5-溴吲唑-3-甲酸 | 1077-94-7

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-溴吲唑-3-甲酸
• 中文别名: 5-溴-1H-吲唑-3-甲酸
• 英文名称: 5-bromo-1H-indazole-3-carboxylic acid
• 英文别名: 5-bromoindazole-3-carboxylic acid
• CAS: 1077-94-7
• 化学式: C₈H₅BrN₂O₂
• mdl: MFCD05663979
• 分子量: 241.044
• InChiKey: AMJVXOOGGBPVCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  289-292°C
• 沸点：
  493.4±25.0 °C(Predicted)
• 密度：
  1.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R22
• 海关编码：
  2933990090
• 安全说明：
  S22,S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Name:	5-Bromo-1H-indazole-3-carboxylic acid Material Safety Data Sheet
Synonym:
CAS:	1077-94-7

Section 1 - Chemical Product MSDS Name:5-Bromo-1H-indazole-3-carboxylic acid Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1077-94-7	5-Bromo-1H-indazole-3-carboxylic acid	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1077-94-7: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Off white
Odor: Characteristic odour
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 289.5 - 292 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H5BrN2O2
Molecular Weight: 241.05

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases, amines.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1077-94-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Bromo-1H-indazole-3-carboxylic acid - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 1077-94-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1077-94-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1077-94-7 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

吲唑-3-羧酸的多种衍生物具有抗精子生成、抗关节炎及镇吐等生物活性。其中，盐酸格拉司琼是一种高度选择性的5-HT₃受体拮抗剂，已广泛用于预防和治疗肿瘤患者因化疗引起的恶心呕吐。近年来，随着医药工业的快速发展，5-溴吲唑-3-羧酸作为一种重要的化工产品受到了越来越多的关注。

制备

以5-溴靛红为起始原料合成5-溴吲唑-3-甲酸的方法如下：将5-溴靛红的碱性溶液与亚硝酸钠溶液混合，在冷却条件下加至稀硫酸溶液中进行重氮化，所得重氮盐溶液用二氧化硫饱和后再加入氯化亚锡还原即可得5-溴吲唑-3-甲酸。在粗产品中含有大量难去除的含锡杂质，可通过反复使用冰醋酸结晶精制。其合成反应式如图1所示。


反应信息

• 作为反应物：
  描述：

  5-溴吲唑-3-甲酸 在 吡啶 、 lithium aluminium tetrahydride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 5-溴吲唑-3-甲醛
  参考文献：
  名称：

  通过Wittig-Horner反应获得2-氮杂色氨酸和脱氢衍生物的新实用途径

  摘要：

  受保护的3-甲酰基吲唑1与（±）-N-（苄氧羰基）-α-膦酰基甘氨酸三甲酯2的Wittig-Horner反应已被开发为脱氢2-氮杂色氨酸和氨基酸衍生物的新型实用合成方法。讨论了5-溴-3-甲酰基吲唑的制备。

  DOI：

  10.1016/j.tetlet.2007.02.042
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 铬 、 溶剂黄146 作用下， 生成 5-溴吲唑-3-甲酸
  参考文献：
  名称：

  Fischer,E.; Tafel, Justus Liebigs Annalen der Chemie, 1885, vol. 227, p. 305,316

  摘要：

  DOI：

文献信息

• Discovery of 2-(cyclopropanecarboxamido)-N-(5-((1-(4-fluorobenzyl)piperidin-4-yl)methoxy)pyridin-3-yl)isonicotinamide as a potent dual AChE/GSK3β inhibitor for the treatment of Alzheimer's disease: Significantly increasing the level of acetylcholine in the brain without affecting that in intestine
  作者：Xueyang Jiang、Chang Liu、Manxing Zou、Huanfang Xie、Tailiang Lin、Weiping Lyu、Jian Xu、Yuan Li、Feng Feng、Haopeng Sun、Wenyuan Liu

  DOI：10.1016/j.ejmech.2021.113663

  日期：2021.11

  impairment-improvement effects. In this study, we characterized a new backbone of the AChE/GSK3β inhibitor 11c. It was identified as a highly potent AChE inhibitor and was found superior to donepezil, the first-line drug for the treatment of AD. In vivo studies confirmed that 11c significantly inhibited the activity of AChE in the brain but had little effect on the activity of AChE in the intestine. This advantage

