甲基乙基酮-DNPH | 958-60-1

• 物质功能分类: 分析化学 - 标准品 - 有机污染物标样
• 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: 甲基乙基酮-DNPH
• 中文别名: 甲基乙基酮-2,4-二硝基苯肼；甲基乙基甲酮-2,4-二硝基苯腙；丁酮(甲乙酮)-二硝基苯肼；乙基甲基甲酮-2,4-二硝基苯基腙；甲基乙基酮-2,4-二硝基苯基腙；2-丁酮--DNPH衍生物
• 英文名称: 2-butanone 2,4-dinitrophenylhydrazone
• 英文别名: Butanon-2,4-dinitrophenylhydrazon；Butanon-<2.4-dinitro-phenylhydrazon>；Butan-2-on-(2,4-dinitro-phenylhydrazon)；Butan-2-on-<2.4-dinitro-phenylhydrazon>；Butanon-(2)-<2.4-dinitro-phenylhydrazon>；Methyl-aethyl-keton-<2.4-dinitro-phenylhydrazon>；Methylaethylketon-(2.4-dinitro-phenylhydrazon)；N-(butan-2-ylideneamino)-2,4-dinitroaniline
• CAS: 958-60-1
• 化学式: C₁₀H₁₂N₄O₄
• mdl: MFCD00438715
• 分子量: 252.23
• InChiKey: WPWSANGSIWAACK-UHFFFAOYSA-N

物化性质

• 熔点：
  115-115.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  381.9±52.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)
• 闪点：
  2 °C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 保留指数：
  2288

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 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：
  116
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn,F,Xi
• 安全说明：
  S16,S26,S36,S36/37
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2928000090
• 危险品运输编号：
  UN 1648 3
• 储存条件：
  -20°C密封储存

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2-Butanone-2,4-dinitrophenylhydrazone
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. : 958-60-1
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
Classification according to Regulation (EC) No 1272/2008
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
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
Xi Irritant R36/37/38
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)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 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
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 2-Butanone 2,4-DNPH
Formula : C10H12N4O4
Molecular Weight : 252,23 g/mol
CAS-No. : 958-60-1
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
2-Butanone-2,4-dinitrophenylhydrazone
Skin Irrit. 2; Eye Irrit. 2; STOT -
SE 3; H315, H319, H335
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. Evacuate personnel to safe areas. 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.
Recommended storage temperature: -20 °C
Handle and store under inert gas.
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
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).
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 Melting point/range: 239 - 241 °C
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- 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
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
LDLO Intraperitoneal - mouse - 500 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
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
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
Additional Information
RTECS: EL8400000
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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Eye Irrit. Eye irritation
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Full text of R-phrases referred to under sections 2 and 3
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2013 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.

反应信息

• 作为反应物：
  描述：

  甲基乙基酮-DNPH 在 bismuth (III) oxychloride 作用下， 以 水 、 乙腈 为溶剂， 反应 2.58h， 以92%的产率得到丁酮
  参考文献：
  名称：

  BiOCl作为将2，4-二硝基苯基hydr裂成羰基化合物的有效选择试剂的新颖用途

  摘要：

  据报道，在温和条件下，氯氧化铋（BiOCl）作为一种有效和选择性的氧化催化剂，可用于清洁裂解C = N键。反应进行得非常顺利，收率良好至极好。没有观察到醛过度氧化为羧酸和副产物的形成。催化剂可以回收并重复使用至少4个反应周期而不会明显降低反应活性。

  DOI：

  10.2298/jsc150504071m
• 作为产物：
  描述：

  N-[(E)-3-Chloro-2-methyl-but-2-en-(E)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine 在 苯胺 作用下， 以 乙醇 为溶剂， 生成 甲基乙基酮-DNPH
  参考文献：
  名称：

