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乙二醇二甲醚溴化镍 | 28923-39-9

中文名称
乙二醇二甲醚溴化镍
中文别名
镍(II)溴化乙烯二醇二甲基醚络合物
英文名称
nickel(II) bromide dimethoxyethane
英文别名
[(DME)NiBr2];NiBr2*DME;nickel(II) bromide ethylene glycol dimethyl ether;dibromo(1,2-dimethoxyethane)nickel(II);NiBr2*dimethoxyethane;(1,2-dimethoxyethane)NiBr2;NiBr2(1,2-dimethoxyethane);NiBr2*digylme;NiBr2*glyme;Ni(DME)Br2;nickel(II) bromide ethylene glycol dimethyl ether complex;(dimethoxyethane)NiBr2;Dibromo(glyme)nickel;1,2-dimethoxyethane;nickel(2+);dibromide
乙二醇二甲醚溴化镍化学式
CAS
28923-39-9
化学式
C4H10Br2NiO2
mdl
——
分子量
308.62
InChiKey
VHSVJTYBTJCDFL-UHFFFAOYSA-L
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    186-188 °C
  • 闪点:
    124 °F
  • 溶解度:
    甲醇(微溶)、水(微溶)
  • 稳定性/保质期:

    遵照规定使用和储存,则不会分解。

计算性质

  • 辛醇/水分配系数(LogP):
    1.97
  • 重原子数:
    9
  • 可旋转键数:
    0
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    18.5
  • 氢给体数:
    0
  • 氢受体数:
    2

安全信息

  • 危险品标志:
    Xn,F
  • 安全说明:
    S16,S22,S26,S36/37/39,S45
  • 危险类别码:
    R20/21/22,R36/37/38,R11
  • WGK Germany:
    3
  • 危险品运输编号:
    UN 1325 4.1/PG 2
  • 包装等级:
    II
  • 危险类别:
    4.1
  • 危险性防范说明:
    P210,P261,P264,P280,P302+P352+P312,P370+P378
  • 危险性描述:
    H228,H302+H312+H332,H315,H319,H335,H350,H360
  • 储存条件:
    保持贮藏器密封,并将其放入一个紧密封装的容器中。应存放在阴凉、干燥处。

SDS

SDS:fed0e578b46cb13d7ea24661a491531e
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Section 1: Product Identification
Chemical Name: Nickel(II) bromide, dimethoxyethane adduct, min. 97%
CAS Registry Number: 28923-39-9
Formula: NiBr2.CH3O(CH2)2OCH3
EINECS Number: none
Chemical Family: metal halide
Synonym: Nickelous bromide, dimethoxyethane adduct

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 28923-39-9 100% 0.1mg/m3 (as Ni) 1mg/m3 (as Ni)

Section 3: Hazards Identification
Toxic if swallowed. Ingestion of nickel salts may cause intestinal disorders, convulsions and asphyxia. Irritating
Emergency Overview:
to skin, eyes and respiratory tract. May cause cancer and heritable genetic damage.
Primary Routes of Exposure: Ingestion, inhalation of dust
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin. Prolonged exposure to nickel salts may lead to dermatitis.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract. May cause sensitization by inhalation.
Toxic if swallowed. Ingestion may lead to dizziness, abdominal cramps, vomiting, bloody diarrhea, weakness
Ingestion:
and convulsions.
Toxic if swallowed. Irritating to skin, eyes and respiratory tract. May cause intestinal disorders, convulsions,
Acute Health Affects:
asphyxia, sensitization dermatitis, allergic asthma and pneumonitis.
Prolonged exposure to nickel and nickel compounds may lead to skin irritation and dermatitis. May cause
Chronic Health Affects:
cancer and heritable genetic damage. Dimethoxyethane may be a teratogen.
NTP: Yes
IARC: Yes
OSHA: No

SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

SECTION 5: Fire Fighting Measures
Flash Point: not applicable
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: None. Material is non-flammable.
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire, this material may emit toxic fumes of hydrogen bromide.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

SECTION 6: Accidental Release Measures
Small spills may be mixed with diatomaceous earth, sand, vermiculite or other suitable inert material and
Spill and Leak Procedures:
swept up. Avoid raising dust.

