奠定了基础。证明了活细胞和组织中HOCl的双光子显微镜（TPM）比例成像。

  DOI：

  10.1002/anie.201711188
• 作为产物：
  描述：

  1,3-二甲基咪唑 碘 在 sodium hexamethyldisilazane 、 硼烷-三甲胺络合物 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以50%的产率得到(1,3-dimethylimidazol-2-ylidene)borane
  参考文献：
  名称：

  用胺和膦-硼烷进行路易斯碱交换制备NHC硼烷配合物

  摘要：

  报道了一种从两种稳定的，易于获得的反应物-杂环盐和胺或膦-硼烷开始制备NHC硼烷的通用新方法。它在硼上使用路易斯碱交换，并易于获得新的NHC硼烷，特别是B取代的硼烷硼烷。

  DOI：

  10.1021/jo101301d
• 作为试剂：
  描述：

  1-bromo-4-(((trifluoromethyl)sulfonyl)ethynyl)benzene 在 (1,3-dimethylimidazol-2-ylidene)borane 、 重水 、 N-氯代丁二酰亚胺 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到(E)-1-bromo-4-(2-((trifluoromethyl)sulfonyl)vinyl-2-d)benzene
  参考文献：
  名称：

  炔基砜的无催化剂 α-反式选择性硼氢化和 (E)-选择性氘代半氢化

  摘要：

  在这里，我们提出了炔基砜与 NHC-硼烷的直接 α-反式选择性硼氢化反应，无需催化剂。该反应与多种底物兼容，能够以令人满意的产率有效生产结构多样的α-硼基化乙烯基砜。通过密度泛函理论 (DFT) 计算反式硼氢化反应，研究了从 NHC-硼烷2a到炔基三氟酮1b的氢化物转移。此外，还开发了使用D 2 O作为氘源的炔基三氟酮的区域发散氘化半氢化反应。多种面向多样性的含 D 乙烯基三氟乙烯以良好至优异的产率制备，并且具有优异的氘掺入比。实现了氘化产物的合成操作，将其转化为有价值的氘化分子，表明了该方案的实用性。

  DOI：

  10.1021/acs.joc.3c02833

文献信息

• Dirhodium‐Catalyzed Enantioselective B−H Bond Insertion of <i>gem</i> ‐Diaryl Carbenes: Efficient Access to <i>gem</i> ‐Diarylmethine Boranes
  作者：Yu‐Tao Zhao、Yu‐Xuan Su、Xiao‐Yu Li、Liang‐Liang Yang、Ming‐Yao Huang、Shou‐Fei Zhu

  DOI：10.1002/anie.202109447

  日期：2021.11.2

  We report highly enantioselective dirhodium-catalyzed B−H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance.

  我们报告了以二芳基重氮甲烷作为卡宾前体的高对映选择性二铑催化的 B-H 键插入反应。这些反应以高产率（高达 99 % 的产率）、高活性（高达 14 300 的转化率）、高对映选择性（高达 99 % ee）提供了手性 gem-二芳基次甲基硼烷化合物，并显示出前所未有的广泛官能团耐受性。
• Radical-Hydroboration-Involved One-Pot Synthesis of Boron-Handled Glycol Derivatives
  作者：Feng-Lian Zhang、Yi-Feng Wang、Bi-Yang Zhuang、Ji-Kang Jin

  DOI：10.1055/s-0040-1707142

  日期：2021.3

  A one-pot two-step protocol for the direct synthesis of boron-handled glycol derivatives is reported. The procedure starts by an NHC–boryl-radical-promoted regioselective hydroboration of glycol-protected cinnamaldehydes. After that, the reaction mixture is treated with pinacol in the presence of HCl, leading to the direct formation of pinacol boronate handled glycol monoalkyl ethers. In this acid-triggered

