2,6-二羟基-3-氰基-4-甲基吡啶 | 5444-02-0

• 物质功能分类: 医药中间体 - 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: 2,6-二羟基-3-氰基-4-甲基吡啶
• 中文别名: 3-氰基-4-甲基-2,6-二羟基吡啶；6-羟基-3-腈基-4-甲基-1,2-二氢-2-吡啶酮；2,6-二羟基-4-甲基烟腈；3-氰基-2,6-二羟基-4-甲基吡啶；2,6-二羟基-4-甲基吡啶-3-腈；3-氰基-6-羟基-4-甲基-2-吡啶酮；3-氰基-2,6-双羟基-4-甲基吡啶；2,6-二羟基-4-甲基吡啶腈；3-氰基-4-甲基-6-羟基-2-吡啶酮；2,6-二羟基-4-甲基-3-吡啶甲腈；2,6-二羟基-3-氰基4-甲基吡啶；6-羟基-3-氰基-4-甲基吡啶酮；3-氰基-4-甲基-6-羟基-吡啶酮
• 英文名称: 2,6-dihydroxy-3-cyano-4-methylpyrimidine
• 英文别名: 3-cyano-2,6-dihydroxy-4-methylpyridine；2,6-dihydroxy-4-methylnicotinonitrile；2,6-dihydroxy-3-cyano-4-methylpyridine；2,6-Dihydroxy-4-methyl-3-pyridinecarbonitrile；2-hydroxy-4-methyl-6-oxo-1H-pyridine-3-carbonitrile
• CAS: 5444-02-0
• 化学式: C₇H₆N₂O₂
• mdl: MFCD00023471
• 分子量: 150.137
• InChiKey: YRGYYQCOWUULNF-UHFFFAOYSA-N

物化性质

• 熔点：
  315 °C (dec.)(lit.)
• 沸点：
  339.0±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，未有已知危险发生。

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2933399090
• 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：
  密闭、阴凉干燥处保存，并确保有良好的通风。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Cyano-2,6-dihydroxy-4-methylpyridine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
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: 3-Cyano-2,6-dihydroxy-4-methylpyridine
CAS number: 5444-02-0

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.

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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: C7H6N2O2
Molecular weight: 150.1

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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.

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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

制备方法与用途

用途：用于制备染料的中间体。

反应信息

• 作为反应物：
  描述：

  2,6-二羟基-3-氰基-4-甲基吡啶 在 盐酸 作用下， 生成 2,6-二羟基-4-甲基吡啶
  参考文献：
  名称：

  Basu, Journal of the Indian Chemical Society, 1931, vol. 8, p. 323

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氨 作用下， 生成 2,6-二羟基-3-氰基-4-甲基吡啶
  参考文献：
  名称：

  Hope, Journal of the Chemical Society, 1922, vol. 121, p. 2219

  摘要：

  DOI：
• 作为试剂：
  描述：

  氰乙酸甲酯 、 氨 、 乙酰乙酸甲酯 在 2,6-二羟基-3-氰基-4-甲基吡啶 、 水 作用下， 以 水 、 硫酸 为溶剂， 反应 5.0h， 以This gives 147.0 parts (98% of theory) of 3-cyano-4-methyl-6-hydroxypyrid-2-one with a melting point above 305° C.的产率得到
  参考文献：
  名称：

  Process for the manufacture of 6-hydroxypyrid-2-ones

  摘要：

  制备6-羟基吡啶-2-酮的方法是在水溶液或悬浮液中，在氨基存在下，将氰乙酰胺与乙酰乙酸酯在50℃至200℃的温度和0.5至50巴的压力下反应，氨基的摩尔量至少等于氰乙酰胺反应物的摩尔量。

  公开号：

  US04284782A1

文献信息

• Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties
  作者：Mijin, Dušan、Božić Nedeljković, Biljana、Božić, Bojan、Kovrlija, Ilijana、Ladarević, Jelena、Ušćumlić, Gordana

  DOI：10.3906/kim-1711-97

  日期：——

  New azo dyes bearing 2-pyridone and benzimidazole moieties were prepared using diazotization of 4-(1H-benzo[d]imidazol-2-yl)aniline and coupling of the obtained diazonium salt with substituted 3-cyano-2-pyridones. Obtained compounds were characterized via UV-Vis, FT-IR, and $^1}$H and $^13}$C NMR spectroscopy as well as by elemental analysis data. The UV-Vis spectra of the synthesized dyes were measured in thirteen solvents of different properties at room temperature. Solvatochromism and tautomerism of novel azo dyes were discussed. An MTT (3,4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl tetrazolium bromide) test was performed to prove the biocompatibility of the investigated dyes. The investigated dyes exhibited satisfying antiproliferative activities against both tumor cell lines, MDA-MB-231 and HCT-116, demonstrating the potent capacity for treatment of tumors.

  含有2-吡啶酮和苯并咪唑结构的新型偶氮染料是通过4-(1H-苯并[d]咪唑-2-基)苯胺的重氮化以及所得的重氮盐与取代的3-氰基-2-吡啶酮的偶联反应制备的。所得化合物通过UV-Vis、FT-IR、$^1}$H和$^13}$C NMR光谱以及元素分析数据进行表征。合成的染料在室温下在十三种不同性质的溶剂中的UV-Vis光谱被测定。讨论了新型偶氮染料的溶剂化色变和互变异构现象。通过MTT（3,4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴盐）测试证明了所研究染料的生物相容性。所研究的染料对MDA-MB-231和HCT-116两种肿瘤细胞系表现出满意的抗增殖活性，显示出强大的肿瘤治疗能力。
• Online Monitoring of Microwave-Enhanced Reactions by UV/Vis Spectroscopy
  作者：Eberhard Heller、Jessica Klöckner、Werner Lautenschläger、Ulrike Holzgrabe

