biphenyl-4-carbaldehyde oxime | 40143-27-9

• 物质功能分类: 分析化学 - 标准品 - 法医和兽医标准品
• 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: biphenyl-4-carbaldehyde oxime
• 英文别名: 4-phenylbenzaldehyde oxime；4-Phenylbenzaldoxime；N-[(4-phenylphenyl)methylidene]hydroxylamine
• CAS: 40143-27-9
• 化学式: C₁₃H₁₁NO
• mdl: MFCD00016415
• 分子量: 197.236
• InChiKey: OUNAWNXTMKAPFT-UHFFFAOYSA-N

物化性质

• 熔点：
  142-147 °C
• 沸点：
  334.8±21.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2928000090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-Phenylbenzaldoxime
CAS-No. : 40143-27-9
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 : C13H11NO
Molecular Weight : 197,2 g/mol
Component Concentration
4-Phenylbenzaldoxime
CAS-No. 40143-27-9 -

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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. FIRE-FIGHTING 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
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.
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 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- 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

反应信息

• 作为反应物：
  描述：

  biphenyl-4-carbaldehyde oxime 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以82%的产率得到4-氨基乙基联苯
  参考文献：
  名称：

  항암 활성을 갖는 신규 피리미딘-4-카르복시산 유도체

  摘要：

  这项发明涉及一种具有抗癌活性的新型嘧啶-4-羧酸衍生物，该发明的化合物在治疗和预防肿瘤疾病的药物中是有用的。

  公开号：

  KR101725292B1
• 作为产物：
  描述：

  联苯-4-甲醇 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 盐酸羟胺 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 biphenyl-4-carbaldehyde oxime
  参考文献：
  名称：

  将一元醇轻松地一锅转化为3-芳基和3-烷基异恶唑和-吡唑

  摘要：

  抽象的 通过在TEMPO，NH 2 OH和NCS的存在下依次用PhI（OAc）2连续处理，然后与炔烃反应，在一个锅中将各种伯醇顺利地转化成高产率的3-芳基-和3-烷基异恶唑。的Et存在下3 N.类似地，多种伯醇被顺利转化为3-芳基-和3- alkylpyrazoles以良好的收率以一锅煮的通过用岛（OAC）连续处理2在TEMPO，PhNHNH存在2，然后NCS和癸基甲基硫醚，然后在Et 3存在下与炔烃反应因此，3-芳基-和3-烷基异唑和3-芳基和3-烷基吡唑都可以在无过渡金属的条件下由易得的伯醇在一个罐中制备。 通过在TEMPO，NH 2 OH和NCS的存在下依次用PhI（OAc）2连续处理，然后与炔烃反应，在一个锅中将各种伯醇顺利地转化成高产率的3-芳基-和3-烷基异恶唑。的Et存在下3 N.类似地，多种伯醇被顺利转化为3-芳基-和3- alkylpyrazoles以良好的收率以一锅煮的

  DOI：

  10.1055/s-0039-1690102

文献信息

• Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes
  作者：Thirumanavelan Gandhi、Kishorkumar Kadam、Amol Gupte、A. Gangopadhyay、Rajiv Sharma

  DOI：10.1055/s-0035-1561464

  日期：——

  from substituted aldoximes (mixture of E and Z) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either tert-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent in situ [3+2] dipolar cycloaddition to the substituted alkynes

  摘要 已经描述了一种有效的一锅法，该方法用于在常规加热条件下，使用亚硝酸烷基酯，由取代的醛肟（E和Z的混合物）和炔烃合成3,5-二取代的异恶唑。合成异恶唑所需的关键腈氧化物中间体是通过用亚硝酸叔丁酯或亚硝酸异戊酯处理取代的醛肟而形成的。生成的腈氧化物在取代的炔烃上进行原位[3 + 2]偶极环加成反应，以高选择性或极高的产率选择性地生成3,5-二取代的异恶唑。已开发的合成方法用于合成先前报道的有效hDGAT1抑制剂。 已经描述了一种有效的一锅法，该方法用于在常规加热条件下，使用亚硝酸烷基酯，由取代的醛肟（E和Z的混合物）和炔烃合成3,5-二取代的异恶唑。合成异恶唑所需的关键腈氧化物中间体是通过用亚硝酸叔丁酯或亚硝酸异戊酯处理取代的醛肟而形成的。生成的腈氧化物在取代的炔烃上进行原位[3 + 2]偶极环加成反应，以高选择性或极高的产率选择性地生成3,5-二取代的异恶唑。已开发的合成方法用于合成先前报道的有效hDGAT1抑制剂。
• Catalytic Enantioselective [3 + 2] Cycloaddition of α-Keto Ester Enolates and Nitrile Oxides
  作者：Samuel L. Bartlett、Yoshihiro Sohtome、Daisuke Hashizume、Peter S. White、Miki Sawamura、Jeffrey S. Johnson、Mikiko Sodeoka

