2,2-dimethyl-5-(4-nitrobenzylidene)-1,3-dioxane-4,6-dione | 15795-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dimethyl-5-(4-nitrobenzylidene)-1,3-dioxane-4,6-dione
• 英文别名: 5-(4-nitrobenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione；isopropylidene p-nitrobenzalmalonate；2,2-Dimethyl-5-[(4-nitrophenyl)methylidene]-1,3-dioxane-4,6-dione
• CAS: 15795-62-7
• 化学式: C₁₃H₁₁NO₆
• 分子量: 277.233
• InChiKey: FCDZHNDUCXHXLS-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C(Solv: ethanol (64-17-5))
• 沸点：
  523.2±50.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2,2-DIMETHYL-5-(4-NITRO-BENZYLIDENE)-
(1,3)DIOXANE-4,6-DIONE
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 15795-62-7

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Eye irritation (Category 2), H319
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22, R36
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
Harmful if swallowed.
Causes serious eye irritation.
Precautionary statement(s)
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C13H11NO6
Molecular Weight : 277,24 g/mol
CAS-No. : 15795-62-7
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2,2-DIMETHYL-5-(4-NITRO-BENZYLIDENE)-(1,3)DIOXANE-4,6-DIONE
Acute Tox. 4; Eye Irrit. 2; -
H302, H319
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
2,2-DIMETHYL-5-(4-NITRO-BENZYLIDENE)-(1,3)DIOXANE-4,6-DIONE
Xn, R22 - R36 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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 vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
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.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
Safety glasses with side-shields conforming to EN166 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).
Control of environmental exposure
Do not let product enter drains.

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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) Evapouration 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: -0,157
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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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 sensitisation
no data available
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
Further information
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(4-nitrobenzylidene)-1,3-dioxane-4,6-dione 在 Oxone 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以75%的产率得到对硝基苯甲醛
  参考文献：
  名称：

  无过渡金属的权宜方法可用于芳基芳烃Meldrum的酸和丙二腈衍生物的C C键裂解

  摘要：

  讨论了一种用于无电子烯烃（例如亚芳基迈德鲁姆酸和丙二腈衍生物）的C C键裂解的无过渡金属的简便方法。这些化合物的C C键在高温下以高收率裂解为苯甲酸。最重要的是，与过硫酸氢钾CH 3 CN / H 2 O不连到45℃或米-CPBA在DCM或次氯酸钠2的THF / H 2 O或PIDA在THF中在室温下布置的苯甲醛衍生物选择性地在良好的产率。

  DOI：

  10.1016/j.tet.2019.130573
• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 水 为溶剂， 生成 2,2-dimethyl-5-(4-nitrobenzylidene)-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Nucleophilic addition to olefins. 6. Structure-reactivity relationships in the reactions of substituted benzylidene Meldrum's acids with water, hydroxide ion, and aryloxide ions

  摘要：

  DOI：

  10.1021/ja00383a024

文献信息

• Microwave‐associate synthesis of Co ₃ O ₄ nanoparticles as an effcient nanocatalyst for the synthesis of arylidene barbituric and Meldrum's acid derivatives in green media
  作者：Mahdieh Yahyazadehfar、Enayatollah Sheikhhosseini、Sayed Ali Ahmadi、Dadkhoda Ghazanfari

  DOI：10.1002/aoc.5100

  日期：——

  conditions using controlled, effective, and facile microwave method. The final nanostructures were characterized by SEM, XRD, and TEM analyses. The products had a small size distribution, homogeneous morphology, and crystallographic structures associated with the formation of Co3O4 nanostructures. Moreover, EDS mapping analysis confirmed the existence of Co and O elements in the final structure, and the

  在这项研究中，使用可控，有效且简便的微波方法，在环境适宜的条件下构建了Co 3 O 4纳米催化剂。通过SEM，XRD和TEM分析来表征最终的纳米结构。产物具有较小的尺寸分布，均匀的形态和与Co 3 O 4形成相关的晶体结构纳米结构。此外，EDS作图分析证实了最终结构中存在Co和O元素，并通过VSM研究了样品的磁性。此纳米结构中的催化方法中的应用进一步检查，结果表明，它可作为一种新的候选为亚芳基巴比妥和麦德鲁姆的合成， s至由巴比妥和麦德鲁姆醛的Knoevenagel缩合酸， S酸性中水性介质。这些纳米催化剂的高产率将由纳米结构的性质以及本研究开发的实验程序来证明，这影响了产物的理化特性。
• Asymmetric synthesis of multi-substituted spiro[5,5]undecane-1,5,9-triones via organocatalytic three-component reaction
  作者：Jian Shi、Yangbin Liu、Min Wang、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.tet.2011.01.037

  日期：2011.3

  The asymmetric domino three-component Knoevanagel-Diels–Alder addition (ATCDA) reaction, as an important methodology, has been utilized to construct complex product from ordinary starting materials. In this report, many typical organoamine catalysts were investigated to achieve highly efficient asymmetric three-component reaction of enones 2, aldehydes 3 and Meldrum’s acid 4. Various pharmacological

  作为一种重要的方法，非对称多米诺三组分Knoevanagel-Diels-Alder加成反应（ATCDA）已被用于从普通起始原料构建复杂的产物。在本报告中，研究了许多典型的有机胺催化剂，以实现烯酮2，醛3和Meldrum酸4的高效不对称三组分反应。各种药理学上多取代的螺[5,5]十一烷-1,5,9-三酮一锅得到9 g的9-氨基-9-脱氧表位-奎宁促进，中等至良好的收率（高达81％），具有极好的非对映异构体（> 99：1 dr）和对映选择性（高达97 ％ee）。同时，根据控制实验和分析数据，提出了该反应双重活性的合理机理。
• Uncatalyzed Knoevenagel Condensation in PEG-600 at Room Temperature
  作者：Babasaheb P. Bandgar、Balaji L. Korbad、Sachin A. Patil、Sunita B. Bandgar、Hemant V. Chavan、Baliram S. Hote

  DOI：10.1071/ch08106

  日期：——

  A rapid, efficient, and ecofriendly protocol has been developed for the Knoevenagel condensation of active methylene compounds with aromatic, aliphatic, conjugated and heteroaromatic aldehydes in polyethylene glycol-600 (PEG-600) with good to excellent yields.

  针对活性亚甲基化合物与芳香族、脂肪族、共轭族和杂芳香族醛类化合物在聚乙二醇-600（PEG-600）中的克诺文纳格尔缩合反应，我们开发出了一种快速、高效和环保的方案，并取得了良好甚至优异的收率。
• Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes
  作者：Franca Bigi、Silvia Carloni、Leonetto Ferrari、Raimondo Maggi、Alessandro Mazzacani、Giovanni Sartori

  DOI：10.1016/s0040-4039(01)00978-9

  日期：2001.7

  The environment-friendly condensation of Meldrum's acid and aromatic, heteroaromatic and hindered aliphatic aldehydes is performed carrying out the reaction in water at 75°C for 2 h, avoiding the addition of any catalyst.

  Meldrum的酸与芳族，杂芳族和受阻脂族醛的环保缩合反应是在75°C的水中进行2小时的反应，而无需添加任何催化剂。
• Bentonite Catalyzed an Efficient and Green Synthesis of Arylidene Meldrum's Acid Derivatives in Aqueous Media
  作者：Mahdieh Yahyazadehfar、Sayed Ali Ahmadi、Enayatollah Sheikhhosseini、Dadkhoda Ghazanfari

  DOI：10.2174/1570178617999200807155325

  日期：2021.7