5-(4-氯苯胺甲基)噻吩-2-磺酰氯 | 166964-34-7

• 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: 5-(4-氯苯胺甲基)噻吩-2-磺酰氯
• 英文名称: 5-({[1-(4-Chloro-phenyl)-methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride
• 英文别名: 5-({[1-(4-chlorophenyl)methanoyl]amino}methyl)thiophene-2-sulfonyl chloride；5-((4-chloro-benzoylamino)-methyl)-thiophene-2-sulfonyl chloride；5-(4-chlorobenzamidomethyl)thiophene-2-sulphonyl chloride；5-({[1'-(4-Chloro-phenyl)-methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride；5-{[(4-chlorobenzoyl)amino]methyl}-2-thiophenesulfonyl chloride；5-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride；5-[[(4-chlorobenzoyl)amino]methyl]thiophene-2-sulfonyl chloride
• CAS: 166964-34-7
• 化学式: C₁₂H₉Cl₂NO₃S₂
• mdl: MFCD00084934
• 分子量: 350.246
• InChiKey: HWAXMFYECKQLDX-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2934999090
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P501,P260,P234,P264,P280,P390,P303+P361+P353,P301+P330+P331,P363,P304+P340+P310,P305+P351+P338+P310,P406,P405
• 危险品运输编号：
  3261
• 危险性描述：
  H314,H290

SDS

Name:	5-{[(4-Chlorobenzoyl)amino]methyl}thiophene-2-sulfonyl chloride 97% Material Safety Data Sheet
Synonym:	5-(4-Chlorobenzamidomethyl)thiophene -2-sulfonyl chlorid
CAS:	166964-34-7

Section 1 - Chemical Product MSDS Name:5-{[(4-Chlorobenzoyl)amino]methyl}thiophene-2-sulfonyl chloride 97% Material Safety Data Sheet
Synonym:5-(4-Chlorobenzamidomethyl)thiophene -2-sulfonyl chlorid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
166964-34-7	5-{[(4-Chlorobenzoyl)amino]methyl}thio	97%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Store under nitrogen.

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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# 166964-34-7: Personal Protective Equipment Eyes: Not available.
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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 131 - 135 deg C
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: C12H9Cl2NO3S2
Molecular Weight: 350

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, reducing agents, bases, amines.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 166964-34-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-{[(4-Chlorobenzoyl)amino]methyl}thiophene-2-sulfonyl chloride - 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
Shipping Name: CORROSIVE SOLID, N.O.S.*
Hazard Class: 8
UN Number: 1759
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 166964-34-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 166964-34-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 166964-34-7 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：

  5-(4-氯苯胺甲基)噻吩-2-磺酰氯 在 polymer-bound morpholine 、 氨 、 polymer-bound aminobenzene 、 polymer-bound isocyanate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4-chloro-N-[(5-sulfamoylthiophen-2-yl)methyl]benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Novel, Potent, and Selective (Benzoylaminomethyl)thiophene Sulfonamide Inhibitors of c-Jun-N-Terminal Kinase

  摘要：

  Several lines of evidence support the hypothesis that c-Jun N-terminal kinases (JNKs) play a critical role in a wide range of disease states including cell death (apoptosis)-related and inflammatory disorders (epilepsy, brain, heart and renal ischemia, neurodegenerative diseases, multiple sclerosis, rheumatoid arthritis, and inflammatory bowel syndrome). The screening of a compound collection led to the identification of a 2-(benzoylaminomethyl)thiophene sulfonamide (AS004509, compound I) as a potent and selective JNK inhibitor. Chemistry and structure-activity relationship (SAR) studies performed around this novel kinase-inhibiting motif indicated that the left and central parts of the molecule were instrumental to maintaining potency at the enzyme. Accordingly, we investigated the JNK-inhibiting properties of a number of variants of the right-hand moiety of the molecule, which led to the identification of 2-(benzoylaminomethyl)thiophene sulfonamide benzotriazole (AS600292, compound 50a), the first potent and selective JNK inhibitor of this class which demonstrates a protective action against neuronal cell death induced by growth factor and serum deprivation.

