二溴乙酸乙酯 | 617-33-4

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 二溴乙酸乙酯
• 中文别名: 二溴以乙酸乙酯
• 英文名称: ethyl dibromoacetate
• 英文别名: Dibrom-essigsaeure-aethylester；ethyl 2,2-dibromoacetate
• CAS: 617-33-4
• 化学式: C₄H₆Br₂O₂
• 分子量: 245.898
• InChiKey: NIJGVVHCUXNSLL-UHFFFAOYSA-N

物化性质

• 沸点：
  77 °C (12 mmHg)
• 密度：
  1.902
• 闪点：
  76-78°C/12mm
• 溶解度：
  易溶于己烷、乙醚、二氯甲烷、丙酮、乙酸乙酯、乙醇。
• 保留指数：
  1044.9
• 稳定性/保质期：
  具有催泪作用，应避免吸入，并在通风橱中进行操作。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN 3265
• 海关编码：
  2915900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  将密器密封，存放在主藏器中，并置于阴凉、干燥处。

SDS

Name:	Ethyl dibromoacetate tech. 83% Material Safety Data Sheet
Synonym:	Acetic acid, dibromo-, ethyl este
CAS:	617-33-4

Section 1 - Chemical Product MSDS Name:Ethyl dibromoacetate tech. 83% Material Safety Data Sheet
Synonym:Acetic acid, dibromo-, ethyl este

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
617-33-4	Acetic acid, dibromo-, ethyl ester	83	210-510-7

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Corrosive.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
May cause skin irritation. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause irritation of the digestive tract. May cause systemic effects.
Inhalation:
Aspiration may lead to pulmonary edema. May cause systemic effects.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed.
Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately 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 immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do not use mouth-to-mouth resuscitation if victim ingested or inhaled the substance; induce artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device.
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.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Use only in a chemical fume hood. Discard contaminated shoes. Do not breathe vapor.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives area.

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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# 617-33-4: 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: Liquid
Color: clear, colorless
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 77 deg C @ 12.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: 1.9020g/cm3
Molecular Formula: C4H6Br2O2
Molecular Weight: 245.90

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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:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 617-33-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Acetic acid, dibromo-, ethyl ester - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
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# 617-33-4: No information available.
Canada
CAS# 617-33-4 is listed on Canada's NDSL List.
CAS# 617-33-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 617-33-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生产方法：乙酸乙酯在赤磷的存在下与溴作用而得到。

反应信息

• 作为反应物：
  描述：

  二溴乙酸乙酯 在 氨 作用下， 生成 2,2-二溴代乙酰胺
  参考文献：
  名称：

  Schaeffer, Chemische Berichte, 1871, vol. 4, p. 366

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-二溴-2,2-二乙氧基乙烷 在 溴 作用下， 生成 二溴乙酸乙酯
  参考文献：
  名称：

  Magnani; McElvain, Journal of the American Chemical Society, 1938, vol. 60, p. 2212

  摘要：

  DOI：

文献信息

• Fe(0)-Mediated Synthesis of Tri- and Tetra-Substituted Olefins from Carbonyls:  An Environmentally Friendly Alternative to Cr(II)
  作者：J. R. Falck、Romain Bejot、Deb K. Barma、Anish Bandyopadhyay、Suju Joseph、Charles Mioskowski

  DOI：10.1021/jo061445u

  日期：2006.10.1

  carbonyls by activated polyhalides. In many instances, Fe(0) was equivalent or superior to Cr(II). Notably, Fe(0), but not Cr(II), proved compatible with a wide range of functionality, inter alia, unprotected phenol, aryl nitro, carboxylic acid, and alkyl nitrile. A surprising reversal of stereoselectivity for aldehydes versus ketones was observed using both metals. The resultant α-halo-α,β-unsaturated or α

  研究了Fe（0）作为Cr（II）的一种经济高效，环保的替代品，用于活化多卤化物对羰基进行烯化。在许多情况下，Fe（0）等于或优于Cr（II）。值得注意的是，事实证明，Fe（0）而不是Cr（II）与广泛的官能度兼容，尤其是与未保护的苯酚，芳基硝基，羧酸和烷基腈。使用两种金属均观察到醛相对于酮的立体选择性出乎意料的逆转。所得的α-卤代-α，β-不饱和或α，β-不饱和的羧酸，酯和腈是许多目标化合物中常见的结构元素，也是制备其他官能团的关键中间体。
• Vicarious Nucleophilic Substitution of Nitrobenzenes
  作者：Gerath A. DeBoos、David J. Milner

