2-碘苯甲醛 | 26260-02-6

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醛(含缩醛,半缩醛)
• 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: 2-碘苯甲醛
• 中文别名: 邻碘苯甲醛
• 英文名称: 2-iodobenzaldehyde
• 英文别名: o-iodobenzaldehyde；2-iodobenzenealdehyde；ortho-iodobenzaldehyde
• CAS: 26260-02-6
• 化学式: C₇H₅IO
• mdl: MFCD00039570
• 分子量: 232.021
• InChiKey: WWKKTHALZAYYAI-UHFFFAOYSA-N

物化性质

• 熔点：
  36-39 °C (lit.)
• 沸点：
  129 °C (14 mmHg)
• 密度：
  1.8576 (estimate)
• 闪点：
  >230 °F
• 溶解度：
  溶于甲醇
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会分解。 应避免接触氧化物、空气以及光线。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT, AIR SENSITIVE, KEEP COLD
• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2913000090
• 危险品运输编号：
  NONH for all modes of transport
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  在干性保护气体中处理，并保持贮藏容器密封。将其存放在阴凉、干燥处，并置于紧密的容器中保存。

SDS

Name:	2-Iodobenzaldehyde Material Safety Data Sheet
Synonym:
CAS:	26260-02-6

Section 1 - Chemical Product MSDS Name:2-Iodobenzaldehyde Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
26260-02-6	2-Iodobenzaldehyde		unlisted

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.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with 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:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.) Store under nitrogen.

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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# 26260-02-6: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 129 deg C @14mmHg
Freezing/Melting Point: 36 - 39 deg C
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H5IO
Molecular Weight: 232.02

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen iodide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 26260-02-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Iodobenzaldehyde - 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: 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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 26260-02-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 26260-02-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 26260-02-6 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

制备方法与用途

应用

2-碘苯甲醛是一种有机中间体，可由2-碘苯甲醇通过二氧化锰氧化或Swern氧化制备。

制备过程如下：

在烧瓶中，将4克（17.09毫米摩尔）2-碘苯甲醇溶解于85毫升二氯甲烷中，随后加入14.86克（170.92毫米摩尔）二氧化锰。反应产物在回流下搅拌直至完成。冷却至室温后，通过硅藻土过滤并浓缩，最终得到2-碘苯甲醛，产率为75～90％。

反应信息

• 作为反应物：
  描述：

  2-碘苯甲醛 在 potassium permanganate 、 四丁基溴化铵 、 水 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 25.0h， 生成 二氢-3-(异十二碳烯基)呋喃-2,5-二酮
  参考文献：
  名称：

  丝素蛋白上的钯支持铃木-宫浦的交叉偶联反应

  摘要：

  丝纤蛋白负载的Pd催化剂（Pd / SF）已在Suzuki-Miyaura偶联剂中制备和测试，与其他生物聚合物负载的钯催化剂相比，具有更好的活性，更大的底物范围和较高的可回收性。

  DOI：

  10.1002/ejoc.202001120
• 作为产物：
  描述：

  2-甲酰基苯硼酸 在 七氟-2-碘代丙烷 、 铜 、 对苯二酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以83%的产率得到2-碘苯甲醛
  参考文献：
  名称：

  在室温下用（CF 3）2 CFI进行铜介导的硼酸好氧碘化和硼酸的全氟烷基化

  摘要：

  描述了支链（CF 3）2 CFI和硼酸（RB（OH）2）之间的铜介导的好氧反应。不同于线性全氟烷基类似物CF 3（CF 2）n I（n = 2、3、5、7 ），（CF 3）2 CFI在室温，空气中，催化性Cu存在下与RB（OH）2反应粉末仅提供相应的碘化物（RI），而芳基硼酸与（CF 3）2 CFI在室温下在Cu（OAc）2存在下的需氧反应产生了全氟烷基化产物（R-CF（CF 3）2）可接受到中等产量。氢醌可进一步促进碘化反应，对苯二酚的添加提高了（CF 3）2 CFI的氧化能力，并以高收率提供了碘代碘化产物。羧酸铜促进了全氟烷基化，因为将这些盐添加到反应混合物中可以成功地生成Ar-CF（CF 3）2。

