617-33-4

• 常用中文名：二溴乙酸乙酯
• 常用英文名：ethyl dibromoacetate
• CAS号：617-33-4
• 分子式：C₄H₆Br₂O₂
• 分子量：245.89700
• 相关类别： 化学试剂 有机试剂 酯类 乙酯类化合物
• 发布时间：2018-07-02 17:39:37
• 更新时间：2024-01-02 22:48:22

• 在叔丁醇钾或位阻大的苯氧化物作用下，二溴乙酸乙酯与有机硼烷发生烷基化反应，根据所用试剂的量和反应温度不同可以生成α-溴代酯或α,α-二烷基取代酯 (式1)。用苯氧基 (pK 11.7) 可以减少起始物或产物的自身缩合反应。这是一个可以替代传统丙二酸酯合成法的方法。

  

  低温条件下，在锌/银-石墨作用下，二溴乙酸乙酯发生Reformatsky反应，生成α-溴-β-羟基酯 (式2)，再用适当的基团处理α-溴-β-羟基酯可以得到多种产物。锌/银-碳试剂也可用在醛糖内酯上。向Reformatsky反应有机锌试剂中加入二乙基氯化铝可以改进反应，得到α,β-不饱和酯，这是一种可以替代Wadsworth-Emmons反应的方法。氯化钐或氯化铬也可以用于这个反应 (式3)。

  

  在三乙基甲硼烷催化作用下，二溴乙酸乙酯对烯酮缩醛发生加成反应得到1,4-二酯 (式4)。

  

  控制反应条件，苯硫醇可以与二溴乙酸乙酯反应生成相应的硫缩醛 (式5)。进一步发生烷基化可以得到丙酮酸衍生物。

  

  在铜或锌粉作用下，单烯烃可以与二溴乙酸乙酯发生乙氧基羰基环丙烷化反应 (式6)。

  

名称

• 中文名: 二溴乙酸乙酯
• 英文名: ethyl 2,2-dibromoacetate
• 中文别名: 二溴以乙酸乙酯
• 英文别名: Dibrom-essigsaeure-aethylester; Acetic acid,dibromo-,ethyl ester; MFCD00041718; Dibromoacetic acid,ethyl ester; Ethyl dibromoacetate; EINECS 210-510-7; Acetic acid,2,2-dibromo-,ethyl ester

物化性质

• 密度: 1.902
• 沸点: 77ºC (12 mmHg)
• 分子式: C₄H₆Br₂O₂
• 分子量: 245.89700
• 闪点: 76-78°C/12mm
• 精确质量: 243.87300
• PSA: 26.30000
• LogP: 1.66540
• 外观性状: 透明无色至淡棕色液体
• 折射率: 1.492-1.502
• 储存条件:

  将密器密封，储存密封的主藏器内，并放在阴凉，干爽的位置。

• 稳定性:

  有催泪作用，应避免吸入，在通风橱中进行操作。

• 水溶解性: Soluble in hexane, ether, CH2Cl2, acetone, EtOAc, ethanol.
• 分子结构:

  1、 摩尔折射率：37.77

  2、 摩尔体积（cm³/mol）：124.7

  3、 等张比容（90.2K）：317.6

  4、 表面张力（dyne/cm）：42.0

  5、 极化率（10^-24cm³）：14.97

• 计算化学:

  1.疏水参数计算参考值（XlogP）:2.2

  2.氢键供体数量:0

  3.氢键受体数量:2

  4.可旋转化学键数量:3

  5.互变异构体数量:无

  6.拓扑分子极性表面积26.3

  7.重原子数量:8

  8.表面电荷:0

  9.复杂度:82.1

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.性状：无色或淡黄色液体

  2.沸点（℃，1.0 mmHg）：194

  3.沸点（℃，12 mmHg）：77

  4.密度：d 1.9025 g/cm³

  5.溶解性：不溶于水，微溶于己烷、乙醚、二氯甲烷、丙酮、乙酸乙酯、乙醇。

  6.相对密度（20℃，4℃）：1.8991

  7.常温折射率（n²⁰）：1.4633

MSDS

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 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 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. 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: 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. 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. 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. 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. 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 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 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. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA No information available. IMO No information available. RID/ADR No information available. 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. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

生态学数据: 1、其它有害作用：该物质对环境可能有危害，对水体应给予特别注意。

安全

• 危害码 (欧洲): Xi
• 风险声明 (欧洲): 36/37/38
• 安全声明 (欧洲): 37/39-26
• 危险品运输编码: UN 3265
• 海关编码: 2915900090

合成路线

上下游产品

上游产品  8
141-52-6 42520-11-6 761-17-1 631-22-1
631-64-1 64-17-5 623-73-4 138000-26-7
下游产品  10
10035-10-6 7726-95-6 42716-73-4 20461-96-5
7605-25-6 882-33-7 77-83-8 7367-88-6
6974-87-4 121-39-1

制备

由乙酸乙酯在赤磷存在下与溴作用而得。

海关

海关编码	2915900090
中文概述	2915900090. 其他饱和无环一元羧酸及其酸酐（酰卤、过氧）化物、过氧酸及其卤化、硝化、磺化、亚硝化衍生物. 增值税率:17.0%. 退税率:9.0%. 监管条件:AB(入境货物通关单,出境货物通关单). 最惠国关税:5.5%. 普通关税:30.0%
申报要素	品名, 成分含量, 用途
监管条件	A.入境货物通关单 B.出境货物通关单
检验检疫	R.进口食品卫生监督检验 S.出口食品卫生监督检验 M.进口商品检验 N.出口商品检验
Summary	2915900090 other saturated acyclic monocarboxylic acids and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:5.5% General tariff:30.0%