3-羟基-2-甲基吡啶 | 1121-25-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-羟基-2-甲基吡啶
• 中文别名: 2-甲基-3-羟基吡啶；2甲基3羟基吡啶
• 英文名称: 2-methyl-3-pyridinol
• 英文别名: 2-methylpyridin-3-ol；2-methyl-3-hydroxypyridine；3-hydroxy-2-methylpyridine
• CAS: 1121-25-1
• 化学式: C₆H₇NO
• mdl: MFCD00082538
• 分子量: 109.128
• InChiKey: AQSRRZGQRFFFGS-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C (lit.)
• 沸点：
  204.59°C (rough estimate)
• 密度：
  1.1143 (rough estimate)
• 溶解度：
  可溶于二甲基亚砜、甲醇
• LogP：
  0.314 (est)
• 保留指数：
  2140
• 稳定性/保质期：
  常温常压下稳定，避免氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39,S37/39
• 危险类别码：
  R22,R36/37/38,R41
• WGK Germany：
  3
• 海关编码：
  2933399090
• 危险品运输编号：
  NONH for all modes of transport
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H315,H318,H335
• 危险性防范说明：
  P261,P280,P305 + P351 + P338
• 储存条件：
  请将容器密封保存，并储存在阴凉、干燥的地方。

SDS

Name:	3-Hydroxy-2-methylpyridine 99% Material Safety Data Sheet
Synonym:	2-Methyl-3-pyridino
CAS:	1121-25-1

Section 1 - Chemical Product MSDS Name:3-Hydroxy-2-methylpyridine 99% Material Safety Data Sheet
Synonym:2-Methyl-3-pyridino

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1121-25-1	3-Hydroxy-2-methylpyridine	99%	214-327-3

Hazard Symbols: XI
Risk Phrases: 36/37/38

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

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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:

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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.

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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.

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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.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1121-25-1: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: off-white to tan
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 168-169 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: C6H7NO
Molecular Weight: 109.0551

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1121-25-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Hydroxy-2-methylpyridine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 1121-25-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1121-25-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1121-25-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

3-羟基-2-甲基吡啶

简介 3-羟基-2-甲基吡啶是一种医药中间体，可通过将2-乙酰基呋喃与氨水一步反应制备得到。进一步地，它可与N-溴代琥珀酰亚胺反应生成2,4-二溴-3-羟基-6-甲基吡啶，后者再通过特定步骤转化为2-溴-5-羟基-6-甲基吡啶。

用途 3-羟基-2-甲基吡啶用于取代吡啶和嘧啶衍生物的制备，并在治疗病毒感染中具有潜在的应用价值。

应用 该化合物可作为化工医药中间体，在实验室研发及化工医药合成过程中发挥重要作用。

制备 将0.03摩尔2-乙酰基呋喃、35毫升甲醇以及适量铵盐加入100毫升定制的高温消解罐中，再加入20.4克25%氨水。在油浴温度为170℃下磁力搅拌反应16小时。反应完成后进行过滤，并将滤液用活性炭脱色三次，然后旋蒸去除溶剂得到灰色固体。最后通过50%乙醇水溶液重结晶纯化。最终产物2-甲基-3-羟基吡啶的熔点为167～171℃，摩尔收率为33.2%。

生物活性 3-羟基-2-甲基吡啶是从可可碱提取物中分离出来的化合物，可用于嘧啶的合成。

反应信息

• 作为反应物：
  描述：

  3-羟基-2-甲基吡啶 在 [1,3-bis(diphenylphosphino)propane]nickel(II) dichloride 、 rhodium on alumina 盐酸 、 sodium hydroxide 、 magnesium 、 1,2-二溴乙烷 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0~25.0 ℃ 、9.0 MPa 条件下， 反应 24.08h， 生成 (+/-)-spicigerinate de methyle
  参考文献：
  名称：

  Hasseberg, Hans-Albrecht; Gerlach, Hans, Liebigs Annalen der Chemie, 1989, p. 255 - 262

  摘要：

  DOI：
• 作为产物：
  描述：

  碳酸甲丙酯 在 双氧水 、 copper(II) nitrate 作用下， 以 phosphate buffer 、 乙腈 为溶剂， 反应 4.0h， 以82%的产率得到3-羟基-2-甲基吡啶
  参考文献：
  名称：

  AN EFFICIENT FACILE AND SELECTIVE HYDROXYLATION OF NITROGEN HETEROCYCLES

  摘要：

  DOI：

  10.1515/hc.2001.7.5.501
• 作为试剂：
  描述：

  果糖二丙酮 在 3-羟基-2-甲基吡啶 、 磺酰氯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 果糖二丙酮氯磺酸酯
  参考文献：
  名称：

  一种托吡酯的合成工艺

  摘要：

  本发明提供一种托吡酯的合成工艺，涉及药物合成技术领域，所述托吡酯的合成工艺包括以下步骤：(1)双丙酮果糖和磺酰氯在弱碱性环境下酯化得到氯磺酸酯，(2)将氯磺酸酯在四氢呋喃/二氯甲烷的混合溶剂中氨化，得到托吡酯粗品；(3)精制：托吡酯粗品重结晶，得到精制托吡酯；本发明提供了一种操作安全、简单的制备托吡酯的方法，它避免了多步重结晶，降低了成本，简化了生产工艺，适合工业化大规模生产。