  DOI：

  10.1016/j.jfluchem.2016.07.021
• 作为试剂：
  描述：

  1-乙炔基萘 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 2-碘苯甲醛 、 potassium tert-butylate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 0.75h， 生成 1-((4-(prop-2-ynyloxy)-3-vinylphenyl)ethynyl)naphthalene
  参考文献：
  名称：

  含乙炔基和乙烯基取代基的芳基配体在配位构架中银-碳键的系统研究

  摘要：

  一系列十种包含设计的配体的晶体的单晶X射线衍射，这些配合物包含设计的配体，每个配体均由芳香族系统组成，该系统经末端和内部乙炔基团以及乙烯基取代基官能化，提供了详细信息有关配体位置和方向，配位偏好以及不同类型的银（I）-碳键相互作用（银-乙炔，银-乙炔基，银-乙烯基和银-芳族化合物）共存影响的信息亲和性和弱分子间/分子间相互作用巩固了协调网络的建设。复杂的Ag L10⋅ 6的AgCF 3 CO 2 ⋅ ħ 2 ö ⋅MeOH（HL10 = 1-{[4-（丙-2-炔氧基）-3-乙烯基苯基]乙炔基}萘）是第一个报告的实例，在固态时表现出所有四种银（I）-碳键相互作用。

  DOI：

  10.1002/chem.201204225

文献信息

• Palladium-Catalyzed Carbonylation of 2-Bromoanilines with 2-Formylbenzoic Acid and 2-Halobenzaldehydes: Efficient Synthesis of Functionalized Isoindolinones
  作者：Kishore Natte、Jianbin Chen、Haoquan Li、Helfried Neumann、Matthias Beller、Xiao-Feng Wu

  DOI：10.1002/chem.201404446

  日期：2014.10.27

  versatile method for the synthesis of functionalized isoindolinones is reported. Various 2‐bromoanilines undergo palladium‐catalyzed carbonylation with 2‐formylbenzoic acid under a convenient and mild procedure to give good to excellent yields of the corresponding isoindolinones. Additionally, 2‐halobenzaldehydes can be applied as substrates in palladium‐catalyzed double‐carbonylation to provide identical

  报告了一种简明且用途广泛的方法，用于合成官能化的异吲哚啉酮。在方便，温和的程序下，各种2-溴苯胺与2-甲酰基苯甲酸进行钯催化的羰基化反应，可以使相应的异吲哚啉酮的收率高至优异。另外，2-卤代苯甲醛可作为钯催化的双羰基化反应的底物，以中等到良好的收率提供相同的化合物。
• Isomer Dependence in the Assembly and Lability of Silver(I) Trifluoromethanesulfonate Complexes of the Heteroditopic Ligands, 2-, 3-, and 4-[Di(1<i>H</i>-pyrazolyl)methyl]phenyl(di-<i>p</i>-tolyl)phosphine
  作者：James R. Gardinier、Jeewantha S. Hewage、Sergey V. Lindeman

  DOI：10.1021/ic5019357

  日期：2014.11.17

  and its solid-state and solution spectroscopic properties were studied for comparison purposes. These studies suggest that the cyclic structures of 1 and 2 are likely preserved but are dynamic in solution at room temperature. Moreover, both 3 and 4 have dynamic solution structures where 3 is likely extensively dissociated in CH3CN or acetone rather than being polymeric as in the solid state.

