[ CAS No. 58687-83-5 ] {[proInfo.proName]}

Name: 58687-83-5|4-Amino-N-propylbenzenesulfonamide|96%
Brand: Ambeed
SKU: A596263
Rating: 93 (25 reviews)

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Quality Control of [ 58687-83-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 58687-83-5 ]

Product Details of [ 58687-83-5 ]

CAS No. :	58687-83-5	MDL No. :	MFCD05666729
Formula :	C₉H₁₄N₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PEDHCXVSNZZLSR-UHFFFAOYSA-N
M.W :	214.29	Pubchem ID :	2065546
Synonyms :

Safety of [ 58687-83-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P280-P305+P351+P338-P310	UN#:	1759
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 58687-83-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 58687-83-5 ]

[ 58687-83-5 ] Synthesis Path-Downstream 1~15

1
<i>N</i>-acetyl-sulfanilic acid propylamide [ No CAS ]
[ 58687-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride
	With sodium hydroxide; water for 1h; Reflux;

Reference： [1]Mangini [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1940, vol. <7> 1, p. 452,457]
[2]Location in patent: experimental part El-Mariah, Fatma; Nassar, Ekhlass; Hosny, Mona; Deeb, Ali [Phosphorus, Sulfur and Silicon and the Related Elements, 2009, vol. 184, # 1, p. 92 - 102]

2
[ 58687-83-5 ]
[ 98-88-4 ]
<i>N</i>-benzoyl-sulfanilic acid propylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Mangini [Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1940, vol. 1, p. 143]

4
[ 121-60-8 ]
[ 58687-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; water 2: aqueous hydrochloric acid

Reference： [1]Mangini [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1940, vol. <7> 1, p. 452,457]

5
[ 58687-83-5 ]
[ 94011-79-7 ]
[ 1167997-38-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In butan-1-ol for 3h; Reflux;

Reference： [1]Location in patent: experimental part El-Mariah, Fatma; Nassar, Ekhlass; Hosny, Mona; Deeb, Ali [Phosphorus, Sulfur and Silicon and the Related Elements, 2009, vol. 184, # 1, p. 92 - 102]

6
dimethyl 4-(methoxymethylene)-2-pentenedioate [ No CAS ]
[ 58687-83-5 ]
[ 1160499-32-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide at 20℃; for 0.25h;

Reference： [1]Location in patent: experimental part El-Mariah, Fatma; Nassar, Ekhlass [Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 12, p. 3145 - 3155]

7
[ 1228268-12-9 ]
[ 58687-83-5 ]
[ 1228268-21-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	In benzene for 5h; Reflux;

Reference： [1]Location in patent: experimental part El Mariah, Fatma [Journal of Chemical Research, 2009, # 10, p. 593 - 598]

8
[ 58687-83-5 ]
[ 189894-90-4 ]
[ 1228268-28-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	In butan-1-ol for 3h; Reflux;

Reference： [1]Location in patent: experimental part El Mariah, Fatma [Journal of Chemical Research, 2009, # 10, p. 593 - 598]

9
[ 106-94-5 ]
[ 63-74-1 ]
[ 58687-83-5 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate at 20℃; for 120h;	Formation of compound 11: 4-amino-N-(propyl)benzenesulfonamide To a solution of 172 mg of sulfanilamide (1 mmol) and 304 mg of K2CO3 (2.2 mmol) in 2.5 mL of DMF was added dropwise 91 μL of 1-bromopropane (1 mmol). The mixture was stirred at room temperature for 5 days. Then, DMF was evaporated and the crude was dissolved with water and the solution was extracted with ethylacetate ( 3). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by combi-flash with the eluent petroleum ether/ethylacetate: 70/30, thereby obtaining compound 11 (90 mg, 42%) as a white solid (mp: 80-82 °C). 1H NMR (CDCl3, 400 MHz, ppm) δ: 0.83 (t, CH3, J = 7.4 Hz, H3'), 1.45 (qt, CH2, J = 7.3 Hz, J = 7.2 Hz, H2’), 2.78 (dd, CH2, J = 7.1 Hz, J = 6.3 Hz, H1'), 5.39 (broad s, 2H, SO2NH2), 6.02 (t, 1H, J = 6.1 Hz, NH), 6.74 (d, 2CH, J = 8.8 Hz, H3 and H5), 7.53 (d, 2CH, J = 8.7 Hz, H2, H6). 13C NMR (CDCl3, 100 MHz, ppm) δ: 11.5 (CH3, C3'), 23.4 (CH2, C20), 45.5 (CH2, C1'), 113.9 (2CH, C3 and C5), 127.9 (C1), 129.5 (2CH, C2 and C6), 153.0 (C4). MS (IES+, ACN): m/z 215 [M+H]+, 137 [M+Na]+. HRMS (ESI, CH3OH): m/z 237.0672 (m/z theoretical: 237.06737) [M+Na]+.

