4-甲基-1-萘醛 | 33738-48-6

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-甲基-1-萘醛
• 英文名称: 4-methyl-1-naphthaldehyde
• 英文别名: 1-methyl-4-naphthaldehyde；4-methylnaphthaldehyde；4-methylnaphthalene-1-carboxaldehyde；4-methylnaphthalene-1-carbaldehyde
• CAS: 33738-48-6
• 化学式: C₁₂H₁₀O
• mdl: MFCD00060691
• 分子量: 170.211
• InChiKey: LANRGTXVAPBSIA-UHFFFAOYSA-N

物化性质

• 熔点：
  32-36 °C(lit.)
• 沸点：
  259.85°C (rough estimate)
• 密度：
  1.1252
• 闪点：
  >230 °F
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，未有已知危险发生。

  避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2912299000
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉干燥处，并保持良好通风。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-Methyl-1-naphthaldehyde
CAS-No. : 33738-48-6
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C12H10O
Molecular Weight : 170,21 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
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
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
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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
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
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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: 32 - 36 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point 110 °C - closed cup
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause 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.
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

制备方法与用途

用途

4-甲基-1-萘醛是一种醛类有机化合物，可用于有机合成的中间体。

反应信息

• 作为反应物：
  描述：

  4-甲基-1-萘醛 在 2-氨基苯磺酸 、 [双(三氟乙酰氧基)碘]苯 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 1,2-二氯乙烷 为溶剂， 以60%的产率得到4-methyl-8-hydroxy-1-naphthaldehyde
  参考文献：
  名称：

  Palladium-Catalyzed Regiospecific peri- and ortho-C–H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups

  摘要：

  DOI：

  10.1021/acs.orglett.0c03701
• 作为产物：
  描述：

  甲基萘 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 1.25h， 生成 4-甲基-1-萘醛
  参考文献：
  名称：

  Dearomative Allylation of Naphthyl Cyanohydrins by Palladium Catalysis: Catalyst-Enhanced Site Selectivity

  摘要：

  A dearomative allylation of naphthyl cyanohydrins with allyl borates and allyl stannanes under palladium catalysis was developed. At the initial stage of this study, the dearomative reaction (C4 substitution of the aromatics) was competing with benzyl substitution. To circumvent this issue, the use of palladium and meta-disubstituted triarylphosphine as the catalyst in a 1:1 ratio was found to enhance the site selectivity, furnishing the desired dearomatized products. Further derivatizations of products were also successful.

  DOI：

  10.1021/acs.orglett.0c00897

文献信息

• In Silico Driven Design and Synthesis of Rhodanine Derivatives as Novel Antibacterials Targeting the Enoyl Reductase InhA
  作者：Liudas Slepikas、Gianpaolo Chiriano、Remo Perozzo、Sébastien Tardy、Agata Kranjc、Ophélie Patthey-Vuadens、Hajer Ouertatani-Sakouhi、Sébastien Kicka、Christopher F. Harrison、Tiziana Scrignari、Karl Perron、Hubert Hilbi、Thierry Soldati、Pierre Cosson、Eduardas Tarasevicius、Leonardo Scapozza

  DOI：10.1021/acs.jmedchem.5b01620

  日期：2016.12.22

  computational studies. Their antimicrobial activity was assessed against Mycobacterium marinum (Mm) (a model for Mtb), Pseudomonas aeruginosa (Pa), Legionella pneumophila (Lp), and Enterococcus faecalis (Ef) by using anti-infective, antivirulence, and antibiotic assays. Nineteen out of 34 compounds reduced Mm virulence at 10 μM. 33 exhibited promising antibiotic activity against Mm with a MIC of 0.21 μM and showed

  在这里，我们报告针对结核分枝杆菌结核（Mtb）反-2-烯酰基酰基载体蛋白还原酶（InhA）的4-噻唑烷酮（若丹宁）衍生物的设计，合成和生物学评估。在罗丹宁环第5位具有庞大芳族取代基且在N -3位具有色氨酸残基的化合物对InhA的活性最高，IC 50值为2.7至30μM。实验数据显示与计算研究一致的相关性。他们的抗菌活性评估了对结核分枝杆菌（Mm）（铜绿假单胞菌（Mtb）的模型）。Pa），嗜肺军团菌（Lp）和粪肠球菌（Ef），方法是使用抗感染，抗毒力和抗生素检测方法。34种化合物中有19种降低了10μM的Mm毒力。33的MIC为0.21μM，对Mm表现出有希望的抗生素活性，在30μM的抗感染试验中，Lp的生长降低了89％。32显示对Ef的高抗生素活性，MIC为0.57μM。
• INHIBITORS OF HEMOPOIETIC CELL KINASE (P59-HCK) AND THEIR USE IN THE TREATMENT OF INFLUENZA INFECTION
  申请人：Charron Catherine Elisabeth

  公开号：US20120244120A1

  公开（公告）日：2012-09-27

  The present invention relates inter alia to the treatment or prevention of influenza virus infection (including subtypes influenza A virus, influenza B virus, avian strain H5N1, A/H1N1, H3N2 and/or pandemic influenza) using compounds which inhibit the activity of p59-HCK and to a method of screening for a candidate drug substance intended to prevent or treat influenza virus infection in a subject, said method comprising identifying a test substance capable of inhibiting p59-HCK activity.