  DOI：

  10.1021/jm031112e
• 作为产物：
  描述：

  2-噻吩甲胺 在 氯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 5-(4-氯苯胺甲基)噻吩-2-磺酰氯
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Novel, Potent, and Selective (Benzoylaminomethyl)thiophene Sulfonamide Inhibitors of c-Jun-N-Terminal Kinase

  摘要：

  Several lines of evidence support the hypothesis that c-Jun N-terminal kinases (JNKs) play a critical role in a wide range of disease states including cell death (apoptosis)-related and inflammatory disorders (epilepsy, brain, heart and renal ischemia, neurodegenerative diseases, multiple sclerosis, rheumatoid arthritis, and inflammatory bowel syndrome). The screening of a compound collection led to the identification of a 2-(benzoylaminomethyl)thiophene sulfonamide (AS004509, compound I) as a potent and selective JNK inhibitor. Chemistry and structure-activity relationship (SAR) studies performed around this novel kinase-inhibiting motif indicated that the left and central parts of the molecule were instrumental to maintaining potency at the enzyme. Accordingly, we investigated the JNK-inhibiting properties of a number of variants of the right-hand moiety of the molecule, which led to the identification of 2-(benzoylaminomethyl)thiophene sulfonamide benzotriazole (AS600292, compound 50a), the first potent and selective JNK inhibitor of this class which demonstrates a protective action against neuronal cell death induced by growth factor and serum deprivation.

  DOI：

  10.1021/jm031112e

文献信息

• Sulfonamides having antiangiogenic and anticancer activity
  申请人：——

  公开号：US20040157836A1

  公开（公告）日：2004-08-12

  Compounds having methionine aminopeptidase-2 inhibitory (MetAP2) are described. Also described are pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, methods of inhibiting angiogenesis, and methods of treating cancer.

  描述了具有蛋氨酸氨基肽酶-2抑制剂（MetAP2）的化合物。还描述了包括这些化合物的药物组合物、使用这些化合物的治疗方法、抑制血管生成的方法以及治疗癌症的方法。
• Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin
  申请人：——

  公开号：US20020095041A1

  公开（公告）日：2002-07-18

  Biphenylsulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, bicyclic or tricyclic carbon or heterocyclic ring biphenylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.

  提供了二苯基磺胺类化合物和调节或改变内皮素家族肽活性的方法。具体包括使用双环或三环碳或杂环环二苯基磺胺类化合物的方法，通过将该磺胺类化合物与内皮素受体接触来抑制内皮素肽与内皮素受体的结合。还提供了通过给予有效剂量的这些磺胺类化合物或其前药来治疗内皮素介导的疾病的方法，这些化合物能够抑制或增加内皮素的活性。
• Pharmaceutically active sulfonyl hydrazide derivatives
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP1088822A1

  公开（公告）日：2001-04-04

  The present invention is related to sulfonyl hydrazide derivatives according to formula I with its geometrical isomers, in an optically active form as enantiomers, diastereomers, as well as in the form of racemates, as well as pharmaceutically acceptable salts thereof, wherein Ar1 and Ar2 are independently from each other an unsubstituted or substituted aryl or heteroaryl group, X1 and X2 are independently from each other O or S; R1, R2, R3 are independently from each other hydrogen or a C1-C6-alkyl substituent or R1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar1; or R2 and R3 form a substituted or unsubstituted 5-6-membered saturated or unsaturated ring; n is an integer from 0 to 5; G is selected from a group comprising or consisting of an unsubstituted or substituted 4-8-membered heterocycle containing at least one heteroatom, or G is a substituted or unsubstituted C1-C6-alkyl group; for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such sulfonyl hydrazide derivatives. Said sulfonyl hydrazide derivatives are efficient modulators of the JNK pathway, they are in particular efficient inhibitors of JNK 2 and 3. The present invention is furthermore related to novel sulfonyl hydrazide derivatives as well as to methods of their preparation.

