4-氨基-N-甲基苯磺酰胺 | 1709-52-0

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸盐/亚磺酸盐
• 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-氨基-N-甲基苯磺酰胺
• 英文名称: N-methyl-4-aminobenzenesulfonamide
• 英文别名: 4-amino-N-methylbenzenesulfonamide
• CAS: 1709-52-0
• 化学式: C₇H₁₀N₂O₂S
• mdl: MFCD01683104
• 分子量: 186.235
• InChiKey: OISQSDKFWKJEBA-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  359.2±44.0 °C(Predicted)
• 密度：
  1.2900 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2935009090
• RTECS号：
  WP0670000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件：2-8℃，避免光照，保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Methyl 4-aminobenzenesulfonamide
Synonyms: 4-Amino-N-methylbenzenesulfonamide

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

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Section 3. Composition/information on ingredients.
Ingredient name: N-Methyl 4-aminobenzenesulfonamide
CAS number: 1709-52-0

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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.

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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.

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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.

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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:

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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.

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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: C7H10N2O2S
Molecular weight: 186.2

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

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  磺胺	sulfanilamide	63-74-1	C6H8N2O2S	172.208
  ——	N-methyl-4-(acetamido)benzenesulfonamide	6884-87-3	C9H12N2O3S	228.272
  4-硝基-N-甲基-苯磺酰胺	N-methyl-4-nitro-benzenesulfonamide	6319-45-5	C7H8N2O4S	216.218

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-氨基-N,N-二甲基苯磺酰胺	4-amino-N,N-dimethylbenzenesulphonamide	1709-59-7	C8H12N2O2S	200.261
  4-异硫代氰酰基-N-甲基苯磺酰胺	4-isothiocyanato-N-methylbenzenesulfonamide	223785-90-8	C8H8N2O2S2	228.296
  ——	N-methyl-4-(acetamido)benzenesulfonamide	6884-87-3	C9H12N2O3S	228.272
  ——	N-acryloyl-sulfanilic acid methylamide	146447-87-2	C10H12N2O3S	240.283
  ——	2-bromo-N-[4-(methylsulfamoyl)phenyl]acetamide	1339155-51-9	C9H11BrN2O3S	307.168
  4-氨基-N-[4-(甲基氨基磺酰基)苯基]苯磺酰胺	Sulfanilsulfanilmethylamid	547-53-5	C13H15N3O4S2	341.412
  ——	4,4'-dithiobis-N-methylbenzenesulfonamide	917761-25-2	C14H16N2O4S4	404.556
  4-(5-氨基-1H-1,2,4-噻唑-3-基氨基)-N-甲基苯磺酰胺	4-(5-amino-1H-[1,2,4]triazol-3-ylamino)-N-methylbenzenesulfonamide	443799-42-6	C9H12N6O2S	268.299
  ——	N-methyl-4-(2-oxopyrrolidin-1-yl)benzenesulfonamide	——	C11H14N2O3S	254.31
  ——	N-(N-acetyl-sulfanilyl)-sulfanilic acid methylamide	71119-14-7	C15H17N3O5S2	383.449

反应信息

• 作为反应物：
  描述：

  4-氨基-N-甲基苯磺酰胺 在 1,1'-双(二苯基膦)二茂铁 、 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-amino-5-(methylsulfamoyl)benzoate
  参考文献：
  名称：

  [EN] NLRP MODULATORS
  [FR] MODULATEURS DE NLRP

  摘要：

  在一个方面，公式AA的化合物或其药用可接受盐被描述：或其药用可接受盐，其中在公式A中显示的变量可以如本文中的任何地方所定义。

  公开号：

  WO2020010140A1
• 作为产物：
  描述：

  对乙酰胺基苯磺酰氯 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 4-氨基-N-甲基苯磺酰胺
  参考文献：
  名称：

  新型2-氯-4-苯胺基喹唑啉衍生物作为EGFR和VEGFR-2双重抑制剂

  摘要：

  合成了设计为EGFR和VEGFR-2双重抑制剂的新型2-氯-4-苯胺基喹唑啉并评估了其抑制作用。EGFR和VEGFR-2在癌症治疗中是经过验证的靶标，联合抑制可能在抗肿瘤活性和耐药性预防方面具有协同作用。获得的生物学数据证明了2-氯-4-苯胺基喹唑啉衍生物作为EGFR和VEGFR-2双重抑制剂的潜力，突出了化合物8o，其对VEGFR-2的效力大约高7倍，而效力则高11倍。在EGFR上与原型相比7。SAR和对接研究允许鉴定两种激酶的药效基团，并证明了氢键供体在对位的重要性苯胺部分与EGFR和VEGFR-2结合位点中保守的Glu和Asp氨基酸相互作用的位置。

