重氮基乙酰乙酸乙酯 - CAS号 2009-97-4

物化性质

沸点：

102-103 °C(Press: 12 Torr)
密度：

1.131 g/mL at 25 °C (lit.)
闪点：

185 °F
稳定性/保质期：

在常温常压下，该物质保持稳定。

计算性质

辛醇/水分配系数(LogP)：

0.6
重原子数：

11
可旋转键数：

4
环数：

0.0
sp3杂化的碳原子比例：

0.5
拓扑面积：

45.4
氢给体数：

0
氢受体数：

4

安全信息

危险品标志：

Xi
安全说明：

S26,S36
危险类别码：

R36/37/38
海关编码：

2927000090
储存条件：

常温下，请将产品存放在阴凉、通风的地方。

SDS

SDS：cd14b2a406273ac270ef57cffb748120

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Ethyl diazoacetoacetate
CAS-No. : 2009-97-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
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
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6H8N2O3
Molecular Weight : 156,14 g/mol
Component Concentration
Ethyl diazoacetoacetate
CAS-No. 2009-97-4 -

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
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

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

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
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.

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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
no data available

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).

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 85 °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 24,814 hPa at 20 °C
37,910 hPa at 55 °C
l) Vapour density no data available
m) Relative density 1,131 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

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

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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious 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

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

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.

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

SECTION 15 - REGULATORY INFORMATION
N/A

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

重氮基乙酰乙酸乙酯是一种α-重氮酯类化合物，可用作合成材料的中间体。

反应信息

作为反应物：

描述：

重氮基乙酰乙酸乙酯在 potassium hydroxide 作用下，以乙醚、水为溶剂，生成重氮乙酸乙酯

参考文献：

名称：

以重氮化合物为自由基前体光催化合成茚满酮、吡喃酮和吡啶酮衍生物

摘要：

我们在此公开了重氮烷烃的光催化自由基级联环化，用于重要碳环和杂环的发散合成。在最佳反应条件下，可以以中等至良好的收率得到各种茚满酮、吡喃酮和吡啶酮衍生物。机理实验支持重氮烷通过质子耦合电子转移过程形成以碳为中心的自由基。使用连续流技术的放大反应和所形成的杂环的有用下游应用进一步使该策略具有吸引力和价值。

DOI：

10.1021/acs.orglett.3c04331
作为产物：

描述：

乙酰乙酸乙酯在对甲苯磺酰叠氮、 caesium carbonate 作用下，以四氢呋喃为溶剂，反应 0.5h，以92%的产率得到重氮基乙酰乙酸乙酯

参考文献：

名称：

活性亚甲基化合物重氮转移反应的改进和有效方法

摘要：

摘要在碳酸铯的存在下，活性亚甲基化合物和对甲苯磺酰叠氮化物之间的重氮转移反应可以有效地介导。

DOI：

10.1080/00397919508011762
作为试剂：

描述：

苯乙烯在重氮基乙酰乙酸乙酯、 copper(II) bis(trifluoromethanesulfonate) 、 tetrabutylammonium dichlorobromate 作用下，以二氯甲烷为溶剂，反应 2.0h，生成 (2-溴-1-氯-乙基)苯

参考文献：

名称：

Tetrabutylammonium dichlorobromide: an efficient and mild reagent for geminal bromochlorination of α-diazo carbonyl compounds

摘要：

An efficient and mild one-pot procedure for geminal bromochlorination of alpha-diazo carbonyl compounds has been developed for the first time using tetrabutylammonium dichlorobromide (TBADCB) via metal carbenoids. This protocol was found to be highly selective and does not result in dichlorination or dibromination products. The reagent, TBADCB, is commercially available, easy to prepare and handle. (C) 2015 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.tetlet.2014.12.117

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文献信息

Rh(III)-Catalyzed Regio- and Chemoselective [4 + 1]-Annulation of Azoxy Compounds with Diazoesters for the Synthesis of 2H-Indazoles: Roles of the Azoxy Oxygen Atom

作者：Zhen Long、Zhigang Wang、Danni Zhou、Danyang Wan、Jingsong You

DOI：10.1021/acs.orglett.7b00631

日期：2017.6.2

tandem C–H alkylation/intramolecular decarboxylative cyclization of azoxy compounds with diazoesters for the synthesis of 3-acyl-2H-indazoles is disclosed. The azoxy instead of the azo group enables a distinct approach for cyclative capture, leading to a [4 + 1]-annulation rather than a classic [4 + 2] manner. The azoxy oxygen atom is traceless after annulation, and further removal from the product is

揭示了用Rh（III）催化的重氮化合物与重氮酸酯的串联C–H烷基化/分子内脱羧环化反应，可合成3-酰基-2 H-吲唑。取代偶氮基团的是偶氮氧基团，从而实现了一种独特的环化捕获方法，从而导致了[4 +1]环化，而不是经典的[4 + 2]方式。环氧化后，z氧基氧原子是无痕的，不需要进一步从产物中除去。该反应具有对不对称的乙氧基苯的完全区域选择性和单芳基二烯氧化物的相容性。
Multiple Roles of the Pyrimidyl Group in the Rhodium‐Catalyzed Regioselective Synthesis and Functionalization of Indole‐3‐carboxylic Acid Esters