  乙酰胆碱酯酶（AChE）抑制剂是目前 FDA 批准用于治疗阿尔茨海默病（AD）的一线药物。然而，较短的有效窗口限制了它们的治疗效果。临床研究证实，AChE 抑制剂和神经保护剂的组合表现出更好的抗 AD 作用。我们之前曾报道过双重 AChE/GSK3β（糖原合酶激酶 3β）调节剂具有神经保护作用和认知障碍改善作用。在这项研究中，我们表征了 AChE/GSK3β 抑制剂11c的新骨架。它被确定为一种高效的 AChE 抑制剂，并且优于多奈哌齐，后者是治疗 AD 的一线药物。体内研究证实，11c显着抑制脑内 AChE 的活性，但对肠内 AChE 的活性影响不大。预计11c 的这一优势将减少多奈哌齐引起的外周副作用。此外，生物标志物研究表明，11c还提高了大脑中乙酰胆碱和突触素的水平，并表现出神经保护作用。初步的体内和体外研究结果强调化合物的励磁潜在11C在AD的治疗。
• [EN] ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF IMMUNE AND INFLAMMATORY DISORDERS<br/>[FR] COMPOSÉS ARYLE, HÉTÉROARYLE, ET HÉTÉROCYCLIQUES POUR LE TRAITEMENT DE TROUBLES IMMUNITAIRES ET INFLAMMATOIRES
  申请人：ACHILLION PHARMACEUTICALS INC

  公开号：WO2017035409A1

  公开（公告）日：2017-03-02

  Compounds, methods of use, and processes for making inhibitors of complement Factor D are provided comprising Formula I, I" and I'" or a pharmaceutically acceptable salt or composition thereof. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade. The inhibitors of Factor D described herein reduces the excessive activation of complement.

  提供含有公式I、I"和I'"的补体因子D抑制剂、使用方法和制备过程，或其药物可接受的盐或组合物。本文所述的抑制剂针对因子D并抑制或调节补体级联反应。本文所述的因子D抑制剂减少了补体的过度激活。
• Development of Potent Serotonin-3 (5-HT3) Receptor Antagonists. II. Structure-Activity Relationships of N-(1-Benzyl-4-methylhexahydro-lH-1,4-diazepin-6-yl)carboxamides.
  作者：Hiroshi HARADA、Toshiya MORIE、Yoshimi HIROKAWA、Hideo TERAUCHI、Iwao FUJIWARA、Naoyuki YOSHIDA、Shiro KATO

  DOI：10.1248/cpb.43.1912

  日期：——

  reflex in rats are described. Heteroaromatic rings such as pyrrole, thiophene, furan, pyridine, pyridazine, 1,2-benzisoxazole, indole, quinoline, and isoquinoline rings showed weak 5-HT3 receptor antagonistic activity. Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H-indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3

  我们对4-氨基-5-氯-2-乙氧基苯甲酰胺的研究导致发现N-（1,4-二甲基六氢-1H-1,4-二氮杂-6-6基）苯甲酰胺9和1-苄基-4 -甲基六氢-1H-1,4-二氮杂analogue类似物10是有效的血清素3（5-HT3）受体拮抗剂。描述了结构和活性关系（SAR）研究9和10的芳香核对大鼠von Bezold-Jarisch反射的抑制作用。杂芳族环，如吡咯，噻吩，呋喃，吡啶，哒嗪，1,2-苯并恶唑环，吲哚，喹啉和异喹啉环显示弱的5-HT3受体拮抗活性。在这个系列中，使用1H-吲唑环作为芳族部分会导致活性的大幅提高。1H-吲唑基羧酰胺54、57、97和102显示出有效的5-HT3受体拮抗活性。
• IMIDAZOPYRAZINES AS LSD1 INHIBITORS
  申请人：Incyte Corporation

  公开号：US20160009720A1

  公开（公告）日：2016-01-14

  The present invention is directed to imidazo[1,2-a]pyrazine derivatives which are LSD1 inhibitors useful in the treatment of diseases such as cancer.

  本发明涉及咪唑并[1,2-a]吡嗪衍生物，这些衍生物是LSD1抑制剂，可用于治疗癌症等疾病。
• [EN] ALKYNYL ALCOHOLS AND METHODS OF USE<br/>[FR] ALCOOLS D'ALCYNYLE ET PROCÉDÉS D'UTILISATION CORRESPONDANTS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015025025A1

  公开（公告）日：2015-02-26

  The invention relates to compounds of Formula (0): wherein Q, A1-A8, R4 and R5 and each has the meaning as described herein. Compounds of Formula (0) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over- activation of NF-kB signaling is observed.

  这项发明涉及以下式的化合物（0）：其中Q，A1-A8，R4和R5分别具有如本文所述的含义。式（0）的化合物及其药物组成物在治疗观察到NF-kB信号通路的不良或过度活化的疾病和紊乱中是有用的。