SECTION 7: Handling and Storage
Store the material in a tightly sealed container away from moisture. Handle in a fume hood under a dry
Handling and Storage:
atmosphere of argon or nitrogen. Prolonged exposure to the atmosphere may degrade the product.

SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

SECTION 9: Physical and Chemical Properties
Color and Form: peach powder
Molecular Weight: 308.62
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: soluble

SECTION 10: Stability and Reactivity
Stability: moisture sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: contact with moisture
Incompatibility: active metals and chlorine
Decomposition Products: Nickel oxybromide, hydrogen bromide, carbon dioxide, carbon monoxide, organic fumes

SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: Carcinogen (as Ni)
Mutagenic Effects: no data
Tetratogenic Effects: no data

SECTION 12: Ecological Information
Ecological Information: No information available

SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

SECTION 14: Transportation
Shipping Name (CFR): Toxic solid, Inorganic, N.O.S.
Hazard Class (CFR): 6.1
Additional Hazard Class (CFR): NA
Packaging Group (CFR): III
UN ID Number (CFR): UN# 3288
Shipping Name (IATA): Toxic solid, Inorganic, N.O.S.
Hazard Class (IATA): 6.1
Additional Hazard Class (IATA): NA
Packaging Group (IATA): III
UN ID Number (IATA): UN# 3288

SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Title compound: See Category Code N495 for reporting.
Second Ingredient: none


SECTION 16 - ADDITIONAL INFORMATION
N/A




制备方法与用途

用途

乙二醇二甲醚溴化镍是一种有机属化合物,可用作催化剂。

应用

乙二醇二甲醚溴化镍是人工合成的早期应用最广泛的化学药品之一。它具有广谱抗菌、价格低廉、化学性质稳定以及使用方便的特点。该物质既可用于注射也可用于内服,尤其对鸟兽类动物。自高效、长效且广谱的乙二醇二甲醚溴化镍与增效剂合成以来,其在兽医临床上的应用仅次于抗生素。

制备

乙二醇二甲醚溴化镍可通过一步反应制备得到。具体步骤为:将100克NiCl2溶解于300毫升甲醇和50毫升原甲酸三甲酯的混合物中,并在回流下搅拌过夜。反应结束后,通过过滤去除未反应的NiCl2,然后在减压下除去80%的溶液以获得绿色凝胶。将该凝胶溶于适量甲醇中,并加入300毫升1,2二甲氧基乙烷DME)。混合物在回流下搅拌过夜后,会形成黄色粉末[NiCl2(DME)]沉淀并进行过滤分离。用戊烷洗涤后,在氮气流下干燥,最终获得橙色粉末的乙二醇二甲醚溴化镍,产率为80%。

合成路线

如图2所示为该化合物的合成路线:

<a href=https://www.molaid.com/MS_76903 target="_blank">乙二醇二甲醚溴化镍</a>的合成路线

副作用

乙二醇二甲醚溴化镍被吸收进入血液后,在肝脏中通过已酰辅酶的作用产生有毒代谢产物,导致溶解度降低。这些结晶体容易在肾脏、输尿管等处形成沉淀,从而引发刺激和阻塞现象。

