2,3-二溴丙酸甲酯 | 1729-67-5

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 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: 2,3-二溴丙酸甲酯
• 中文别名: 一缩二乙二醇一(2-乙基已基)醚；二甘醇(2-乙己基)醚；2-乙己基卡必醇；二甘醇一(2-乙己基)醚；二乙二醇单辛醚；一缩二乙二醇单(2-乙基已基)醚；D-哌可酸；2-{(2-[(2-乙基己基)氧基]乙氧基}乙醇；二甘醇单(2-乙己基)醚
• 英文名称: Methyl 2,3-dibromopropionate
• 英文别名: 2,3-dibromo-propionic acid methyl ester；methyl 2,3-dibromopropanoate
• CAS: 1729-67-5
• 化学式: C₄H₆Br₂O₂
• mdl: MFCD00017882
• 分子量: 245.898
• InChiKey: ROXQOUUAPQUMLN-UHFFFAOYSA-N

物化性质

• 沸点：
  83-86 °C/10 mmHg (lit.)
• 密度：
  1.944 g/mL at 20 °C (lit.)
• 闪点：
  -33 °C
• LogP：
  2
• 保留指数：
  1070
• 稳定性/保质期：
  常温常压下稳定，避免与强酸接触以及氧化物的生成。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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

• 危险品标志：
  Xi
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R36/37
• WGK Germany：
  3
• 危险品运输编号：
  UN 2398 3/PG 2
• 海关编码：
  2915900090
• 危险类别：
  6.1
• 包装等级：
  III
• 储存条件：
  请将容器密封保存，并储存在阴凉、干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Methyl 2,3-dibromopropionate
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
H335: May cause respiratory irritation
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

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 2,3-dibromopropionate
CAS number: 1729-67-5

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C4H6Br2O2
Molecular weight: 245.9

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,3-二溴丙酸甲酯 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到methyl 2-azidoacrylate
  参考文献：
  名称：

  通过β，γ-C，S硫-迈克尔加成反应化学合成N-末端半胱氨酸硫酯

  摘要：

  脱氢丙氨酸（ΔAla）是高度亲电的残基，可与硫亲核试剂有效反应，提供半胱氨酰类似物。本文中，我们报告了基于β，γ-C，S硫醇-迈克尔加成法的N端半胱氨酸硫酯的有效合成方法，适用于S，N-酰基转移。发现基于离子方法和基于自由基的方法对于该过程都是有效的。

  DOI：

  10.1021/acs.orglett.9b01013
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 在 四氢吡咯 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 为溶剂， 以27%的产率得到2,3-二溴丙酸甲酯
  参考文献：
  名称：

  溴阳离子有机催化还原的光谱和计算研究：加速立体选择性二溴化方案**

  摘要：

  报道了一种新开发的使用胺有机催化剂从N-溴代琥珀酰亚胺 (NBS) 中原位还原阳离子溴的方法。中间体试剂及其反应性已通过光谱和计算方法得到了很好的表征。NBS 分子的战略结构变化可以引起足够的极性反转，以加速需要两个“Br”合成子的二溴化反应。这已进一步用于具有广泛底物范围的烯烃的加速二溴化反应。

  DOI：

  10.1002/chem.202300675
• 作为试剂：
  描述：

  2-amino-5-methyl-benzoic acid ethyl ester; thiocyanate 在 2,3-二溴丙酸甲酯 作用下， 反应 2.5h， 生成 ethyl 7-methyl-5-oxo-1,2-dihydro-[1,3]thiazolo[3,2-a]quinazoline-2-carboxylate;hydrobromide
  参考文献：
  名称：

  Gakhar, H. K.; Kiran, Sushma; Gupta, Shashi Bhushan, Journal of the Indian Chemical Society, 1982, vol. 59, # 5, p. 666 - 667

  摘要：

  DOI：

文献信息

• Efficient Synthesis of Highly Functionalized Cyclic Aminimides
  作者：Bongjin Moon、Sangbae Han、Dohyung Kim

  DOI：10.1021/ol051270v

  日期：2005.7.1

  [reaction: see text]. Simple condensation reactions of various alpha,beta-epoxy or alpha,beta-aziridinyl methyl esters with 1,1-dialkyl hydrazines provided cyclic aminimides (1,1-dialkyl-3-oxopyrazolidines) with a heteroatom substituent at the 4-position in good yields. The reaction proceeds smoothly, without any coreagent, providing the product as an easily isolable precipitate. The reaction is expected

  [反应：请参见文字]。各种α，β-环氧或α，β-叠氮基甲基酯与1,1-二烷基肼的简单缩合反应可提供环状氨基胺（1,1-二烷基-3-氧杂唑烷），在4位具有杂原子取代基产量。反应平稳进行，没有任何核心试剂，提供了易于分离的沉淀产物。预期该反应将是高度官能化的五元环骨架的组合合成的良好候选者。通过改变取代基R（1）-R（5），研究了该反应的范围和局限性。
• [EN] ROR-GAMMA INHIBITORS<br/>[FR] INHIBITEURS DE ROR-GAMMA
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2019063748A1

  公开（公告）日：2019-04-04

  The present invention relates to compounds of formula I and pharmaceutical compositions comprising compounds of formula I. Compounds of Formula I are useful in treatment of inflammatory, metabolic or autoimmune diseases which are mediated by RORy.

