2-羟基甲基-5-硝基苯硼酸半酯 | 118803-40-0

• 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 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-羟基甲基-5-硝基苯硼酸半酯
• 中文别名: 2-羟甲基-5-硝基苯基硼酸
• 英文名称: 6-nitrobenzo[c][1,2]oxaborol-1(3H)-ol
• 英文别名: 6-nitrobenzoboroxole；6-nitrobenzoxaborole；1-hydroxy-6-nitro-3H-2,1-benzoxaborole；5-Nitro-boronophthalid
• CAS: 118803-40-0
• 化学式: C₇H₆BNO₄
• mdl: MFCD04115657
• 分子量: 178.94
• InChiKey: GFFKBQCIGADRSN-UHFFFAOYSA-N

物化性质

• 熔点：
  178-181°C
• 沸点：
  330.6±52.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

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，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Hydroxymethyl-5-nitrophenylboronic acid, dehydrated
Product Name:
Synonyms: 1-Hydroxy-6-nitro-2,1-benzoxaborolane

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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.
2-Hydroxymethyl-5-nitrophenylboronic acid, dehydrated
Ingredient name:
CAS number: 118803-40-0

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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: C7H6BNO4
Molecular weight: 178.9

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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, nitrogen 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

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
  2-甲基-5-硝基苯硼酸频哪醇酯	4,4,5,5-tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane	957062-84-9	C13H18BNO4	263.101
  2-(羟甲基)苯硼酸环状单酯	3H-benzo[c][1,2]oxaborol-1-ol	5735-41-1	C7H7BO2	133.942
  2-(2-(溴甲基)-5-硝基苯基)-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷	2-(2-(bromomethyl)-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	2096333-96-7	C13H17BBrNO4	341.997

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1,3-二氢-1-羟基-2,1-苯并噁硼-6-胺	6-aminobenzo[c][1,2]oxaborol-1(3H)-ol	117098-94-9	C7H8BNO2	148.957
  ——	1-hydroxy-N-methyl-3H-2,1-benzoxaborol-6-amine	1222510-67-9	C8H10BNO2	162.984
  ——	6-(benzylamino)benzo[c][1,2]oxaborol-1(3H)-ol	——	C14H14BNO2	239.082
  ——	1-(4-fluorophenyl)-3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)urea	1266681-38-2	C14H12BFN2O3	286.07
  ——	1-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-3-(4-(trifluoromethyl)phenyl)urea	1266681-31-5	C15H12BF3N2O3	336.078
  5-BOC-氨基-2-羟甲基苯基硼酸	tert-butyl (1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)carbamate	850568-79-5	C12H16BNO4	249.074
  ——	N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-4-nitrobenzene sulfonamide	1196115-63-5	C13H11BN2O6S	334.117
  ——	1-benzyl-3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)urea	1266681-55-3	C15H15BN2O3	282.107
  ——	4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)amino)-4-oxobutanoic acid	126545-08-2	C11H12BNO5	249.031

反应信息

• 作为反应物：
  描述：

  2-羟基甲基-5-硝基苯硼酸半酯 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 5-<2-Hydroxy-3-carboxy-naphthalinazo>-boronophthalid
  参考文献：
  名称：

  芳基硼酸。四、硼苯酞的反应1

  摘要：

  报道了硼苯酞衍生物的制备。硼苯酞硝化的产物，5-硝基硼苯酞，被还原为5-氨基硼苯酞。5-氨基硼苯酞转化为Nsuccinyl-5-氨基硼苯酞和硼苯酞5-重氮氯化物。最后，重氮化合物与 3-羧基-2-萘酚偶联。讨论了硼苯酞的硼酸内酯环的几种尝试转化。

  DOI：

  10.1021/ja01494a021
• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 sodium nitrite 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 26.5h， 生成 2-羟基甲基-5-硝基苯硼酸半酯
  参考文献：
  名称：

  氨基和羟甲基苯并恶唑硼酸酯的合成：进一步功能化的著名支架

  摘要：

  本文描述了一种短，简单而有效的合成氨基和羟甲基取代的苯并氧杂硼酸的方法的开发。关键步骤是通过苯胺的硼化使硼早期掺入。然后将形成的硼酸盐分两步精加工成最终产品，收率很高。

  DOI：

  10.1002/ejoc.201900013

文献信息

• Protection of the Benzoxaborole Moiety: Synthesis and Functionalization of Zwitterionic Benzoxaborole Complexes
  作者：James M. Gamrat、Giulia Mancini、Sarah J. Burke、Rebecca C. Colandrea、Nicholas R. Sadowski、Bryan C. Figula、John W. Tomsho

  DOI：10.1021/acs.joc.8b00677

  日期：2018.6.1

  incompatible reactions (oxidations, substitutions, and mild reductions) to be achieved in the presence of the benzoxaborole moiety. 3-(N,N-Dimethylamino)-1-propanol was determined to be useful in one-step sequences and is readily cleaved upon workup. Two other groups, N-methylsalicylidenimine and 2-[1-(methylimino)ethyl]phenol, are suitable for multistep syntheses. Deprotection with mild aqueous acid

  报道了三个苯并氧杂硼杂环保护基的合成和实用性。这些保护基团提高了有机溶解度，并在存在苯并氧杂硼烷部分的情况下实现了不相容的反应（氧化，取代和轻度还原）。经确定3-（N，N-二甲基氨基）-1-丙醇可用于一步步骤，并且在后处理时容易裂解。另外两个组，N-甲基水杨亚胺和2- [1-（甲基亚氨基）乙基]苯酚适用于多步合成。用弱酸水溶液脱保护可高产率地进行无色谱分离的苯并氧杂硼烷。
• [EN] PROTECTIVE GROUPS AND METHODS FOR PROTECTING BENZOXABOROLES OR OXABOROLES<br/>[FR] GROUPES PROTECTEURS ET PROCÉDÉS DE PROTECTION DE BENZOXABOROLES OU D'OXABOROLES
  申请人：UNIV OF THE SCIENCES

  公开号：WO2019173814A1

  公开（公告）日：2019-09-12

  The present invention relates in part protective groups that can be used to reversibly protect benzoxaboroles and/or oxaboroles and yield the corresponding protected complexes. The invention further relates to the use of these protective groups to protect benzoxaboroles and/or oxaboroles.