  DOI：10.1002/ejoc.201000441

  日期：2010.7

  Microwave-enhanced reactions are very fast in comparison to thermal reactions. They are often finished within a few minutes. Thus, the determination of the end point often fails, because conventional analytical methods are too slow. We developed a fast method using a UV/Vis sensor, which allows a direct online monitoring of the reaction process. The potency of the method is demonstrated by means of

  与热反应相比，微波增强反应的速度非常快。它们通常在几分钟内完成。因此，终点的确定常常失败，因为传统的分析方法太慢了。我们开发了一种使用 UV/Vis 传感器的快速方法，可以直接在线监测反应过程。该方法的效力通过五个有代表性的反应来证明。
• PROCESS FOR PREPARING SUBSTITUTED PYRIDONE COMPOUNDS
  申请人：Xerox Corporation

  公开号：US20040006234A1

  公开（公告）日：2004-01-08

  Disclosed is a process for preparing substituted pyridone compounds which comprises (a) admixing in the absence of a solvent (1) an amine of the formula R 1 —NH 2 wherein R 1 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and (2) a first ester of the formula 1 wherein R 2 is an electron withdrawing group and R 3 is an alkyl group; (b) heating the mixture containing the amine and the first ester to form an intermediate compound of the formula 2 (c) admixing the intermediate compound with (1) a base and (2) a second ester of the formula 3 wherein R 4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group and R 5 is an alkyl group, said second ester being present in a molar excess relative to the intermediate compound, said base being present in a molar excess relative to the intermediate compound, and (d) heating the mixture containing the intermediate compound, the second ester, and the base to form a pyridone compound of the formula 4 or a salt thereof. Also disclosed is a process for preparing diazopyridone colorants which comprises preparing a pyridone compound by the above process and reacting the pyridone compound with a diazonium salt to form a diazopyridone compound.

  揭示了一种制备取代吡啶酮化合物的过程，包括(a)在无溶剂的情况下混合（1）具有R1—NH2式的胺，其中R1是烷基、芳基、芳基烷基或烷基芳基，以及（2）具有R2为电子吸引基团和R3为烷基的第一酯的混合；（b）加热含有胺和第一酯的混合物以形成具有式2的中间化合物；（c）将中间化合物与（1）碱和（2）具有R4为烷基、芳基、芳基烷基或烷基芳基以及R5为烷基的第二酯混合，其中所述第二酯相对于中间化合物存在摩尔过量，所述碱相对于中间化合物存在摩尔过量，并且（d）加热含有中间化合物、第二酯和碱的混合物以形成具有式4的吡啶酮化合物或其盐。还揭示了一种制备重氮吡啶酮染料的过程，包括通过上述过程制备吡啶酮化合物，并将吡啶酮化合物与重氮盐反应以形成重氮吡啶酮化合物。
• [EN] 2, 6-DISUBSTITUTED PYRIDINES AND 2, 4-DISUBSTITUTED PYRIMIDINES AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS<br/>[FR] PYRIDINES 2, 6-DISUBSTITUÉES ET PYRIMIDINES 2, 4-DISUBSTITUÉES EN TANT QU'ACTIVATEURS DE GUANYLATE CYCLASE SOLUBLE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009068652A1

  公开（公告）日：2009-06-04

  Disclosed are compounds of formula (I): wherein n represents 1 or 2; each R1 independently represents halo or trifluoromethyl; wherein halo represents fluoro, chloro or bromo; R2 represents hydrogen or C1-3alkyl; X represents N or CH; wherein -Z- represents a group selected from: (A), (B) or (C), wherein R3 represents trifluoromethyl or C1-3alkyl; and R4 represents hydrogen, trifluoromethyl or C1-3alkyl; with the proviso that where Z represents a thiophene group and X represents N, R2 cannot represent C1-3alkyl; and when X represents CH, -Z- can additionally represent a group selected from: (D) or (E) or salts thereof which activate soluble guanylate cyclase (sGC) pharmaceutical compositions containing them, their use is medicine, and processes for their preparation.

  化合物的结构式（I）如下：其中n代表1或2；每个R1独立地代表卤素或三氟甲基；其中卤素代表氟、氯或溴；R2代表氢或C1-3烷基；X代表N或CH；其中-Z-代表从以下选取的基团：（A）、（B）或（C），其中R3代表三氟甲基或C1-3烷基；R4代表氢、三氟甲基或C1-3烷基；但是当Z代表噻吩基团且X代表N时，R2不能代表C1-3烷基；当X代表CH时，-Z-还可以代表从以下选取的基团：（D）或（E）或它们的盐，这些化合物激活可溶性鸟苷酸环化酶（sGC），含有它们的药物组合物，其用途是医药学，以及它们的制备方法。
• 2-substituted 1,2-benzisothiazol-3(2H)-one 1,1-dioxide useful as an
  申请人：American Home Products Corporation

  公开号：US04859671A1

  公开（公告）日：1989-08-22

  There is disclosed the compound 2-[4-[4-(2,7-naphthyridin-1-yl)-1-piperazinyl]butyl]-1,2-benzisothiazol-3( 2H)-one 1,1-dioxide, and the method of producing said compound, and the pharmaceutically acceptable salts thereof, and the use of said compound as an anxiolytic agent having a low liability for extrapyramidal side effects.

  披露了化合物2-[4-[4-(2,7-萘啶基-1-基哌嗪基)丁基]-1,2-苯并异噻唑-3(2H)-酮-1,1-二氧化物，以及制备该化合物的方法，以及其药用可接受的盐，以及将该化合物用作具有低额外锥体副作用风险的抗焦虑剂的用途。