Reference： [1]Compain, Guillaume; Martin-Mingot, Agnes; Maresca, Alfonso; Thibaudeau, Sebastien; Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 6, p. 1555 - 1563]

10
[ 110-87-2 ]
[ 58687-83-5 ]
[ 2043-61-0 ]
(4aSR*,5RS*,10bSR*)-5-cyclohexyl-N-propyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-9-sulfonamide [ No CAS ]
C₂₁H₃₂N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium(II) perchlorate In acetonitrile at 20℃; for 16h; Inert atmosphere;

Reference： [1]Díaz, José Luis; Christmann, Ute; Fernández, Ariadna; Luengo, Mónica; Bordas, Magda; Enrech, Raquel; Carro, Mónica; Pascual, Rosalia; Burgueño, Javier; Merlos, Manuel; Benet-Buchholz, Jordi; Cerón-Bertran, Jordi; Ramírez, Jesús; Reinoso, Raquel F.; Fernández De Henestrosa, Antonio R.; Vela, José Miguel; Almansa, Carmen [Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3656 - 3665]

11
[ 67132-17-6 ]
[ 58687-83-5 ]
N-((4-(N-propylsulfamoyl)phenyl)carbamothioyl)-[1,1'-biphenyl]-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.09 g	In acetone Reflux;	50 4.6.3. General procedure C (step 3) General procedure: 4-Phenylbenzoyl chloride (15, 1.2 mmol, 1-1.2 eq) in acetone (10 mL) was added slowly to a mixture of potassium thiocyanate (1-1.2 eq) in acetone (10 mL). The reaction mixture was refluxed 1.5-3 h and the reaction was monitored by TLC. The reaction mixture was cooled down to rt and an appropriate benzenesulfonamide or benzamide analog (14a-q, 1 eq) in acetone (10 mL) was slowly added. The reaction mixture was refluxed for 2-4 h orovernight. When starting material was disappeared (detected by TLC plate), the mixture was poured on ice cold water which pH was adjusted to 5 with HCl. If the product crystallized, it was filtered and washed with small amount of cold water. Otherwise the mixture was extracted with EA. The product was purified by column chromatography, recrystallization or washing with hexane. 4.6.4.50 N-((4-(N-Propylsulfamoyl)phenyl)carbamothioyl)-[1,1'-biphenyl]-4-carboxamide (17o) From 14o (0.11 g, 0.5 mmol) with general procedure C. Light yellow solid (0.09 g, 38%). 1H NMR (DMSO-d6): δ 0.81 (3H, t, J = 7.3 Hz), 1.39 (2H, m), 2.73 (2H, m), 7.45 (1H, t, J = 7.3 Hz), 7.53 (2H, t, J = 7.5 Hz), 7.60 (1H, t, J = 5.8 Hz), 7.78 (2H, d, J = 7.4 Hz), 7.82 (2H, d, J = 8.5 Hz), 7.86 (2H, d, J = 8.5 Hz), 7.98 (2H, d, J = 8.4 Hz), 8.10 (2H, d, J = 8.4 Hz), 11.73 (1H, s), 12.78 (1H, s); 13C NMR (DMSO-d6): δ 11.1, 22.4, 44.4, 124.3, 126.6, 127.0, 127.1, 128.5, 129.1, 129.5, 130.8, 137.7, 138.7, 141.3, 144.6, 167.8, 179.3; ESI-MS 452.00 [M-H]-; Anal. Calcd for C23H23N3O3S2: C 60.90, N 9.26, H 5.11, S 14.14; found: C 60.83, N 9.29, H 5.27, S 13.33.

