2-碘代甲苯 | 615-37-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 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-碘代甲苯
• 中文别名: 2-甲基碘苯；邻碘甲苯；2-碘甲苯
• 英文名称: 2-Iodotoluene
• 英文别名: ortho-methylphenyl iodide；1-iodo-2-methylbenzene；2-methyliodobenzene；o-iodotoluene；1-iodo-2-toluene
• CAS: 615-37-2
• 化学式: C₇H₇I
• 分子量: 218.037
• InChiKey: RINOYHWVBUKAQE-UHFFFAOYSA-N

物化性质

• 熔点：
  11.27°C (estimate)
• 沸点：
  211 °C(lit.)
• 密度：
  1.713 g/mL at 25 °C(lit.)
• 闪点：
  194 °F
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• 蒸汽压力：
  0.45 mmHg
• 保留指数：
  1122.4;1150;1150;1149
• 稳定性/保质期：
  性质与稳定性： 在常温常压下，不会分解产生其他物质。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  T
• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29036990
• 危险品运输编号：
  UN 2810
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  贮存： 将密器密封后，放入密封的主容器中，并存放在阴凉、干燥的地方。

SDS

Name:	2-Iodotoluene 98% Material Safety Data Sheet
Synonym:
CAS:	615-37-2

Section 1 - Chemical Product MSDS Name:2-Iodotoluene 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
615-37-2	2-Iodotoluene	98	210-422-9

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. May cause chemical conjunctivitis and corneal damage.
Skin:
May cause irritation and dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Aspiration may lead to pulmonary edema. Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. Use water spray to keep fire-exposed containers cool. Combustible liquid.
Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use agent most appropriate to extinguish fire. 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. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 615-37-2: 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 yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 211 deg C @ 760.00 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 90 deg C ( 194.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.7130 g/cm3
Molecular Formula: C7H7I
Molecular Weight: 218.04

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen iodide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 615-37-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Iodotoluene - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
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# 615-37-2: No information available.
Canada
CAS# 615-37-2 is listed on Canada's NDSL List.
CAS# 615-37-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 615-37-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

2-碘代甲苯是一种碘代芳烃类化合物，卤代芳烃化合物如碘代芳烃类化合物是重要的化工原料和中间体。以常见的碘苯为例，碘苯相比溴苯和氯苯具有更高的化学活性，在催化C-C键合成及C-杂原子键合反应中应用更广泛。

制备 方法一

在装有磁搅拌子的圆底烧瓶中加入0.2 mL氧化亚铜/NH₃催化体系，135.8 mg邻甲基苯硼酸，0.830 g碘化钾以及2 mL水。室温下开放体系反应24小时后，向其中加入1.5 mL 2 mol/L的氢氧化钠溶液并用二氯甲烷萃取三次（每次2 mL），合并后的有机相经浓缩得到2-碘代甲苯176 mg，产率为81%。

方法二

精确称取邻溴甲苯(42.8 mg, 0.25 mmol)、四甲基碘化铵(150.79 mg, 0.75 mmol)、氧化亚铜(3.6 mg, 0.025 mmol)和L-脯氨酸(5.8 mg, 0.05 mmol)，依次加入到25 mL的Schlenk瓶中，加入精制过的乙醇(1.5 mL)，置于110℃油浴中反应30小时。反应结束后，通过硅胶柱过滤至10 mL容量瓶，并用乙酸乙酯将溶液体积定量至指定刻度。使用气相色谱进行分析，2-碘代甲苯的产率为28%。

用途

主要作为生物制药中的医药中间体。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-碘苄醇	2-iodobenzyl alcohol	5159-41-1	C7H7IO	234.036
  2-碘苯甲基溴	2-Iodobenzyl bromide	40400-13-3	C7H6BrI	296.933
  2-碘苄基碘	2-iodobenzyliodide	4622-38-2	C7H6I2	343.934
  邻碘氯苄	2-(chloromethyl)iodobenzene	59473-45-9	C7H6ClI	252.482

