2-chloroethanesulfonyl fluoride | 762-70-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 英文名称: 2-chloroethanesulfonyl fluoride
• 英文别名: 2-Chlorethansulfonylfluorid
• CAS: 762-70-9
• 化学式: C₂H₄ClFO₂S
• mdl: MFCD01937909
• 分子量: 146.57
• InChiKey: UWHZNPZESCRRJT-UHFFFAOYSA-N

物化性质

• 沸点：
  66 °C(Press: 14 Torr)
• 密度：
  1.5007 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2904909090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Chloroethanesulfonyl fluoride
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Chloroethanesulfonyl fluoride
CAS number: 762-70-9

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C2H4ClFO2S
Molecular weight: 146.6

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride, hydrogen fluoride, sulfur oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-chloroethanesulfonyl fluoride 在 magnesium oxide 作用下， 以 水 为溶剂， 反应 16.0h， 以73%的产率得到乙烯磺酰氟
  参考文献：
  名称：

  乙磺酰氟和有机叠氮化物的无金属合成功能性1-取代的1,2,3-三唑

  摘要：

  特别是自2000年代初期以来，1,4-二取代三唑产品的增长迅速，在很大程度上可归因于点击化学的诞生以及CuI催化的叠氮化物-炔烃环加成反应（CuAAC）的发现。然而，相对简单但重要的1-取代的1,2,3-三唑的合成却令人惊讶地更具挑战性。此处报道的是一种直接且可扩展的点击启发式方案，用于从有机叠氮化物和稳定的乙炔代用品乙磺酰氟（ESF）合成1-取代-1,2,3-三唑。新的转化工艺可以耐受多种基材，并且可以在无金属的条件下顺利进行，从而使产品具有出色的产量。在控制的酸性条件下，1-取代的1,2，

  DOI：

  10.1002/anie.201912728
• 作为产物：
  描述：

  2-氯乙烷磺酰氯 在 potassium hydrogen bifluoride 作用下， 以 水 为溶剂， 反应 2.0h， 以99.3%的产率得到2-chloroethanesulfonyl fluoride
  参考文献：
  名称：

  乙磺酰氟（ESF）：千克级制备的水上程序

  摘要：

  描述了用于合成乙磺酰氟（ESF）的两步水上程序。2-氯乙烷磺酰氟是通过与几乎饱和的氟化氢钾水溶液进行纯反应，由易于获得的2-氯乙烷磺酰氯制得。随后的2-氯乙烷磺酰氟的脱氯化氢以氧化镁为碱，在水性悬浮液中进行纯净，得到ESF。该配方允许以千克规模以98％的收率制备ESF。

  DOI：

  10.1021/acs.joc.6b01423

文献信息

• 2-Azidoethane-1-sulfonylfluoride (ASF): A Versatile<i>Bis</i>-clickable Reagent for SuFEx and CuAAC Click Reactions
  作者：Xu Zhang、Balakrishna Moku、Jing Leng、K. P. Rakesh、Hua-Li Qin

  DOI：10.1002/ejoc.201801825

  日期：2019.2.28

  3‐triazole‐derived S(VI)‐F library for medicinal chemistry, chemical biology, and drug discovery in a quick, efficient and atom‐economical manner applying click chemistry. A new class of dendrimers was developed using this reagent through orthogonal CuAAC and SuFEx click reactions.

  使用2-叠氮基乙烷-1-磺酰氟（ASF）制备了一个独特的1,2,3-三唑衍生的S（VI）-F库，用于快速，高效且原子化的药物化学，化学生物学和药物发现。应用点击化学的经济方式。通过正交CuAAC和SuFEx点击反应，使用该试剂开发了新型树状聚合物。
• Sulfur(VI) fluoride compounds and methods for the preparation thereof
  申请人：The Scripps Research Institute

  公开号：US10117840B2

  公开（公告）日：2018-11-06

  This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.

  该应用描述了由式(I)表示的化合物：(I)其中：Y是一个生物活性有机核心基团，包括芳基、杂芳基、非芳香烃基和非芳香杂环基中的一个或多个，其中Z与之以共价键结合；n为1、2、3、4或5；m为1或2；Z为O、NR或N；X1为共价键或—CH2CH2—，X2为O或NR；R包括H或从芳基、杂芳基、非芳香烃基和非芳香杂环基中选择的取代或未取代基团。还描述了制备这些化合物的方法、使用这些化合物的方法以及包含这些化合物的药物组合物。
• Process for producing a fluorine atom-containing sulfonyl fluoride compound
  申请人：ASAHI GLASS COMPANY LIMITED

