2,2,2-三氟乙酰基异氰酸酯 | 14565-32-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,2,2-三氟乙酰基异氰酸酯
• 中文别名: 三氟乙酰基异氰酸酯
• 英文名称: 2,2,2-trifluoroacetyl isocyanate
• 英文别名: trifluoroacetyl isocyanate；Trifluoracetyl-isocyanat
• CAS: 14565-32-3
• 化学式: C₃F₃NO₂
• mdl: MFCD01320688
• 分子量: 139.034
• InChiKey: GDCXCDOQEWMQSO-UHFFFAOYSA-N

物化性质

• 沸点：
  37.5°C (estimate)
• 密度：
  1.6603 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2929109000

SDS

Name:	Trifluoroacetylisocyanate Material Safety Data Sheet
Synonym:	None
CAS:	14565-32-3

Section 1 - Chemical Product MSDS Name:Trifluoroacetylisocyanate Material Safety Data Sheet
Synonym:None

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14565-32-3	Trifluoroacetylisocyanate	100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Moisture sensitive.Stench.
Potential Health Effects
Eye:
Causes eye irritation. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Exposure produces central nervous system depression. At high concentrations, isocyanates affect mucous membranes of the respiratory tract and may lead to fatal pulmonary edema. Exposure to low and often even unmeasurable isocyanate concentration results in sensitization.
Chronic:
May cause lung damage. Inhalation of product may aggravate existing chronic repiratory problems such as asthma, emphysema or bronchitis.

---

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. Do NOT allow victim to rub eyes or keep eyes closed.
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. Wash mouth out with 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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

---

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 water spray, dry chemical, carbon dioxide, or chemical foam. Do NOT get water inside containers.

---

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. Provide ventilation. Do not get water inside containers.

---

Section 7 - HANDLING and STORAGE
Handling:
Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas.
Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Do not allow contact with water. Keep from contact with moist air and steam.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.

---

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# 14565-32-3: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 37.5 deg C @ 760 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C3F3NO2
Molecular Weight: 139.04

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Moisture, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas, hydrocarbons.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14565-32-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Trifluoroacetylisocyanate - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 14565-32-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14565-32-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14565-32-3 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟乙酰基异氰酸酯 在 氨 作用下， 反应 15.0h， 以31%的产率得到N-氨基甲酰-2,2,2-三氟乙酰胺
  参考文献：
  名称：

  Kiemstedt, Wolfgang; Sundermeyer, Wolfgang, Chemische Berichte, 1982, vol. 115, # 3, p. 919 - 925

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-bis(2,2,2-trifluoroacetyl)-1-<2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl>urea 生成 2,2,2-三氟乙酰基异氰酸酯
  参考文献：
  名称：

  TANAKA, CHIAKI;NASU, KEIKO;YAMAMOTO, NORIKO;SHIBATA, MEGUMI, CHEM. AND PHARM. BULL., 1982, 30, N 9, 3374-3376

  摘要：

  DOI：

文献信息

• Preparation of fluorinated imides
  作者：F. Ye、R.E. Noftle

  DOI：10.1016/s0022-1139(96)03526-9

  日期：1997.3

  A direct method for the preparation of trifluoroacetimides has been extended to the preparation of trifluoroacetyl trifluoracetimide and the new compound trifluoromethylsulfuryl trifluoroacetimide. Points concerning previously reported syntheses of trifluoroacetyl isocyanate have also been clarified.

  制备三氟乙酰亚胺的直接方法已扩展到三氟乙酰基三氟乙酰亚胺和新的化合物三氟甲基磺酰基三氟乙酰亚胺的制备。关于先前报道的三氟乙酰基异氰酸酯的合成的要点也已经阐明。
• Raman and infrared spectra, conformational stability, barriers to internal rotation, and ab initio calculations of trifluoroacetyl isocyanate
  作者：J.R. Durig、G.A. Giurgis、K.A. Krutules

  DOI：10.1016/0022-2860(94)08362-2

  日期：1994.12

  conformer have been assigned. The experimental conformational stability, barriers to internal rotation, structural parameters, and fundamental vibrational frequencies are compared with those obtained from ab initio gradient calculations employing the RHF/3-21G, RHF/6-31G* and/or MP2/6-31G* basis sets and to the corresponding quantities obtained for some similar molecules.

