3-氰基-2-(甲硫基)吡啶-6-甲醛 | 175277-27-7

• 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-氰基-2-(甲硫基)吡啶-6-甲醛
• 中文别名: 6-甲酰基-2-(甲基硫代)烟腈；6-甲酰-2-甲磺酰)-烟酰腈
• 英文名称: 6-formyl-2-(methylthio)nicotinonitrile
• 英文别名: 6-formyl-2-(methylsulfanyl)nicotinonitrile；6-formyl-2-(methylsulfanyl)pyridine-3-carbonitrile；6-formyl-2-methylsulfanylpyridine-3-carbonitrile
• CAS: 175277-27-7
• 化学式: C₈H₆N₂OS
• mdl: MFCD00173824
• 分子量: 178.214
• InChiKey: UBGVOMZGBKLUOU-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  79
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2933399090

SDS

Name:	6-Formyl-2-(methylsulfanyl)nicotinonitrile 95+% Material Safety Data Sheet
Synonym:	3-Cyano-2-(methylthio)pyridine-6-carboxaldehyd
CAS:	175277-27-7

Section 1 - Chemical Product MSDS Name:6-Formyl-2-(methylsulfanyl)nicotinonitrile 95+% Material Safety Data Sheet
Synonym:3-Cyano-2-(methylthio)pyridine-6-carboxaldehyd

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175277-27-7	6-Formyl-2-(methylsulfanyl)nicotinonit	95+%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
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:
Treat symptomatically and supportively.

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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# 175277-27-7: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 137 - 139 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: C8H6N2OS
Molecular Weight: 178

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, acids, bases, amines.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175277-27-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Formyl-2-(methylsulfanyl)nicotinonitrile - 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
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
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 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 175277-27-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175277-27-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175277-27-7 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

反应信息

• 作为反应物：
  描述：

  3-氰基-2-(甲硫基)吡啶-6-甲醛 在 咪唑 、 sodium chlorite 、 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 乙基溴化镁 、 二异丁基氢化铝 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 乙醇 、 氯仿 、 甲苯 为溶剂， 生成 2-ethyl-N-(2-(4-isopropoxy-3-methylphenyl)-2-oxoethyl)-6-(((triisopropylsilyl)oxy)methyl)nicotinamide
  参考文献：
  名称：

  Synthesis and SAR of 1,3-thiazolyl thiophene and pyridine derivatives as potent, orally active and S1P3-sparing S1P1 agonists

  摘要：

  We have previously disclosed 1,2,4-oxadiazole derivative 3 as a potent S1P(3)-sparing S1P(1) agonist. Although compound 3 exhibits potent and manageable immunosuppressive efficacy in various in vivo models, recent studies have revealed that its 1,2,4-oxadiazole ring is subjected to enterobacterial decomposition. As provisions for unpredictable issues, a series of alternative compounds were synthesized on the basis of compound 3. Extensive SAR studies led to the finding of 1,3-thiazole 24c with the EC50 value of 3.4 nM for human S1P(1), and over 5800-fold selectivity against S1P(3). In rat on host versus graft reaction (HvGR), the ID50 value of 24c was determined at 0.07 mg/kg. The pharmacokinetics in rat and monkey is also reported. Compared to compound 3, 24c showed excellent stability against enterobacteria. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.067
• 作为产物：
  描述：

  6-(二甲氧基甲基)-2-硫代-1,2-二氢-3-吡啶甲腈 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 乙腈 为溶剂， 生成 3-氰基-2-(甲硫基)吡啶-6-甲醛
  参考文献：
  名称：

  Synthesis and SAR of 1,3-thiazolyl thiophene and pyridine derivatives as potent, orally active and S1P3-sparing S1P1 agonists

  摘要：

  We have previously disclosed 1,2,4-oxadiazole derivative 3 as a potent S1P(3)-sparing S1P(1) agonist. Although compound 3 exhibits potent and manageable immunosuppressive efficacy in various in vivo models, recent studies have revealed that its 1,2,4-oxadiazole ring is subjected to enterobacterial decomposition. As provisions for unpredictable issues, a series of alternative compounds were synthesized on the basis of compound 3. Extensive SAR studies led to the finding of 1,3-thiazole 24c with the EC50 value of 3.4 nM for human S1P(1), and over 5800-fold selectivity against S1P(3). In rat on host versus graft reaction (HvGR), the ID50 value of 24c was determined at 0.07 mg/kg. The pharmacokinetics in rat and monkey is also reported. Compared to compound 3, 24c showed excellent stability against enterobacteria. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.067

文献信息

• A phase-switch purification approach for the expedient removal of tagged reagents and scavengers following their application in organic synthesis
  作者：Jason Siu、Ian R. Baxendale、Russell A. Lewthwaite、Steven V. Ley

  DOI：10.1039/b503778f

  日期：——

  In this paper we wish to report on a variety of expedient chemical transformations and purifications achieved via a generic ‘catch and release’ methodology, based on a synthetically inert bipyridyl chelating tag that can be selectively captured with a resin-bound copper(II) species. Utilising this approach we are able to derive many of the same benefits associated with both solid phase synthesis and supported reagent methods.

