2,3-二甲基-2,3-二苯基丁烷 | 1889-67-4

• 物质功能分类: 原料药 - 抗生素类药物 - 其它抗生素类药
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2,3-二甲基-2,3-二苯基丁烷
• 中文别名: 1,1’-(1,1,2,2-四甲基-1,2-亚乙基)二苯；异丙苯(2,3-二甲基-2,3-二苯基丁烷)1，1'(1,1,2,2-四甲基-1,2-乙二基)双苯；异丙苯(2,3-二甲基-2,3-二苯基丁烷)1,1'(1,1,2,2-四甲基-1,2-乙二基)双苯
• 英文名称: dicumene
• 英文别名: 2,3-dimethyl-2,3-diphenylbutane；bicumyl；(2,3-dimethylbutane-2,3-diyl)dibenzene；(2,3-dimethyl-3-phenylbutan-2-yl)benzene
• CAS: 1889-67-4
• 化学式: C₁₈H₂₂
• 分子量: 238.373
• InChiKey: HGTUJZTUQFXBIH-UHFFFAOYSA-N

物化性质

• 熔点：
  90-110 °C
• 沸点：
  335.97°C (estimate)
• 密度：
  0.9859 (estimate)
• LogP：
  6.68 at 25℃
• 物理描述：
  PelletsLargeCrystals

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2902909090
• 危险品标志：
  T+
• WGK Germany：
  3
• RTECS号：
  MV1407370
• 包装等级：
  I; II; III
• 危险类别：
  6.1
• 危险类别码：
  R28
• 危险品运输编号：
  UN 2811 6.1/PG 2
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  | 冰箱 (+4°C) |

SDS

Name:	2 3-Dimethyl-2 3-diphenylbutane Material Safety Data Sheet
Synonym:	None Known
CAS:	1889-67-4

Section 1 - Chemical Product MSDS Name:2 3-Dimethyl-2 3-diphenylbutane Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1889-67-4	2,3-Dimethyl-2,3-diphenylbutane	95	217-568-2

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:
Non-irritating to the eyes.
Skin:
Non-irritating to the skin. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
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:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
Call a poison control center. If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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. 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 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

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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# 1889-67-4: 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:
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: Flakes
Color: white to yellow
Odor: faint odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 90 - 110 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C18H22
Molecular Weight: 238.37

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1889-67-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3-Dimethyl-2,3-diphenylbutane - 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.
WGK (Water Danger/Protection)
CAS# 1889-67-4: No information available.
Canada
CAS# 1889-67-4 is listed on Canada's NDSL List.
CAS# 1889-67-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1889-67-4 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：

• 用于非过氧化物的高能塑料引发剂、接枝剂及阻燃助剂。

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-2,3-二苯基丁烷 在 NaY 作用下， 生成 cumyl cation
  参考文献：
  名称：

  Direct Observation of Cumyl Cations in Nonacidic Zeolites. Absolute Lifetime and Reactivity with Coabsorbed Alcohols

  摘要：

  DOI：

  10.1021/ja970690f
• 作为产物：
  描述：

  2-苯基-2-丙醇 在 LDMAN 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.67h， 生成 2,3-二甲基-2,3-二苯基丁烷
  参考文献：
  名称：

  枯基苯基硫化物在还原锂化作用下形成双枯基而不是枯基锂。SET亲核取代中的噻吩基作为离去基团

  摘要：

  在用芳族自由基阴离子还原后，枯基苯基硫化物（1 S）主要产生双枯基（2）而不是预期的枯基锂（3），尽管此处有文献报道错误地表明产生了阴离子3。汇编了文献中的相关示例。建议的机理涉及从产生的枯基锂（3）到枯基苯基硫化物（1 S）的单电子转移，产生噻吩二氧阴离子和两个枯基，它们主要在溶剂笼中偶联。实验证明了这种被阴离子3取代的噻吩氧化物。对叔苯基或枯基环上的-丁基基团可能通过空间抑制被认为是电子转移所必需的pi络合物而增加了枯基锂与双枯基的比例。

  DOI：

  10.1016/s0040-4020(97)00544-9
• 作为试剂：
  描述：

  甲基二氯硅烷 、 氯苯 在 2,3-二甲基-2,3-二苯基丁烷 作用下， 590.0 ℃ 、100.0 kPa 条件下， 生成 甲基苯基二氯硅烷
  参考文献：
  名称：

  Process for preparing organosilanes

  摘要：

  该发明涉及一种制备通式为1R3Si—R′（1）的有机硅烷的过程，其中通式为2R3Si—H（2）的氢硅烷与通式为3R′—X（3）的卤代烃反应，其中R为一价的C1-C18碳氢基团、氢或卤素，R′为一价的C1-C18碳氢基团，X为卤素，在存在自由基引发剂的情况下，所述自由基引发剂选自烷烃、二氮烯和有机二硅烷。

  公开号：

  US20050137413A1

文献信息

• Controlling parameters for radical cation fragmentation reactions: Origin of the intrinsic barrier
  作者：Deepak Shukla、Guanghua Liu、Joseph P Dinnocenzo、Samir Farid

  DOI：10.1139/v03-078

  日期：2003.6.1

  C—C bond cleavages of radical cations of 2-substituted benzothiazoline derivatives were investigated to determine the parameters controlling the fragmentation rate constants. In spite of the low oxidation potentials of the compounds, fragmentation rate constants greater than 1 × 10⁶ s^–1 could be achieved through weakening of the fragmenting bond by substituents that stabilize the radical fragment and exert steric crowding. A quantitative assessment of the relative roles of radical stabilization vs. steric effects to weaken the fragmenting C—C bond was achieved through DFT calculations. The calculated activation enthalpies matched reasonably well with the experimentally determined values. A thermokinetic analysis revealed that the fragmentations of benzothiazoline radical cations have relatively large intrinsic kinetic barriers, ascribed to the delocalized nature of the product radical and cation fragments. Interestingly, the same factors that lead to the large intrinsic barriers led, simultaneously, to large thermodynamic driving forces for the fragmentations, which should lead to lower activation barriers. These effects oppose each other kinetically and provide important insight into the design of fast radical ion fragmentation reactions.Key words: benzothiazoline, radical cation, fragmentation, steric effects, DFT.

