环丙基苯甲烷 | 1667-00-1

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 环烃
• 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: 环丙基苯甲烷
• 英文名称: benzylcyclopropane
• 英文别名: Benzyl-cyclopropan；(cyclopropylmethyl)benzene；Cyclopropyl-phenyl-methan；Cyclopropylphenylmethane；cyclopropylmethylbenzene
• CAS: 1667-00-1
• 化学式: C₁₀H₁₂
• mdl: MFCD00019257
• 分子量: 132.205
• InChiKey: GUGXBRGATQTAFP-UHFFFAOYSA-N

物化性质

• 熔点：
  4.8°C
• 沸点：
  179.15°C (rough estimate)
• 密度：
  0.9059 (estimate)
• 闪点：
  62 °C
• 保留指数：
  1056.4;1059.5

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  2
• 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

• 安全说明：
  S24/25
• 海关编码：
  2902909090

SDS

Name:	Cyclopropylphenylmethane 99% Material Safety Data Sheet
Synonym:	None
CAS:	1667-00-1

Section 1 - Chemical Product MSDS Name:Cyclopropylphenylmethane 99% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1667-00-1	Cyclopropylphenylmethane, 99%	99%	216-782-3

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Combustible liquid.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 gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation.
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:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
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 if cough or other symptoms appear.
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. Will burn if involved in a fire.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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. Scoop up with a nonsparking tool, then place into a suitable container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas.
Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage:
Keep away from sources of ignition. Store in a cool, dry place.
Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 1667-00-1: 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: Liquid
Color: clear, colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 62 deg C ( 143.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H12
Molecular Weight: 132.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Mechanical shock, incompatible materials, ignition sources, temperatures above 65C.
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# 1667-00-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cyclopropylphenylmethane, 99% - 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# 1667-00-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1667-00-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1667-00-1 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

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
  4-苯基-1-丁基溴	1-Bromo-4-phenylbutane	13633-25-5	C10H13Br	213.117
  ——	4-phenyl-1-iodobutane	64283-87-0	C10H13I	260.118
  ——	(3-iodo-2-iodomethylpropyl)benzene	40548-59-2	C10H12I2	386.014
  2-苄基丙烷-1,3-二醇	2-benzyl-1,3-propanediol	2612-30-8	C10H14O2	166.22
  (3-溴-2-溴甲基丙基)苯	2-Benzyl-1,3-dibrom-propan	35694-75-8	C10H12Br2	292.013
  环丙基苯基碳酸酯	1-phenyl-1-cyclopropylmethanol	1007-03-0	C10H12O	148.205
  苯基环丙基甲酮	cyclopropyl phenyl ketone	3481-02-5	C10H10O	146.189
  ——	1,1-dibromo-2-(phenylmethyl)cyclopropane	99058-02-3	C10H10Br2	289.997
  ——	2-benzyl-1,1-dichlorocyclopropane	939-78-6	C10H10Cl2	201.095

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  丁苯	1-butylbenzene	104-51-8	C10H14	134.221
  4-(环丙基甲基)苯甲醛	4-(Cyclopropylmethyl)benzaldehyde	146922-94-3	C11H12O	160.21
  ——	(S)-cyclopropyl(phenyl)methanol	110548-56-6	C10H12O	148.205
  ——	(R)-cyclopropyl(phenyl)methanol	110548-55-5	C10H12O	148.205
  环丙基苯基碳酸酯	1-phenyl-1-cyclopropylmethanol	1007-03-0	C10H12O	148.205
  苯基环丙基甲酮	cyclopropyl phenyl ketone	3481-02-5	C10H10O	146.189
  ——	(phenyl)bromomethylcyclopropane	18926-26-6	C10H11Br	211.101
  ——	2-(cyclopropylmethyl)aniline	1224733-72-5	C10H13N	147.22
  ——	1-Phenyl-1-cyclopropyl-hexan	5557-99-3	C15H22	202.34
  ——	N-(4-phenylbutyl)acetamide	34059-11-5	C12H17NO	191.273

反应信息

• 作为反应物：
  描述：

  环丙基苯甲烷 在 C₉H₂₄B₁₁N₂⁽¹⁺⁾*C₂₄BF₂₀^(1-) 、 氢气 作用下， 以 苯 为溶剂， 反应 24.0h， 以76%的产率得到丁苯
  参考文献：
  名称：

  通过σ键复分解活化CC键：氢硼催化环丙烷的氢解

  摘要：

  高价过渡金属或主族络合物介导的σ键易位在共价H–E键的活化中起重要作用。但是，其参与C–C键的活化作用仍然难以捉摸。在这里，我们描述了氢硼配合物对环丙烷的C–C键的直接氢硼化。我们的机理研究表明该反应通过σ键复分解途径进行。使用这种氢硼配合物作为催化剂，可以实现未官能化环丙烷的氢解，这对于均相催化剂而言是前所未有的，并且可以在不存在金属的情况下为C–C键官能化提供非常规方法。

  DOI：

  10.1021/acs.organomet.0c00099
• 作为产物：
  描述：

  亚苯甲基丙二酸二乙酯 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三苯基氢化锡 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 48.0h， 生成 环丙基苯甲烷
  参考文献：
  名称：