  本发明涉及公式I的化合物和包含公式I化合物的药物组合物。公式I的化合物在治疗由RORγ介导的炎症性、代谢性或自身免疫性疾病方面是有用的。
• Reaction of N-Haloamide. XX. Bromo-formyloxylation of α, β-Unsaturated Esters with N, N-Dibromobenzenesulfonamide and Formic Acid
  作者：YOSHIO UENO、AKEMI YAMASAKI、HIROMI TERAUCHI、SHOJI TAKEMURA

  DOI：10.1248/cpb.22.1646

  日期：——

  α, β-Unsaturated esters were made to react with N, N-dibromobenzenesulfonamide and formic acid in chloroform to give bromo-formyloxyesters. Methyl acrylate (1a), ethyl crotonate (2a), ethyl trans-cinnamate (3a), methyl tiglate (4a), methyl methacrylate (5a), and methyl phenylacrylate (6a) gave methyl 2-bromo-3-formyloxypropionate (1b), ethyl erythro-2-bromo-3-formyloxybutyrate (2b), ethyl erythro-2-bromo-3-formyloxy-3-phenylpropionate (3b), methyl erythro-2-bromo-3-formyloxy-2-methylbutyrate (4b), a mixture of methyl 3-bromo-2-formyloxy-2-methylpropionate (5b) and methyl 2-bromo-3-formyloxy-2-methylpropionate (5c), and methyl 3-bromo-2-formyloxy-2-phenylpropionate (6b) respectively in good yields.

  α, β-不饱和酯与N, N-二溴苯磺酰胺和甲酸在氯仿中反应，生成溴代甲酰氧基酯。甲基丙烯酸酯（1a）、乙基巴豆酸酯（2a）、乙基反式肉桂酸酯（3a）、甲基惕格酸酯（4a）、甲基甲基丙烯酸酯（5a）和甲基苯基丙烯酸酯（6a）分别以良好的产率生成甲基2-溴-3-甲酰氧基丙酸酯（1b）、乙基erythro-2-溴-3-甲酰氧基丁酸酯（2b）、乙基erythro-2-溴-3-甲酰氧基-3-苯基丙酸酯（3b）、甲基erythro-2-溴-3-甲酰氧基-2-甲基丁酸酯（4b）、甲基3-溴-2-甲酰氧基-2-甲基丙酸酯（5b）和甲基2-溴-3-甲酰氧基-2-甲基丙酸酯（5c）的混合物以及甲基3-溴-2-甲酰氧基-2-苯基丙酸酯（6b）。
• Hybridized and isosteric analogues of N 1 -acetyl- N 4 -dimethyl-piperazinium iodide (ADMP) and N 1 -phenyl- N 4 -dimethyl-piperazinium iodide (DMPP) with central nicotinic action
  作者：Dina Manetti、Alessandro Bartolini、Pier Andrea Borea、Cristina Bellucci、Silvia Dei、Carla Ghelardini、Fulvio Gualtieri、Maria Novella Romanelli、Serena Scapecchi、Elisabetta Teodori、Katia Varani

  DOI：10.1016/s0968-0896(98)00259-4

  日期：1999.3

  tertiary bases (2, 4) with arecoline (5) and arecolone (6) or by isosteric substitution of the phenyl ring of DMPP, has been synthesized. Hybridization afforded compounds that, both as tertiary bases and as iodomethylates, have no affinity for the nicotinic receptor. On the contrary, isosteric substitution gave compounds that maintain affinity for the receptor; among them, two tertiary bases (37, 38)

  通过将N1-乙酰基-N4-二甲基哌嗪碘化物（1，ADMP）和N1-苯基-N4-二甲基哌嗪碘化物（3，DMPP）或相应的叔碱基（2， 4）用槟榔碱（5）和槟榔酮（6）或通过等规取代DMPP的苯环。杂交提供了既作为叔碱又作为碘甲基化物的化合物，其对烟碱样受体没有亲和力。相反，等位取代使化合物对受体保持亲和力。其中，两个叔碱基（37、38）对烟碱样受体具有纳摩尔级的亲和力。这些异构化合物的药理学特征非常有趣，因为它们的外周和中枢作用存在差异，
• [EN] QUINOLIN-, ISOQUINOLIN-, AND QUINAZOLIN-OXYALKYLAMIDES AND THEIR USE AS FUNGICIDES<br/>[FR] OXYALKYLAMIDES DE QUINOLINE, D'ISOQUINOLINE ET DE QUINAZOLINE ET LEUR UTILISATION COMME FONGICIDES
  申请人：SYNGENTA LTD

  公开号：WO2004047538A1

  公开（公告）日：2004-06-10

  Fungicidal compounds of the general formula (1) wherein one of X and Y is N or N-oxide and the other is CR or both of X and Y are N.

  通用公式（1）中的杀真菌化合物，其中X和Y中的一个是N或N-氧化物，另一个是CR，或者X和Y都是N。

表征谱图