反应信息

  • 作为反应物:
    描述:
    乙二醇二甲醚溴化镍2-吡唑-1-吡啶二氯甲烷 为溶剂, 反应 18.0h, 以90%的产率得到[NiBr2(2-pyrazol-1-ylpyridine)]
    参考文献:
    名称:
    含有混合的吡唑,嘧啶和吡啶芳环的双齿N–N'配体的镍(II)配合物,作为乙烯聚合的催化剂
    摘要:
    这项工作描述了以下含有吡唑(pz),嘧啶(pm)和吡啶(py)芳香环的中性双齿氮配体的Ni(II)配合物的合成和表征:2-pyrazol-1-yl-pyrimidine(pzpm) ,2-(4-甲基-吡唑-1-基)-嘧啶(4-Mepzpm),2-(4-溴-吡唑-1-基)-嘧啶(4-Brpzpm),2-(3,5-二甲基-吡唑-1-基)-嘧啶(pz * pm),2-吡唑-1-基-吡啶(pzpy)和双(3,5-二甲基吡唑-1-基)苯基甲烷(bpz * mph)。配合物[NiBr 2(pzpm)](1),[NiBr 2(4-Mepzpm)](2),[NiBr 2(4-Brpzpm)](3),[NiBr 2(pz * pm)](4),[NiBr 2(pzpy)](5)和[NIBR 2(BPZ *英里每小时)](6)进行测试作为催化剂用于乙烯聚合中,助催化剂甲基铝氧烷(MAO)或二乙基氯化铝(ALET存在2
    DOI:
    10.1016/j.jorganchem.2015.09.004
  • 作为产物:
    描述:
    乙二醇二甲醚 、 nickel dibromide 以 乙二醇二甲醚 为溶剂, 生成 乙二醇二甲醚溴化镍
    参考文献:
    名称:
    含 β-二酮亚胺基配体和硫醚系链的铁和镍配合物
    摘要:
    通过乙酰丙酮和 2-甲硫基苯胺的反应合成了一种含有硫醚系链的新型 β-二酮亚氨基配体前体 LH (II)。II 被去质子化并用于合成两种铁 (II) 配合物 [LFeCl] (1) 和 [LFeOTf] (2),以及一种镍 (II) 配合物 [LNiBr] (3)。所有三种化合物都通过单晶 X 射线衍射表征并讨论了它们的结构。
    DOI:
    10.1002/zaac.200800411
  • 作为试剂:
    描述:
    4-乙基苯甲醚 、 在 乙二醇二甲醚溴化镍potassium phosphate monohydrate 、 [Ir(dF(CF3)-ppy)2(4,4'dCF3-bpy)]PF6 、 C23H20N2O2 作用下, 以61 %的产率得到
    参考文献:
    名称:
    金属光氧化还原催化实现立体选择性苯甲基 C(sp3)–H 烯基化
    摘要:
    选择性激活苄基 C(sp 3 )–H 键对于构建复杂的有机框架至关重要。在具有可比能量和空间分布的 C-H 键之间实现精确选择性仍然是一个深刻的合成挑战。在此,我们揭示了利用金属光氧化还原催化的位点和立体选择性苄基 C(sp 3 )–H 烯基化。可以顺利获得各种直链和环状( Z )-全碳三取代和四取代烯烃。该策略可应用于具有多个苄基位点的复杂底物,以前由于位点选择性不可控而被认为不适合。此外,敏感官能团如末端烯基和TMS基团在温和条件下是相容的。卓越的位点选择性和广泛的基材兼容性归因于可见光催化中继电子转移-质子转移过程。更重要的是,我们扩展了这种方法来实现对映选择性苄基 C(sp 3 )–H 烯基化,产生高度对映体富集的产品。通过复杂结构和克级操作的后期功能化,进一步验证了我们协议的适用性和可扩展性,强调了其实用性和鲁棒性。
    DOI:
    10.1039/d4sc02830a
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文献信息

