(2,2-二氯-1-甲基环丙基)苯 | 3591-42-2

• 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: (2,2-二氯-1-甲基环丙基)苯
• 中文别名: (2,2-二氯-1-甲基环丙基Z)苯；2,2-二氯-1-甲基环丙基苯
• 英文名称: 1,1-dichloro-2-methyl-2-phenylcyclopropane
• 英文别名: (2,2-dichloro-1-methylcyclopropyl)benzene；2,2-dichloro-1-methyl-1-phenyl-cyclopropane
• CAS: 3591-42-2
• 化学式: C₁₀H₁₀Cl₂
• mdl: MFCD00012260
• 分子量: 201.095
• InChiKey: NXYPRVQXSWVEOB-UHFFFAOYSA-N

物化性质

• 沸点：
  70-72°C 0,8mm
• 密度：
  1.1720
• 闪点：
  70-72°C/0.8mm
• 稳定性/保质期：

  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  Yes
• 安全说明：
  S24/25
• 海关编码：
  2903999090
• 储存条件：
  请将药品存放在避光、通风干燥的地方，并密封保存。

SDS

Name:	(2 2-Dichloro-1-methylcyclopropyl)benzene 95% Material Safety Data Sheet
Synonym:	None
CAS:	3591-42-2

Section 1 - Chemical Product MSDS Name:(2 2-Dichloro-1-methylcyclopropyl)benzene 95% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3591-42-2	(2,2-Dichloro-1-methylcyclopropyl)benz	95	222-734-2

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:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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.
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. 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, 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:
Avoid runoff into storm sewers and ditches which lead to waterways.
Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Absorb spill using an absorbent, non-combustible material such as earth, sand, or vermiculite. Do not use combustible materials such as sawdust.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep away from sources of ignition. 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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3591-42-2: 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 brown
Odor: benzene-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 75-77C @ 1mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 94 deg C ( 201.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.172
Molecular Formula: C10H10Cl2
Molecular Weight: 201.09

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3591-42-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(2,2-Dichloro-1-methylcyclopropyl)benzene - 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# 3591-42-2: No information available.
Canada
CAS# 3591-42-2 is listed on Canada's DSL List.
CAS# 3591-42-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3591-42-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (2,2-二氯-1-甲基环丙基)苯 在 1,3-二溴-5,5-二甲基海因 、 双氧水 、 sodium 、 叔丁醇 作用下， 反应 60.0h， 生成 1-溴-4-(1-甲基环丙基)苯
  参考文献：
  名称：

  Cyclic peroxides. 60. Prostanoid endoperoxide model compounds: preparation of 1,2-dioxolanes from cyclopropanes

  摘要：

  DOI：

  10.1021/jo00400a028
• 作为产物：
  描述：

  2-苯基-2-丙醇 在 金刚烷 、 potassium tert-butylate 、 potassium hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 180.0h， 生成 (2,2-二氯-1-甲基环丙基)苯
  参考文献：
  名称：

  KOtBu 作为单电子供体？用 CBr4 和 CCl4 重新审视烷烃的卤化

  摘要：

  对 KOtBu 和其他叔醇盐可能表现为单电子供体的反应的探索，使我们在金刚烷的存在下探索了它们与四卤甲烷 CX4 的反应。我们最近报道了在这些条件下金刚烷的卤化。这些反应似乎反映了 NaOH 与 CBr4 在相转移条件下的类似已知反应，其中引发的特征是从氢氧根离子到 CBr4 的单电子转移。我们现在报告来自实验和计算研究的证据，即 KOtBu 和其他醇盐试剂不会通过类似的电子转移。相反，醇盐在与 CBr4 或 CCl4 反应时形成次卤酸盐，并且适当次卤酸盐的均裂引发金刚烷的卤化。

  DOI：

  10.3390/molecules23051055

文献信息

• gem-Dihalocyclopropane formation by iron/copper activation of tetrahalomethanes in the presence of nucleophilic olefins. Evidence for a carbene pathway
  作者：Eric Léonel、Michael Lejaye、Sylvain Oudeyer、Jean Paul Paugam、Jean-Yves Nédélec

  DOI：10.1016/j.tetlet.2004.01.124

  日期：2004.3

  The activation of CBr4 and CCl4 by a bimetallic iron/copper couple in acetonitrile is a new, inexpensive, nontoxic and efficient procedure for gem-dibromo- and gem-dichloromethylenation of nucleophilic alkenes. This new route to gem-dihalocyclopropanes involves dihalocarbene species.

