烯丙基丙二酸 | 2583-25-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 烯丙基丙二酸
• 英文名称: allylmalonic acid
• 英文别名: 2-allylmalonic acid；Allyl-malonsaeure；2-prop-2-enylpropanedioic acid
• CAS: 2583-25-7
• 化学式: C₆H₈O₄
• mdl: MFCD00014347
• 分子量: 144.127
• InChiKey: ZDZVKPXKLLLOOA-UHFFFAOYSA-N

物化性质

• 熔点：
  102-105 °C
• 沸点：
  182.71°C (rough estimate)
• 密度：
  1.1311 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 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
• WGK Germany：
  3
• 海关编码：
  2917190090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Allylmalonic acid
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. : 2583-25-7
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
Formula : C6H8O4
Molecular Weight : 144,13 g/mol
CAS-No. : 2583-25-7
EC-No. : 219-958-8
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Allylmalonic acid
CAS-No. 2583-25-7 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
EC-No. 219-958-8 SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Allylmalonic acid
CAS-No. 2583-25-7 Xi, R36/37/38 <= 100 %
EC-No. 219-958-8
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
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.
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
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.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
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: powder
Colour: beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 102 - 105 °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
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
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
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

烯丙基丙二酸可作为有机合成中间体和医药中间体，主要应用于实验室研发及化工生产过程。

反应信息

• 作为反应物：
  描述：

  烯丙基丙二酸 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 磺酰氯 、 氯仿 、 溶剂黄146 作用下， 生成 cis-1-acetyl-4-hydroxy-DL-proline
  参考文献：
  名称：

  New Syntheses of Hydroxyproline¹

  摘要：

  DOI：

  10.1021/ja01630a038
• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 烯丙基丙二酸
  参考文献：
  名称：

  探索莫能菌素生物合成的体内和体外非天然聚酮化合物延长单元的混杂酶促活化。

  摘要：

  在聚酮化合物合成中引入新的自然扩展剂是多样性的重要来源，但由于体内适当活化的构建基团的有限可用性而受到限制。我们在这里描述了用于商业上可利用的新的自然扩展剂单元的生物激活的简单工作流程。首先，表征了来自肉桂链霉菌的高柔性丙二酸辅酶A合成酶的底物范围。该结果与体内实验相匹配，在体内实验中，所述扩展剂单元被莫能菌素生物合成途径的聚酮化合物合酶和辅助酶所接受。通过利用酰基转移酶的固有底物混杂和下游酶功能，实验产生了一系列可预测的莫能菌素衍生物。

  DOI：

  10.1002/cbic.201800734
• 作为试剂：
  描述：

  氢氧化钾 、 水 、 Allyldiethylmalonate 、 正庚烷 在 乙醇 、 resultant product 、 final solution 、 乙醚 、 magnesium sulfate 、 烯丙基丙二酸 、 petroleum ether 作用下， 生成 烯丙基丙二酸
  参考文献：
  名称：

  Organosilicon-containing materials useful for biomedical devices

  摘要：

  含有有机硅材料在生物医学器械中非常有用，例如隐形眼镜。这些材料包括末端带有至少一个乙烯基不饱和基团的大分子单体和单体。这些大分子单体和单体包括以下式子的单元：##STR1## 其中：每个Y是--O--或--NR.sup.30--，其中R.sup.30为H或C.sub.1-C.sub.6烷基；每个R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5独立地选自H、C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6卤代烷基、C.sub.2-C.sub.6烷基，其中至少一个亚甲基被替换为--O--，C.sub.2-C.sub.6卤代烷基，其中至少一个亚甲基被替换为--O--，和--R.sup.Si；m和n独立地为0或1到6的整数；每个R.sup.Si独立地是有机硅基团；而R是.alpha.、.omega.-二羟基化合物或.alpha.、.omega.-二氨基化合物的二价残基。

  公开号：

  US05510442A1

文献信息

• Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters
  作者：Alistair J. M. Farley、Christopher Sandford、Darren J. Dixon

  DOI：10.1021/jacs.5b10226

  日期：2015.12.30

  The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated α-substituted acrylate esters catalyzed by a bifunctional iminophosphorane organocatalyst under mild conditions is described. The strong Brønsted basicity of the iminophosphorane moiety of the catalyst provides the necessary activation of the alkyl thiol pro-nucleophile, while the two tert-leucine residues flanking a