  本发明涉及按照式I的磺酰基腙衍生物及其几何异构体，以对映体、二对映体的光学活性形式，以及它们的盐的药学上可接受的形式，其中Ar1和Ar2分别独立地是未取代或取代的芳基或杂环芳基，X1和X2分别独立地是O或S；R1、R2、R3分别独立地是氢或C1-C6-烷基取代基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环；或R2和R3形成取代或未取代的5-6元饱和或不饱和环；n是0到5的整数；G选自包含或仅包含至少一个杂原子的未取代或取代的4-8元杂环的群，或G是取代或未取代的C1-C6烷基基团；用作药学活性化合物，以及含有这种磺酰基腙衍生物的制药配方。所述磺酰基腙衍生物是JNK途径的高效调节剂，特别是JNK 2和3的高效抑制剂。本发明还涉及新型磺酰基腙衍生物以及其制备方法。
• N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
  申请人：Texas Biotechnology Corp.

  公开号：US06342610B2

  公开（公告）日：2002-01-29

  Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.

  提供了噻吩基、呋喃基和吡咯基磺酰胺以及用于调节或改变内皮素肽家族活性的方法。特别是，提供了N-(异恶唑基)噻吩磺酰胺、N-(异恶唑基)呋喃磺酰胺和N-(异恶唑基)吡咯磺酰胺以及使用这些磺酰胺通过将受体与磺酰胺接触来抑制内皮素肽与内皮素受体结合的方法。还提供了通过施用有效量的一个或多个这些磺酰胺或其前药来治疗内皮素介导的疾病的方法，这些磺酰胺或其前药抑制或增加内皮素的活性。
• Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP1193268A1

  公开（公告）日：2002-04-03

  The present invention is related to sulfonamide derivatives having a lipophilic moiety and which are substantially soluble under physiological conditions. Said compounds are notably for use as pharmaceutically active compounds. The present invention also related to pharmaceutical formulations containing such sulfonamide derivatives. Said sulfonamide derivatives are efficient modulators of the JNK pathway, they are in particular efficient and selective inhibitors of JNK 2 and 3. The present invention is furthermore related to novel sulfonamide derivatives as well as to methods of their preparation. The compounds of formula I according to the present invention being suitable pharmaceutical agents are those wherein Ar1 and Ar2 are independently from each other substituted or unsubstituted aryl or heteroaryl groups, X is O or S, preferably O; R1 is hydrogen or a C1-C6-alkyl group, or R1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar1; n is an integer from 0 to 5, preferably between 1-3 and most preferred 1; Y within formula I is an unsubstituted or a substituted 4-12-membered saturated cyclic or bicyclic alkyl which is substituted with at least one ionisable moiety to which a lipophilic chain is attached and which is containing at least one nitrogen atom, whereby one nitrogen atom within said ring is forming a bond with the sulfonyl group of formula I thus providing a sulfonamide.ring is forming a bond with the sulfonyl group of formula I thus providing a sulfonamide.

  本发明涉及具有亲脂基团并在生理条件下基本可溶的磺胺基衍生物。所述化合物特别适用作药用活性化合物。本发明还涉及含有这种磺胺基衍生物的药物配方。所述磺胺基衍生物是JNK途径的高效调节剂，特别是JNK 2和3的高效和选择性抑制剂。本发明还涉及新型磺胺基衍生物以及它们的制备方法。 根据本发明的式I化合物适用于药用剂的那些化合物是这样的： Ar1和Ar2分别独立地是取代或未取代的芳基或杂环芳基， X是O或S，优选为O； R1是氢或C1-C6烷基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环； n是0到5的整数，优选为1-3之间，最优选为1； 式I中的Y是未取代或取代的4-12元饱和环或双环烷基，其上取代有至少一个可离子化基团，该基团连接有一个亲脂链，并且含有至少一个氮原子，其中所述环中的一个氮原子与式I的磺酰基形成键合，从而提供磺胺基。