4-二甲氨基-2-硝基苯甲醛 | 56670-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-二甲氨基-2-硝基苯甲醛
• 英文名称: 2-nitro-4-dimethylaminobenzaldehyde
• 英文别名: 4-(dimethylamino)-2-nitrobenzaldehyde
• CAS: 56670-20-3
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD03427165
• 分子量: 194.19
• InChiKey: DHLFXZQEAWYQLC-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C (dec.) (lit.)
• 沸点：
  365.5±32.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2922399090
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。储存时，请置于阴凉、干燥处。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-Dimethylamino-2-nitrobenzaldehyde
CAS-No. : 56670-20-3

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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]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
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.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C9H10N2O3
Molecular Weight : 194,19 g/mol
Component Concentration
4-Dimethylamino-2-nitrobenzaldehyde
CAS-No. 56670-20-3 -

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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
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
impervious clothing, 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 Melting point/range: 117 °C - dec.
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- no data available
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
Strong 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
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
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 May be 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
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-二甲氨基-2-硝基苯甲醛 在 copper diacetate 、 尿素 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 以88%的产率得到4-(dimethylamino)-2-nitrobenzonitrile
  参考文献：
  名称：

  铜催化 2-硝基苯甲醛与醛一锅法合成喹唑啉酮：在天然产物合成中的应用

  摘要：

  首次通过铜催化的腈形成、水解和还原在一个锅中揭示了一种从 2-硝基苯甲醛构建喹唑啉酮的新型、高效和原子经济的方法。在该反应中，尿素用作生成腈的氮源，水合肼用于硝基的还原和腈的水解，大气中的氧气用作唯一的氧化剂。该方法描绘了具有良好官能团耐受性的宽底物范围。此外，该方法还用于合成裂殖菌素、色胺菊酯、phaitanthrin-A、phaitanthrin-B和8 H-喹唑啉[4,3 - b ]quinazolin-8-one。

  DOI：

  10.1021/acs.joc.1c02343
• 作为产物：
  描述：

  N,N-二甲基-3-硝基苯胺 、 丙酮 在 sodium acetate 、 三氯氧磷 作用下， 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 为溶剂， 以33%的产率得到4-二甲氨基-2-硝基苯甲醛
  参考文献：
  名称：

  Caged amino acids

  摘要：

  根据本发明，被囚禁的氨基酸具有以下式1所表示的结构：其中X和Y分别表示卤素原子、烷基基团、烷氧基团、烷基氨基团或苯基；R1表示氢原子或烷基基团；R2和R3分别表示氢原子或烷基基团；A表示氨基酸残基；M表示氢原子、碱金属或碱土金属。

  公开号：

  US06329546B1

文献信息

• NOVEL CURCUMIN DERIVATIVE
  申请人：Sugimoto Hachiro

  公开号：US20110082295A1

  公开（公告）日：2011-04-07

  To develop a highly safe measure to treat Alzheimer's disease using a secretase-inhibiting substance, there is provided a compound represented by the following general formula (I) or a salt thereof: wherein A represents a phenyl group or the like, R 1 represents a chlorine atom, a bromine atom, or a nitro group or the like, R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or the like, and L represents CH 2 —CH 2 or CH═CH.

  为了开发一种高度安全的措施来治疗阿尔茨海默病，提供了一种由以下一般式（I）或其盐表示的化合物： 其中A代表苯基或类似物，R1代表氯原子、溴原子或硝基团等，R2、R3、R4和R5各自代表氢原子或类似物，L代表CH2— 或CH═CH。
• Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
  作者：Manar Ahmed Fouad、Francesco Ferretti、Dario Formenti、Fabio Milani、Fabio Ragaini

  DOI：10.1002/ejoc.202100789

  日期：2021.9.14

  A very efficient, general and scalable protocol for the preparation of indoles and other N-heterocycles from suitably substituted nitroarenes using alkyl and phenyl formates as CO surrogates was described. Using phenyl formate, the products were isolated in yields often higher than those previously achieved by using gaseous CO. The mechanism of both the decarbonylation reaction of phenyl formate and