  DOI：10.1080/00397919408020772

  日期：1994.4

  Abstract Vicarious nucleophilic substitution (VNS) by dichloroacetate and other reagents has been applied in good yield to various ortho-substituted nitrobenzenes including 2-nitrotoluene and 2-nitro ethylbenzene. For alkyl nitrobenzenes, ease of VNS increased para < ortho < meta and methyl < ethyl < iso-propyl. Formation of chlorine-free products upon VNS by methyl dichloroacetate suggests the involvement

  摘要 二氯乙酸酯和其他试剂的替代亲核取代（VNS）已以良好的收率应用于各种邻位取代的硝基苯，包括2-硝基甲苯和2-硝基乙苯。对于烷基硝基苯，VNS 的易用性增加了对 < 邻 < 间和甲基 < 乙基 < 异丙基。二氯乙酸甲酯在 VNS 上形成无氯产物表明自由基阴离子的参与。
• The Addition Reaction of Samarium Enolates and 2-Haloenolates Derived from Esters, and Amides to Imines. Totally Stereoselective Synthesis of Enantiopure 3,4-Diamino Esters or Amides
  作者：José M. Concellón、Humberto Rodríguez-Solla、Carmen Simal、Vicente del Amo、Santiago García-Granda、M. Rosario Díaz

  DOI：10.1002/adsc.200900534

  日期：2009.11

  addition reaction of samarium enolates and 2-haloenolates derived from esters and amides to imines takes place in an efficient manner. A novel protocol to perform the addition reaction of samarium enolates derived from esters or amides to chiral 2-aminoimines, with total stereoselectivity and without racemization, is also reported. The use of samarium enolates in place of other classic metallic enolates

  衍生自酯和酰胺的烯醇盐和2-卤代烯醇盐以有效的方式发生加成反应。还报道了一种新颖的方案，该方案可以进行酯或酰胺衍生的烯醇sa到手性2-氨基亚胺的加成反应，该反应具有总的立体选择性且没有消旋作用。当需要低碱性的烯醇盐时，使用sa烯醇盐代替其他经典的金属烯醇盐（锂，镁等）可能是获得对映纯3,4-二氨基酯或酰胺的有价值的选择。
• Molecular water oxidation catalysis by zwitterionic carboxylate bridge-functionalized bis-NHC iridium complexes
  作者：Raquel Puerta-Oteo、M. Victoria Jiménez、Jesús J. Pérez-Torrente

  DOI：10.1039/c8cy02306a

  日期：——

  transformed into the same active molecular species resulting from the degradation of the hydrocarbon ligands which is partially supported by the similarity of the oxygen evolution profiles at moderate oxidant/catalyst ratios for both catalyst precursors and the same chemical oxidant. In addition, DLS studies provide evidence for the participation of homogeneous iridium molecular species as intermediates likely

  两性离子水溶性[Cp * Ir III Cl （MeIm）2 CHCOO}]和[Ir I（cod）（MeIm）2 CHCOO}]配合物，具有羧酸酯桥官能化的双-N-杂环卡宾配体，可有效催化水使用硝酸铈铈（IV）或高碘酸钠作为牺牲氧化剂进行氧化。TOF 50值高达1000 h -1时，产量极高使用CAN作为电子受体以[CAN] / [Ir]的比率高于700已经实现了这一目标。通过紫外可见光谱对反应机理的研究似乎证明了两种催化剂前体均因降解而转化为相同的活性分子。对于催化剂前体和相同的化学氧化剂，在适中的氧化剂/催化剂比下，由氧释放曲线的相似性部分支持了烃配体的一部分。此外，DLS研究提供了均质铱分子物质作为中间体的证据，这些中间体很可能被羧酸盐官能化的双-NHC配体稳定。
• 一种唑来膦酸中间体化合物
  申请人：鲁南制药集团股份有限公司

  公开号：CN112574113A

  公开（公告）日：2021-03-30

  本发明属于医药合成技术领域，具体涉及一种唑来膦酸中间体化合物。本发明以2,2‑双取代乙酸酯和咪唑为起始原料，经过取代反应、水解反应合成2,2‑咪唑乙酸盐酸盐中间体，该方法原料简单易得，反应条件温和，操作过程简便，经济环保；利用该中间体化合物制备的唑来膦酸收率可达到85.27％，且无双膦酸杂质，纯度高达99.8％以上。

表征谱图