  通过3-碘丙基自由基的均相取代反应形成环丙烷的制备和速率研究

  摘要：

  用氢化锡还原2-取代的1，3-二碘丙烷衍生物，得到取代的环丙烷。该反应通过3-碘丙基的均质取代而发生，所述3-碘丙基在80℃下具有约5×10 5 s -1的速率常数。

  DOI：

  10.1016/s0040-4020(98)01144-2

文献信息

• Clean and Efficient Benzylic C−H Oxidation in Water Using a Hypervalent Iodine Reagent: Activation of Polymeric Iodosobenzene with KBr in the Presence of Montmorillonite-K10
  作者：Toshifumi Dohi、Naoko Takenaga、Akihiro Goto、Hiromichi Fujioka、Yasuyuki Kita

  DOI：10.1021/jo8012435

  日期：2008.9.19

  We have found that unreactive and insoluble polymeric iodosobenzene [PhIO] n induced aqueous benzylic C-H oxidation to effectively give arylketones, in the presence of KBr and montmorillonite-K10 (M-K10) clay. Water-soluble and reactive species 1 having the unique I(III)-Br bond, in situ generated from [PhIO]n and KBr, was considered to be the key radical initiator during the reactions.

  我们已经发现，在KBr和蒙脱土-K10（M-K10）粘土的存在下，不活泼且不溶的聚合碘代苯[PhIO] n可以诱导苄基CH水溶液氧化，从而有效地产生芳基酮。由PhIOn和KBr原位产生的具有独特的I（III）-Br键的水溶性和反应性物质1被认为是反应过程中的关键自由基引发剂。
• Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent
  作者：Matthew H. Gieuw、Zhihai Ke、Ying-Yeung Yeung

  DOI：10.1002/anie.201713422

  日期：2018.3.26

  A facile and effective system has been developed for the regio‐ and chemoselective ring‐opening/electrophilic functionalization of cyclopropanes through C−C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p‐toluenesulfonamide. The p‐toluenesulfonamide‐promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3‐diol products

  已经开发了一种简便有效的系统，借助路易斯（Lewis）碱性促进剂对甲苯磺酰胺，通过[双（三氟乙酰氧基）碘]苯的CC键活化，对环丙烷的区域和化学选择性开环/亲电子官能化。所述p -toluenesulfonamide促进的系统可以很好地用于宽范围的环丙烷，得到1,3-二醇产物以良好产率选择性和区域选择性的形成。
• Metal–Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols
  作者：Neha Antil、Ajay Kumar、Naved Akhtar、Rajashree Newar、Wahida Begum、Kuntal Manna

  DOI：10.1021/acs.inorgchem.1c01008

  日期：2021.6.21

  Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal–organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones

  通过多相贱金属催化剂使用氢对羰基和醇进行化学选择性脱氧对于精细化学品和生物燃料的可持续生产至关重要。我们报告了一种铝金属有机骨架 (DUT-5) 节点负载钴 (II) 氢化物，它是一种高度化学选择性和可回收的多相催化剂，用于一系列芳香族和脂肪族酮、醛以及伯和仲醇的脱氧，包括1 bar H 2下的生物质衍生底物。通过用 CoCl 2对 DUT-5 的二级构建单元 (SBU) 进行后合成金属化，然后与 NaEt 3反应，可以轻松制备单点钴催化剂 (DUT-5-CoH)BH。X 射线光电子能谱和 X 射线吸收近边光谱 (XANES) 表明催化后 DUT-5-CoH 和 DUT-5-Co 中存在 Co II和 Al III中心。通过扩展X射线精细结构光谱（EXAFS）和密度泛函理论建立了催化前后DUT-5-Co钴中心的配位环境。动力学和计算数据表明，在转换限制步骤之前，羰基与钴的可逆配位，包括配位的羰基
• Bismuth-Catalyzed Benzylic Oxidations with <i>tert</i>-Butyl Hydroperoxide
  作者：Yannick Bonvin、Emmanuel Callens、Igor Larrosa、David A. Henderson、James Oldham、Andrew J. Burton、Anthony G. M. Barrett

  DOI：10.1021/ol051765k

  日期：2005.10.1

  oxidation of methyl arenes gave the corresponding substituted benzoic acids (50-95%). Preliminary mechanistic studies were consistent with a radical mechanism rather than a bismuth(III)-bismuth(V) cycle.

  [反应：见正文]在吡啶和乙酸中，铋和吡啶甲酸在叔丁基过氧化氢催化下用叔丁基氢过氧化物氧化烷基和环烷基芳烃，得到相应的苄基酮（48-99％）。或者，甲基芳烃的氧化得到相应的取代的苯甲酸（50-95％）。初步的机理研究与激进机理一致，而不是与铋（III）-铋（V）循环一致。
• Deoxygenation of benzylic alcohols using chloroboranes
  作者：Min-Liang Yao、Adam B. Pippin、George W. Kabalka

  DOI：10.1016/j.tetlet.2009.12.018

  日期：2010.2

  New boron-based methods for deoxygenating benzylic alcohols via the corresponding alkoxides are reported.

  据报道，新的基于硼的通过相应的醇盐使苄醇脱氧的方法。

表征谱图