  CBR的活化4和CCl 4通过双金属铁/铜偶在乙腈为一个新的，便宜的，无毒的和有效的程序宝石-dibromo-和宝石亲核烯烃-dichloromethylenation。这种通往宝石-二卤代环丙烷的新途径涉及二卤卡宾类。
• Kinetics of cyclopropyl radical reactions. 2. Studies on the inversion of cyclopropyl and 1-methylcyclopropyl radicals and on the kinetics of some addition and abstraction reactions of 1-methylcyclopropyl and 1-methoxycyclopropyl radicals
  作者：Linda J. Johnston、K. U. Ingold

  DOI：10.1021/ja00269a034

  日期：1986.4

  To investigate this possibility we decided to use the same stereospecific pattern of deuterium labeling of the cyclopropyl radical that had been previously employed by Kobayashi and LambertI5 in their (unsuccessful) attempt to trap cyclopropyl before it could invert. These workers generated their labeled radicals from the corresponding labeled cyclopropane carboxylic acid in the Hunsdiecker reaction

  由于氢隧道效应，反转速度更快。与其他两个基团相比，1-甲氧基环丙基对苯乙烯和 1,4- 环己二烯的反应性较低。无法获得该自由基的 EPR 谱。在第 1 部分）中，我们报道了环丙基自由基在环境温度下在溶液中的一些加成和脱去反应的第一个绝对速率常数。这些通过激光闪光光解获得的动力学数据表明，环丙基的反应性比苯基低，但比伯烷基自由基的反应性强。在某些吸氢反应的后续工作中，我们表明 4 在环境温度下，自由基反应性下降系列：Ph' > Me2C=CH' > c-C3HS > CH3' > RCH2CH2'。我们的结果在很大程度上证实了 Walborsky 的结论 〜基于相对反应性的研究，“环丙基自由基表现为高反应性的快速反转 0 自由基”。已经进行了大量实验，试图确定各种取代的环丙基自由基能够保持其原始构型的程度。 6 这些研究中的大多数都涉及化学捕集，其中由适当取代的环丙基自由基形成的产物被用于确
• Dihalomethanes as C-H acids in the catalytic two-phase (CTP) system - a new method for the synthesis of gem-dichlorocyclopropanes
  作者：A. Jończyk、P. Balcerzak

  DOI：10.1016/s0040-4039(01)80777-2

  日期：1989.1

  Dihalomethanes react with carbon tetrachloride and alkanes in the CTP system affording gem-dichlorocyclopropanes.

  在CTP系统中，二卤甲烷与四氯化碳和烷烃反应，生成宝石-二氯环丙烷。
• Selective mono- or dimetalation of arenes by means of superbasic reagents
  作者：Manfred Schlosser、Hoon Choi Jung、Sadahito Takagishi

  DOI：10.1016/s0040-4020(01)87763-2

  日期：1990.1

  of two mono-and ten di-substituted derivatives. - Alkyl groups, as present in tert-butylbenzene, retard the metalation at both m- and p- positions, while trialkylsilyl groups deactive only m-positions. In either case exclusive monosubstitution occurs. -Perdeuterobenzene undergoes metalation and subsequent electrophilic mono-or disubstitution to afford isotope labeled compounds with moderate, through

  如果用于四氢呋喃中，则在纯净单金属化下，化学计量的丁基锂和叔丁醇钾与苯反应。但是，在己烷悬浮液中，获得了大量的间位和对位双取代副产物（约10％）。如果使用三倍过量的金属化剂，它们将成为优势。在相同条件下，萘导致两种单或十个双取代衍生物的混合物。-叔丁基苯中存在的烷基会延迟m和p位的金属化，而三烷基甲硅烷基仅在m时会失活-位置。在这两种情况下，都将发生排他性单取代。-全氘苯经过金属化处理，随后进行亲电性单或双歧化反应，以合成上有吸引力的收率得到中等价的同位素标记的化合物。动力学同位素效应和产物比率可以作为在超碱性金属化试剂和有机金属中间体两者水平上聚集体形成的证据。
• Synthesis of 1,1-Bis(trimethylstannyl)cyclopropanes by the S_RN1 Mechanism
  作者：Javier F. Guastavino、Roberto A. Rossi

  DOI：10.1021/om801104e

  日期：2009.4.27

  dichlorocarbene to alkenes, with Me3Sn− anions are reported. The process is described in terms of a photoinduced SRN1 substitution. The 1,1-bis(trimethylstannyl)cyclopropanes were obtained in good to excellent isolated yield (71−90%); 7,7-dichloro-2-oxa-bicyclo[4.1.0]heptane gave the 1,1-bis(trimethylstannyl) product in only 40% yield.

  容易获得的1,1- dichlorocyclopropanes的的反应中，通过加入二氯卡宾为烯烃得到的，与我3的Sn -报道阴离子。根据光诱导的S RN 1取代来描述该过程。得到的1,1-双（三甲基锡烷基）环丙烷的分离收率良好至优异（71-90％）；7,7-二氯-2-氧杂双环[4.1.0]庚烷仅以40％的收率得到1,1-双（三甲基锡烷基）产物。

表征谱图