  公开号：

  CN106397502A

文献信息

• Design and synthesis of novel, potent and selective hypoxanthine analogs as adenosine A 1 receptor antagonists and their biological evaluation
  作者：Summon Koul、Vidya Ramdas、Dinesh A. Barawkar、Yogesh B. Waman、Neela Prasad、Santosh Kumar Madadi、Yogesh D. Shejul、Rajesh Bonagiri、Sujay Basu、Suraj Menon、Srinivasa B. Reddy、Sandhya Chaturvedi、Srinivas Rao Chennamaneni、Gaurav Bedse、Rhishikesh Thakare、Jayasagar Gundu、Sumit Chaudhary、Siddhartha De、Ashwinkumar V. Meru、Venkata Palle、Anita Chugh、Kasim A. Mookhtiar

  DOI：10.1016/j.bmc.2017.02.029

  日期：2017.3

  Multipronged approach was used to synthesize a library of diverse C-8 cyclopentyl hypoxanthine analogs from a common intermediate III. Several potent and selective compounds were identified and evaluated for pharmacokinetic (PK) properties in Wistar rats. One of the compounds 14 with acceptable PK parameters was selected for testing in in vivo primary acute diuresis model. The compound demonstrated

  多管齐下的方法用于从常见的中间体III合成各种C-8环戊基次黄嘌呤类似物的文库。鉴定了几种有效的和选择性的化合物，并评估了Wistar大鼠的药代动力学（PK）特性。选择具有可接受的PK参数的化合物14之一用于体内原发性急性利尿模型的测试。该化合物在该模型中显示出明显的利尿活性。
• BENZOFURAN-2-SULFONAMIDES DERIVATIVES AS CHEMOKINE RECEPTOR MODULATORS
  申请人：ALLERGAN, INC.

  公开号：US20130231338A1

  公开（公告）日：2013-09-05

  The present invention relates to novel benzofuran-2-sulfonamide derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of chemokine receptors.

  本发明涉及新型苯并呋喃-2-磺酰胺衍生物，制备它们的方法，含有它们的药物组合物以及它们作为化学受体调节剂的药用。
• [EN] TRIAZOLONE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE TRIAZOLONE ET LEURS UTILISATIONS
  申请人：INCEPTION 2 INC

  公开号：WO2013134562A1

  公开（公告）日：2013-09-12

  The invention disclosed herein is directed to compounds of Formula (I) and pharmaceutically acceptable salts thereof, which are useful in the treatment of prostate, breast, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention also comprises pharmaceutical compositions comprising a therapeutically effective amount of compound of Formula (I), or a pharmaceutically acceptable salt thereof. The invention disclosed herein is also directed to methods of treating prostate, breast, ovarian, liver, kidney, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention disclosed herein is further directed to methods of treating prostate, breast, colon, pancreatic, chronic lymphocytic leukemia, melanoma and other cancers comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist. The compounds and pharmaceutical compositions of the invention are also useful in the treatment of viral infections, such as HCV infections and HIV infections. The invention disclosed herein is also directed to a methods of preventing the onset of and/or recurrence of acute and chronic myeloid leukemia, as well as other cancers, comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist.

  本发明涉及的化合物属于式(I)及其药学上可接受的盐，可用于治疗前列腺、乳腺、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症。该发明还包括含有式(I)化合物的治疗有效量或其药学上可接受的盐的药物组合物。本发明还涉及治疗前列腺、乳腺、卵巢、肝脏、肾脏、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法。本发明还涉及治疗前列腺、乳腺、结肠、胰腺、慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法，包括给予选择性PPARα拮抗剂的治疗有效量。本发明的化合物和药物组合物还可用于治疗病毒感染，如HCV感染和HIV感染。本发明还涉及一种预防急性和慢性骨髓性白血病以及其他癌症发作和/或复发的方法，包括给予选择性PPARα拮抗剂的治疗有效量。
• Substituted triazole derivatives as oxytocin antagonists
  申请人：Brown Daniel Alan

  公开号：US20060160786A1

  公开（公告）日：2006-07-20

  The present invention relates to substituted triazoles of formula (I), uses thereof, processes for the preparation thereof and compositions containing said compounds. These inhibitors have utility in a variety of therapeutic areas including sexual dysfunction.

  本发明涉及公式（I）的取代三唑化合物，其用途，制备方法以及含有该化合物的组合物。这些抑制剂在包括性功能障碍在内的各种治疗领域具有用途。
• Substituted N, N-disubstituted diamino compounds useful for inhibiting cholesteryl ester transfer protein activity
  申请人：——

  公开号：US20020120011A1

  公开（公告）日：2002-08-29

  The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted diamines. A preferred specific N,N-disubstituted diamine is the compound: 1

  这项发明涉及替代多环芳基和杂环芳基的三级杂烷基胺化合物，可用作胆固醇酯转移蛋白（CETP；血浆脂质转移蛋白-I）的抑制剂，以及用于治疗动脉粥样硬化和其他冠状动脉疾病的化合物、组合物和方法。首选的三级杂烷基胺化合物是取代的N,N-二取代二胺。首选的具体N,N-二取代二胺化合物是：1

表征谱图