(1R,3S)-2,2-二甲基-3-(2-氧丙基)-环丙烷乙腈 | 110847-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,3S)-2,2-二甲基-3-(2-氧丙基)-环丙烷乙腈
• 中文别名: 2-[(1R,3S)-3-丙酮基-2,2-二甲基环丙基]乙腈；2-[(1R,3S)-2,2-二甲基-3-(2-氧代丙基)环丙基]乙腈；2-[(1R,3S)-2,2-二甲基-3-(2-氧代丙基)环丙基]乙烷腈
• 英文名称: [(1R,3S)-2,2-dimethyl-3-(2-oxopropyl)-cyclopropyl]-acetonitrile
• 英文别名: (1R,3S)-2,2-dimethyl-3-(2-oxopropyl)-cyclopropaneacetonitrile；(1R,3S)-2,2-dimethyl-3(2-oxopropyl)-cyclopropaneacetonitrile；(1R,3S)-2,2-dimethyl-3-(2-oxopropyl)cyclopropaneacetonitrile；2-((1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropyl)acetonitrile；2-[(1R,3S)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetonitrile
• CAS: 110847-02-4
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: KRZTYSCUOUIFHR-BDAKNGLRSA-N

物化性质

• 沸点：
  132-133 °C (7 mmHg)
• 密度：
  0.96
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R20/21/22
• 海关编码：
  2926909090

SDS

Name:	(1R 3S)-2 2-Dimethyl-3-(2-oxopropyl)-cyclopropaneacetonitrile 99% Material Safety Data Sheet
Synonym:	None
CAS:	110847-02-4

Section 1 - Chemical Product MSDS Name:(1R 3S)-2 2-Dimethyl-3-(2-oxopropyl)-cyclopropaneacetonitrile 99% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
110847-02-4	(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)-c	99	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin. May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. No data found on whether or not this chemical would be likely to cause an allergic skin reaction.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed. Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration. Chronic exposure to cyanide solutions may lead to the development of a "cyanide" rash, characterized by itching, and by macular, papular, and vesicular eruptions, and may be accompanied by secondary infections.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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 breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
May be partially metabolized to cyanide in the body.
Antidote: Always have a cyanide antidote kit on hand when working with cyanide compounds. Get medical advice to use.

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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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. 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 container closed when not in use. Store in a tightly closed container. 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# 110847-02-4: 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 minimize contact with skin.
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: Viscous liquid
Color: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 132-133 deg C @ 7 mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: practically insoluble
Specific Gravity/Density: .960 g/ml
Molecular Formula: C10H15NO
Molecular Weight: 165.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, cyanide fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 110847-02-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)-cyclopropaneacetonitrile - 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: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 110847-02-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 110847-02-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 110847-02-4 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

反应信息

• 作为反应物：
  描述：

  (1R,3S)-2,2-二甲基-3-(2-氧丙基)-环丙烷乙腈 在 吡啶 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 47.0h， 生成 (1R,3S)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropaneacetonitrile
  参考文献：
  名称：

  Synthesis of (1R)-cis-Chrysanthemylamine from (+}-3-Carene

  摘要：

  通过涉及多个步骤的两种合成方法，将由(+)-3-蒈烯(1)制备的氧代腈2转化为(1R)-顺式菊胺(7a)。

  DOI：

  10.1055/s-1992-26226
• 作为产物：
  描述：

  3-morpholinocaran-4-one oxime 在 五氯化磷 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以58%的产率得到(1R,3S)-2,2-二甲基-3-(2-氧丙基)-环丙烷乙腈
  参考文献：
  名称：

  Tkachev, A.V.; Rukavishnikov, A.V.; Chibirjaev, A.M., Synthetic Communications, 1990, vol. 20, # 14, p. 2123 - 2132

  摘要：

  DOI：

文献信息

• Conversion of Cyclic Aziridines and 2-Amino-1-cycloalkanols to Keto Nitriles by Using Electrogenerated Reactive Halogen Species
  作者：Sigeru Torii、Tsutomu Inokuchi、Sadahito Takagishi、Etsuji Sato、Hiromi Tsujiyama

  DOI：10.1246/cl.1987.1469

  日期：1987.7.5

  Oxidative cleavage of C(1)–C(2) bond of aziridines and 2-amino-1-cycloalkanols, giving the corresponding keto nitriles, exclusively, have been performed by oxidation with electrogenerated reactive halogen species (e.g., [Cl]+).

