4-甲苯磺酰丙酮 | 5366-49-4

• 物质功能分类: 有机原料 - 酮类化合物
• 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-甲苯磺酰丙酮
• 中文别名: 对甲苯磺酰丙酮
• 英文名称: 4-toluenesulfonylacetone
• 英文别名: 1-tosylpropan-2-one；tosylacetone；1-(p-toluenesulfonyl)-propan-2-one；1-(4-methylphenylsulfonyl)propan-2-one；(p-tolylsulfonyl)acetone；1-(4-methylphenyl)sulfonylpropan-2-one
• CAS: 5366-49-4
• 化学式: C₁₀H₁₂O₃S
• mdl: MFCD00026240
• 分子量: 212.269
• InChiKey: NDQXJNHOGLQSMB-UHFFFAOYSA-N

物化性质

• 熔点：
  52 °C
• 沸点：
  167 °C(Press: 0.1 Torr)
• 密度：
  1.195±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914399090
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将药品存放在避光、阴凉干燥的地方，并密封保存。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1-(P-Tolylsulfonyl)-2-Propanone
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.
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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 212,27 g/mol
No components need to be disclosed according to the applicable regulations.

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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
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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 vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
No special environmental precautions required.
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.
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.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart 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
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).
Control of environmental exposure
No special environmental precautions required.

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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) 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
No data available
Hazardous decomposition products
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

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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
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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
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
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	1-(4-methylphenylsulfonyl)propan-2-ol	85870-05-9	C10H14O3S	214.285
  1-甲基-4-(2-丙炔磺酰基)-苯	4-tosylacetonitrile	16192-07-7	C10H10O2S	194.254
  (4-甲基苯基硫)丙酮	1-(p-tolylsulfanyl)propan-2-one	1200-13-1	C10H12OS	180.271
  ——	4-methylphenyl prop-1-enyl sulfone	32228-15-2	C10H12O2S	196.27
  ——	p-tolylsulfonylallene	16192-08-8	C10H10O2S	194.254
  ——	1-(p-toluenesulfonyl)propyne	14027-53-3	C10H10O2S	194.254

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3-氯-1-((4-甲基苯基)磺酰基)乙酮	3-chloro-1-((4-methylphenyl)sulfonyl)acetone	57122-47-1	C10H11ClO3S	246.715
  ——	1-bromo-3-(toluene-4-sulfonyl)-acetone	874009-26-4	C10H11BrO3S	291.166
  ——	1,3-bis-(toluene-4-sulfonyl)-acetone	39180-21-7	C17H18O5S2	366.459
  1-甲基-4-(丙基磺酰基)苯	1-(4-tolylsulfonyl)propane	90926-25-3	C10H14O2S	198.286
  ——	1-chloro-1-p.toluenesulphonylacetone	101246-34-8	C10H11ClO3S	246.715
  ——	(S)-1-(4-methylphenylsulfonyl)propan-2-ol	109610-75-5	C10H14O3S	214.285
  ——	1-tosylpropan-2-ol	——	C10H14O3S	214.285
  ——	1-(4-methylphenylsulfonyl)propan-2-ol	85870-05-9	C10H14O3S	214.285
  ——	3-(4-Methylbenzene-1-sulfonyl)hex-5-en-2-one	67605-00-9	C13H16O3S	252.334
  ——	1-diazo-1-tosylpropan-2-one	2725-60-2	C10H10N2O3S	238.267

反应信息

• 作为反应物：
  描述：

  4-甲苯磺酰丙酮 在 双氧水 、 碘 、 palladium diacetate 、 caesium carbonate 、 溶剂黄146 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 15.0h， 生成 1-(cinnamylsulfonyl)-4-methylbenzene
  参考文献：
  名称：

  官能化烷基卤化物与乙烯基芳烃/杂芳烃的可见光诱导室温 Heck 反应

  摘要：

  第一个可见光诱导的 Pd 催化的 α-杂原子取代的烷基碘化物和-溴化物与乙烯基芳烃/杂芳烃的 Heck 反应已经开发出来。这种转化在室温下有效进行，并能够从相应的α-取代甲基碘合成有价值的官能化烯丙基系统，例如烯丙基硅烷、硼酸酯、锗烷、锡烷、新戊酸酯、膦酸酯、邻苯二甲酰亚胺和甲苯磺酸酯。值得注意的是，后一种底物的合成在现有的热诱导钯催化条件下失败，这凸显了可见光对于这种转变的重要性。

  DOI：

  10.1002/anie.201706554
• 作为产物：
  描述：

  4-甲基苯硫氯 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.5h， 生成 4-甲苯磺酰丙酮
  参考文献：
  名称：