  本文旨在报道通过一种基于合成不活跃的双吡啶螯合标签的通用“捕获与释放”方法，实现的一系列便捷的化学转化和纯化。该方法可以选择性地利用树脂结合的铜(II)物种来捕获双吡啶螯合标签。采用这种方法，我们能够获得与固相合成和支持试剂法相关的许多相同益处。
• [EN] 2-(SUBSTITUTED-PHENYL)-CYCLOPENTANE-1,3-DIONE COMPOUNDS, AND DERIVATIVES THEREOF<br/>[FR] COMPOSÉS DE 2-(PHÉNYL SUBSTITUÉ)-CYCLOPENTANE-1,3-DIONES ET LEURS DÉRIVÉS
  申请人：SYNGENTA LTD

  公开号：WO2013079708A1

  公开（公告）日：2013-06-06

  The present invention relates to a compound of formula (I): wherein: X is methyl or chlorine; R1 is methyl or chlorine; R2 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, ethoxy or fluoromethoxy; and G, R3, R4, R5 and R6 are as defined herein; wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof. These compounds are suitable for use as herbicides. The invention therefore also relates to a method of controlling weeds, especially grassy monocotyledonous weeds, in crops of useful plants, comprising applying a compound of formula (I), or a herbicidal composition comprising such a compound, to the plants or to the locus thereof.

  本发明涉及一种具有以下式（I）的化合物：其中：X为甲基或氯；R1为甲基或氯；R2为氢、甲基、乙基、正丙基、环丙基、乙烯基、乙炔基、氟、氯、溴、甲氧基、乙氧基或氟甲氧基；以及G、R3、R4、R5和R6如本文所定义；其中式（I）的化合物可以作为农药中可接受的盐存在。这些化合物适用于用作除草剂。因此，本发明还涉及一种控制杂草，特别是草本单子叶杂草，在有用植物作物中的方法，包括将式（I）的化合物或包含这种化合物的除草剂组合物施用于植物或其生长地点。
• 2-(SUBSTITUTED-PHENYL)-CYCLOPENTANE-1,3-DIONE COMPOUNDS, AND DERIVATIVES THEREOF
  申请人：Syngenta Limited

  公开号：US20140323303A1

  公开（公告）日：2014-10-30

  The present invention relates to a compound of formula (I): wherein: X is methyl or chlorine; R 1 is methyl or chlorine; R 2 is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, methoxy, ethoxy or fluoromethoxy; and G, R 3 , R 4 , R 5 and R 6 are as defined herein; wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof. These compounds are suitable for use as herbicides. The invention therefore also relates to a method of controlling weeds, especially grassy monocotyledonous weeds, in crops of useful plants, comprising applying a compound of formula (I), or a herbicidal composition comprising such a compound, to the plants or to the locus thereof.

  本发明涉及一种具有以下式（I）的化合物：其中：X为甲基或氯；R1为甲基或氯；R2为氢、甲基、乙基、正丙基、环丙基、乙烯基、乙炔基、氟、氯、溴、甲氧基、乙氧基或氟甲氧基；以及G、R3、R4、R5和R6如本文所定义；其中该式（I）的化合物可以作为农药可接受的盐存在。这些化合物适用于用作除草剂。因此，本发明还涉及一种控制杂草，特别是草本单子叶杂草，在有用植物作物中的方法，包括将式（I）的化合物或包含这种化合物的除草剂组合物施用于植物或其生长地点。
• A Photoredox Coupling Reaction of Benzylboronic Esters and Carbonyl Compounds in Batch and Flow
  作者：Yiding Chen、Oliver May、David C. Blakemore、Steven V. Ley

  DOI：10.1021/acs.orglett.9b02307

  日期：2019.8.2

  Mild cross-coupling reaction between benzylboronic esters with carbonyl compounds and some imines was achieved under visible-light-induced iridium-catalyzed photoredox conditions. Functional group tolerance was demonstrated by 51 examples, including 13 heterocyclic compounds. Gram-scale reaction was realized through the use of computer-controlled continuous flow photoreactors.

  在可见光诱导的铱催化的光氧化还原条件下，苄基硼酸酯与羰基化合物和一些亚胺之间实现了温和的交叉偶联反应。通过51个实例（包括13个杂环化合物）证明了官能团的耐受性。革兰氏反应是通过使用计算机控制的连续流光反应器实现的。
• 6-O-substituted erythromycin derivatives having improved gastrointestinal tolerance
  申请人：Ma Zhenkun

  公开号：US20060166906A1

  公开（公告）日：2006-07-27

  Compounds having formula (I) are useful for treating bacterial infections while avoiding the concomitant liability of gastrointestinal intolerance. Compositions containing the compounds and methods of treatment using the compounds are also disclosed.

  具有化学式（I）的化合物可用于治疗细菌感染，同时避免胃肠不耐受的风险。含有这些化合物的组合物以及使用这些化合物进行治疗的方法也被揭示。