4-氰基-2-硝基苯硼酸 | 850568-46-6

• 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: 4-氰基-2-硝基苯硼酸
• 中文别名: 2-硝基-4-氰基苯硼酸；4-氰基-2-硝基苯基硼酸
• 英文名称: (4-CYANO-2-NITROPHENYL)BORONIC ACID
• 英文别名: 4-Cyano-2-nitrophenylboronic acid
• CAS: 850568-46-6
• 化学式: C₇H₅BN₂O₄
• mdl: MFCD04115646
• 分子量: 191.939
• InChiKey: YDIOTBNYNPBRFF-UHFFFAOYSA-N

物化性质

• 熔点：
  110-116°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  UN 3439
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温，惰性气体

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Cyano-2-nitrophenylboronic acid
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Cyano-2-nitrophenylboronic acid
CAS number: 850568-46-6

---

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.
Storage: Store in closed vessels.

---

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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H5BN2O4
Molecular weight: 191.9

---

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

反应信息

• 作为反应物：
  描述：

  4-氰基-2-硝基苯硼酸 在 盐酸 、 aluminum (III) chloride 、 四(三苯基膦)钯 、 铁粉 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 氯苯 为溶剂， 反应 55.0h， 生成 8-bromo-9-methoxy-6-oxo-5,6-dihydrophenanthridine-3-carbonitrile
  参考文献：
  名称：

  Development of potent macrocyclic inhibitors of genotype 3a HCV NS3/4A protease

  摘要：

  A series of macrocyclic compounds containing 2-substituted-quinoline moieties have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155K mutant activity while maintaining the high rat liver exposure. Cyclization of the 2-substituted quinoline substituent led to a series of tricyclic P2 compounds which also display superb gt3a potency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.106

文献信息

• Nickel(II)-Promoted Amide N–H Arylation of Pyroglutamate–Histidine with Arylboronic Acid Reagents
  作者：Kengo Hanaya、Mary K. Miller、Zachary T. Ball

  DOI：10.1021/acs.orglett.9b00759

  日期：2019.4.5

  Small and simple bioorthogonal reactive handles that can be readily encoded by natural processes are important for bioconjugation. A rapid nickel-promoted N–H arylation of pyroglutamate–histidine sequences with 2-nitroarylboronic acids proceeds under mild aqueous conditions. Chemoselective activation of a lactam amide N–H within a peptide or protein provides a new approach to selective conjugation

  可以通过自然过程轻松编码的小而简单的生物正交反应手柄对于生物缀合非常重要。焦谷氨酸-组氨酸序列与2-硝基芳基硼酸的快速镍促进NH芳基化反应在温和的水性条件下进行。肽或蛋白质中内酰胺酰胺N–H的化学选择性活化为聚酰胺结构的选择性偶联提供了一种新方法。
• Direct formation and site-selective elaboration of methionine sulfoximine in polypeptides
  作者：Yuxuan Ding、Simon S. Pedersen、Alex Lin、Ruoyu Qian、Zachary T. Ball

  DOI：10.1039/d2sc04220g

  日期：——

  sulfoximine (MSO) and its derivatives are well studied, structures with methionine sulfoximine residues within complex polypeptides have been generally inaccessible. This paper describes a straightforward means of late-stage one-step oxidation of methionine residues within polypeptides to afford NH-sulfoximines. We also present chemoselective subsequent elaboration, most notably by copper(II)-mediated N–H cross-coupling

  亚砜亚胺是药物和生物化学的新兴成分，部分原因在于它们在选择性抑制酰胺形成酶（例如 γ-谷氨酰半胱氨酸合成酶）方面的功效。虽然小分子亚砜亚胺如甲硫氨酸亚砜亚胺 (MSO) 及其衍生物得到了很好的研究，但复杂多肽中具有甲硫氨酸亚砜亚胺残基的结构通常是不可接近的。本文描述了一种直接的方法，用于后期一步氧化多肽中的甲硫氨酸残基以提供 NH-亚砜亚胺。我们还介绍了化学选择性后续阐述，最显着的是铜 ( II)-介导的甲硫氨酸亚砜亚胺残基与芳基硼酸试剂的 N-H 交叉偶联。这一发展可作为将多种亚砜亚胺结构整合到天然多肽中的策略，并将甲硫氨酸亚砜亚胺残基鉴定为生物正交、化学选择性生物偶联的新位点。
• CN115838372
  申请人：——

  公开号：——

  公开（公告）日：——
• Development of potent macrocyclic inhibitors of genotype 3a HCV NS3/4A protease
  作者：Michael T. Rudd、John A. McCauley、Joseph J. Romano、John W. Butcher、Kimberly Bush、Charles J. McIntyre、Kevin T. Nguyen、Kevin F. Gilbert、Terry A. Lyle、M. Katharine Holloway、Bang-Lin Wan、Joseph P. Vacca、Vincenzo Summa、Steven Harper、Michael Rowley、Steven S. Carroll、Christine Burlein、Jillian M. DiMuzio、Adam Gates、Donald J. Graham、Qian Huang、Steven W. Ludmerer、Stephanie McClain、Carolyn McHale、Mark Stahlhut、Christine Fandozzi、Anne Taylor、Nicole Trainor、David B. Olsen、Nigel J. Liverton

  DOI：10.1016/j.bmcl.2012.08.106

  日期：2012.12

  A series of macrocyclic compounds containing 2-substituted-quinoline moieties have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155K mutant activity while maintaining the high rat liver exposure. Cyclization of the 2-substituted quinoline substituent led to a series of tricyclic P2 compounds which also display superb gt3a potency. (C) 2012 Elsevier Ltd. All rights reserved.