乙酰乙酸乙酯-3,4-13C2 | 89186-80-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 乙酰乙酸乙酯-3,4-13C2
• 英文名称: ethyl acetoacetate-3,4-¹³C₂
• 英文别名: ethyl <3,4-(13)C2>acetoacetate；ethyl <3,4-13C 2>acetoacetate；ethyl acetoacetate-3,4-¹³C2；ethyl 3,4-di-(13)C-3-oxobutanoate；3,4-13C2-ethyl acetoacetate；ethyl (3,4-(13)C2)acetoacetate；Ethyl acetoacetate-3,4-13C2；ethyl 3-oxo(3,4-13C2)butanoate
• CAS: 89186-80-1
• 化学式: C₆H₁₀O₃
• 分子量: 132.122
• InChiKey: XYIBRDXRRQCHLP-BFQMUAMKSA-N

物化性质

• 熔点：
  −43 °C(lit.)
• 沸点：
  181 °C(lit.)
• 密度：
  1.037 g/mL at 25 °C
• 闪点：
  184 °F
• 稳定性/保质期：
  避免强氧化剂、强碱、强酸和强还原剂。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R41,R37/38

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Ethyl acetoacetate-3,4-13C2
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. : 89186-80-1
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
Serious eye damage (Category 1), H318
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 R37/38, R41
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 Danger
Hazard statement(s)
H315 Causes skin irritation.
H318 Causes serious eye damage.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P280 Wear protective gloves/ eye protection/ face protection.
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
Chemical characterization : Isotopically labeled
Formula : 13C2C4H10O3
Molecular Weight : 132,13 g/mol
CAS-No. : 89186-80-1
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Ethyl acetoacetate-3,4-13C2
Skin Irrit. 2; Eye Dam. 1; -
STOT SE 3; H315, H318,
H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Ethyl acetoacetate-3,4-13C2
Xi, R37/38 - R41 -
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
Do NOT induce vomiting. 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
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or
spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of
water.
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
Use water spray to cool unopened containers.

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13). 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 inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
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. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Store under inert gas. hygroscopic
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
Tightly fitting safety goggles. Faceshield (8-inch minimum). 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 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: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: -43 °C - lit.
point
f) Initial boiling point and 181 °C - lit.
boiling range
g) Flash point 84 °C - closed cup
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 1,037 g/mL at 25 °C1,037 g/cm3 at 25 °C
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
Heat, flames and sparks.
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
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
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: Not available
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
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material.
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：

  乙酰乙酸乙酯-3,4-13C2 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到ethyl 2-diazoacetoacetate-β,γ-di-(13)C
  参考文献：
  名称：

  Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates

  摘要：

  Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.

  DOI：

  10.1021/ol203331r
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 乙酰氯-13C2 生成 乙酰乙酸乙酯-3,4-13C2
  参考文献：
  名称：

  TOWNSEND, CRAIG A.;CHRISTENSEN, SIEGFRIED B.;DAVIS, STEVEN G., J. CHEM. SOC. PERKIN TRANS.,(1988) N 4, 839-861

  摘要：

  DOI：

文献信息

• Atom arrangement strategy for designing a turn-on¹H magnetic resonance probe: a dual activatable probe for multimodal detection of hypochlorite
  作者：Tomohiro Doura、Hiroshi Nonaka、Shinsuke Sando

  DOI：10.1039/c1cc12044a

  日期：——

  The first dual activatable hypochlorite (−OCl)-sensing probe was developed, based on a new proof-of-concept design involving signal-activatable 1H chemical probes using the triple-resonance NMR technique. The probe enabled fluorescence–1H MR dual turn-on detection of−OCl in solution and in crude tissue extracts.

  首个双活化次氯酸盐（−OCl）传感器被开发出来，其基于一种新的概念验证设计，涉及使用三共振核磁共振技术的信号活化1H化学探针。该探针能够在溶液和粗组织提取物中实现荧光与1H磁共振双开关检测−OCl。
• Synthetic Studies on Natural Diterpenoid Glyceryl Esters
  作者：Nicon Ungur、Margherita Gavagnin、Angelo Fontana、Guido Cimino

  DOI：10.1016/s0040-4020(00)00097-1

  日期：2000.4

  Synthesis of natural bicyclic and tricyclic diterpenoid diacylglycerols has been performed by regioselective coupling of terpenoid acid with glycerol at 1′-sn position. This method may be considered a general approach to obtain optically active acylglycerols. The preparation of 13C-labelled geranylgeranoic acid glyceryl esters is also described here.