  • The Asymmetric Synthesis of Amines via Nickel-Catalyzed Enantioconvergent Substitution Reactions
    作者:Ze-Peng Yang、Dylan J. Freas、Gregory C. Fu
    DOI:10.1021/jacs.0c13034
    日期:2021.2.24
    dialkyl carbinamines do not provide general access to amines wherein the two alkyl groups are of similar size (e.g., CH2R versus CH2R1). Herein, we report two mild methods for the catalytic enantioconvergent synthesis of protected dialkyl carbinamines, both of which use a chiral nickel catalyst to couple an alkylzinc reagent (1.1–1.2 equiv) with a racemic partner, specifically, an α-phthalimido alkyl chloride
    手性二烷基卡宾胺在有机化学、药物化学生物化学等领域具有重要意义,例如用作生物活性分子、手性配体和手性催化剂。不幸的是,大多数用于合成二烷基卡宾胺的催化不对称方法不提供获得其中两个烷基具有相似大小的胺的一般途径(例如,CH 2 R与CH 2 R 1 )。在此,我们报道了两种催化对映异构合成受保护的二烷基卡宾胺的温和方法,这两种方法都使用手性催化剂将烷基锌试剂(1.1-1.2当量)与外消旋伙伴偶联,特别是α-邻苯二甲酰亚基烷基或受保护的 α-氨基酸的N-羟基邻苯二甲酰亚胺 (NHP) 酯。该方法用途广泛,可提供带有一系列官能团的二烷基卡宾胺衍生物。对于NHP酯的偶联,我们进一步描述了一种一锅变体,其中NHP酯原位生成,允许从市售氨基酸生物一步生成对映体富集的受保护的二烷基卡宾胺;我们通过将其应用于一系列有趣的目标分子的有效催化对映选择性合成来证明该方法的实用性。
  • Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling
    作者:Hai-Yong Tu、Fang Wang、Liping Huo、Yuanbo Li、Shengqing Zhu、Xian Zhao、Huan Li、Feng-Ling Qing、Lingling Chu
    DOI:10.1021/jacs.0c03708
    日期:2020.5.27
    A nickel-catalyzed, enantioselective, three-component fluoroalkylarylation of unactivated alkenes with aryl halides and perfluoroalkyl iodides has been described. This cross-electrophile coupling protocol utilizes a chiral nickel/BiOx system as well as a pendant chelating group to facilitate the challenging three-component, asymmetric difunctionalization of unactivated alkenes, providing direct access
    催化、对映选择性、三组分氟烷基芳基化未活化的烯烃与芳基卤化物和全氟烷基化物已被描述。这种交叉亲电偶联方案利用手性/BiOx 系统以及悬垂的螯合基团来促进未活化烯烃的具有挑战性的三组分不对称双官能化,从而以高效和出色的对映选择性直接获得有价值的手性 β-氟烷基芳基烷烃. 温和的条件允许广泛的底物范围以及良好的官能团耐受性。
  • Stable Nickel Catalysts for Fast Norbornene Polymerization: Tuning Reactivity
    作者:Juan A. Casares、Pablo Espinet、José M. Martín‐Alvarez、Jesús M. Martínez‐Ilarduya、Gorka Salas
    DOI:10.1002/ejic.200500121
    日期:2005.10
    have been determined by X-ray diffraction and show an almost perfect square-planar geometry in all cases. Their catalytic activity in insertion polymerization of norbornene have been tested showing a strong dependence of the yield and molecular mass of the polymer on the ligand used and the solvent. High yield and high molecular mass values are obtained using complexes with ligands easy to displace from
    空气稳定的反式-[Ni(C6CL2F3)2L2] 配合物 (L = SbPh3, 1; AsPh3, 2; AsCyPh2, 3; AsMePh2, 4; PPh3, 5) 已通过 [NiBr2(dme)] 的芳基化合成 ( dme = 1,2-二甲氧基乙烷)在相应配体 L 的存在下(对于化合物 1-4)或通过从 1 开始的配体取代(对于化合物 5)。1、2 和 5 的结构已通过 X 射线衍射确定,并且在所有情况下都显示出几乎完美的方形平面几何形状。已经测试了它们在降冰片烯插入聚合中的催化活性,表明聚合物的产率和分子量对所使用的配体和溶剂有很强的依赖性。使用具有易于从 NiII(SbPh3 是最好的)和非配位溶剂中置换的配体的配合物可以获得高产率和高分子量值。建议将配合物 1-3 作为方便的实验室催化剂使用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451
  • Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp<sup>3</sup>–sp<sup>2</sup> Cross-Coupling of Oxalates with Aryl Halides
    作者:Xiaheng Zhang、David W. C. MacMillan
    DOI:10.1021/jacs.6b09533
    日期:2016.10.26
    Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This
    由相应的醇制备的草酸烷基酯首次在属光氧化还原催化中作为碳自由基碎片参与。在本报告中,我们证明醇类,天然有机官能团,可以很容易地用简单的草酰氯活化,成为与各种芳基卤化物交叉偶联的净氧化还原中性 Csp3-Csp2 中的自由基前体。这种醇-活化偶联已成功应用于天然类固醇的功能化和医学相关药物先导药物的便利合成。
  • Photo–nickel dual catalytic benzoylation of aryl bromides
    作者:Tobias Emanuel Schirmer、Alexander Wimmer、Florian Wolfgang Clemens Weinzierl、Burkhard König
    DOI:10.1039/c9cc04726c
    日期:——
    The dual catalytic arylation of aromatic aldehydes by aryl bromides using UV-irradiation and a nickel catalyst is reported. The reaction product serves as a photocatalyst and a hydrogen atom transfer agent for this transformation.
    报道了使用紫外线辐射和催化剂,芳基化物对芳族醛的双重催化芳基化反应。反应产物用作该转化的光催化剂和氢原子转移剂。
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