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2,4-diiodo-toluene	32704-08-8	C7H6I2	343.934
  1,3,5-三碘-2-甲基苯	2,4,6-triiodo-toluene	36994-79-3	C7H5I3	469.83
  2-碘苯甲醛	2-iodobenzaldehyde	26260-02-6	C7H5IO	232.021
  2-碘苄醇	2-iodobenzyl alcohol	5159-41-1	C7H7IO	234.036
  2-碘苯甲基溴	2-Iodobenzyl bromide	40400-13-3	C7H6BrI	296.933
  2-碘氰基苯	2-iodobenzonitrile	4387-36-4	C7H4IN	229.02
  2-碘苄胺	2-iodobenzylamine	39959-51-8	C7H8IN	233.052
  ——	iodosyl-o-toluene	64297-59-2	C7H7IO	234.036
  5-溴-2-碘甲苯	2-methyl-4-bromoiodobenzene	116632-39-4	C7H6BrI	296.933
  2-碘异丙基苯	2-isopropyliodobenzene	19099-54-8	C9H11I	246.091

反应信息

• 作为反应物：
  描述：

  2-碘代甲苯 在 盐酸 、 RhCl(COD)(P(n-Pr)3) 、 potassium carbonate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 66.0h， 生成 2-甲基二苯甲酮
  参考文献：
  名称：

  涉及碳-杂原子双键的 Heck 型反应。铑(I)-催化的芳基卤化物与N-吡唑醛亚胺的偶联

  摘要：

  DOI：

  10.1021/ja003306e
• 作为产物：
  描述：

  1lambda6,3lambda6,2-Benzodithiazol-2-ide 1,1,3,3-tetraoxide;2-methylbenzenediazonium 在 四丁基碘化铵 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以75%的产率得到2-碘代甲苯
  参考文献：
  名称：

  在有电子转移催化剂存在或不存在的情况下，干燥的Arenediazonium o-Benzenedisulfonimides的卤代重氮化作用。制备芳基氯化物，溴化物和碘化物的简单通用程序。

  摘要：

  该论文报告了一项广泛研究的结果，该研究旨在通过将干燥的芳基重氮邻苯二磺酰亚胺1与卤化四烷基铵2进行卤代重氮化来制备芳基氯化物3（19例），溴化物4（19例）和碘化物5（9例）。在无水乙腈中，在室温（约20℃）下，在铜粉存在下，在60℃或室温下，在无催化剂的条件下进行。在最佳条件下，收率从良好到优异（60个反应，产率61-94％），只有少数例外（8个反应，产率51-55％）。总是从反应中回收大量的邻苯二磺酰亚胺（7），然后可以将其重新用于制备盐1。

  DOI：

  10.1021/jo9819537
• 作为试剂：
  描述：

  1,3,5-三甲基环己烷 在 十二羰基三钌 、 2-碘代甲苯 、 N,N'-1,2-tetrakis(4-fluorophenyl)ethane-1,2-diimine 、 caesium carbonate 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以17%的产率得到1,3-二甲基-5-亚甲基环己烷
  参考文献：
  名称：

  通过分子间氢原子转移机制的钌催化脱氢

  摘要：

  烷烃直接脱氢是获得有价值的烯烃产品的最有效方法之一。尽管已经设计了几种催化剂来促进这种转变，但不幸的是它们在精细化学合成中的应用有限。在这里，我们报告了一种使用钌催化剂催化烷烃分子间脱氢的概念新颖的策略。氧化还原活性配体和空间位阻芳基自由基中间体的组合释放了这种新策略。重要的是，已经进行了机理研究，为进一步开发这种新型催化脱氢系统提供了概念框架。

  DOI：

  10.1002/anie.202015837

文献信息

• Nickel(II) N‐Heterocyclic Carbene Complexes: Versatile Catalysts for C–C, C–S and C–N Coupling Reactions
  作者：Lourdes Benítez Junquera、Francys E. Fernández、M. Carmen Puerta、Pedro Valerga

  DOI：10.1002/ejic.201700057

  日期：2017.5.18

  A variety of Ni(II) complexes with a wide range of electronic and steric properties, bearing picolyl-imidazolidene ligands (a-g) and Cp (2a-f) or Cp* (3a,c,g) groups, have been synthesised and characterised using NMR and single crystal X-ray crystallography. The complexes have been used as precatalysts for a wide range of catalytic transformations most likely involving a Ni0/NiII catalytic cycle. In