  天然双环和三环二萜类二酰基甘油的合成已通过萜类酸与甘油在1'- sn位置的区域选择性偶联而进行。该方法可以被认为是获得旋光酰基甘油的通用方法。这里还描述了13 C-标记的香叶基香叶酸甘油酯的制备。
• Investigation of the Mechanism for the Preparation of 6-Phenyl-2,4-dioxotetrahydropyrans by the Potassium Carbonate Promoted Condensation between Acetoacetate Esters and Benzaldehyde
  作者：Brad Andersh、Elizabeth T. Nguyen、Ryan J. Van Hoveln、Dylan K. Kemmerer、David A. Baudo、Jessica A. Graves、Mollie E. Roark、Wayne B. Bosma

  DOI：10.1021/jo400213s

  日期：2013.5.3

  4-dioxotetrahydropyran. Based upon results from deuterium exchange experiments, carbon-13 labeling experiments, 1H NMR monitoring studies, and reactivity studies, our proposed mechanism for this reaction involves deprotonation at the α-carbon, intramolecular proton transfer to form a γ-anion, addition of the resulting γ-anion to the carbonyl carbon of benzaldehyde, and intramolecular transesterification.

  在醇溶剂中用碳酸钾处理苯甲醛和乙酰乙酸酯是通过γ-C-烷基化而不是α-C-烷基化进行的，导致形成6-苯基-2,4-二氧代四氢吡喃。根据氘交换实验，碳13标记实验，1 H NMR监测研究和反应性研究的结果，我们提出的该反应机理涉及α-碳的去质子化，分子内质子转移形成γ-阴离子，添加生成的γ阴离子与苯甲醛的羰基碳发生分子内酯交换反应。
• Synthesis of (R, S)-[2,3-13C2]-1-(1′-methyl-2′-pyrrolidinyl)propan-2-one; {(R, S)-[2′,3′-13C2]hygrine}
  作者：Timothy W. Abraham、Edward Leete

  DOI：10.1002/(sici)1099-1344(199605)38:5<419::aid-jlcr859>3.0.co;2-l

  日期：1996.5

  give (R,S)-[2,3- 13 C 2 ]-1-(1'-methyl-5'-oxo-2'-pyrrolidinyl)propan-2-one (4) in 91% yield. Protection of the ketone as a ketal (ethylene glycol, H + ), followed by reduction of the amide to the amine using LiAlH 4 and subsequent deprotection of the ketal gave (R,S)-[2,3- 13 C 2 ]-1-(1'-methyl-2'-pyrrolidinyl)propan-2-one ((R,S)-[2',3'- 13 C 2 ]Hygrine) (8) in 78% yield. (61% overall yield from ethyl

  2-乙氧基-1-甲基-5-吡咯烷酮(1)与[3,4- 13 C 2 ]-乙酰乙酸乙酯(2)在TiCl 4 存在下反应得到[3,4- 13 C 2 ]乙酯-2-(1'-methyl-5'-oxo-2'-pyrrolidinyl)-3-oxobutanoate (3)，产率为 85%。[3,4- 13 C 2 ] -2-(1'-甲基-5'-氧代-2'-吡咯烷基)-3-氧代丁酸乙酯 (3) 的脱碳乙氧基化使用 NaCl 和 H 2 O 在 DMSO 中完成，得到(R,S)-[2,3- 13 C 2 ]-1-(1'-甲基-5'-氧代-2'-吡咯烷基)丙-2-一 (4)，产率为 91%。将酮保护为缩酮（乙二醇，H + ），然后使用 LiAlH 4 将酰胺还原为胺，随后将缩酮脱保护得到 (R,S)-[2,3- 13 C 2 ]- 1-(1'-甲基-2'-吡咯烷基)propan-2-one ((R,S)-[2'
• Townsend, Craig A.; Christensen, Siegfried B.; Davis, Steven G., Journal of the Chemical Society. Perkin transactions I, 1988, p. 839 - 862
  作者：Townsend, Craig A.、Christensen, Siegfried B.、Davis, Steven G.

  DOI：——

  日期：——