4-溴-1,3-二甲基-1H-吡唑 | 5775-82-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 4-溴-1,3-二甲基-1H-吡唑
• 中文别名: 1,3-二甲基-4-溴吡唑；4-溴-1,3-二甲基吡唑
• 英文名称: 4-bromo-1,3-dimethyl-1H-pyrazole
• 英文别名: 4-bromo-1,3-dimethylpyrazole；1,3-Dimethyl-4-brom-pyrazol；4-Brom-1,3-dimethyl-pyrazol
• CAS: 5775-82-6
• 化学式: C₅H₇BrN₂
• mdl: MFCD00985488
• 分子量: 175.028
• InChiKey: UESOBPUTZLYSGI-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 30 Torr)
• 密度：
  1.487 g/mL at 25 °C
• 闪点：
  103 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-1,3-dimethylpyrazole
Synonyms: 4-Bromo-1,3-dimethyl-1H-pyrazole

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
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

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromo-1,3-dimethylpyrazole
CAS number: 5775-82-6

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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.

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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, refrigerated.

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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
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H7BrN2
Molecular weight: 175.0

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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.

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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

反应信息

• 作为反应物：
  描述：

  4-溴-1,3-二甲基-1H-吡唑 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 生成 4-溴-3-二氟甲基-1-甲基吡唑
  参考文献：
  名称：

  一种3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸 乙酯的制备方法

  摘要：

  本发明公开了一种3‑(二氟甲基)‑1‑甲基‑1H‑吡唑‑4‑羧酸乙酯的制备方法，属于有机合成技术领域。以1,3‑二甲基吡唑为原料，通过卤代得到4‑卤‑1,3‑二甲基‑1H‑吡唑，接着在溴代试剂和AIBN条件下反应，六亚甲基四胺水解得到4‑卤‑1‑甲基‑1H‑吡唑‑3‑甲醛，随后采用氟化试剂反应得到4‑卤‑3‑二氟甲基‑1‑甲基吡唑，最后与格氏试剂进行交换/氯甲酸乙酯反应得到3‑(二氟甲基)‑1‑甲基‑1H‑吡唑‑4‑羧酸乙酯。该方法操作简便，反应收率高，得到的产品纯度可达99.5％以上，具备潜在的工艺放大前景。

  公开号：

  CN111233768B
• 作为产物：
  描述：

  1,3-二甲基-1H-吡唑-4-羧酸 在 sodium hydroxide 、 溴 作用下， 以 水 为溶剂， 反应 1.0h， 以80%的产率得到4-溴-1,3-二甲基-1H-吡唑
  参考文献：
  名称：

  Bromination of 1,3-dimethyl-and 1,5-dimethyl-1H-pyrazole-4-carboxylic acids

  摘要：

  DOI：

  10.1134/s1070363207020193

文献信息

• NITROGEN-CONTAINING HETEROCYCLIC COMPOUND OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20150322063A1

  公开（公告）日：2015-11-12

  A compound represented by Formula [1] (in the formula, Z 1 represents N, CH, or the like; X 1 represents NH or the like; R 1 represents a heteroaryl group or the like; each of R 2 , R 3 , and R 4 represents a hydrogen atom, a halogen atom, an alkoxy group, or the like; and R 5 represents a heteroaryl group or the like) or salt thereof.

  由式[1]表示的化合物（在该式中，Z表示N、CH或类似物；X表示NH或类似物；R表示杂环烷基或类似物；R2、R3和R4中的每一个表示氢原子、卤原子、烷氧基或类似物；R5表示杂环烷基或类似物）或其盐。
• [EN] PYRIDINE DERIVATIVES AS MUSCARINIC M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS<br/>[FR] DÉRIVÉS DE LA PYRIDINE EN TANT QUE MODULATEURS ALLOSTÉRIQUES POSITIFS DU RÉCEPTEUR M1 MUSCARINIQUE
  申请人：PFIZER

  公开号：WO2016009297A1

  公开（公告）日：2016-01-21

  The present invention provides, in part, compounds of Formula I: (I) N-oxides thereof, and pharmaceutically acceptable salts of the compounds or N-oxides; processes for the preparation of; intermediates used in the preparation of; and compositions containing such compounds,N-oxides, or salts, and their uses for treating M1-mediated (or M1-associated) disorders including, e.g., Alzheimer's disease, schizophrenia (e.g., its cognitive and negative symptoms), pain, addiction, and a sleep disorder.

