((4-(二甲基氨基)苯基)亚甲基)甲烷-1,1-二甲腈 | 2826-28-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: ((4-(二甲基氨基)苯基)亚甲基)甲烷-1,1-二甲腈
• 英文名称: 4-dimethylaminobenzylidenemalononitrile
• 英文别名: p-(N-dimethylamino benzylidene) malononitrile；2-(4-(dimethylamino)benzylidene)malononitrile；2-[[4-(dimethylamino)phenyl]methylidene]propanedinitrile
• CAS: 2826-28-0
• 化学式: C₁₂H₁₁N₃
• mdl: MFCD00100708
• 分子量: 197.239
• InChiKey: IYNONQVNLZATDK-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C
• 沸点：
  370.4±32.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: α-(4-(Dimethylamino)benzylidene)malononitrile
Product name
CAS-No. : 2826-28-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Respiratory sensitization (Category 1)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin. May cause sensitization by skin
contact.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P342 + P311 If experiencing respiratory symptoms: Call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
R43 May cause sensitization by skin contact.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37 Wear suitable protective clothing and gloves.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C12H11N3
Molecular Weight : 197,24 g/mol
Component Concentration
α-(4-(Dimethylamino)benzylidene)malononitrile
CAS-No. 2826-28-0 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 2,741
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
May cause allergic respiratory reaction.
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  ((4-(二甲基氨基)苯基)亚甲基)甲烷-1,1-二甲腈 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 50.0h， 以47%的产率得到(E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide
  参考文献：
  名称：

  Mishriky, Nawal; Ibrahim; Girgis, Pharmazie, 2000, vol. 55, # 4, p. 269 - 272

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苄亚基丙二腈 在 3,4-二氢-2H-吡咯 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 ((4-(二甲基氨基)苯基)亚甲基)甲烷-1,1-二甲腈
  参考文献：
  名称：

  A Facile Transfer of Dicyano Methylene Group Between Arylidenemalononitrile and Aldehyde

  摘要：

  Arylidenemalononitrile undergoes facile exchange of dicyano methylene group with beta-formyl steroidal enamide as well as aromatic aldehydes under mild base catalysed reaction.

  DOI：

  10.1080/00397910008087379

文献信息

• Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
  作者：Shoaib Muhammad、Muhammad Naveed Javed、Firdous Imran Ali、Ahmed Bari、Imran Ali Hashmi

  DOI：10.1016/j.molliq.2019.112372

  日期：2020.2

  (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs

  离子液体（ILs）自组装形成超分子聚合物簇/聚集体。IL的聚集行为影响其在有机合成中的活性。但是，IL在有机反应中的确切作用仍是未知的。因此，重要的是要理解IL的超分子聚合聚集行为。我们正在使用电喷雾电离质谱（ESI-MS）探索IL的超分子聚合聚集行为。我们已经合成了四个亲水性IL（1-4），并研究了它们的聚集行为及其对碳-碳键形成（Knoevenagel和Claisen-Schmidt缩合）催化活性的影响。在这里，我们表明IL的聚集行为取决于阳离子和阴离子的类型和性质。ESI-MS（-ve）光谱揭示了两种不同类型的聚集，即[C n A n + 1 ] -和[A 2  + H + ] -。我们发现，催化活性随[C n A n + 1 ] -超分子聚集的增加而增加。因此，在IL中获得的最高收率的产品显示出阴离子-阴离子聚集的减少[A 2  + H +] – ESI-MS中的丰度。我们预计我们
• Structure−Activity Relationship Study of Prion Inhibition by 2-Aminopyridine-3,5-dicarbonitrile-Based Compounds:  Parallel Synthesis, Bioactivity, and in Vitro Pharmacokinetics
  作者：Barnaby C. H. May、Julie A. Zorn、Juanita Witkop、John Sherrill、Andrew C. Wallace、Giuseppe Legname、Stanley B. Prusiner、Fred E. Cohen

  DOI：10.1021/jm061045z

  日期：2007.1.1

  2-Aminopyridine-3,5-dicarbonitrile compounds were previously identified as mimetics of dominant-negative prion protein mutants and inhibit prion replication in cultured cells. Here, we report findings from a comprehensive structure-activity relationship study of the 6-aminopyridine-3,5-dicarbonitrile scaffold. We identify compounds with significantly improved bioactivity (approximately 40-fold) against