  对氮杂环和2-氨基-1-环烷醇的C(1)–C(2)键进行氧化裂解，专门生成相应的酮腈，已通过与电生成的反应性卤素物种（如[Cl]+）的氧化反应完成。
• APPLICATION OF THE HURD-MORI REACTION FOR THE SYNTHESIS OF CHIRAL 1,2,3-THIA(SELENO)DIAZOLE DERIVATIVES FROM (+)-3-CARENE AND α-PINENE
  作者：Yu.Yu. Morzherin、T.V. Glukhareva、V.S. Mokrushin、A.V. Tkachev、V.A. Bakulev

  DOI：10.1515/hc.2001.7.2.173

  日期：2001.1

  methylene and methyl groups of the substituted acetone moiety in compound 7 could take part in the cyclization process to form isomeric products 1a and 9. Nevertheless, we have shown that the reaction of oxo nitrile 7 with thionyl chloride proceeds with high regioselectivity on the methylene group to form thiadiazole 1a as the only product and isomeric 1,2,3-thiadiazole 9 is not detected. The formation of compound

  s 含有环丙基或环丁基的手性 1,2,3-噻二唑衍生物是通过 Hurd-Mori 反应从 (+)-3-carene 和 α-蒎烯的二级衍生物合成的。引言 已知 1,2,3-噻二唑是有机合成中有用的合成子 (4,5)。最近在其中发现了非常活跃的棉花脱叶剂和植物活化剂（1-3）。在我们的研究工作过程中，我们对作为潜在杀菌剂的功能化手性 1,2,3-噻二唑 1,2 感兴趣。为了制备 1,2,3-噻二唑 1,2，我们使用 Hurd 和 Mori (6,7) 反应。将通过已知方法(8)由天然单萜(+)-3-蒎烯5和α-蒎烯6制备的氧代腈3,4作为起始试剂。结果和讨论 缩氨基脲 7、8 很容易从相应的氧代腈 3、4 在室温下与氨基脲盐酸盐反应。当化合物7、8在室温下在CH 2 Cl 2 中用亚硫酰氯处理时，以78％和60％的产率形成噻二唑1a、2a。如果该反应在较高温度下进行，则仅发现环破坏的产物。通常，化合物
• Baker's yeast-induced asymmetric reduction of the keto group activated by the cyclopropane unit.
  作者：Alexey V. Tkachev、Alexey V. Rukavishnikov、Yuri V. Gatilov、Irina Yu. Bagrjanskaja

  DOI：10.1016/s0957-4166(00)82103-5

  日期：1992.9

  Certain cis-3-substituted 2,2-dimethyl-1-(2-oxopropyl)-cyclopropanes are effectively reduced by baker's yeast to give predominantly (s)-isomers of the corresponding 2-hydroxypropyl derivatives. Reduction of the 2-oxopropyl group proceeds more rapidly (ca. 3.5 times) and with higher stereoselectivity [(S):(R) = 98:2] when the group is attached to the (s)-carbon of the cyclopropane unit than of the keto group attached to the (R)-carbon [(S):(R) = (88):(12)]. Yeast reduction of the keto derivatives is effectively carried out when substituents at C-3 are as follows: CH2COOCH3, -CH2COCH3, -CN, -CH2CN, -CH2CH2OH, and the relative rates of reduction are 36:36:15:13:7. No reduction occurs when substituents at C-3 are propyl, 2-methyl-2-hydroxypropyl or 2-methyl-1,3-dioxolan-2-yl methyl groups.
• A Novel Synthetic Pathway to 1R- and 1S-Dihidro-Ghrisanthemolactone5 from (+)-3-Carene
  作者：Alexey V. Rukavishnikov、Alexey V. Tkaohev

  DOI：10.1080/00397919208019296

  日期：1992.4

  A novel synthetic approach to the enantiomeric dihydrochrysanthemolactones is described.
• RUKAVISHNIKOV, A. V.;POPOV, S. A.;TKACHEV, A. V.;VOLODARSKIJ, L. B., XIMIYA, PRIMENENIE I MEXANIZM DEJSTVIYA INSEKTITSIDOV I AKARITSIDOV: TEZ.+
  作者：RUKAVISHNIKOV, A. V.、POPOV, S. A.、TKACHEV, A. V.、VOLODARSKIJ, L. B.

  DOI：——

  日期：——