苄基乙基丙二酸 | 42998-51-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 苄基乙基丙二酸
• 英文名称: benzyl ethyl malonate
• 英文别名: BEM；ethyl benzyl malonate；3-O-benzyl 1-O-ethyl propanedioate
• CAS: 42998-51-6
• 化学式: C₁₂H₁₄O₄
• mdl: MFCD00009194
• 分子量: 222.241
• InChiKey: CGNOCUSLPSCMLL-UHFFFAOYSA-N

物化性质

• 沸点：
  138-139 °C
• 密度：
  1.087
• 闪点：
  145°C/4mm
• LogP：
  2.020 (est)
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S23,S24/25
• 海关编码：
  2917190090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封、阴凉、干燥保存。

SDS

Name:	Benzyl ethyl malonate Material Safety Data Sheet
Synonym:	None listed
CAS:	42998-51-6

Section 1 - Chemical Product MSDS Name:Benzyl ethyl malonate Material Safety Data Sheet
Synonym:None listed

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
42998-51-6	Benzyl ethyl malonate	ca. 100	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Cover with sand, dry lime or soda ash and place in a closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 42998-51-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Clear liquid
Color: clear colorless
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 138 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: 1.0870g/cm3
Molecular Formula: C12H14O4
Molecular Weight: 222.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 42998-51-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Benzyl ethyl malonate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 42998-51-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 42998-51-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 42998-51-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

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
  丙二酸单苯甲酯	malonic acid monobenzyl ester	40204-26-0	C10H10O4	194.187
  ——	dibenzyl ethylmalonate	74254-53-8	C19H20O4	312.365
  乙酸苄酯	Benzyl acetate	140-11-4	C9H10O2	150.177

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	benzyloxycarbonylmethyl ethyl malonate	——	C14H16O6	280.277
  ——	(±)-1-benzyl 3-ethyl 2-(3-oxobutyl)malonate	1405679-53-9	C16H20O5	292.332
  ——	(±)-1-benzyl 3-ethyl 2-(3-(hydroxyimino)butyl)malonate	1405679-66-4	C16H21NO5	307.346

反应信息

• 作为反应物：
  描述：

  苄基乙基丙二酸 在 palladium dihydroxide 氢气 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 monoethyl DL-ethyl-malonate
  参考文献：
  名称：

  N-芳基，N'-烷基巴比妥酸酯的三组分一锅顺序合成。

  摘要：

  [反应：见正文] N-烷基，N'-芳基碳二亚胺和丙二酸单酯之间的缩合导致N-酰基脲衍生物的高收率形成，可以通过在其中加入合适的碱将其环化为C-单取代的巴比妥酸酯。一锅顺序的方式。在亲电子试剂的存在下，最后一步导致完全取代的巴比妥酸酯的一锅三组分顺序合成。

  DOI：

  10.1021/ol063074+
• 作为产物：
  描述：

  乙酸苄酯 在 pumice stone 作用下， 300.0~310.0 ℃ 、666.61 Pa 条件下， 生成 苄基乙基丙二酸
  参考文献：
  名称：

  DE427856

  摘要：

  公开号：

文献信息

• Substituted guanidine derivatives and process for producing the same
  申请人：Sumitomo Pharmaceuticals Company

  公开号：US06369110B1

  公开（公告）日：2002-04-09

  A compound represented by the general formula (1): wherein each of R1, R2, R3, R4 and R5 is a hydrogen atom, an alkyl group, a substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a saturated heterocyclic group, an aromatic group, an acyl group or the like; each of Y1, Y2, Y3 and Y4 is a single bond, —CH2—, —O—, —CO— or the like, provided that at least two of Y1 through Y4 are independently a group other than a single bond; and Z may be absent, or one or more Zs may be present and are independently an alkyl group, a substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a saturated heterocyclic group, a halogen atom, a carboxyl group, an alkoxycarbonyl group, an aromatic group, an acyl group or the like, is useful as a therapeutic or prophylactic agent for diseases caused by the acceleration of the sodium/proton exchange transport system.