  β-氯乙烯基醛的立体化学

  摘要：

  由N-亚甲基酮通过Vilsmeier反应制备的β-氯乙烯-醛的立体化学已经通过nmr光谱法进行了研究，包括溶剂迁移研究。一种轻微的方法被用于他们的准备。

  DOI：

  10.1039/j39700002484

文献信息

• Functionalisation of saturated hydrocarbons. Part XI. Oxidation of cedrol, ?- and ?-eudesmol, sclareol, manoyl oxide, 1,9-dideoxyforskolin, methyltrans-dihydroiasmonate, and tetrahydrolinalool by the ?Gif system?
  作者：Derek H. R. Barton、Jean-Clauude Beloeil、Annick Billion、Jean Boivin、Jean-Yves Lallemand、Patrick Lelandais、Simone Mergui

  DOI：10.1002/hlca.19870700824

  日期：1987.12.16

  The oxidation of cedrol (1), β- and γ-eudesmol (6 and 7, resp.), sclareol (14) manoyl oxide (15), 1,9-dideoxyforskolin (22) (±)-methyl trans-dihydrojasmonate (28), and tetrahydrolinalool (32) nearly all of natural terpenoid origin, by the ‘Gif system’ has afforded a number of novel products (3, 11, and 12, 16/17, 18/19, 26, 29–31, and ketones corresponding to 34–35, res.). The structures of these compounds

  头孢（1），β-​​和γ-地摩尔（分别为6和7），香紫苏醇（14）氧化锰（15），1,9-二脱氧伏夫林（22）（±）-反式-二氢茉莉酸甲酯（（1））的氧化。28），和四氢芳樟醇（32）几乎所有天然萜类来源的，由'的Gif系统'已经得到了许多的新产品（的3，11，和12，16/17，18/19，26，29-31，和对应于34–35的酮，res。）。这些化合物的结构是通过包括2D-NMR在内的光谱技术确定的，并在适当情况下通过与真实样品进行比较来确定。
• The synthesis of ketones viaα-silyl sulphides
  作者：David J. Ager

  DOI：10.1039/p19860000195

  日期：——

  an alkyl- lithium to 1-phenylthio-1-trimethylsilylethene (7), and transmetallation of a tributylstannyl moiety. The formation of an alkyl-lithium by reaction of lithium naphthalenide with a phenyl sulphide provided an additional route to (2) from bis(phenylthio)acetals (8). An alternative path to the α-phenylthiosilanes (2) was to reduce the corresponding α-phenylsulphonylsilane (15); these, in turn

  α-苯硫基硅烷（2）已经通过衍生自1-苯硫基-1-三甲基甲硅烷基烷（1）的阴离子（4）的烷基化而制备。这些阴离子（4）已经通过多种方法制备，包括：（1）的直接去质子化，萘锂置换苯硫基，在1-苯基硫-1-三甲基甲硅烷基乙烯中添加烷基锂（7），以及三丁基锡烷基部分的金属转移。通过萘二甲酸锂与苯硫醚的反应形成烷基锂，提供了从双（苯硫基）缩醛（8）到（2）的另一条路线。α-苯基硫代硅烷的替代途径（2）是还原相应的α-苯基磺酰基硅烷（15）; 这些反过来很容易从α-磺酰基阴离子的烷基化或甲硅烷基化获得。通过sila-Pummerer重排将α-苯基硫代硅烷（2）转化为O-三甲基甲硅烷基苯基硫代缩醛（18），尽管在某些情况下这会因硫化乙烯基（20）的形成而变得复杂。随后将（18）和（20）水解，得到酮（3）。
• Revisiting the reaction of hydroxyl radicals with vicinal diols in water
  作者：Dong Jiang、Sebastián Barata-Vallejo、Bernard T. Golding、Carla Ferreri、Chryssostomos Chatgilialoglu

  DOI：10.1039/c1ob06538f

  日期：——

  The carbonyl products of the reactions of hydroxyl radicals with three vicinal diols (ethane-1,2-diol, propane-1,2-diol and butane-2,3-diol) have been identified and quantified. Hydroxyl radicals were produced by γ-radiolysis of N2O-saturated aqueous solutions. The reactions result in the formation of alkoxyl radicals (∼15%) followed by β-fragmentation, and α-hydroxyl alkyl radicals that undergo H2O elimination. The latter process is part of a radical chain reaction at higher diol concentrations.

