2-异丙基-6-甲基-4-吡啶醇 | 2814-20-2

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 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: 2-异丙基-6-甲基-4-吡啶醇
• 中文别名: 2-异丙基-6-甲基-4-嘧啶醇；安石榴苷；2-异丙基-4-甲基-6-羟基嘧啶；2-异丙基-6-甲基-4-羟基嘧啶
• 英文名称: 2-isopropyl-6-methyl-4-pyrimidinol
• 英文别名: 2-isopropyl-6-methylpyrimidin-4-ol；2-isopropyl-4-hydroxy-6-methylpyrimidine；2-Isopropyl-4-methyl-6-hydroxypyrimidin；4-hydroxy-2-isopropyl-6-methyl-pyrimidine；2-Isopropyl-6-methyl-4-pyrimidone；4-methyl-2-propan-2-yl-1H-pyrimidin-6-one
• CAS: 2814-20-2
• 化学式: C₈H₁₂N₂O
• mdl: MFCD00044811
• 分子量: 152.196
• InChiKey: AJPIUNPJBFBUKK-UHFFFAOYSA-N

物化性质

• 熔点：
  172-175 °C(lit.)
• 沸点：
  274.67°C (rough estimate)
• 密度：
  1.0996 (rough estimate)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

自由生活的土壤线虫秀丽环毛蚓（Panagrellus redivivus）和对植物寄生的线虫短尾滑刃线虫（Bursaphelenchus xylophilus）在接触(14)C标记的敌百虫溶液时，显著吸收了放射性碳。短尾滑刃线虫的代谢产物包括嘧啶醇。秀丽环毛蚓消除放射性碳的速度比短尾滑刃线虫快，这导致在秀丽环毛蚓的培养介质中存在高水平的极性嘧啶醇代谢物。

THERE WAS APPRECIABLE UPTAKE OF RADIOCARBON BY PANAGRELLUS REDIVIVUS, A FREE-LIVING SOIL NEMATODE; AND BURSAPHELENCHUS XYLOPHILUS, A PLANT PARASITIC NEMATODE, WHEN EXPOSED TO A SOLUTION OF (14)C-LABELED DIAZINON. METABOLITES FROM BURSAPHELENCHUS XYLOPHILUS INLUDED PYRIMIDINOL. ELIMINATION OF RADIOCARBON WAS MORE RAPID WITH PANAGRELLUS REDIVIVUS THAN WITH BURSAPHELENCHUS XYLOPHILUS, & THIS RESULTED IN THE PRESENCE OF HIGH LEVELS OF THE POLAR PYRIMIDINOL METABOLITE IN THE INCUBATION MEDIUM OF PANAGRELLUS REDIVIVUS.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Pyrimidinol 是 Diazinon 和 Diazoxon 的人类已知代谢物。

Pyrimidinol is a known human metabolite of Diazinon and Diazoxon.

来源:NORMAN Suspect List Exchange

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• 海关编码：
  2933599090
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  UW7525000
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  密封储存，应存放在阴凉、干燥的库房中。

SDS

Name:	2-Isopropyl-6-Methyl-4-Pyrimidinol 99% Material Safety Data Sheet
Synonym:	6-Methyl-2-(1-Methylethyl)-4(1H)-Pyrimidinone; 2-Isopropyl-4-Methyl-6-Oxypyrimidine; 2-Isopropyl-6-Methyl-3H-Pyrimidin-4-One
CAS:	2814-20-2

Section 1 - Chemical Product MSDS Name:2-Isopropyl-6-Methyl-4-Pyrimidinol 99% Material Safety Data Sheet
Synonym:6-Methyl-2-(1-Methylethyl)-4(1H)-Pyrimidinone; 2-Isopropyl-4-Methyl-6-Oxypyrimidine; 2-Isopropyl-6-Methyl-3H-Pyrimidin-4-One