12
[ 98-74-8 ]
[ 58687-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 20 °C 2: hydrogenchloride; tin / ethanol; water / Reflux
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h

Reference： [1]Yrjölä, Sari; Parkkari, Teija; Navia-Paldanius, Dina; Laitinen, Tuomo; Kaczor, Agnieszka A.; Kokkola, Tarja; Adusei-Mensah, Frank; Savinainen, Juha R.; Laitinen, Jarmo T.; Poso, Antti; Alexander, Amy; Penman, June; Stott, Lisa; Anskat, Marie; Irving, Andrew J.; Nevalainen, Tapio J. [European Journal of Medicinal Chemistry, 2016, vol. 107, p. 119 - 132]
[2]Myers, Stephanie M.; Bawn, Ruth H.; Bisset, Louise C.; Blackburn, Timothy J.; Cottyn, Betty; Molyneux, Lauren; Wong, Ai-Ching; Cano, Celine; Clegg, William; Harrington, Ross. W.; Leung, Hing; Rigoreau, Laurent; Vidot, Sandrine; Golding, Bernard T.; Griffin, Roger J.; Hammonds, Tim; Newell, David R.; Hardcastle, Ian R. [ACS Combinatorial Science, 2016, vol. 18, # 8, p. 444 - 455]

13
[ 23530-47-4 ]
[ 58687-83-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; tin In ethanol; water Reflux;	32 4.6.2. General procedure B (step 2) General procedure: Concentrated HCl (10-15 ml) was added slowly to a mixture of 4-nitrobenzenesulfonamide or 4-nitrobenzamide analog (13a-q,1.4 mmol, 1 eq) and Sn granules (2-2.5 eq) in ethanol (10 mL). The reaction mixture was refluxed for 3.5-6 h. When the TLC plates howed that there is no more starting material left, the reaction mixture was cooled down to rt. NaOH (30% or 5M, aq) was added to the mixture until it became basic. The mixture was extracted with EA or DCM and the organic layer was dried with Na2SO4. The solvent was evaporated. The product was purified with column chromatography when required. 4.6.4.32 4-Amino-N-propylbenzenesulfonamide (14o) From 13o (0.75 g, 3.1 mmol) with general procedure B. Solid (0.84 g, 100%) that was used without further purification. 1H NMR (DMSO-d6): δ 0.78 (3H, t, J = 7.4 Hz), 1.34 (2H, m), 2.60 (2H, t, J = 7.0 Hz), 5.87 (2H, s), 6.60 (2H, d, J = 8.7 Hz), 7.03 (1H, s), 7.40 (2H, d, J = 8.7 Hz).
95%	With palladium 10% on activated carbon; hydrogen In ethyl acetate for 18h;

14
[ 58687-83-5 ]
[ 333-20-0 ]
2-amino-N-propylbenzo[d]thiazole-6-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(II) sulfate In methanol for 3h; Reflux;

Reference： [1]Myers, Stephanie M.; Bawn, Ruth H.; Bisset, Louise C.; Blackburn, Timothy J.; Cottyn, Betty; Molyneux, Lauren; Wong, Ai-Ching; Cano, Celine; Clegg, William; Harrington, Ross. W.; Leung, Hing; Rigoreau, Laurent; Vidot, Sandrine; Golding, Bernard T.; Griffin, Roger J.; Hammonds, Tim; Newell, David R.; Hardcastle, Ian R. [ACS Combinatorial Science, 2016, vol. 18, # 8, p. 444 - 455]

15
[ 58687-83-5 ]
2-(piperidin-1-yl)benzenesulfonyl chloride [ No CAS ]
2-(piperidin-1-yl)-N-(4-(N-propylsulfamoyl)phenyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With pyridine at 120℃; for 1h; Microwave irradiation;	175 Example 175 2-(piperidin-l-yl)-N-(4-(N-propylsulfamoyl)phenyl)benzenesulfonamide General procedure: A solution of 4-amino-N-propylbenzenesulfonamide (0.107 g, .5 mmol) in Pyridine (E000 ml) was treated with 2-(piperidin-l-yl)benzenesulfonyl chloride (0.130 g, 0.500 mmol). The solution was stirred at 120° C for 1 hour. The crude product was purified by reversed-phase chromatography (4-100% CEECN over 15 min) to give desired product (0.107g, 24% yield). (LCMS, ESI pos.) Calculated for C20H27N3O4S2: 438.6 (M + H), Measured: 438.1.

Reference： [1]Current Patent Assignee: UNIVERSITY OF MICHIGAN; NAT CENTER FOR ADVANCING TRANSLATIONAL SCIENCES - WO2021/41866, 2021, A1 Location in patent: Page/Page column 148

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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Deprotonation of Methylbenzene • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nitrosation of Amines • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of LDA • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Ugi Reaction • Vilsmeier-Haack Reaction

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 58687-83-5 ] {[proInfo.proName]}

Quality Control of [ 58687-83-5 ]

Related Doc. of [ 58687-83-5 ]

Product Details of [ 58687-83-5 ]

Safety of [ 58687-83-5 ]

Application In Synthesis of [ 58687-83-5 ]

[ 58687-83-5 ] Synthesis Path-Downstream 1~15

Technical Information

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