3-氰基-6,7-二甲基色酮 | 94978-86-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3-氰基-6,7-二甲基色酮
• 英文名称: 3-cyano-6,7-dimethylchromone
• 英文别名: 6,7-dimethyl-3-cyanochromone；MFCD00191957；6,7-dimethyl-4-oxochromene-3-carbonitrile
• CAS: 94978-86-6
• 化学式: C₁₂H₉NO₂
• mdl: MFCD00191957
• 分子量: 199.209
• InChiKey: YBBAUISOAUXLKI-UHFFFAOYSA-N

物化性质

• 熔点：
  206-209 °C(lit.)
• 沸点：
  347.8±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2926909090

SDS

Name:	3-Cyano-6 7-dimethylchromone Material Safety Data Sheet
Synonym:	6,7-Dimethyl-4-oxo-4H-1-benzopyran-3-carbonitril
CAS:	94978-86-6

Section 1 - Chemical Product MSDS Name:3-Cyano-6 7-dimethylchromone Material Safety Data Sheet
Synonym:6,7-Dimethyl-4-oxo-4H-1-benzopyran-3-carbonitril

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
94978-86-6	3-Cyano-6,7-dimethylchromone		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:

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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. Avoid generating dusty conditions.

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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# 94978-86-6: 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: orange-brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 208-210 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: C12H9NO2
Molecular Weight: 199.21

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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.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 94978-86-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Cyano-6,7-dimethylchromone - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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# 94978-86-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 94978-86-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 94978-86-6 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-6,7-二甲基色酮 在 吗啉 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以61%的产率得到2-氨基-3-甲酰基-6,7-二甲基色酮
  参考文献：
  名称：

  抗过敏药的研究。7.合成抗过敏的5-氧代-5H- [1]苯并吡喃并[2，3-b]吡啶。

  摘要：

  由4-氧代-4H-1-苯并吡喃-3-甲腈3或2-氨基合成5-氧代-5H- [1]苯并吡喃并[2,3-b]吡啶-3-羧酸23及其四唑类似物24。 -4-氧代-4H-1-苯并吡喃-3-甲醛4.静脉内给药时，它们在大鼠的PCA试验中表现出抗过敏​​活性。在羧酸系列中，活性受2-位取代基的影响，并按以下顺序显着增加：Me，OMe小于NH2小于OH，H小于NHOMe。另一方面，在四唑系列中，2-未取代的衍生物显示出最高的活性。不管位置2和3上的取代基种类如何，带有烷基，尤其是7位上的异丙基的化合物的活性均优于相应的未取代的化合物。在这些烷基衍生物中，3-羧酸衍生物，即23c（7-乙基），23g（2-氨基-7-异丙基），23r [2-（甲氧基氨基）-7-异丙基]和3-四唑衍生物。 24c（7-异丙基）的效力是色甘氨酸二钠的41-184倍。口服时它们还表现出显着的活性。23g（AA-673）的临床研究正在进行中。

  DOI：

  10.1021/jm50001a005
• 作为产物：
  描述：

  6,7-二甲基-3-甲酰基查尔酮 在 sodium iodide 盐酸羟胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到3-氰基-6,7-二甲基色酮
  参考文献：
  名称：

  将 3-甲酰基色素高效地一步转化为 3-氰基色素

  摘要：

  3-氰基色酮构成一类重要的中间体，因为它们用于合成抗过敏物质。cyan0 基团增强了环烯酮系统的碳-碳双键的亲二烯性，因此 3-氰基色酮已被广泛用作合成具有选择性乙酰胆碱酯酶抑制活性的化合物的亲二烯体？已经报道了几种通过相应醛肟 (2) 脱水合成 3 氰基色酮 (3) 的方法。这些包括在盐酸 3 甲酸钠在乙酸中 4 和乙酸酐的存在下在乙醇中回流 12 小时。据报道，硫酸促进从 0-甲基肟中消除甲醇，用于合成 3-氰基色酮。6 大多数这些方法涉及 i) 肟的预先制备和 ii) 脱水，具有强酸性条件、46 昂贵的试剂、6 反应时间长的缺点？产品分离繁琐，总收率低。3-氰基色酮的合成潜力和药用价值以及3-氰基色酮合成中遇到的困难促使人们寻找一种方便的方法。