  描述了使用烷基和苯基甲酸酯作为 CO 替代物从适当取代的硝基芳烃制备吲哚和其他N-杂环的非常有效、通用和可扩展的方案。使用甲酸苯酯，产物的分离产率通常高于以前使用气态 CO 实现的产率。通过动力学和机理研究阐明了甲酸苯酯的脱羰反应和环化反应的机理。
• Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines
  作者：Douglas J. Fansher、Richard Granger、Satinderpal Kaur、David R. J. Palmer

  DOI：10.1021/acscatal.1c01398

  日期：2021.6.18

  Quinoline derivatives are important natural products and pharmaceuticals, but their synthesis can be challenging due to poor yields, harsh reaction conditions, and instability of starting materials. Here we report the chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase, trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (NahE, or HBPA). A series of 2-aminobenzaldehydes

  喹啉衍生物是重要的天然产物和药物，但由于收率低、反应条件苛刻和起始材料不稳定，它们的合成具有挑战性。在这里，我们报告了使用醛缩酶、反式-o-羟基亚苄基丙酮酸水合酶-醛缩酶（NahE 或 HBPA）在温和条件下化学酶法合成喹哪二酸。在 NahE 存在下，一系列源自相应硝基类似物还原的 2-氨基苯甲醛与丙酮酸反应，以高达 93% 的分离产率得到取代的喹啉。该反应不同于体内NahE 催化的羟醛缩合，而是类似于由其同源物二氢吡啶二羧酸合酶催化的杂环形成。
• A Biphilic Phosphetane Catalyzes N–N Bond-Forming Cadogan Heterocyclization via P^III/P^V═O Redox Cycling
  作者：Trevor V. Nykaza、Tyler S. Harrison、Avipsa Ghosh、Rachel A. Putnik、Alexander T. Radosevich

  DOI：10.1021/jacs.7b03260

  日期：2017.5.24

  chemoselective catalytic synthesis of 2H-indazoles, 2H-benzotriazoles, and related fused heterocyclic systems with good functional group compatibility. On the basis of both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV═O cycling, where DFT modeling suggests a turnover-limiting (3+1) cheletropic addition between the phosphetane catalyst and nitroarene

  发现小环磷环 1,2,2,3,4,4-六甲基膦烷在氢硅烷末端还原剂存在下催化邻硝基苯扎二亚胺、邻硝基偶氮苯和相关底物的脱氧 NN 键形成 Cadogan 杂环化. 该反应提供了具有良好官能团兼容性的 2H-吲唑、2H-苯并三唑和相关稠合杂环系统的化学选择性催化合成。在化学计量和催化机理实验的基础上，该反应被提议通过催化 PIII/PV=O 循环进行，其中 DFT 模型表明磷烷催化剂和硝基芳烃底物之间存在限制周转的 (3+1) 螯合加成。
• Gold-Catalyzed Synthesis of Quinolines from Propargyl Silyl Ethers and Anthranils through the Umpolung of a Gold Carbene Carbon
  作者：Hongming Jin、Bin Tian、Xinlong Song、Jin Xie、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/anie.201606043

  日期：2016.10.4

  proceeds through a sequential ring opening/1,2‐H‐shift/protodeauration/Mukaiyama aldol cyclization. This method offers a regiospecific and modular access to 2‐aminoquinolines and other quinoline derivatives under mild conditions and with a broad functional‐group tolerance. The conversion is possible on a gram scale, which underlines the synthetic practicability of this methodology. The versatility of the

  炔丙基甲硅烷基醚与蒽的金催化级联环化通过顺序开环/ 1,2-H-移位/原脱硫/ Mukaiyama羟醛环化进行。该方法在温和条件下具有对区域2氨基喹啉和其他喹啉衍生物的区域特异性和模块化接近性，并且具有宽泛的官能团耐受性。克量级的转换是可能的，这突显了该方法的综合实用性。所获得的支架的多功能性已通过有用的后功能化得到证明。