1,1,1-三氟-3-甲基-丁烷-2-酮 | 382-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1,1-三氟-3-甲基-丁烷-2-酮
• 英文名称: 1,1,1-trifluoro-3-methylbutan-2-one
• CAS: 382-03-6
• 化学式: C₅H₇F₃O
• 分子量: 140.105
• InChiKey: NLCCAFQWEKMQLM-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 密度：
  1.080 g/mL at 25 °C
• 闪点：
  -19℃
• 沸点：
  52-60°C/760 mmHg

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914700090
• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1,1,1-TRIFLUORO-3-METHYL-2-BUTANONE, 97&
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 382-03-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Flammable liquids (Category 2), H225
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H225 Highly flammable liquid and vapour.
H302 Harmful if swallowed.
Precautionary statement(s)
P210 Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 1,1,1-Trifluoro-3-methyl-2-butanone
Formula : C5H7F3O
Molecular Weight : 140,10 g/mol
CAS-No. : 382-03-6
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
1,1,1-Trifluoro-3-methyl-2-butanone
CAS-No. 382-03-6 Flam. Liq. 2; Acute Tox. 4; <= 100 %
H225, H302
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
1,1,1-Trifluoro-3-methyl-2-butanone
CAS-No. 382-03-6 Xn, R22 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Hydrogen fluoride
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13).
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, Flame retardant antistatic protective clothing, The type
of protective equipment must be selected according to the concentration and amount of the
dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type AXBEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 52 - 60 °C
boiling range
g) Flash point -19 °C
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure 179 hPa at 25 °C
l) Vapour density no data available
m) Relative density 1,0804 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,007
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks. Extremes of temperature and direct sunlight.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 1993 IMDG: 1993 IATA: 1993
UN proper shipping name
ADR/RID: FLAMMABLE LIQUID, N.O.S. (1,1,1-Trifluoro-3-methyl-2-butanone)
IMDG: FLAMMABLE LIQUID, N.O.S. (1,1,1-Trifluoro-3-methyl-2-butanone)
IATA: Flammable liquid, n.o.s. (1,1,1-Trifluoro-3-methyl-2-butanone)
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: II IMDG: II IATA: II
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,1,1-三氟-3-甲基-丁烷-2-酮 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-cyclohexyl-4-methyl-3-(trifluoromethyl)pent-1-yn-3-yl hydroxy(methyl)carbamate
  参考文献：
  名称：

  （Z）-三氟甲基-三取代的烯烃或异恶唑啉：来自同一个丙二烯的不同途径。

  摘要：

  由于涉及氟上非键合电子对的电荷-偶极相互作用，三氟甲基烯丙基的质子化导致具有高（Z）选择性的三或四取代的烯烃。用催化的Au（I）处理相同的烯基会引发反应级联反应，该反应级联可高产率生产异恶唑啉。

  DOI：

  10.1021/acs.orglett.0c02546
• 作为产物：
  描述：

  异丙基溴化镁 、 N-甲氧基-N-甲基-2,2,2-三氟乙酰胺 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1,1,1-三氟-3-甲基-丁烷-2-酮
  参考文献：
  名称：

  （Z）-三氟甲基-三取代的烯烃或异恶唑啉：来自同一个丙二烯的不同途径。

  摘要：

  由于涉及氟上非键合电子对的电荷-偶极相互作用，三氟甲基烯丙基的质子化导致具有高（Z）选择性的三或四取代的烯烃。用催化的Au（I）处理相同的烯基会引发反应级联反应，该反应级联可高产率生产异恶唑啉。

  DOI：

  10.1021/acs.orglett.0c02546

文献信息

• Indium-catalyzed C(sp³)–H functionalization of 2-methylazaarenes through direct benzylic addition to trifluoromethyl ketones
  作者：Zaini Jamal、Yong-Chua Teo

  DOI：10.1039/c4ra17182a

  日期：——

  The application of trivalent indium for the Lewis acid-catalyzed C(sp3)–H functionalization of 2-methylazaarenes is reported. InCl3 was discovered to catalyze the direct addition of the benzylic C–H bond in the azaarenes to trifluoromethyl ketones. An ample number of substrates were cogently demonstrated to give the products as trifluoromethylated alcohols whereby in some cases, up to quantitative

  报道了三价铟在路易斯酸催化的2-甲基氮杂芳烃的C（sp 3）–H官能化中的应用。发现InCl 3可以催化氮杂芳烃中苄基C–H键直接加成到三氟甲基酮上。令人信服地证明了足够数量的底物将产物提供为三氟甲基化醇，因此在某些情况下，可以获得高达定量的收率（99％）。
• Pyridine and Pyrazine derivative for the Treatment of CF
  申请人：BAETTIG Urs

  公开号：US20110230483A1

  公开（公告）日：2011-09-22

  The present invention provides pyridine and pyrazine derivatives which restore or enhance the function of mutant and/or wild type CFTR to treat cystic fibrosis, primary ciliary dyskinesia, chronic bronchitis, chronic obstructive pulmonary disease, asthma, respiratory tract infections, lung carcinoma, xerostomia and keratoconjunctivitis sire, or constipation (IBS, IBD, opioid induced). Pharmaceutical compositions comprising such derivatives are also encompassed.