  报告了直接合成硼处理的乙二醇衍生物的一锅两步协议。该过程从乙二醇保护的肉桂醛的 NHC-硼基自由基促进的区域选择性硼氢化反应开始。之后，反应混合物在 HCl 存在下用频哪醇处理，导致直接形成频哪醇硼酸酯处理的二醇单烷基醚。在这种酸引发的转化中，乙二醇衍生的缩醛部分发生还原性开环，在此期间 NHC-硼烷单元作为氢化物源。
• Radical Borylation/Cyclization Cascade of 1,6-Enynes for the Synthesis of Boron-Handled Hetero- and Carbocycles
  作者：Shi-Chao Ren、Feng-Lian Zhang、Jing Qi、Yun-Shuai Huang、Ai-Qing Xu、Hong-Yi Yan、Yi-Feng Wang

  DOI：10.1021/jacs.7b01889

  日期：2017.5.3

  construct boron-handled cyclic molecules was developed based on a radical borylation/cyclization cascade of 1,6-enynes. The process was initiated by the chemo- and regio-controlled addition of an N-heterocyclic carbene-boryl radical to an alkene or alkyne, followed by ring closure to afford boron-substituted cyclic skeletons. Further molecular transformations of the cyclic products to synthetically

  基于 1,6-烯炔的自由基硼化/环化级联，开发了一种构建硼处理环状分子的合成方法。该过程由化学和区域控制的 N-杂环卡宾硼基与烯烃或炔烃的加成开始，然后闭环以提供硼取代的环状骨架。还证明了环状产物向合成有用的结构单元的进一步分子转化。
• Rhodium-Catalyzed B–H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated <i>in Situ</i> from Tosylhydrazones
  作者：Yue Pang、Qiao He、Zi-Qi Li、Ji-Min Yang、Jin-Han Yu、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1021/jacs.8b05946

  日期：2018.8.29

  situ from tosylhydrazones. In addition, by using chiral dirhodium catalysts, we also achieved an asymmetric version of the reaction with good to excellent enantioselectivities (up to 98:2 e.r.). This is the first enantioselective heteroatom-hydrogen bond insertion reaction to use unstabilized diazo compounds as carbene precursors. The protocol exhibited good functional group tolerance and could be carried

  尽管过渡金属催化的 BH 键插入卡宾到稳定的硼烷加合物中已成为有机硼烷合成的一种有前途的方法，但迄今为止用作卡宾前体的所有重氮化合物都具有吸电子基团来稳定它们。在此，我们报告了由甲苯磺酰腙原位生成的不稳定重氮化合物的铑催化 BH 键插入反应的协议。此外，通过使用手性二铑催化剂，我们还实现了具有良好至优异对映选择性（高达 98:2 er）的不对称反应。这是第一个使用不稳定的重氮化合物作为卡宾前体的对映选择性杂原子 - 氢键插入反应。该方案表现出良好的官能团耐受性，可以在克规模上进行。它还能够对映选择性地将羰基一锅法转化为硼基。BH 键插入产物可以很容易地转化为手性醇和其他广泛使用的具有对映体保真度的有机硼试剂。
• Radical Deoxygenation of Xanthates and Related Functional Groups with New Minimalist N-Heterocyclic Carbene Boranes
  作者：Shau-Hua Ueng、Louis Fensterbank、Emmanuel Lacôte、Max Malacria、Dennis P. Curran

  DOI：10.1021/ol101015m

  日期：2010.7.2

  Minimalist N-heterocyclic carbene boranes 1,3-dimethylimidazol-2-ylideneborane and 2,4-dimethyl-1,2,4-triazol-3-ylideneborane are readily available and have low molecular weights. They exhibit superior performance to first-generation NHC−boranes, providing improved yields in reductions of xanthates and related functional groups.

  极简主义的N-杂环卡宾硼烷1,3-二甲基咪唑-2-亚基硼烷和2,4-二甲基-1,2,4-三唑-3-亚基硼烷很容易获得，并且分子量低。它们表现出优于第一代NHC-硼烷的性能，在减少黄药和相关官能团方面提供了更高的收率。