4-氟-2-甲基苯磺酰胺 | 489-17-8

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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: 4-氟-2-甲基苯磺酰胺
• 英文名称: 4-fluoro-2-methyl-1-benzenesulfonamide
• 英文别名: 4-fluoro-2-methylbenzenesulfonamide
• CAS: 489-17-8
• 化学式: C₇H₈FNO₂S
• mdl: MFCD02709831
• 分子量: 189.21
• InChiKey: NNYVGGHJPLSSRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  180-184 °C (lit.)
• 沸点：
  324.0±52.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• WGK Germany：
  3
• 海关编码：
  2921420090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 4-Fluoro-2-methylbenzenesulfonamide
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. : 489-17-8

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C7H8FNO2S
Molecular Weight : 189,21 g/mol
CAS-No. : 489-17-8
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
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, nitrogen oxides (NOx), Sulphur oxides, Hydrogen fluoride
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
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.
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
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
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: crystalline
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 180 - 184 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
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 no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
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
no data available
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

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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
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: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-氟-2-甲基苯磺酰胺 在 甲酸铵 作用下， 反应 7.0h， 以72%的产率得到4-氟-2-甲基苯硫酚
  参考文献：
  名称：

  Solvent-Free Synthesis of Thiophenol Using Uncatalyzed Transfer Hydrogenation

  摘要：

  Clean and sustainable transfer hydrogenation for aryl sulfonamides and sulfonyl chlorides is described. The protocol is chemoselective and uses neither catalyst nor solvent.

  DOI：

  10.1080/00397911.2011.559317
• 作为产物：
  描述：

  4-氟-2-甲基苯磺酰氯 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以79%的产率得到4-氟-2-甲基苯磺酰胺
  参考文献：
  名称：

  Synthesis and Cyclooxygenase-2 Inhibiting Property of 1,5-Diarylpyrazoles with Substituted Benzenesulfonamide Moiety as Pharmacophore:  Preparation of Sodium Salt for Injectable Formulation^†

  摘要：

  A series of 1,5-diarylpyrazoles having a substituted benzenesulfonamide moiety as pharmacophore was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Through SAR and molecular modeling, it was found that fluorine substitution on the benzenesulfonamide moiety along with an electron-donating group at the 4-position of the 5-aryl ring yielded selectivity as well as potency for COX-2 inhibition in vitro. Among such compounds 3-fluoro-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl]-1-benzenesulfonamide 3 displayed interesting pharmacokinetic properties along with antiinflammatory activity in vivo. Among the sodium salts tested in vivo, 10, the propionyl analogue of 3, showed excellent antiinflammatory activity and therefore represents a new lead structure for the development of injectable COX-2 specific inhibitors.

  DOI：

  10.1021/jm020563g

文献信息

• [EN] N-TYPE CALCIUM CHANNEL INHIBITOR<br/>[FR] INHIBITEUR DE CANAL DE CALCIUM DE TYPE N
  申请人：ONO PHARMACEUTICAL CO

  公开号：WO2006038594A1

  公开（公告）日：2006-04-13

  　本発明は、一般式（Ｉ） （式中の記号は明細書中に記載の通り）で示されるＮ型カルシウムチャネル阻害作用を有する化合物、その塩もしくはそれらの溶媒和物またはそのプロドラッグを含有してなるＮ型カルシウムチャネル阻害薬に関する。　本発明化合物は、Ｎ型カルシウムチャネル阻害作用を有するので、Ｎ型カルシウムチャネル介在性疾患、例えば疼痛（例えば、急性痛、慢性痛、術後痛、癌性疼痛、神経痛、感染性疼痛等）、脳梗塞、一過性脳虚血発作、心臓手術後の脳脊髄障害、脊髄血管障害、ストレス性高血圧、神経症、てんかん、喘息、頻尿、眼疾患等の予防および／または治療剤として有用である。

  This invention relates to an N-type calcium channel inhibitor drug containing a compound having an N-type calcium channel inhibitory action represented by the general formula (I) (wherein the symbols are as described in the specification), its salt, solvate, or prodrug. Since the compound of the present invention has an N-type calcium channel inhibitory action, it is useful as a preventive and/or therapeutic agent for N-type calcium channel-mediated diseases such as pain (e.g., acute pain, chronic pain, postoperative pain, cancer pain, neuropathic pain, infectious pain, etc.), cerebral infarction, transient cerebral ischemic attack, brain and spinal cord disorders after cardiac surgery, spinal cord vascular disorders, stress-induced hypertension, neurosis, epilepsy, asthma, frequent urination, eye diseases, etc.
• Iridium‐Catalyzed <i>ortho‐</i> C−H Amidation of Benzenesulfonamides with Sulfonyl Azides
  作者：Hongcen Hou、Yongli Zhao、Shouri Sheng、Junmin Chen