  羟自由基与三种邻二醇（乙二醇、丙二醇和丁二醇）反应的羰基产物已被鉴定并定量。羟自由基通过γ射线辐照饱和N2O水溶液产生。反应导致烷氧自由基（约15%）的形成，随后发生β-断裂，以及经历H2O消除的α-羟基烷基自由基。后者过程在较高二醇浓度下是自由基链反应的一部分。
• Effect of CHAPS and CPC micelles on Ir(III) catalyzed Ce(IV) oxidation of aliphatic alcohols at room temperature and pressure
  作者：Aniruddha Ghosh、Rumpa Saha、Bidyut Saha

  DOI：10.1016/j.molliq.2014.03.037

  日期：2014.8

  Kinetics of cerium(IV) oxidation of aliphatic alcohols: ethanol, propanol, propan-2-ol, 1-butanol and 2-butanol were studied at 30 °C in the presence and absence of surfactants in acidic medium. The reaction was studied under pseudo-first-order conditions, [alcohol]T ≫ [Ce(IV)]T. Ir(III)-salt used as catalyst had a significant effect on reaction rate. Cationic surfactant CPC (N-cetylpyridinium chloride)

  在酸性介质中存在和不存在表面活性剂的条件下，在30°C下研究了脂肪族醇：乙醇，丙醇，丙-2-醇，1-丁醇和2-丁醇的铈（IV）氧化的动力学。将反应物伪一级条件下研究，[醇] Ť  »[CE（IV）] Ť。用作催化剂的Ir（III）盐对反应速率有重要影响。阳离子表面活性剂CPC（N-氯化十六烷基吡啶鎓）抑制了反应速率，但是两性离子表面活性剂CHAPS（3-[（（3-苯甲酰氨基丙基）二甲基铵基] -1-丙烷磺酸盐）显着催化氧化反应。CHAPS的CMC值通过荧光分光光度计确定。反应速率随介质酸浓度的增加而增加。NMR和FTIR光谱证实了氧化产物。通过扫描电子显微镜（SEM）和透射电子显微镜（TEM）研究了反应条件下表面活性剂的聚集。动态光散射（DLS）用于表征聚集体的形状变化。根据Berezin模型，表面活性剂的性质，表面活性剂的性质，定性地讨论了在表面活性剂和金属离子催化剂存在下不同醇的反应速
• A Facile Mild Deprotection Protocol for 1,3-Dithianes and 1,3-Dithiolanes with 30% Hydrogen Peroxide and Iodine Catalyst in Aqueous Micellar System
  作者：Nemai Ganguly、Sujoy Barik

  DOI：10.1055/s-0028-1088023

  日期：2009.4

  A simple clean expeditious protocol for the deprotection of 1,3-dithianes and 1,3-dithiolanes has been developed using 30% aqueous hydrogen peroxide activated by iodine catalyst (5 mol%) in water in the presence of sodium dodecyl sulfate (SDS) under essentially neutral conditions. The method showed tolerance for a number of phenol protecting groups such as allyl, benzyl, TBDMS, TBDPS ethers, phenolic

  在十二烷基硫酸钠（SDS）存在下，使用30％的碘催化剂活化的过氧化氢水溶液（5 mol％），已经开发出一种简单，清洁，快速的脱保护1,3-二硫杂环戊烷和1,3-二硫杂环戊烷的方法。在基本上中立的条件下。该方法显示出对许多酚保护基团的耐受性，例如烯丙基，苄基，TBDMS，TBDPS醚，酚醛乙酸酯和苯甲酸酯，以及氨基保护的BOC，Cbz氨基甲酸酯，没有任何可检测的过氧化。 1,3-二硫烷-1,3-二硫杂环戊烷-碘-30％过氧化氢-十二烷基硫酸钠（SDS）

表征谱图