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2814-20-2	2-Isopropyl-6-Methyl-4-Pyrimidinol	99	220-561-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 2814-20-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Needles
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 172.00 - 174.00 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: C8H12N2O
Molecular Weight: 152.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2814-20-2: UW7525000 LD50/LC50:
CAS# 2814-20-2: Oral, mouse: LD50 = 2200 mg/kg; Oral, rat: LD50 = 2700 mg/kg.
Carcinogenicity:
2-Isopropyl-6-Methyl-4-Pyrimidinol - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 2814-20-2: No information available.
Canada
CAS# 2814-20-2 is listed on Canada's NDSL List.
CAS# 2814-20-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2814-20-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
本品为白色结晶，熔点172～175℃，不溶于水。

用途
2-异丙基-4-甲基-6-羟基嘧啶是杀虫剂二嗪磷的中间体，并用作医药中间体。此外，它也是有机磷农药二嗪磷的关键组成部分。

生产方法
其制备方法是由异丁醛生成的异丁腈与甲醇和氯化氢反应，形成亚胺醚盐酸盐。随后通过该亚胺醚盐酸盐与氨反应生成异丁脒，再在氢氧化钠存在下与乙酰乙酸乙酯环合，最终生成2-异丙基-4-甲基-6-羟基嘧啶。

反应信息

• 作为反应物：
  描述：

  2-异丙基-6-甲基-4-吡啶醇 在 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 生成 N-(4-chlorobenzyl)-2-[furan-2-ylmethyl-(5-iodo-2-isopropyl-6-methylpyrimidin-4-yl)-amino]-acetamide
  参考文献：
  名称：

  钯催化呋喃的开环，作为通往α，β-不饱和醛的途径。

  摘要：

  呋喃可以通过帕拉多催化的反应而开环，从而导致α，β-不饱和醛和酮束缚在吲哚和异喹啉部分上。除了它们的合成兴趣外，这些片段化还为围绕富电子杂环的钯CH活化所涉及的反应机理的讨论带来了有趣的元素。

  DOI：

  10.1039/c0cc04164e
• 作为产物：
  描述：

  二嗪磷 在 水 作用下， 反应 960.0h， 生成 2-异丙基-6-甲基-4-吡啶醇
  参考文献：
  名称：

  Influence of Natural Dissolved Organic Matter, Temperature, and Mixing on the Abiotic Hydrolysis of Triazine and Organophosphate Pesticides

  摘要：

  Abiotic hydrolysis of simazine, atrazine, diazinon, methylparathion, and chlorpyrifos was studied in three different natural waters and buffered Milli-Q water. The triazines showed no detectable decrease in concentration in any of the waters over 43 days at pH 8.0 and 40 degrees C. The rates of hydrolysis for diazinon and methylparathion were statistically similar in all waters tested. Chlorpyrifos exhibited a similar to 32% decrease in hydrolysis rate in the presence of a high concentration of dissolved organic matter (DOM) (34.5 mg/L dissolved organic carbon). The activation energies are larger, and thus the predicted hydrolysis rates are significantly slower than those previously reported. The effect of continuous vigorous mixing on hydrolysis rates was investigated and found to have only a minor effect. The results suggest that uncatalyzed abiotic hydrolysis is very slow for these compounds at the temperatures and pH's typical of most natural waters and affirm the need for a greater understanding of the relative influence of DOM, catalysis, and biodegradation on the fate of organophosphate and triazine pesticides.

  DOI：

  10.1021/jf960315r

文献信息

• [EN] DISUBSTITUTED OCTAHY-DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS<br/>[FR] OCTAHYDROPYRROLO [3,4-C] PYRROLES DISUBSTITUÉS UTILISÉS COMME MODULATEURS DU RÉCEPTEUR DE L'OREXINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012145581A1

  公开（公告）日：2012-10-26

  Disubstituted octahydropyrrolo[3,4-c]pyrrole compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

  描述了二取代的八氢吡咯[3,4-c]吡咯化合物，这些化合物可用作促进睡眠素受体的调节剂。这些化合物可能在药物组合物和治疗由促进睡眠素活性介导的疾病状态、紊乱和病况的方法中有用，比如失眠。
• Convenient Syntheses of Biologically Relevant Vinyl and Divinyl Phosphates by Selective Dealkylation of the Corresponding Phosphites
  作者：Nanjing Zhang、John E. Casida

  DOI：10.1055/s-2000-7109

  日期：——

  Reactions of diethyl vinyl phosphite and divinyl methyl phosphite with iodine produce exclusively dealkylated intermediates, the highly reactive vinyl and divinyl phosphoroiodidates, which can be used as efficient phosphorylation reagents to prepare a variety of vinyl and divinyl organophosphorus compounds. Examples are given for the ethyl vinyl and divinyl analogs of the potent diethyl phosphate anticholinesterase agents diazoxon, chlorpyrifos oxon and paraoxon.