  DOI：10.1021/jacs.7b03782

  日期：2017.6.28

  An enantioselective [3 + 2] cycloaddition reaction between nitrile oxides and transiently generated enolates of α-keto esters has been developed. The catalyst system was found to be compatible with in situ nitrile oxide-generation conditions. A versatile array of nitrile oxides and α-keto esters could participate in the cycloaddition, providing novel 5-hydroxy-2-isoxazolines in high chemical yield

  已开发出腈氧化物与瞬时生成的 α-酮酯烯醇化物之间的对映选择性 [3 + 2] 环加成反应。发现该催化剂体系与原位氧化腈生成条件相容。一系列多功能的腈氧化物和 α-酮酯可以参与环加成，以高化学产率提供新型 5-羟基-2-异恶唑啉，具有高水平的非对映选择性和对映选择性。值得注意的是，最佳反应条件避免了通过 O-亚氨酰化和杂 [3 + 2] 途径的并发反应。
• A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH₂ OH) to Nitriles (RCN) Mediated by SO₂ F₂
  作者：Ying Jiang、Bing Sun、Wan-Yin Fang、Hua-Li Qin

  DOI：10.1002/ejoc.201900478

  日期：2019.6.2

  A new transition‐metal‐free one‐pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.

  在不引入“额外碳原子”的情况下，开发了一种新的无过渡金属的单锅级联工艺，用于将醇直接转化为腈。该方案允许将容易获得，廉价和丰富的醇转化为高价值的腈。
• Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene-based chiral sulfides as organocatalysts
  作者：Meng-Ting Huang、Hsin-Yi Wu、Rong-Jie Chein

  DOI：10.1039/c3cc47550f

  日期：——

  This work describes catalytic and asymmetric aziridinations (15 examples, 95-98% ee) of benzyl bromide and imines via the imino Corey-Chaykovsky reaction using (thiolan-2-yl)diarylmethanol benzyl ether as an organocatalyst. The catalyst and analogues thereof were prepared through an expeditious and efficient synthetic route featuring a double nucleophilic substitution and Shi epoxidation as key steps

  这项工作描述了使用（thiolan-2-yl）diarylmethanol苄基醚作为有机催化剂通过亚氨基Corey-Chaykovsky反应进行的苄基溴和亚胺的催化和不对称叠氮化（15例，95-98％ee）。通过快速有效的合成途径制备催化剂及其类似物，所述合成途径以双亲核取代和Shi环氧化为关键步骤。
• Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime
  作者：Zhanyu Li、Jinbo Zhao、Baozhen Sun、Tingting Zhou、Mingzhu Liu、Shuang Liu、Mengru Zhang、Qian Zhang

  DOI：10.1021/jacs.7b06523

  日期：2017.8.30

  We report realization of the first enantioselective Cope-type hydroamination of oximes for asymmetric nitrone synthesis. The ligand promoted asymmetric cyclopropene “hydronitronylation” process employs a Cu-based catalytic system and readily available starting materials, operates under mild conditions and displays broad scope and exceptionally high enantio- and diastereocontrol. Preliminary mechanistic

  我们报告实现了不对称硝酮合成肟的第一个对映选择性Cope型加氢胺化反应。配体促进的不对称环丙烯“氢硝基化”工艺采用基于铜的催化体系和易于获得的原料，在温和的条件下运行，显示范围广，对映体和非对映体的控制非常高。初步机理研究证实在Cu我-catalytic轮廓设有烯烃metalla -retro-柯普aminocupration过程作为密钥C-N键形成事件。这种概念上新颖的反应性使高对映选择性催化硝酮形成过程的第一个例子成为可能，并有可能刺激进一步的发展，从而可能大大加快手性硝酮的合成。