  通式（1）所代表的化合物： 其中R1、R2、R3、R4和R5中的每一个是氢原子、烷基、取代烷基、烯基、炔基、环烷基、环烯基、饱和杂环基、芳香基、酰基或类似物；Y1、Y2、Y3和Y4中的每一个是单键、—CH2—、—O—、—CO—或类似物，前提是至少两个Y1到Y4中的独立团是单键以外的团；以及Z可以不存在，或者一个或多个Z可以存在且独立地是烷基、取代烷基、烯基、炔基、环烷基、环烯基、饱和杂环基、卤素原子、羧基、烷氧羰基、芳香基、酰基或类似物，对于由于钠/质子交换传输系统加速而引起的疾病，具有治疗或预防作用。
• Multicomponent, One-Pot Sequential Synthesis of 1,3,5- and 1,3,5,5-Substituted Barbiturates
  作者：Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/jo801288s

  日期：2008.10.3

  represents a general and straightforward one-pot sequential synthesis of 1,3,5-trisubstituted barbiturates in very mild conditions (organic solvent/2 N NaOH aqueous solution, 20 degrees C). Performing the reaction in the presence of an electrophile resulted in the formation of fully substituted (namely, 1,3,5,5-tetrasubstituted) barbiturates through a three-component one-pot sequential process. The latter

  碳二亚胺和丙二酸单乙酯容易反应，得到N-酰脲衍生物，可以通过添加合适的碱原位环化。该方法代表在非常温和的条件下（有机溶剂/ 2 N NaOH水溶液，20摄氏度）进行的简单直接的一锅顺序合成1,3,5-三取代的巴比妥酸盐。在亲电子试剂的存在下进行反应，通过三组分一锅法连续反应形成了完全取代的（即1,3,5,5-四取代的）巴比妥酸酯。然而，后者仅在高反应性亲电试剂例如苄基和在某些情况下是烯丙基卤的情况下发生。为了扩大该方法的范围，我们寻求开发一种用于1,3,5-三取代的巴比妥酸酯的C-烷基化的通用方法。我们发现，在无水K2CO3存在下于120℃下在CH3CN中用烷基卤处理1,3,5-三取代的巴比妥酸酯时发生C-烷基化，从而以良好的收率提供目标1,3,5,5-四取代的巴比妥酸酯。多组分工艺是通过以下三个步骤以一锅顺序方式组合完成的，即碳二亚胺与丙二酸单乙酯的缩合，所得N-酰基脲的环化以及所得1,3的C-烷基化，
• Amino Acids and Peptides. XII. Phosphorus in Organic Synthesis. VIII. Reaction of Malonic Acid Half Esters with Diphenyl Phosphorazidate
  作者：KUNIHIRO NINOMIYA、TAKAYUKI SHIOIRI、SHUNICHI YAMADA

  DOI：10.1248/cpb.22.1398

  日期：——

  Application of the modified Curtius reaction by DPPA to some malonic acid half esters revealed that esterification occurred in a one-step process but the rearrangement reaction took place in a two-in-one-reaction procedure, the results of which are summarized in Tables I and II. The latter procedure may provide a new simple method for the synthesis of α-amino acids.

  通过DPPA对一些丙二酸半酯进行改良的Curtius反应的应用发现，酯化过程是一步完成的，但重排反应是在一个二合一反应程序中进行的，其结果总结在表I和表II中。后一程序可能为α-氨基酸的合成提供了一种新的简单方法。
• Enantioselective Synthesis of Substituted δ-Lactones by Cooperative Oxidative N-Heterocyclic Carbene and Lewis Acid Catalysis
  作者：Srikrishna Bera、Constantin G. Daniliuc、Armido Studer

  DOI：10.1021/acs.orglett.5b01932

  日期：2015.10.16

  Efficient construction of complex cylcopentane- or cyclohexane-fused δ-lactones employing redox activation of enals using a chiral N-heterocyclic carbene and LiCl as cooperative catalysts is described. The organocascade proceeds with excellent diastereo- (>99:1) and enantioselectivity (up to >99% ee) and comprises the formation of three bonds with three contiguous stereocenters.

  描述了使用手性N-杂环卡宾和LiCl作为协同催化剂，通过烯类的氧化还原活化，高效构建复杂的环戊烷或环己烷稠合的δ-内酯的方法。有机级联反应具有出色的非对映异构体（> 99：1）和对映选择性（高达> 99％ee），并包括三个连续的立体中心的三个键的形成。
• Use of EP4 receptor ligands in the treatment of IL-6 involved diseases
  申请人：——

  公开号：US20030236260A1

  公开（公告）日：2003-12-25

  Methods of treating IL-6 involved diseases with EP4 receptor ligands, including EP4 receptor antagonists. Assays to determine the effect of test compounds on PGE2-induced whole blood cells activation.

  治疗IL-6相关疾病的方法涉及EP4受体配体，包括EP4受体拮抗剂。用于确定试验化合物对PGE2诱导的全血细胞活化效果的测定。