  2-取代苯并噻唑啉衍生物的自由基阳离子的C-C键裂解进行了研究，以确定控制裂解速率常数的参数。尽管化合物的氧化电位较低，但通过通过取代基使裂解键变弱，从而稳定自由基片段并施加立体阻碍，可以实现大于1×10^6 s^-1的裂解速率常数。通过密度泛函理论（DFT）计算，对自由基稳定与立体效应相对作用于使裂解的C-C键变弱的定量评估取得了成功。计算得到的活化焓与实验测定值相当吻合。热动力学分析显示，苯并噻唑啉自由基阳离子的裂解具有相对较大的固有动力学壁垒，归因于产物自由基和阳离子片段的离域性质。有趣的是，导致大固有壁垒的因素同时导致了裂解的大热力学驱动力，这应该导致较低的活化壁垒。这些效应在动力学上相互对立，并为设计快速自由基离子裂解反应提供了重要见解。关键词：苯并噻唑啉，自由基阳离子，裂解，立体效应，DFT。
• Radical Reactions Using Decacarbonyldimanganese under Biphasic Conditions
  作者：Nathalie Huther、P. Terry McGrail、Andrew F. Parsons

  DOI：10.1002/ejoc.200400025

  日期：2004.4

  cyclisations and intermolecular addition reactions were performed under these conditions. This included the development of a new tandem radical addition−ionic cyclisation sequence that was employed in a short approach to (±)-coronamic acid. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  在十羰基二锰存在下由光解引发的烷基卤化物的自由基反应可以在双相介质中进行。在氢氧化钠水溶液和相转移催化剂存在下的反应可有效去除卤化锰副产物，并导致十羰基二锰的再生。在这些条件下进行了一系列有效的自由基偶联、环化和分子间加成反应。这包括开发了一种新的串联自由基加成 - 离子环化序列，该序列用于（±）-冠酸的短方法。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Photochemistry of some deoxybenzoins in micellar solutions. Cage effects, isotope effects, and magnetic field effects
  作者：Nicholas J. Turro、Jochen Mattay

  DOI：10.1021/ja00404a037

  日期：1981.7

  investigated. It was found that the extent of cage disproprotionation to yield benzaldehydes 6 and ..cap alpha..-methylstyrenes 7 is enhanced by a factor of about 10 compared to the photolyses in homogeneous organic solvents. The advantage of using micelles rather than homogeneous solutions to enhance the magnitude of magnetic isotope and magnetic field effects on cage disproportionation is demonstrated. The

  已经研究了 1,2-二苯基-2-甲基-1-丙酮 (1) 及其 D-、/sup 13/C- 和烷基取代衍生物 2 至 5 在各种胶束溶液中的光解作用。发现笼歧化产生苯甲醛 6 和..cap α..-甲基苯乙烯 7 的程度与均相有机溶剂中的光解相比提高了约 10 倍。证明了使用胶束而不是均匀溶液来增强磁同位素和磁场对笼歧化作用的大小的优势。结果被解释为一种机制，该机制涉及超精细诱导的三重自由基对 (/sup 3/RP) 的系统间交叉形成单线态自由基对 (/sup 1/RP) 和 /sup 3/ 逃逸之间的竞争来自胶束的 RP。
• Oxygen activation and olefin oxygenation by iron(III)porphyrin as a model of cytochrome P-450.
  作者：Tomofumi Santa、Takashi Mori、Masaaki Hirobe

  DOI：10.1248/cpb.33.2175

  日期：——

  Tetraphenylporphinatoiron (III) catalyzed the reductive activation of molecular oxygen in the presence of NaBH4 and Me4NOH. Several olefins were oxidized with this system and oxidized products were isolated in high yields.

  四苯基卟啉铁(III)在NaBH4和Me4NOH的存在下催化分子氧的还原活化。该体系下，多种烯烃被氧化，氧化产物以高产率分离得到。
• Benzylic oxidation and photooxidation by air in the presence of graphite and cyclohexene
  作者：Grigoriy Sereda、Vikul Rajpara

  DOI：10.1016/j.tetlet.2007.03.072

  日期：2007.5

  Graphite is introduced as a convenient catalyst for cyclohexene-promoted photooxidation of p-xylene, ethylbenzene, and cumene by air. Availability of the reagent (air), lack of chemical waste, low toxicity, and reusability of the catalyst make the process a good green alternative of oxidation of these industrially important hydrocarbons.

  引入石墨作为方便的催化剂，以环己烯促进空气中对二甲苯，乙苯和枯烯的光氧化。试剂（空气）的可用性，化学废物的缺乏，低毒性和催化剂的可重复使用性使该方法成为这些工业上重要的烃类氧化的良好绿色替代品。

表征谱图