  DOI：10.1002/adsc.201900573

  日期：2019.9.17

  herein an iridium‐catalyzed direct C−H activation/ C−N bond formation reaction of benzenesulfonamides with sulfonyl azides. The amidation reaction provides a protocol for the synthesis of 2‐aminobenzesulfonamides in good to excellent yields. This strategy features a wide substrate scope, tolerates a broad range of functional groups under external oxidant‐free conditions and only releases molecular nitrogen

  我们在此开发了铱催化的苯磺酰胺与磺酰叠氮化物的铱催化直接CH活化/ CN键形成反应。酰胺化反应为合成2-氨基苯磺酰胺类化合物提供了良好的合成方案。该策略具有广泛的底物范围，在无外部氧化剂的条件下可耐受各种官能团，并且仅释放分子氮作为唯一的副产物。此外，还研究了初步机理并提供了建议的反应途径。
• Rhodium-catalyzed direct C–H bond alkynylation of aryl sulfonamides with bromoalkynes
  作者：Hongcen Hou、Yongli Zhao、Shouzhi Pu、Junmin Chen

  DOI：10.1039/c9ob00061e

  日期：——

  report a novel rhodium-catalyzed ortho-mono-alkynylation of aryl sulfonamides. The reactions of N-tosylacetamides with triisopropylsilyl (TIPS)-substituted bromoalkyne are catalyzed by a [(Cp*RhCl2)2] complex without cyclization, forming ortho-(1-alkynyl) benzenesulfonamides. While triethylsilyl or trimethylsilyl (TES or TMS)-substituted bromoalkyne was also amenable to the alkynylation, affording six-membered

  本文中，我们报道了新颖的铑催化的芳基磺酰胺基的邻-单-炔基化。N-甲苯磺酰基乙酰胺与三异丙基甲硅烷基（TIPS）取代的溴炔烃的反应在没有环化的情况下被[（Cp * RhCl2）2]络合物催化，形成邻-（1-炔基）苯磺酰胺。虽然三乙基甲硅烷基或三甲基甲硅烷基（TES或TMS）取代的溴炔烃也适合进行炔基化反应，但通过炔基化/分子内环化级联反应。本协议显示了高官能团耐受性和良好的高收率在空气气氛下广泛的基板范围。机理研究表明，该反应通过限制C–H活化的周转进行，并提出了合理的机理。
• Efficient Manganese/Copper Bimetallic Catalyst for<i>N</i>-Arylation of Amides and Sulfonamides Under Mild Conditions in Water
  作者：Yong-Chua Teo、Fui-Fong Yong、Idzham Khalid Ithnin、Siew-Hui Trionna Yio、Zhiyin Lin

  DOI：10.1002/ejoc.201201218

  日期：2013.1

  An efficient and mild method using a bimetallic MnF2/CuI catalyst at 60 °C in water was developed for the N-arylation of amides and sulfonamides with aryl halides. A variety of functionalized amides and sulfonamides were coupled with different substituted aryl halides to afford the corresponding N-arylated products in good to excellent yields (up to 97 %).

  开发了一种在 60 °C 下在水中使用双金属 MnF2/CuI 催化剂的有效且温和的方法，用于酰胺和磺酰胺与芳基卤化物的 N-芳基化。各种官能化酰胺和磺酰胺与不同的取代芳基卤化物偶联，以良好至极好的产率（高达 97%）提供相应的 N-芳基化产物。
• Efficient Ligand-Free, Copper-Catalyzed N-Arylation of Sulfonamides
  作者：Yong-Chua Teo、Fui-Fong Yong

  DOI：10.1055/s-0030-1259925

  日期：2011.4

  An efficient and convenient protocol has been developed for the N-arylation of sulfonamides with differently substituted aryl iodides using ligand-free copper iodide to afford the arylated products in good to excellent yields (up to 91%).

  一种高效便捷的协议已经被开发出来，用于在没有配体的情况下，利用铜碘将不同取代的苯磺酰胺与苯碘进行N-arylation反应，以良好至优异的产率（高达91%）得到芳基化产物。