  合成并表征了具有各种电子和位阻性质的各种Ni（II）配合物，它们带有吡啶甲基-咪唑啉配体（ag）和Cp（2a-f）或Cp *（3a，c，g）基团使用NMR和单晶X射线晶体学。该络合物已被用作各种催化转化的预催化剂，最有可能涉及Ni0 / NiII催化循环。特别是，新的定义明确的2a，2c，3a和3c在温和条件下对Suzuki-Miyaura偶联反应，活性烯烃的加氢胺化以及芳基卤化物和硫醇的CS交叉偶联反应表现出了极大的效率和多功能性。
• Microwave-Assisted Simple and Efficient Ligand Free Copper Nanoparticle Catalyzed Aryl-Sulfur Bond Formation
  作者：Brindaban C. Ranu、Amit Saha、Ranjan Jana

  DOI：10.1002/adsc.200700289

  日期：2007.12.10

  A new protocol for the coupling of aryl iodides with thiophenols and alkanethiols catalyzed by copper nanoparticles under ligand-free condition has been developed. A variety of functionalized aryl sulfides are prepared in excellent yields under microwave irradiation for 5–7 min. A plausible radical mechanism has been suggested.

  开发了一种新的协议，用于在无配体条件下用铜纳米粒子催化芳基碘化物与硫酚和烷硫醇的偶联。在微波辐射下5-7分钟以高收率制备了各种功能化的芳基硫化物。已经提出了一种可能的自由基机制。
• Pd(II)-Catalyzed Direct γ-C(sp³)-H Arylation between Free β²-Amino Esters and β³-Amino Esters and Aryl Iodides Using a Catalytic Transient Directing Group
  作者：Zhaohui Wang、Yangjie Fu、Qiyu Zhang、Hong Liu、Jiang Wang

  DOI：10.1021/acs.joc.0c00115

  日期：2020.6.19

  Pd(II)-catalyzed direct γ-C(sp3)-H arylation coupling with free β2-amino esters and β3-amino esters using a commercially available catalytic transient directing group has been developed. This approach features high efficiency, broad substrate tolerance, easily accessible starting materials, and mild reaction conditions.

  钯（II）催化的直接γ-C（SP 3）-H芳基化与耦合游离β 2 -氨基酯和β 3个已经开发使用市售的催化瞬态引导组-氨基酯。该方法具有高效，广泛的底物耐受性，易于获得的原料以及温和的反应条件的特点。
• Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed CH Arylation with Diaryliodonium Salts
  作者：Sharon R. Neufeldt、Melanie S. Sanford

  DOI：10.1002/adsc.201200738

  日期：2012.12.14

  This paper describes a photoredox palladium/iridium-catalyzed C-H arylation with diaryliodonium reagents. Details of the reaction optimization, substrate scope, and mechanism are presented along with a comparison to a related method in which aryldiazonium salts are used in place of diaryliodonium reagents. The unprecedentedly mild reaction conditions (25 masculineC in methanol), the requirement for

  本文描述了光氧化还原钯/铱催化 CH 与二芳基碘试剂的芳基化反应。详细介绍了反应优化、底物范围和机理，并与使用芳基重氮盐代替二芳基碘试剂的相关方法进行了比较。前所未有的温和反应条件（甲醇中 25 摄氏度）、对光和光催化剂的要求、自由基清除剂的抑制作用以及观察到的化学选择性趋势都与二芳基碘试剂的自由基热反应一致，该反应被认为是通过一种“离子”2e - 途径，需要更高的反应温度（100 ℃）。
• Two Stereoinduction Events in One C−H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes
  作者：Quentin Dherbassy、Jean‐Pierre Djukic、Joanna Wencel‐Delord、Françoise Colobert

  DOI：10.1002/anie.201801130

  日期：2018.4.16

  scaffolds—ortho‐orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C−H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an

  在这里，我们公开了原始手性支架的合成-呈现两个阻转异构Ar-Ar轴的邻位三联苯。这些不寻常的结构是通过使用CH活化方法建立的，并且值得注意的是，两个手性轴在一次转化中都具有出色的立体选择性。在反应过程中，不仅会发生联芳基前体的对映选择性官能化以建立一个立体轴，而且还会发生空前的对映立体选择性CH芳基化反应，从而生成第二个立体成因元素。这些对映体纯的邻位叔苯基具有原始的三维结构，因此为建立对映体纯的双齿配体（例如新的配体S / N-Biax和二膦酸BiaxPhos）库提供了独特的基础。

表征谱图