  DOI：

  10.1080/00304940409355968

文献信息

• Synthesis of 1-azaxanthones by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-(cyano)benzopyrylium triflates and subsequent domino ‘retro-Michael/nitrile-addition/heterocyclization’ reaction
  作者：Muhammad A. Rashid、Nasir Rasool、Bettina Appel、Muhammad Adeel、Vahuni Karapetyan、Satenik Mkrtchyan、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2008.02.105

  日期：2008.5

  Functionalized 1-azaxanthones (5-oxo-5H-[1]-benzopyrano[2,3-b]pyridines) were prepared by TMSOTf-mediated condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-cyanochromones and subsequent base-mediated domino ‘retro-Michael/nitrile-addition/heterocyclization’ reaction.

  通过TMSOTf介导的1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯与3的缩合反应制备功能化的1-azaxanthones（5-oxo-5 H- [1]-苯并吡喃并[2,3- b ]吡啶）。 -氰基色酮和随后的碱基介导的多米诺骨牌“复古迈克尔/腈加成/杂环化”反应。
• One-Pot Five-Component Synthesis of Spirocyclopenta[<i>b</i>]chromene Derivatives and Their Acid-Catalyzed Rearrangement
  作者：Michael A. Terzidis、Tryfon Zarganes-Tzitzikas、Constantinos Tsimenidis、Julia Stephanidou-Stephanatou、Constantinos A. Tsoleridis、George E. Kostakis

  DOI：10.1021/jo3014947

  日期：2012.10.19

  tert-butylisocyanide or cyclohexylisocyanide and acetylenedicarboxylates, with 3-cyanochromones is described, whereupon spirochromenofuran derivatives 5 or 6 were obtained in good yields. The subsequent acid-catalyzed rearrangement of the isolated 2-imino-spirochromenofurans 5 to 2-amino-spirochromenofurans 7 has also been studied. Rational mechanistic schemes for the formation of compounds 5, 6, and 7 are proposed

  描述了由叔丁基异氰化物或环己基异氰酸酯与乙炔二羧酸酯原位产生的两性离子中间体与3-氰基色酮的反应，从而以良好的产率获得了螺色呋喃呋喃衍生物5或6。还研究了分离的2-亚氨基-吡咯并呋喃并呋喃5到2-氨基-吡咯并呋喃并呋喃7的随后的酸催化重排。理性机械方案为化合物的形成5，6，和7被提议。产物的结构阐明是通过1D和2D NMR实验完成的，并由X射线晶体学分析证实。借助DFT / GIAO计算已明确实现了所有1 H和13 C NMR化学位移的完全分配。
• Synthesis of Highly Functionalized Biaryls by Condensation of 2-Fluoro-1,3-bis(silyloxy) 1,3-Dienes with 3-Cyanochromones and Subsequent Domino “Retro-Michael/Aldol/Fragmentation”
  作者：Muhammad Farooq Ibad、Obaid-ur-Rahman Abid、Muhammad Adeel、Muhammad Nawaz、Verena Wolf、Alexander Villinger、Peter Langer

  DOI：10.1021/jo1018443

  日期：2010.12.3

  The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)-chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.
• Enantioselective H-Bond-Directing Approach for Trienamine-mediated Reactions in Asymmetric Synthesis
  作者：Łukasz Albrecht、Fabio Cruz Acosta、Alberto Fraile、Anna Albrecht、Jannie Christensen、Karl Anker Jørgensen

  DOI：10.1002/anie.201204790

  日期：2012.9.3

  Right direction: The presented enantioselective strategy for the preparation of diversely functionalized tetrahydroxanthones is based on a trienamine-mediated cycloaddition between 2,4-dieneals and activated chromones. It is possibile to control the stereochemical outcome of such reactions by employing an H-bond-directing aminocatalyst.
• A MILD AND FACILE METHOD FOR THE SYNTHESIS OF 3-CYANOCHROMONES FROM OXIMES DERIVED FROM 3-FORMYLCHROMONES USING DIMETHYLFORMAMIDE - THIONYLCHLORIDE COMPLEX
  作者：G. Jagath Reddy、D. Latha、K. Srinivasa Rao

  DOI：10.1515/hc.2004.10.4-5.279

  日期：2004.1