  本发明涉及治疗或预防流感病毒感染（包括亚型流感A病毒、流感B病毒、禽流感H5N1、A/H1N1、H3N2和/或大流行性流感）的化合物，这些化合物抑制p59-HCK的活性，并涉及一种筛选候选药物物质的方法，该方法旨在预防或治疗受试者的流感病毒感染，所述方法包括识别能够抑制p59-HCK活性的试验物质。
• Highly Regioselective Aromatic C–H Allylation of <i>N</i>-(Arylmethyl)sulfonimides with Allyl Grignard Reagents Involving Benzylic C–N Cleavage
  作者：Meng-Zeng Zhu、Dong Xie、Shi-Kai Tian

  DOI：10.1021/acs.orglett.1c02437

  日期：2021.9.3

  C–H functionalization of benzyl electrophiles with nucleophiles via palladium-catalyzed benzylic C–N cleavage. A range of N-(1-naphthylmethyl)sulfonimides, N-(2-thienylmethyl)sulfonimides, and N-(2-furanylmethyl)sulfonimides smoothly underwent palladium-catalyzed aromatic C–H allylation with allyl Grignard reagents at room temperature, delivering structurally diverse substituted 1-allylnaphthalenes and

  已经建立了一对新的反应伙伴，用于通过钯催化的苄基 C-N 裂解将苄基亲电试剂与亲核试剂的芳族 C-H 官能化。一系列N- (1-萘基甲基)磺酰亚胺、N- (2-噻吩基甲基)磺酰亚胺和N- (2-呋喃基甲基)磺酰亚胺在室温下与烯丙基格氏试剂顺利进行钯催化的芳族 C-H 烯丙基化，在结构上传递多种取代的 1-烯丙基萘和 2-烯丙基杂芳烃，产率中等至极好，具有极高的区域选择性。更换N-(芳甲基)磺酰亚胺与(芳甲基)铵盐、芳甲基氯化物或芳甲基磷酸酯作为苄基亲电试剂导致区域选择性的显着侵蚀。
• Controlled Photochemical Release of Nitric Oxide from <i>O</i>²-Naphthylmethyl- and <i>O</i>²-Naphthylallyl-Substituted Diazeniumdiolates
  作者：K. Mani Bushan、Hua Xu、Patrick H. Ruane、Raechelle A. D'Sa、Christopher M. Pavlos、Joseph A. Smith、Tevye C. Celius、John P. Toscano

  DOI：10.1021/ja027957h

  日期：2002.10.1

  effect on the observed photochemistry, with the appropriate substitution pattern resulting in efficient diazeniumdiolate photorelease. Observed nitric oxide release rates from these photoprecursors are consistent with those expected for normal thermal dissociation of the diazeniumdiolate in aqueous solutions and show the same pH dependence.

  已经研究了 O2-萘基甲基-和 O2-萘基烯丙基-取代的二氮烯鎓二醇的光化学。供电子甲氧基取代对观察到的光化学具有显着影响，适当的取代模式导致有效的二氮烯二醇光释放。从这些光前体观察到的一氧化氮释放速率与二氮烯二醇在水溶液中正常热解离的预期一致，并显示出相同的 pH 依赖性。
• Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid
  作者：Hiroshi Nishino、Katsunori Tsunoda、Kazu Kurosawa

  DOI：10.1246/bcsj.62.545

  日期：1989.2

  the presence of manganese(III) acetate gives naphthalenecarbaldehydes and naphthalenecarboxylic acids. Similar reactions of anthracene, pyrene, and methoxybenzenes also yield formylated and carboxylated products. It was found that the formyl group introduced to the aromatic ring was not derived from carboxymethyl radical generated directly by the thermolysis of manganese(III) acetate, but from a dicarboxymethyl

  在乙酸锰 (III) 存在下，萘与丙二酸反应生成萘甲醛和萘甲酸。蒽、芘和甲氧基苯的类似反应也产生甲酰化和羧化产物。发现引入芳环的甲酰基不是由乙酸锰（III）热解直接产生的羧甲基自由基衍生而来，而是由丙二酸和乙酸锰（III）相互作用形成的二羧甲基自由基衍生而来。此外，还发现二羧甲基自由基攻击芳环上电子密度最高的位置，当芳族化合物的电离电位低于7.8 eV时，这种甲酰化是有效的。

表征谱图