  一个新的异位配体的三个异构体，其包含通过对-，间-或邻-亚苯基间隔基（pL与二（对甲苯基）膦基连接的二（1 H-吡唑基）甲基（-CHpz 2）部分，分别为mL和oL）已通过使用HP（p- tolyl）2与（IC 6 H 4）CHpz 2的适当异构体之间的钯（0）催化偶联反应合成。制备了1：1的三氟甲磺酸银（Ag（OTf））配合物，以检查配体配位的性质以及所获得的超分子异构体（单体，环状低聚或聚合）的类型。单晶X射线衍射研究表明，[Ag（pL）]（OTf）1和[Ag（mL）]（OTf）2 2具有环状二聚体指示，而[Ag（oL）]（OTf） ，3，是配位聚合物。与3苯基膦反应可破坏3中的聚合物链，生成的络合物[Ag（oL）（PPh 3）]（OTf），4，具有其中配体结合于银在螯合一个单金属阳离子κ 2 P，N -配位模式。的解决方案的结构1 - 4经由IR的组合探查，变温多核（1个H，13 C，31
• Reductive arene ortho-silanolization of aromatic esters with hydridosilyl acetals
  作者：Yuanda Hua、Parham Asgari、Udaya Sree Dakarapu、Junha Jeon

  DOI：10.1039/c4cc09850a

  日期：——

  The design and application of a single-pot, reductive arene C–H bond silanolization of esters for synthesis of ortho-formyl arylsilanols.

  一锅法还原芳烃C-H键硅醇化酯的设计与应用，用于合成邻甲酰基芳基硅醇。
• Iridium-Catalyzed <i>ortho</i>-C(sp²)–H Amidation of Benzaldehydes with Organic Azides
  作者：Delong Mu、Xinmou Wang、Gong Chen、Gang He

  DOI：10.1021/acs.joc.7b00531

  日期：2017.4.21

  ortho-C(sp2)–H amidation reaction of benzaldehydes with organic azides has been developed. A catalytic amount of 3,5-di(trifluoromethyl)aniline was used to promote the Ir-catalyzed directed C–H amination reaction through a transient aldimine intermediate. This reaction tolerates a broad scope of benzaldehyde substrates and works well with a range of aryl- and alkylsulfonyl azides.

  已开发出铱催化的苯甲醛与有机叠氮化物的邻位C（sp 2）-H酰胺化反应。催化量的3,5-二（三氟甲基）苯胺用于通过短暂的亚胺中间体促进Ir催化的直接CH胺化反应。该反应可耐受各种范围的苯甲醛底物，并能与多种芳基和烷基磺酰基叠氮化物一起很好地起作用。
• Catalytic oxidation of alcohols with novel non-heme <i>N</i>₄-tetradentate manganese(<scp>ii</scp>) complexes
  作者：Vincent Vermaak、Desmond A. Young、Andrew J. Swarts

  DOI：10.1039/c8dt03808b

  日期：——

  non-heme N4-tetradentate Mn(OTf)2 complexes of the type, [(L)MnOTf2], where L = R,R and S,S enantiomers of BPMCN, its 6-methyl and 6-bromo derivatives as well as the novel ligand BMIMCN (BPMCN = N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-(R,R/S,S)-1,2-diaminocyclohexane, BMIMCN = N,N′-dimethyl-N,N′-bis(1-methyl-2-imidazolemethyl)-(R,R/S,S)-1,2-diaminocyclohexane). Solid state structural analysis of the BMIMCN-ligated

  我们报道了[[L] MnOTf 2 ]类型的一系列新型非血红素N 4-四齿Mn（OTf）2配合物的制备和表征，其中L = BPMCN的R，R和S，S对映体，其6-甲基和6-溴衍生物以及新型配体BMIMCN（BPMCN = N，N'-二甲基-N，N'-双（2-吡啶基甲基）-（R，R / S，S）-1， 2-二氨基环己烷，BMIMCN = N，N'-二甲基-N，N′-双（1-甲基-2-咪唑甲基）-（R，R / S，S）-1,2-二氨基环己烷）。BMIMCN连接的Mn-三氟甲磺酸盐配合物（R，R -C4和S，S -C4）的固态结构分析显示相反的螺旋度，但相同的金属位点可及性。在过氧化氢为氧化剂，乙酸为助催化剂的伯醇和仲醇的催化氧化中，利用了这一特性。配合物R，R -C4和S，S -C4由于BMIMCN配体的供电子特性，苯甲醇具有最高的苯甲醇氧化活性。络合物S，S -C4，对多种伯醇底物显示出高活

表征谱图