  公开号：US20030212297A1

  公开（公告）日：2003-11-13

  The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO 2 R A -E 1 (1) with R B -E 2 (2) to form XSO 2 R A -E—R B (3), then reacting (3) with fluorine in a liquid phase to form FSO 2 R AF -E F -R BF (4), and further, decomposing the compound to obtain FSO 2 R AF -E F1 (5), wherein R A is a bivalent organic group, E 1 is a monovalent reactive group, R B is a monovalent organic group, E 2 is a monovalent reactive group which is reactive with E 1 , E is a bivalent connecting group formed by the reaction of E 1 with E 2 , R AF is a bivalent organic group formed by the fluorination of R A , etc., R BF is the same group as R B , etc., E F is a bivalent connecting group formed by the fluorination of E, etc., E F1 is a monovalent group formed by the decomposition of E F , and X is a halogen atom.

  本发明提供了一种过程，通过该过程，可以高效、低成本地生产含氟原子的磺酰氟化合物，例如用作离子交换膜材料，而且在解决生产困难的同时没有结构限制。换句话说，本发明提供了一种过程，包括将XSO2RA-E1(1)与RB-E2(2)反应形成XSO2RA-E—RB(3)，然后将(3)与液相中的氟反应形成FSO2RAF-EF-RBF(4)，进一步，分解化合物以获得FSO2RAF-EF1(5)，其中RA是二价有机基团，E1是一价反应基团，RB是一价有机基团，E2是与E1反应的一价反应基团，E是由E1与E2反应形成的二价连接基团，RAF是由RA氟化形成的二价有机基团，RBF是与RB相同的基团，EF是由E氟化形成的二价连接基团，EF1是由EF分解形成的一价基团，X是卤素原子。
• Molecular design principles of ionic liquids with a sulfonyl fluoride moiety
  作者：David J. Siegel、Grace I. Anderson、Noah Cyr、Daniel S. Lambrecht、Matthias Zeller、Patrick C. Hillesheim、Arsalan Mirjafari

  DOI：10.1039/d0nj05603k

  日期：——

  The continued success of ionic liquids in applications ranging from energy to medicine poses the challenge to rapidly find new functional ionic liquids with desirable properties while developing practical, scalable syntheses. As a SuFExable functionality, the sulfonyl fluoride has become widely adopted throughout the field of chemical biology due, in part, to its unique stability–reactivity pattern

  离子液体在从能源到医学的各种应用中的持续成功提出了在开发实用，可扩展的合成方法时快速寻找具有所需特性的新型功能性离子液体的挑战。作为SuFExable功能，磺酰氟已在整个化学生物学领域被广泛采用，部分原因是其独特的稳定性-反应性模式，这突出了材料化学中S VI –F基序的潜在价值。我们首次在此报告了通过高效，模块化和正交的氟磺酰基乙基化方法开发的，具有相当大结构多样性的一组磺酰氟官能化离子液体的开发。产生的SO 2F-官能化离子环境具有与其分类为离子液体相一致的特性。我们结合了分子设计，合成，计算模型和X射线晶体学研究，以深入了解它们的结构-特性相关性。所述SO多样化2 F-轴承盐被扩展成包括活性药物的前体，从而允许访问功能材料与先验低毒性。
• Hydrocarbylethyl sulfonyl fluoride
  申请人：Chevron Research Company

  公开号：US04269790A1

  公开（公告）日：1981-05-26

  Hydrocarbylethyl sulfonyl fluorides in which the hydrocarbyl substituent contains at least 3 carbon atoms, can be prepared by reacting 2-mercaptoethanol with chlorine to form chloroethyl sulfonyl chloride which is treated with aqueous potassium fluoride to yield chloroethyl sulfonyl fluoride, followed by treatment with magnesium oxide to yield vinyl sulfonyl fluoride. The vinyl sulfonyl fluoride is adducted to a hydrocarbyl substituent precursor, such as an olefin or halogenated olefin. A representative compound is polyisobutenyl sulfonyl fluoride. The hydrocarbylethyl sulfonamide products for which the hydrocarbylethyl sulfonyl fluorides are intermediates are useful as additives for lubricating oils.

  烃基乙基磺酰氟化物中，烃基取代基含有至少3个碳原子，可以通过将2-巯基乙醇与氯反应制备氯乙基磺酰氯，然后用水合氟化钾处理以得到氯乙基磺酰氟，随后经过氧化镁处理得到乙烯磺酰氟。乙烯磺酰氟与烃基取代物前体（如烯烃或卤代烯烃）结合。代表性化合物为聚异丁烯基磺酰氟。烃基乙基磺酰氟化物是烃基乙基磺酰氟化物产品的中间体，这些产品可用作润滑油的添加剂。