  本发明部分提供了以下化合物的公式I：（I）其N-氧化物，以及该化合物或N-氧化物的药用盐；用于制备的工艺；用于制备的中间体；以及含有这些化合物、N-氧化物或盐的组合物，以及它们用于治疗M1介导（或与M1相关）疾病的用途，例如阿尔茨海默病、精神分裂症（例如其认知和消极症状）、疼痛、成瘾和睡眠障碍。
• PYRROLE COMPOUNDS, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：LES LABORATOIRES SERVIER

  公开号：US20150031673A1

  公开（公告）日：2015-01-29

  Compounds of formula (I): wherein A 1 , A 2 , R a , R b , R c , R d , R 3 , R 4 , R 5 and T are as defined in the description. Medicinal products containing the same which are useful in treating pathologies involving a deficit in apoptosis, such as cancer, auto-immune diseases, and diseases of the immune system.

  式(I)的化合物： 其中A 1 ，A 2 ，R a ，R b ，R c ，R d ，R 3 ，R 4 ，R 5 和T的定义如描述中所述。 含有这些化合物的药物产品对于治疗涉及凋亡缺陷的病理，如癌症、自身免疫疾病和免疫系统疾病，具有益处。
• Synthesis of Conformationally Constrained Esters and Amines by Pd-Catalyzed α-Arylation of Hindered Substrates
  作者：Anthony Martin、Jean-Pierre Vors、Olivier Baudoin

  DOI：10.1021/acscatal.6b00943

  日期：2016.6.3

  The α-arylation of sterically hindered silyl ketene acetals (SKAs) with sterically hindered aryl bromides occurs efficiently using Pd[P(t-Bu)3]2 as the optimal catalyst and ZnF2 as a promoter. Less sensitive P(t-Bu)3-based catalysts could be also employed but showed a lower activity. The reaction showed a broad scope with regard to both coupling partners, including heteroaryl bromides and cyclic SKAs

  使用Pd [P（t- Bu）3 ] 2作为最佳催化剂，并使用ZnF 2作为促进剂，可以有效地发生空间位阻的甲硅烷基烯酮缩醛（SKA）与空间位阻的芳基溴的α-芳基化反应。敏感性较低的P（t- Bu）3基催化剂也可以使用，但显示出较低的活性。对于两种偶合伙伴，包括杂芳基溴化物和环状SKA，反应均显示出广泛的范围。它也被证明可以扩展到几克数量级，这使我们能够进一步转化酯基并获得构象受限的苄基和苯乙胺，这是合成新农药的备受追捧的构建基块。
• Divergent Strategies for the π-Extension of Heteroaryl Halides Using Norbornadiene as an Acetylene Synthon
  作者：Siyeon Jeong、Eunmin Kim、Minkyu Kim、Ye Ji Hwang、Birakishore Padhi、Jonghoon Choi、Yunho Lee、Jung Min Joo

  DOI：10.1021/acs.orglett.0c03732

  日期：2020.12.18

  reactions of five-membered heteroaryl halides and norbornadiene (NBD) were developed. Either direct addition of (benzo)azoles or 2:1 annulation was achieved depending on the propensity of the intermediate complex to undergo palladacycle formation, determined by the nature and substitution pattern of the heteroarene. The obtained exo- and cis-diheteroaryl norbornenes underwent epimerization and retro-Diels–Alder

  开发了五元杂芳基卤化物与降冰片二烯（NBD）的钯催化多组分偶联反应。取决于中间配合物经历palladacycle形成的倾向，可以直接添加（苯并）唑或2：1的环空，这取决于杂芳烃的性质和取代方式。将得到的外-和顺-diheteroaryl降冰片烯后行差向异构化和逆狄尔斯-阿尔德反应，得到相应的反式-异构体和π扩展杂芳族体系，分别展示了NBD的多功能性作为乙炔的合成子。