  2-氨基吡啶-3,5-二甲腈化合物以前被鉴定为显性负病毒蛋白突变体的模拟物，并抑制病毒在培养细胞中的复制。在这里，我们报告从6-氨基吡啶-3,5-二甲腈支架的全面的结构-活性关系研究中发现的结果。我们确定了具有明显改善的生物活性（约40倍）的抗感染性ion病毒同工型（PrPSc）复制和合适的药代动力学特征的化合物，以保证在病毒疾病的动物模型中进行评估。
• Synthesis of novel bis(dihydropyridine) and terpyridine derivatives
  作者：Ali M. S. Hebishy、Ismail A. Abdelhamid、Ahmed H. M. Elwahy

  DOI：10.24820/ark.5550190.p010.498

  日期：——

  A synthesis of novel bis(cyanopyridones) by the reaction of the appropriate bis(cyanoacetamide) with the corresponding arylidenmalononitrile in the presence of basic catalysts was reported. In some cases, the corresponding bis(2-cyano-3-arylacrylamide) derivatives were isolated from these reactions as single products. The multicomponent strategy for the synthesis of the target compounds was also investigated

  报道了在碱性催化剂存在下通过适当的双（氰基乙酰胺）与相应的芳基丙二腈反应合成新型双（氰基吡啶酮）。在某些情况下，相应的双（2-氰基-3-芳基丙烯酰胺）衍生物作为单一产物从这些反应中分离出来。还研究了合成目标化合物的多组分策略。还研究了双（氰基乙酰胺）作为新型双喹啉酮结构单元的效用。
• Molecular modeling of drug-pathophysiological Mtb protein targets: Synthesis of some 2-thioxo-1, 3-thiazolidin-4-one derivatives as anti-tubercular agents
  作者：K.M. Noorulla、Ayyadurai Jerad Suresh、Vinod Devaraji、Bijo Mathew、Devi Umesh

  DOI：10.1016/j.molstruc.2017.07.009

  日期：2017.11

  novel 2 - thioxo - 1 , 3 - thiazolidin - 4 - one derivatives ( 5a - 5t ) were synthesized and evaluated for their antitubercular activity. The structure of the compounds was confirmed by IR, NMR and Mass Spectroscopy methods. In addition, single-crystal X-ray diffraction was performed for compound 5a . All the synthesized compounds were screened for their in - vitro antimycobacterial activity against

  摘要 合成了20种新型2-thioxo-1,3-thiazolidin-4-one衍生物(5a-5t)并评价了它们的抗结核活性。化合物的结构通过红外、核磁共振和质谱方法确认。此外，对化合物5a进行了单晶X射线衍射。所有合成的化合物均通过 Alamar Blue 测定法筛选其对 MTB（H37RV，ATCC 编号：27294）的体外抗分枝杆菌活性。化合物5r、5k、5t显示出最有效的体外活性，MIC分别为0.05、0.1、0.2μg/ml浓度，其比标准品更有效。进行分子对接和动力学模拟以找出标题化合物的合理机制。
• Synthesis of Polyfunctionalized Pyrroles via a Tandem Reaction of Michael Addition and Intramolecular Cyanide-Mediated Nitrile-to-Nitrile Condensation
  作者：Sankar K. Guchhait、Shailendra Sisodiya、Meenu Saini、Yesha V. Shah、Gulshan Kumar、Divine P Daniel、Neha Hura、Vikas Chaudhary

  DOI：10.1021/acs.joc.8b00465

  日期：2018.5.18

  A new approach for the synthesis of tetrasubstituted/functionalized NH-pyrroles from gem-diactivated acrylonitriles and TMSCN has been developed. The strategy utilizes the generation of vic-dinitrile via Michael addition and cyanide-mediated nitrile-to-nitrile cyclocondensation, which proceed in tandem guided by manifold roles of “CN”. An extended application to the production of fused pyrrole has

  从宝石双活化的丙烯腈和TMSCN合成四取代/官能化的NH-吡咯的新方法已经被开发出来。该策略利用了通过迈克尔加成反应和氰化物介导的腈-腈环缩合反应生成的vic- diinitrile，这些反应在“ CN”的多种作用的指导下串联进行。还已经实现了在熔融吡咯的生产中的广泛应用。

表征谱图