  二乙基乙烯膦和二乙烯基甲基膦与碘的反应产生唯一的去烷基化中间体，即高度活泼的乙烯基和二乙烯基膦碘化物，它们可用作高效的膦酰化试剂，用于制备多种乙烯基和二乙烯基有机磷化合物。以强效的二乙基磷酸酯抗胆碱酯酶剂二唑克松、氯吡硫磷氧类似物和对氧磷的乙基乙烯基和二乙烯基类似物为例。
• Visible-Light-Driven Difluoroacetamidation of Unactive Arenes and Heteroarenes by Direct C–H Functionalization at Room Temperature
  作者：Lin Wang、Xiao-Jing Wei、Wen-Liang Jia、Jian-Ji Zhong、Li-Zhu Wu、Qiang Liu

  DOI：10.1021/ol502676y

  日期：2014.11.21

  The directed difluoroacetamidation of unactivated arenes and heteroarenes with bromodifluoroacetamides via visible-light photoredox catalysis has been efficiently achieved at room temperature. Broad utility of this transformation is presented, including electronically deficient heteroaromatic and aromatic systems. The mechanistic pathway of the difluoroacetamidation was discussed based on photoluminescence

  在室温下，已通过可见光光氧化还原催化有效地实现了未活化的芳烃和杂芳烃与溴二氟乙酰胺的直接二氟乙酰胺化反应。提出了这种转化的广泛用途，包括电子缺陷的杂芳族和芳族体系。基于光致发光猝灭，自旋俘获和动力学同位素效应实验，讨论了二氟乙酰胺化的机理。
• [EN] COMBINATION OF CHIMERIC ANTIGEN RECEPTOR THERAPY AND AMINO PYRIMIDINE DERIVATIVES<br/>[FR] THÉRAPIE COMBINÉE PAR RÉCEPTEUR ANTIGÉNIQUE CHIMÉRIQUE ET DÉRIVÉS D'AMINO PYRIMIDINE
  申请人：NOVARTIS AG

  公开号：WO2016164580A1

  公开（公告）日：2016-10-13

  The invention provides compositions and methods for treating diseases associated with expression of CD19, e.g., by administering a recombinant T cell comprising the CD19 CAR as described herein, in combination with a BTK inhibitor, e.g., an amino pyrimidine derivative described herein. The invention also provides kits and compositions described herein.

  这项发明提供了用于治疗与CD19表达相关疾病的组合物和方法，例如，通过给予包含本文所述的CD19 CAR的重组T细胞，结合一种BTK抑制剂，例如，本文所述的氨基嘧啶衍生物。该发明还提供了本文所述的试剂盒和组合物。
• NOVEL AMINO PYRIMIDINE DERIVATIVES
  申请人：ANGST Daniela

  公开号：US20150152068A1

  公开（公告）日：2015-06-04

  The present invention describes new amino pyrimidine derivatives and pharmaceutically acceptable salts thereof which appear to interact with Bruton's tyrosine kinase (Btk). Accordingly, the novel amino pyrimidines may be effective in the treatment of autoimmune disorders, inflammatory diseases, allergic diseases, airway diseases, such as asthma and chronic obstructive pulmonary disease (COPD), transplant rejection, cancers e.g. of hematopoietic origin or solid tumors.

  本发明描述了新的氨基嘧啶衍生物及其药用盐，这些衍生物似乎与布鲁顿酪氨酸激酶（Btk）相互作用。因此，这些新型氨基嘧啶可能在治疗自身免疫性疾病、炎症性疾病、过敏性疾病、气道疾病（如哮喘和慢性阻塞性肺病（COPD））、移植排斥、血液起源或实体肿瘤等癌症方面具有有效性。

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