  描述了在温和条件下由双功能亚氨基正膦有机催化剂催化的烷基硫醇与未活化的 α-取代丙烯酸酯的高度对映选择性磺基-迈克尔加成反应。催化剂亚氨基正膦部分的强布朗斯台德碱性为烷基硫醇亲核试剂提供了必要的活化，而中央硫脲氢键供体侧翼的两个叔亮氨酸残基促进了瞬态烯醇中间体质子化过程中的高对映选择性. 该反应在烷基硫醇、酯部分和 α,β-不饱和酯的 α-取代基方面的范围很广，以优异的产率（高达 >99%）和对映选择性（高达到 96% ee)，并且可以使用低至 0 的催化剂负载量进行十克放大。
• Electrochemistry-Enabled Ir-Catalyzed Vinylic C–H Functionalization
  作者：Qi-Liang Yang、Yi-Kang Xing、Xiang-Yang Wang、Hong-Xing Ma、Xin-Jun Weng、Xiang Yang、Hai-Ming Guo、Tian-Sheng Mei

  DOI：10.1021/jacs.9b11915

  日期：2019.12.4

  Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionaliza-tion. Herein, we report the development of electrochemi-cal vinylic C-H functionalization of acrylic acids with al-kynes. In this reaction an iridium catalyst enables C-H/O-H

  电化学和有机金属催化的协同使用已成为位点选择性 CH 功能化的有力工具，但迄今为止这种类型的转化主要限于芳烃 CH 功能化。在此，我们报告了用炔烃对丙烯酸进行电化学乙烯基 CH 官能化的发展。在该反应中，铱催化剂能够实现 CH/OH 官能化以进行炔环化，从而在未分割的电池中提供具有良好至优异产率的 α-吡喃酮。初步机理研究表明，阳极氧化对于从二烯-Ir(I) 络合物中释放产物和再生 Ir(III) 中间体至关重要，二烯-Ir(I) 络合物是一种配位饱和的 18 电子络合物。重要的，
• Microwave-Assisted Synthesis of Furo[3,2-c]-1,8-naphthyridines
  作者：Mustafa Güllü、Deniz Yiğit

  DOI：10.1080/00397911.2010.493264

  日期：2011.7.1

  Abstract Microwave-assisted ring-conversion reactions of some pyrido[1,2-a]pyrimidine derivatives to 1,8-naphthyridines have been investigated. Novel furo[3,2-c]-1,8-naphthyridine compounds were synthesized in good yields under thermal reaction conditions. Both microwave and classical heating methods have been found to be satisfactory for the synthesis of new 1,8-naphthyridines.

  摘要 已经研究了一些吡啶并[1,2-a]嘧啶衍生物到1,8-萘啶的微波辅助环转换反应。在热反应条件下以良好的收率合成了新型呋喃 [3,2-c]-1,8-萘啶化合物。已发现微波和经典加热方法均可用于合成新的 1,8-萘啶。
• Catalytic Generation of Rhodium Silylenoid for Alkene–Alkyne–Silylene [2 + 2 + 1] Cycloaddition
  作者：Toshimichi Ohmura、Ikuo Sasaki、Michinori Suginome

  DOI：10.1021/acs.orglett.9b00326

  日期：2019.3.15

  2 + 1] cycloaddition takes place in the rhodium-catalyzed reaction of 1,6-enynes with borylsilanes bearing an alkoxy group on the silicon atoms, which react as synthetic equivalents of silylene. The reaction proceeds efficiently in 1,2-dichloroethane at 80–110 °C in the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM) as a ligand to afford 1-silacyclopent-2-enes in good to

  烯烃-炔烃-亚甲基[2 + 2 +1]的环加成反应是在铑催化的1,6-炔烃与在硅原子上带有烷氧基的硼烷基硅烷的反应中进行的，这些硅烷作为合成的甲硅烷基等效物进行反应。在载有双（二苯基膦基）甲烷（DPPM）作为配体的铑催化剂存在下，反应在80-110°C的1,2-二氯乙烷中有效进行，从而以高收率或高收率得到1-silacyclopent-2-enes。
• NOC approach to spiroketals. A total synthesis of (.+-.)-talaromycin B
  作者：Alan P. Kozikowski、James G. Scripko

  DOI：10.1021/ja00314a018

  日期：1984.1

  Synthese de talaromycine B par une reaction NOC a partir de l'oxime du dioxa-1,5 spiro [5.5] undecanepropanal-3 et du vinyl- dioxa-1,5 spiro [5.5] undecane via l'hydrogenolyse de l'isoxazoline-2 obtenue

  合成这些 de talaromycine B parune 反应 NOC a partir de l'oxime du dioxa-1,5 spiro [5.5] undecanepropanal-3 et duvinyl-dioxa-1,5 spiro [5.5] undecane via l'hydrogenolyse de l'isoxazoline- 2 迟钝