5-溴-2-氰基嘧啶 | 38275-57-9

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-溴-2-氰基嘧啶
• 中文别名: 2-氰基-5-溴嘧啶
• 英文名称: 5-bromopyrimidine-2-carbonitrile
• 英文别名: 5-bromo-2-cyanopyrimidine；2-cyano-5-bromopyrimidine
• CAS: 38275-57-9
• 化学式: C₅H₂BrN₃
• mdl: MFCD02940446
• 分子量: 183.995
• InChiKey: VPQICCOHFSGBMA-UHFFFAOYSA-N

物化性质

• 沸点：
  317.7±34.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  No
• 危险等级：
  6.1
• 危险品标志：
  Xn,Xi
• 安全说明：
  S26,S36/37,S39,S61
• 危险类别码：
  R20/21/22,R37/38,R41,R50
• 海关编码：
  29339900
• 危险品运输编号：
  UN 3077
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P273,P280,P301+P312+P330,P302+P352+P312,P304+P340+P312,P305+P351+P338+P310
• 危险性描述：
  H302+H312+H332,H315,H318,H335,H410
• 储存条件：
  室温。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2-cyanopyrimidine
Synonyms: 5-Bromopyrimidine-2-carbonitrile

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H331: Toxic if inhaled
H302: Harmful if swallowed
H312: Harmful in contact with skin
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P273: Avoid release to the environment
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Bromo-2-cyanopyrimidine
CAS number: 38275-57-9

---

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.

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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.

---

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.

---

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: C5H2BrN3
Molecular weight: 184.0

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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, hydrogen bromide.

---

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.

---

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

5-溴-2-氰基嘧啶是一种杂环衍生物，可用作医药中间体。有文献报道其可用于制备5-羟基嘧啶-2-羧酸。

制备

在室温下，将20克（103.40毫摩尔，1.00当量）5-溴代-2-氯代嘧啶、2.32克1,4-二氮杂-双环[2.2.2]辛烷和6.72克腈钾（103.20毫摩尔，1.00当量），溶解于54.2毫升水和80毫升DMSO的混合物中，搅拌过夜。随后加入50毫升水，所得溶液用乙醚萃取三次，每次100毫升。合并后的有机层经无水硫酸钠干燥后，在真空条件下浓缩，得到16克（产率84%）黄色固体5-溴-2-氰基嘧啶。

反应信息

• 作为反应物：
  描述：

  5-溴-2-氰基嘧啶 在 potassium phosphate 、 氯化亚砜 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 水 、 cesium fluoride 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 16.5h， 生成 5-甲基-2-嘧啶羧酸甲酯
  参考文献：
  名称：

  Deuterium-Substituted Pyridin- And Pyrimidin-2-yl-Methylamine Compounds

  摘要：

  描述了结构式(I)的氘代吡啶和嘧啶-2-基甲胺化合物，它们是5-羟色胺受体的激动剂。还描述了包括氘代吡啶和嘧啶-2-基甲胺化合物的药物组合物，以及其使用方法。

  公开号：

  US20180079742A1
• 作为产物：
  描述：

  2-甲基-5-溴嘧啶 在 乙酰氯 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 以71%的产率得到5-溴-2-氰基嘧啶
  参考文献：
  名称：

  亚硝酸钠将含氮甲基杂芳烃直接转化为杂芳基腈

  摘要：

  报道了甲基杂芳烃与乙酰氯和亚硝酸钠通过自由基过程以高收率进行的氰化反应。根据对照实验，反应机理发生了根本性的进展。由于其不含金属且易于处理的条件，它在制药行业非常有用。

  DOI：

  10.1021/acs.orglett.2c02596
• 作为试剂：
  描述：

  5-吲哚甲醛 在 potassium carbonate 、 copper(II) sulfate 、 5-溴-2-氰基嘧啶 、 copper(II) oxide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 (R)-2-methyl-N-((S)-1-(1-phenyl-1H-indol-6-yl)ethyl)propane-2-sulfinamide
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS AS MUTANT IDH INHIBITORS

  摘要：

  本公开涉及一般用于治疗与突变异柠檬酸脱氢酶（mt-IDH）相关的疾病的化合物，特别是突变IDH1酶。具体地，本发明揭示了式（IA）的化合物，该化合物对突变IDH1酶表现出抑制活性。还公开了使用该化合物治疗与突变IDH1酶过度活性相关的疾病的方法。此外，还公开了其用途、药物组合物和试剂盒。