  在布朗斯台德酸中由（芳磺酰基）-和（芳基亚磺酰基）亚芳基生成1，2-氧杂硫鎓离子。NMR和DFT研究这些阳离子及其反应。

  摘要：

  在强布朗斯台德酸（CF3SO3H，FSO3H，D2SO4）中，（芳磺酰基）烯（ArSO2-CR1 = C = CR2R3）和（芳亚磺酰基）烯（ArSO-CR1 = C = CR2R3）环化成相应的稳定的1,2-氧杂硫鎓离子，通过NMR和DFT计算进行了研究。用低亲核介质（HCl水溶液）淬灭这些阳离子的溶液会导致它们的去质子化，并形成立体选择性的（芳磺酰基）丁二烯（例如，ArSO2-CR1 = CC（Me）= CH2，对于R2 = R3 = Me，收率的87-98％）。TfOH（0.1当量）-HFIP（六氟丙烷-2-醇）体系中的（芳磺酰基）丙二烯反应后水解生成烯丙醇（ArSO2-CR1 = CH-C（OH）R2R3，收率78-99％ ）。在（1当量）TfOH（1当量）存在下，（芳磺酰基）丙二烯溶液的回流导致环化成硫代色素1，1-二氧化物产量高。在TfOH或AlX 3（X ＝ Cl，Br）的作

  DOI：

  10.3762/bjoc.14.268

文献信息

• Allylation of Active Methylene Compounds with Allyl Oxime Carbonates Catalyzed by Pd(0)
  作者：Osamu Suzuki、Yoshiharu Hashiguchi、Seiichi Inoue、Kikumasa Sato

  DOI：10.1246/cl.1988.291

  日期：1988.2.5

  Allylation of active methylene compounds catalyzed by a palladium(0)-phosphine system took place highly stereoselectively by employing allyl oxime carbonates as the allylating reagent.

  零价钯-膦配合物体系催化活性的甲川化合物与烯丙基肟碳酸酯进行高度立体选择性的烯丙基化反应。
• α-Diazosulphones and related compounds from the base-induced cleavage of α-diazo-β-ketosulphones
  作者：D. Hodson、G. Holt、D. K. Wall

  DOI：10.1039/j39680002201

  日期：——

  sulphonylformaldehyde hydrazones (70—80%), a previously unknown class of compounds, which arose by hydrolysis of the first formed phosphazine. The acylsulphonyldiazomethanes were prepared by the action of toluene-p-sulphonyl azide and triethylamine on β-ketosulphones in 60% aqueous ethanol. If the diazoketosulphone is retained in solution and the reaction period prolonged, sulphonylformaldehyde hydrazones may be

  当在干燥的甲醇中用三乙胺处理时，酰基磺酰基重氮甲烷会发生酰基裂解，从而生成α-重氮砜（约30％）。收率不佳归因于后处理过程中重氮砜的碱促进反应，因为在后处理中加入三苯基膦会生成磺酰甲醛（70-80％），这是一类以前未知的化合物，是通过水解生成首先形成磷嗪。酰基磺酰基重氮甲烷是通过甲苯-对磺酰基叠氮化物和三乙胺在60％的乙醇水溶液中对β-酮砜的作用制得的。如果重氮酮砜保留在溶液中并延长了反应时间，则可在添加三苯膦后直接分离出磺酰甲醛。
• <i>p</i>-Toluenesulfonic Acid Promoted Annulation of 2-Alkynylanilines with Activated Ketones: Efficient Synthesis of 4-Alkyl-2,3-Disubstituted Quinolines
  作者：Changlan Peng、Yong Wang、Lanying Liu、Honggen Wang、Jiaji Zhao、Qiang Zhu

  DOI：10.1002/ejoc.200901257

  日期：2010.2

  Reactions between readily available 2-alkynylanilines and activated ketones such as β-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2,3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquin-olines, which are difficult to obtain by classical

  容易获得的 2-炔基苯胺和活化酮（如由对甲苯磺酸促进的 β-酮酯）之间的反应以良好至极好的收率提供 4-烷基-2,3-二取代喹啉。2-炔基苯胺三键另一端取代基的普遍性使该方法成为一种有价值的方法，可以通过经典方法如弗里德兰德反应难以获得多样化的4-烷基喹啉。喹啉二聚体可以使用 C-4 处的烷基或芳基接头有效地制备。
• Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
  作者：Youzhi Wu、Peng Sun、Kaifan Zhang、Tie Yang、Hequan Yao、Aijun Lin

  DOI：10.1021/acs.joc.5b02824

  日期：2016.3.4

  Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an

  本文报道的是初级苯甲酰胺与重氮化合物的Rh催化氧化还原中性环化反应，代表了对异喹啉酮的有效和经济方案。该过程表现出良好的官能团耐受性，可伸缩性，和区域选择性，避免了对氧化剂的需要，并且只对环境无害Ñ 2和H 2 ö被释放。该方法的进一步利用为功能化的异喹啉提供了另一种途径。
• (Arylsulfonyl)acetones and -acetonitriles: New Activated Methylenic Building Blocks for Synthesis of 1,2,3-Triazoles
  作者：Nazariy Pokhodylo、Vasyl Matiychuk、Mykola Obushak

  DOI：10.1055/s-0029-1216850

  日期：2009.7

  for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. azides - triazoles - sulfones - Dimroth reaction

  在Dimroth环化反应中，β-酮砜和β-腈砜被用作合成1,2,3-三唑的基础。结果表明，砜试剂在温和的条件下（在室温下）进行碱催化的环化反应，以中等至极好的收率得到1,2,3-三唑。这一事实证实了磺酰基亚甲基化合物的高度亲核性，并允许新的合成应用。 叠氮化物-三唑-砜-Dimroth反应

表征谱图