  本发明部分涉及可用于可逆保护苯并硼酮和/或氧硼酮并产生相应保护复合物的保护基。本发明还涉及使用这些保护基来保护苯并硼酮和/或氧硼酮。
• A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near-Infrared Region
  作者：Cecilia Samaniego Lopez、Jimena Hebe Martínez、María Laura Uhrig、Federico Coluccio Leskow、Carla Cecilia Spagnuolo

  DOI：10.1002/chem.201800790

  日期：2018.4.25

  analyte. The superior selectivity of the probe is displayed by the labeling of mucins present in Calu‐3 cells. The new benzoboroxole fluorescent derivative gathers together key properties to make it a highly rated molecular probe: specificity, excellent solubility in water, and off–on near infrared emission. This probe is expected to be an excellent tool for imaging intracellular mucin to evaluate mucus‐related

  据报道，一种新型的荧光分子探针能够在生物活性窗口内以高灵敏度，开启响应以及较大的斯托克斯位移（> 130 nm）检测糖蛋白，特别是粘蛋白。该探针包含一个氨基三聚氰胺作为荧光报告分子，并带有一个连接的苯并环硼氧烷作为识别单元，该受体通过受体的硼半酸酯残基与顺式之间的动态共价反应进行工作。分析物的二醇。通过在Calu-3细胞中存在的粘蛋白标记，可以显示出探针的优越选择性。新的苯并硼恶唑荧光衍生物集聚了关键特性，使其成为高度评价的分子探针：特异性，在水中的出色溶解性以及近红外发射。预期该探针将是对细胞内粘蛋白进行成像以评估粘液相关疾病的绝佳工具，以及对糖基化结构的传感策略，该方法在生物样品中具有治疗学方法的巨大潜力。
• [EN] BORON CONTAINING COMPOUNDS AND THEIR USES<br/>[FR] COMPOSÉS CONTENANT DU BORE ET LEURS UTILISATIONS
  申请人：BORAGEN INC

  公开号：WO2020051575A1

  公开（公告）日：2020-03-12

  The present disclosure contemplates novel boron-containing compounds and their uses as active agents that exhibit pesticidal activity such as antimicrobial, insecticidal, arachnicidal, and/or anti parasitic activity. An agrochemical composition containing such a compound and its use in, animal health, agriculture, or horticulture is also contemplated. A method for promoting plant performance and/or controlling, reducing, preventing, ameliorating, or inhibiting microbes, insects, arachnids, and/or parasites on or in an animal, a plant, a plant part, plant propagation material, and/or harvested fruits or vegetables is also contemplated.

  本公开涉及新颖的含硼化合物及其作为表现出杀虫活性的活性剂的用途，如抗微生物、杀虫、杀螨和/或抗寄生虫活性。还考虑了含有这种化合物的农药组合物及其在动物健康、农业或园艺中的用途。还考虑了一种促进植物表现和/或控制、减少、预防、改善或抑制动物、植物、植物部分、植物繁殖材料和/或收获的水果或蔬菜中的微生物、昆虫、蜘蛛和/或寄生虫的方法。
• Inhibiting Protein Prenylation with Benzoxaboroles to Target Fungal Plant Pathogens
  作者：Sang Hu Kim、Chunliang Liu、Yasheen Zhou、Yong-Kang Zhang、Cari McGregor、Luke Steere、Brittany H. Frederick、C. Tony Liu、Luke Whitesell、Leah E. Cowen

  DOI：10.1021/acschembio.0c00290

  日期：2020.7.17

  identified mutations in the protein prenylation-related genes, CDC43 and ERG20. Allele-swapping experiments confirmed that point mutations in CDC43, which encodes an essential catalytic subunit within geranylgeranyl transferase I (GGTase I) complex, were sufficient to confer resistance to the benzoxaboroles. Mutations in ERG20, which encodes an upstream farnesyl pyrophosphate synthase in the geranylgeranylation

  真菌病原体通过对主要农作物的破坏性影响以及致癌毒素污染食品供应，对全球粮食安全构成越来越大的威胁。农业杀真菌剂的广泛使用增加了农作物的产量，但正促使人们越来越频繁地对可用药剂产生抗药性，并建立了抗药性真菌的环境储藏库，这种储库也可以感染易感人群。为了揭示抗真菌作用的非交叉耐药模式，我们利用了硼化学的独特化学性质，合成了对多种真菌植物病原体具有广谱活性的新型6-硫代氨基甲酸酯苯并硼酸酯。通过酿酒酵母全基因组测序选择对这些化合物具有稳定抗性的分离株，我们鉴定了与蛋白质异戊二烯化相关的基因CDC43和ERG20的突变。等位基因交换实验证实，CDC43的点突变足以赋予对苯并氧杂硼酸的抗性，该点突变编码香叶基香叶基转移酶I（GGTase I）复合物中的重要催化亚基。ERG20中的突变，其在香叶基香叶基化途径中编码上游法呢基焦磷酸合酶，也赋予抗性。与蛋白质烯丙基化的损害一致，这些化合物破坏了经典香叶基