  公开号：

  US20200206233A1

文献信息

• Rapid and Direct Photocatalytic C(sp ³ )−H Acylation and Arylation in Flow
  作者：Daniele Mazzarella、Antonio Pulcinella、Loïc Bovy、Rémy Broersma、Timothy Noël

  DOI：10.1002/anie.202108987

  日期：2021.9.20

  photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)−C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced

  在此，我们报告了一种光催化程序，该程序可以使未官能化的烷基衍生物在流动中酰化/芳基化。该方法利用十钨酸盐阴离子作为氢原子提取物并产生亲核碳中心自由基的能力，这些自由基被镍催化剂拦截以最终形成 C(sp 3 )-C(sp 2 ) 键。由于流动条件的强化，反应时间可以从 12-48 小时减少到仅 5-15 分钟。最后，动力学测量强调了强化条件如何不改变反应机制，而是可靠地加速整个过程。
• [EN] MACROCYLIC PYRIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRIDINE MACROCYCLIQUES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2015150557A1

  公开（公告）日：2015-10-08

  The present invention relates to substituted macrocylic pyrimidine derivatives of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention have EF2K inhibitory activity and optionally also Vps34 inhibitory activity. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及式（I）的取代大环嘧啶衍生物，其中变量的含义如权利要求中所定义。根据本发明的化合物具有EF2K抑制活性，还可能具有Vps34抑制活性。本发明还涉及制备这种新化合物的方法，包含所述化合物作为活性成分的药物组合物，以及将所述化合物用作药物的用途。
• 苯并咪唑-2-哌嗪杂环类化合物、其药物组合物 及其制备方法和用途
  申请人：上海汇伦生命科技有限公司

  公开号：CN104230898B

  公开（公告）日：2016-06-29

  本发明苯并咪唑-2-哌嗪杂环类化合物、其药物组合物及其制备方法和用途，涉及氰基嘧啶化合物、其制备方法及其在医药上的应用。具体的，本发明涉及一种式（19）所示的新的氰基嘧啶化合物、其制备方法及含有该化合物的药物组合物以及其作为治疗剂特别是作为聚（ADP-核糖）聚合酶（PARP）抑制剂的用途。 。
• [EN] AMINOPYRAZINE COMPOUNDS WITH A2A ANTAGONIST PROPERTIES<br/>[FR] COMPOSÉS AMINOPYRAZINES AYANT DES PROPRIÉTÉS ANTAGONISTES DE L'A2A
  申请人：MERCK SHARP & DOHME

  公开号：WO2016081290A1

  公开（公告）日：2016-05-26

  Disclosed are compounds of Formula A and Formula A-1, or a salt thereof, and pharmaceutical formulations (pharmaceutical compositions) comprising those compounds, or a salt thereof; wherein "R1", "RA-1", "R2", "R3", and "Het" are defined herein above, which compounds are believed suitable for use in selectively antagonizing the A2a receptors, for example, those found in high density in the basal ganglia. Such compounds and pharmaceutical formulations are believed to be useful in treatment or management of neurodegenerative diseases, for example, Parkinson's disease, or movement disorders arising from use of certain medications used in the treatment or management of Parkinson's disease.

  公开的是Formula A和Formula A-1的化合物，或其盐，以及包含这些化合物或其盐的药物配方（药物组合物）；其中“R1”、“RA-1”、“R2”、“R3”和“Het”如上所定义，这些化合物被认为适用于选择性拮抗A2a受体，例如，在基底神经节中高密度存在的受体。这些化合物和药物配方被认为在治疗或管理神经退行性疾病方面有用，例如帕金森病，或由于使用治疗或管理帕金森病的某些药物而引起的运动障碍。
• Direct Cross-Coupling of Allylic C(sp³ )−H Bonds with Aryl- and Vinylbromides by Combined Nickel and Visible-Light Catalysis
  作者：Long Huang、Magnus Rueping

  DOI：10.1002/anie.201805118

  日期：2018.8.6

  An efficient protocol for the direct allylic C(sp3)−H bond activation of unactivated tri‐ and tetrasubstituted alkenes and their functionalization with aryl‐ and vinylbromides by nickel and visible‐light photocatalysis has been developed. The method allows C(sp2)−C(sp3) formation under mild reaction conditions with good functional‐group tolerance and excellent regioselectivity.

  已经开发了一种有效的协议，用于未活化的三取代和四取代的烯烃的直接烯丙基C（sp 3）-H键活化以及镍和可见光光催化作用将它们用芳基和乙烯基溴官能化。该方法可以在温和的反应条件下形成C（sp 2）-C（sp 3），具有良好的官能团耐受性和极好的区域选择性。