作者：Hui Jiang、Shang Gao、Jinyi Xu、Xiaoming Wu、Aijun Lin、Hequan Yao

DOI：10.1002/adsc.201500769

日期：2016.1.21

A regioselective synthesis of indole‐3‐carboxylic acid esters from anilines and diazo compounds has been realized by making use of the pyrimidyl group‐assisted rhodium‐catalyzed CH activation and CN bond formation. The reaction proceeds under mild conditions, exhibits good functional group tolerance and scalability. Reutilization of the pyrimidyl directing group in the resulting products provided

通过利用嘧啶基辅助的铑催化的CH活化和CN键的形成，已经实现了由苯胺和重氮化合物对吲哚-3-羧酸酯进行区域选择性合成。反应在温和的条件下进行，表现出良好的官能团耐受性和可扩展性。所得产物中嘧啶基导向基团的再利用为吲哚的C-7进一步官能化提供了有效的策略。而且，嘧啶基部分可以容易地作为离去基团被除去，以提供各种游离的NH吲哚。
A Chemistry for Incorporation of Selenium into DNA‐Encoded Libraries

作者：Hongtao Xu、Yuang Gu、Shuning Zhang、Huan Xiong、Fei Ma、Fengping Lu、Qun Ji、Lili Liu、Peixiang Ma、Wei Hou、Guang Yang、Richard A. Lerner

DOI：10.1002/anie.202003595

日期：2020.8.3

simple selenation with limited atom economy and complicated reaction system. In this work, we designed benzoselenazolone as a novel bifunctional selenide reagent for both off‐ and on‐DNA C−H selenylation under rhodium(III) catalysis. We show that using benzoselenazolone allowed production of a series of selenylation products containing an adjacent aminoacyl group in a fast and efficient way, with high

常规的直接CH H硒化反应具有简单的硒化，有限的原子经济性和复杂的反应体系。在这项工作中，我们设计了苯并硒氮酮作为一种新型的双功能硒化物试剂，用于在铑（III）催化下进行脱氢和脱氢CHH硒化反应。我们表明，使用苯并硒氮唑酮允许以快速，有效的方式生产一系列含有相邻氨基酰基的硒化产物，并具有较高的原子经济性。通过利用酰胺官能团作为亲核试剂，导向基团和酰胺偶联伙伴，证明了该方法的合成应用。这项工作显示出在促进快速构建含硒DNA编码化学文库（SeDEL）方面的巨大潜力，并为开发含硒药物奠定了基础。
Six-Membered Cyclic Nitroso Acetals: Synthesis and Studies of the Nitrogen Inversion Process ofN-Silyloxy-3,6-dihydro-2H-1,2-oxazines

作者：Alexander S. Shved、Andrey A. Tabolin、Roman A. Novikov、Yulia V. Nelyubina、Vladimir P. Timofeev、Sema L. Ioffe

DOI：10.1002/ejoc.201600952

日期：2016.11

The reaction of silyl nitronates and enol diazoacetates affords N‐silyloxy‐3,6‐dihydro‐2H‐1,2‐oxazines as a new type of nitroso acetal. The scope of the reaction was established. Quantum chemical calculations and kinetic data allowed the nitrogen inversion barrier in the target nitroso acetals to be determined.

甲硅烷基硝酸酯与烯醇重氮乙酸酯的反应提供了N-甲硅烷氧基-3,6-二氢-2 H - 1,2-恶嗪类新型亚硝基缩醛。确定了反应范围。量子化学计算和动力学数据可以确定目标亚硝基缩醛中的氮转化障碍。
Rh(<scp>iii</scp>)-catalyzed relay carbenoid functionalization of aromatic C–H bonds: access to π-conjugated fused heteroarenes

作者：Ying Xie、Xun Chen、Xin Liu、Shi-Jian Su、Jianzhang Li、Wei Zeng

DOI：10.1039/c6cc00254d

日期：——

A novel Rh(iii)-catalyzed relay cross-coupling cascade between arylketoimines and diazoesters is described. This transformation provides a concise access to unique π-conjugated 1-azaphenalenes (1-APLEs) via a double aryl Csp²–H bond carbenoid functionalization process.

描述了一种新颖的Rh（III）催化的芳基酮亚胺和重氮酯之间的继发交叉偶联级联反应。该转化通过双芳基Csp2-H键卡宾功能化过程提供了一种简洁访问独特的π共轭1-氮杂苯并（1-APLEs）。

重氮基乙酰乙酸乙酯 | 2009-97-4

物质功能分类

分子结构分类

物化性质

计算性质

安全信息

SDS

制备方法与用途

反应信息

文献信息

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