  DOI：

  10.1016/j.ejmech.2013.10.058

文献信息

• Efficient Ruthenium-Catalyzed N-Methylation of Amines Using Methanol
  作者：Tuan Thanh Dang、Balamurugan Ramalingam、Abdul Majeed Seayad

  DOI：10.1021/acscatal.5b00606

  日期：2015.7.2

  reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N-dimethylation of primary aliphatic amines in excellent yields at 40–100

  据报道，在5mol％LiOtBu存在下，使用甲醇作为甲基化剂，在中等条件下，由[RuCp * Cl 2 ] 2和dpePhos配体原位生成的络合物是一种有效的催化剂。氢气借用策略。这种简单的催化剂体系可在40–100°C下以优异的收率对取代的伯胺和磺酰胺进行选择性N-单甲基化，以及对脂肪族伯胺进行N，N-二甲基化，并且对可还原的官能团具有良好的耐受性。分离出催化中间体Cp * Ru（dpePhos）H，显示出在不存在碱的情况下对甲基化具有活性。
• [EN] STRAD-BINDING AGENTS AND USES THEREOF<br/>[FR] AGENTS DE LIAISON À STRAD ET LEURS UTILISATIONS
  申请人：UNIV CALIFORNIA

  公开号：WO2021155004A1

  公开（公告）日：2021-08-05

  Disclosed herein, inter alia, are compounds for binding STRAD pseudokinase and uses thereof.

  披露的内容包括，但不限于，用于结合STRAD假激酶的化合物及其用途。
• Buchwald–Hartwig cross-coupling of amides (transamidation) by selective N–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: catalyst evaluation and mechanism
  作者：Guangchen Li、Tongliang Zhou、Albert Poater、Luigi Cavallo、Steven P. Nolan、Michal Szostak

  DOI：10.1039/c9cy02080b

  日期：——

  The Pd–NHC-catalyzed acyl-type Buchwald–Hartwig cross-coupling of amides by N–C(O) cleavage (transamidation) provides a valuable alternative to the classical methods for amide synthesis. Herein, we report a combined experimental and computational study of the Buchwald–Hartwig cross-coupling of amides using well-defined, air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts. Most crucially, we present

  通过N-C（O）裂解（酰胺基转移），Pd-NHC催化的酰胺基酰基型布赫瓦尔德-哈特维格交叉偶联为经典的酰胺合成方法提供了有价值的替代方法。本文中，我们报告了使用定义明确的，对空气和水分稳定的[Pd（NHC）（烯丙基）Cl]预催化剂进行的Buchwald-Hartwig酰胺交叉偶联的实验和计算研究。最关键的是，我们对一系列不同的Pd（II）-NHC预催化剂进行了全面评估，这些催化剂具有不同的NHC支架和可抛弃的配体，用于合成与化学计量无过渡金属的酰胺化方法不兼容的官能化酰胺。此外，我们目前通过DFT方法对一系列不同的Pd（II）的催化循环进行评估）– NHC预催化剂。获得NHC支持的酰基-钯（II）酰胺基配合物的可行性将对涉及稳定酰胺亲电试剂的交叉偶联方法的设计和开发产生影响。
• Fused heterocyclic compounds useful as kinase modulators
  申请人：Vaccaro Wayne

  公开号：US20070078136A1

  公开（公告）日：2007-04-05

  Compounds having the formula (1), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are usefuil as kinase modulators, including MK2 modulation, wherein one of E and F is a nitrogen atom and the other of E and F is a carbon atom, Z is N or CR 3 , and R 1 , R 2 , R 3 , X and Y are as defined herein.

  具有化学式（1）的化合物，以及其对映体、非对映体、药用可接受的盐，可用作激酶调节剂，包括MK2调节，其中E和F中的一个是氮原子，另一个是碳原子，Z是N或CR3，R1、R2、R3、X和Y如本文所定义。
• A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2
  作者：Gong-Bao Wang、Lin-Fa Wang、Chao-Zhang Li、Jing Sun、Guang-Ming Zhou、Da-Cheng Yang

  DOI：10.1007/s11164-011-0327-6

  日期：2012.1

  Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides.

  亚硫酰氯在无水条件下高效且选择性地促进了N-芳基乙酰胺和2-氯-N-芳基乙酰胺的去酰化反应，且不影响酯基、氨基磺酰基或苄氧酰胺基。这种方法已成功应用于多种底物，包括不同的N-芳基乙酰胺和2-氯-N-芳基乙酰胺，具有试剂成本低、选择性好、产率高、反应时间短和操作简便等吸引人的优点。这种新方法可能被用于选择性地在芳香族酰胺和烷基酰胺之间进行去酰化反应。