  摘要 三氟乙酰异氰酸酯CF 3 C(O)NCO 的拉曼(2500 至10 cm -1 ) 和红外(2500 至30 cm -1 ) 光谱已被记录为气体和固体。此外，还记录了液体的拉曼光谱并获得了定性去极化值。观察到的谱带是基于流体相中更稳定的顺式构象异构体（异氰酸酯基团顺式与羰基键）和不太稳定的反式构象异构体而分配的，并且固体中仅存在顺式旋转异构体。从溶解在液化氪中的样品的红外光谱的变温研究来看，1796 和 1781 cm -1 处的构象异构体对已被用于确定 163 ± 12 cm -1 (466 ± 34 cal mol -1 ) 应该接近代表气体的 Δ H 值。控制构象交换的潜在函数已由不对称扭转频率和 ΔH 值确定。电位常数的值为：V 1 = 356 ± 14，V 2 = 1865 ± 60，和 V 3 = -203 ± 6 cm -1 。此外，液体的拉曼光谱的可变温度研究给出了 236
• 2,2,2-Trichloroethylsulphonyl, 2,2,2-trichloroethoxysulphonyl, and trifluoroacetyl isocyanates in β-lactam synthesis
  作者：Anthony G. M. Barrett、Ashley Fenwick、Michael J. Betts

  DOI：10.1039/c39830000299

  日期：——

  Condensation of the title isocyanates with olefins and subsequent dissolving-metal reduction (sulphonyl derivatives) or chromatography on Florisil (trifluoroacetyl derivatives) gave several N-unsubstituted β-lactams including two 8-aza-2-oxabicyclo[4.2.0]octan-7-one derivatives.

  标题异氰酸酯与烯烃的缩合，然后进行溶解金属还原（磺酰基衍生物）或在Florisil上进行色谱分离（三氟乙酰基衍生物），得到几种N-未取代的β-内酰胺，包括两个8-氮杂-2-氧杂双环[4.2.0] octan-7一衍生物。
• [EN] SYNTHESIS OF DISCODERMOLIDE<br/>[FR] SYNTHESE DU DISCODERMOLIDE
  申请人：NOVARTIS AG

  公开号：WO2004009574A1

  公开（公告）日：2004-01-29

  The invention relates to a process for preparing discodermolide, for preparing intermediates for the manufacture of discodermolide and discodermolide analogues and to the intermediates obtained during the process. Wherein the process proceeds via a tetraene of formula (IV).

  该发明涉及一种制备discodermolide的过程，用于制备制造discodermolide和discodermolide类似物的中间体，以及在过程中获得的中间体。其中，该过程通过式（IV）的四烯体进行。
• Diastereoselective reaction of 1,3-dihydroxy calixarene with acylisocyanates: new and easy approach for preparing inherently chiral calyx[4]arenes
  作者：V. I. Boyko、A. B. Rozhenko、V. V. Pirozhenko、S. V. Shishkina、O. V. Shishkin、V. I. Kalchenko

  DOI：10.1007/s11224-015-0706-5

  日期：2016.2

  The facile method of generating internal chirality into the calixarene with two hydroxy groups at the lower rim via an attached chiral substituent has been proposed. The reaction with acylisocyanates, catalyzed by a small amount of triethylamine, proceeds forming predominantly one of the two possible calixarene carbamates. The best diastereomeric excess (60 %) has been achieved in the reaction of trichloroacyl

  已经提出了通过连接的手性取代基在下边缘具有两个羟基的杯芳烃中产生内部手性的简便方法。与酰基异氰酸酯的反应在少量三乙胺的催化下进行，主要形成两种可能的杯芳烃氨基甲酸酯中的一种。在三氯酰基异氰酸酯与被手性苯乙基酰胺部分取代的 1,3-羟基杯芳烃的反应中，已实现最佳非对映体过量 (60%)。三氯乙酰氨基甲酰基杯[4]arenas的单个非对映异构体通过结晶分离，它们的绝对构型通过X射线衍射研究确定。通过量子化学计算预测的 1,3-二羟基杯芳烃结构最受青睐的构象具有非常相似的稳定性。然而，三乙胺分子优选连接到两个可用羟基的一个羟基，提供最有利的加合物，其主要参与与酰基异氰酸酯的反应。这导致观察到的非对映体过量。随后在 NaH 存在下用正丙基溴处理形成的氨基甲酰基并水解烷基化产物很容易提供持久的内部手性杯芳烃。