  本发明提供吡啶和吡嗪衍生物，可恢复或增强突变型和/或野生型CFTR的功能，用于治疗囊性纤维化、原发性纤毛运动障碍、慢性支气管炎、慢性阻塞性肺疾病、哮喘、呼吸道感染、肺癌、口干症和角膜结膜炎，或便秘（肠易激综合征、炎症性肠病、阿片类药物诱导）。还包括含有这些衍生物的药物组合物。
• Chemoenzymatic dynamic kinetic resolution of α-trifluoromethylated amines: influence of substitutions on the reversed stereoselectivity
  作者：Guilin Cheng、Bo Xia、Qi Wu、Xianfu Lin

  DOI：10.1039/c3ra40526e

  日期：——

  Enzymatic resolution of α-trifluoromethylated amines via kinetic resolution (KR), dynamic kinetic resolution (DKR) employing CALB-Pd/Al2O3, and a one-pot sequential process of KR/DKR/KR was investigated comparatively for the first time. Although CALB-catalyzed KR of α-trifluoromethylated amines with substituents of methyl (1a), isopropyl (1c), phenyl (1d) and benzyl group (1e) can provide good stereoselectivity factors E from 31 to >200 respectively, DKR and sequential process of KR/DKR/KR possess better practical application potential because of the higher conversion (62%–84%) and the similar enantiomeric excesses (90%–99%). The enantiopreference and inversion for the α-trifluoromethylated amines displayed by CALB were observed and explained by docking modes. Namely, for 1,1,1-trifluoro-2-propylamine (1a), the product amide with R-configuration was obtained, and the enantiopreference was converted to S for the amines (1b–1e) with substituents larger than methyl group. The catalysts recycle, and scale-up experiments were demonstrated successfully. All these results indicated the high efficiency and green feature of this enzymatic process, and its application significance.

  首次比较研究了通过动力学分辨 (KR)、动态动力学分辨 (DKR) 采用 CALB-Pd/Al2O3 催化，及 KR/DKR/KR 一锅顺序过程对 α-三氟甲基化胺的酶解分辨。尽管 CALB 催化的 α-三氟甲基化胺与甲基 (1a)、异丙基 (1c)、苯基 (1d) 和苄基 (1e) 取代基的 KR 可以提供良好的立体选择性因子 E，从 31 到超过 200，但 DKR 和 KR/DKR/KR 的顺序过程由于更高的转化率 (62%–84%) 和相似的对映体过量 (90%–99%)，具有更好的实际应用潜力。通过分子对接模式观察并解释了 CALB 显示出的对 α-三氟甲基化胺的对映选择性和反转。即对于 1,1,1-三氟-2-丙胺 (1a)，获得了 R 构型的酰胺产物，对于取代基大于甲基的胺 (1b–1e)，对映选择性则转换为 S。催化剂的回收和放大实验成功演示。这些结果表明该酶促过程高效且环保，具有重要的应用意义。
• Economical and Practical Strategies for Synthesis of a-Trifluoromethylated Amines
  作者：C.J. Jiang、C.L. Cheng、S.F. Yuan

  DOI：10.14233/ajchem.2015.17863

  日期：——

  A powerful approach to synthesize a-trifluoromethylated amines has been developed. The method is operationally simple, broad in substrate scope and amenable to scale-up using trifluoroacetic anhydride. Meanwhile, the strategy not only provided a versatile approach to synthesize a-trifluoromethylated amines but also provides a new method for exploring the new reactivity of trifluoroacetic anhydride.

  开发了一种合成α-三氟甲基化胺的有效方法。该方法操作简单，底物范围广泛，并且易于通过三氟乙酸酐进行规模放大。同时，这一策略不仅提供了一种合成α-三氟甲基化胺的多功能途径，还为探索三氟乙酸酐的新反应性提供了新的方法。
• Pyridine and Pyrazine derivative for the Treatment of CF, COPD, and Bronchiectasis
  申请人：NOVARTIS AG

  公开号：US20200383960A1

  公开（公告）日：2020-12-10

  The present invention provides pyridine and pyrazine derivatives which restore or enhance the function of mutant and/or wild type CFTR to treat bronchiectasis, cystic fibrosis, primary ciliary dyskinesia, chronic bronchitis, chronic obstructive pulmonary disease, asthma, respiratory tract infections, lung carcinoma, xerostomia and keratoconjunctivitis sire, or constipation (IBS, IBD, opioid induced). Pharmaceutical compositions comprising such derivatives are also encompassed.

  本发明提供了吡啶和吡嗪衍生物，可以恢复或增强突变型和/或野生型CFTR的功能，用于治疗支气管扩张、囊性纤维化、原发性纤毛运动障碍、慢性支气管炎、慢性阻塞性肺疾病、哮喘、呼吸道感染、肺癌、口干症和角膜结膜炎，或便秘（肠易激综合征、炎症性肠病、阿片类药物诱导）。还包括含有这些衍生物的药物组合物。