[ CAS No. 80-39-7 ]

Name: 80-39-7|N-Ethyl-4-methylbenzenesulfonamide|98%
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Quality Control of [ 80-39-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 80-39-7 ]

Product Details of [ 80-39-7 ]

CAS No. :	80-39-7	MDL No. :	MFCD00048511
Formula :	C₉H₁₃NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OHPZPBNDOVQJMH-UHFFFAOYSA-N
M.W :	199.27	Pubchem ID :	6637
Synonyms :

Calculated chemistry of [ 80-39-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.11
TPSA :	54.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	1.65
Log Po/w (WLOGP) :	2.37
Log Po/w (MLOGP) :	1.28
Log Po/w (SILICOS-IT) :	1.14
Consensus Log Po/w :	1.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.26
Solubility :	1.1 mg/ml ; 0.00551 mol/l
Class :	Soluble
Log S (Ali) :	-2.41
Solubility :	0.777 mg/ml ; 0.0039 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.56
Solubility :	0.0551 mg/ml ; 0.000277 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 80-39-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 80-39-7 ]

* 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 [ 80-39-7 ]

[ 80-39-7 ] Synthesis Path-Downstream 1~69

1
[ 778-28-9 ]
[ 80-39-7 ]
[ 10285-92-4 ]

Reference： [1]Monatshefte fur Chemie,1952,vol. 83,p. 870,872,876

2
[ 75-04-7 ]
[ 98-59-9 ]
[ 80-39-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In ethyl acetate at 0 - 20℃; for 1h;
90%	With triethylamine In dichloromethane
	With alkali

	With indole-3-carboxaldehyde-polystyrene resin; sodium cyanoborohydride; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride Yield given. Multistep reaction;
	In dichloromethane
	With triethylamine In dichloromethane at 0 - 10℃;
	With sodium carbonate In water at 20℃;

Reference： [1]Meyer, Andreas Uwe; Berger, Anna Lucia; König, Burkhard [Chemical Communications, 2016, vol. 52, # 72, p. 10918 - 10921]
[2]Zeng, Xianzhu; Tu, Yongliang; Zhang, Zhenming; You, Changming; Wu, Jiao; Ye, Zhiying; Zhao, Junfeng [Journal of Organic Chemistry, 2019, vol. 84, # 7, p. 4458 - 4466]
[3]Marckwald; v.Droste-Huelshoff [Chemische Berichte, 1899, vol. 32, p. 562] Remsen; Palmer [American Chemical Journal, 1886, vol. 8, p. 242]
[4]Estep, Kimberly G.; Neipp, Christopher E.; Stephens Stramiello, Linda M.; Adam, Mavis D.; Allen, Martin P.; Robinson, Shaughnessy; Roskamp, Eric J. [Journal of Organic Chemistry, 1998, vol. 63, # 16, p. 5300 - 5301]
[5]Brewer, Stuart A.; Burnell, Helen T.; Holden, Ian; Jones, Brian G.; Willis, Colin R. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1231 - 1234]
[6]Saidykhan, Amie; Ebert, Jenessa; Martin, William H.C.; Gallagher, Richard T.; Bowen, Richard D. [European Journal of Mass Spectrometry, 2016, vol. 22, # 4, p. 165 - 173]
[7]Hosseini, Raziyeh; Mohammadiannejad, Kazem; Ranjbar-Karimi, Reza [Journal of Fluorine Chemistry, 2020, vol. 233]

3
[ 80-39-7 ]
[ 599-91-7 ]
N-ethyl-4-methyl-N-propylbenzenesulfonamide [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1952,vol. 83,p. 870,872,876

4
[ 67-56-1 ]
[ 80-39-7 ]
[ 58754-95-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium methylate; potassium bromide at 25℃; anodic oxidation;
59%	With potassium hydroxide; potassium bromide anodic oxidation;

Reference： [1]Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Takeuchi, Kei; Sasaki, Katsushi; Kamada, Tohru; Shimizu, Rie [Journal of the American Chemical Society, 1990, vol. 112, # 6, p. 2368 - 2372]
[2]Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Inoue, Kenji; Matsumoto, Yonetatsu [Tetrahedron Letters, 1986, vol. 27, # 50, p. 6083 - 6086]

5
[ 80-39-7 ]
[ 87010-92-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium <i>tert</i>-butylate; hydroxylamine-O-sulfonic acid In methanol; isopropyl alcohol for 0.5h;

Reference： [1]Hofer, Edgar; Keuper, Regina [Synthesis, 1983, # 6, p. 466 - 467]

6
[ 80-39-7 ]
[ 142-28-9 ]
[ 113812-28-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydride In N,N-dimethyl-formamide at 57℃; for 16h;
	In N,N-dimethyl-formamide	2 EXAMPLE 2 EXAMPLE 2 N-Ethyl-N-(3-chloropropyl)-p-toluenesulfonamide. To N-ethyl-p-toluenesulfonamide (5.01 g, 0.0251 mol) in DMF (50 mL) in a dry flask is added sodium hydride (80% in oil, 0.93 g, 0.031 mol). After gas evolution subsides, 1,3-dichloropropane (22.48 g, 0.199 mol) is added. The mixture is heated at 53°C. for 10 h then cooled and poured into ice water (300 mL), which is extracted twice with ether. The combined extracts are washed with 1% sodium bisulfite, water (3*), and brine. Removal of solvent by rotary evaporation then Kugelrohr distillation gives crude product, which is chromatographed on silica gel (30% hexane/CHCl3) to furnish 2.91 g product (42%) NMR (CDCl3)δ1.15 (t, 3H), 1.9-2.2 (m, 2H), 2.44 (s, 3H), 3.11-3.35 (m, 4H), 3.6 (t, 2H), 7.3 (d, 2H), 7.74 (d, 2H).

Reference： [1]Bergeron, Raymond J.; Neims, Allen H.; McManis, James S.; Hawthorne, Thomas R.; Vinson, John R. T.; et al. [Journal of Medicinal Chemistry, 1988, vol. 31, # 6, p. 1183 - 1190]
[2]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - US5091576, 1992, A

7
[ 675-14-9 ]
[ 80-39-7 ]
2-(N-ethyl-4-methylbenzenesulfonamido)-4,6-difluoro-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 2,4,6-trimethyl-pyridine In acetone at 20℃; for 48h;

Reference： [1]Brewer, Stuart A.; Burnell, Helen T.; Holden, Ian; Jones, Brian G.; Willis, Colin R. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1231 - 1234]

8
[ 108-77-0 ]
[ 80-39-7 ]
4,6-dichloro-2-(N-ethyl-4-methylbenzenesulfonamido)-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With sodium In ethanol for 0.5h; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at -10 - 20℃; for 1h;

Reference： [1]Brewer, Stuart A.; Burnell, Helen T.; Holden, Ian; Jones, Brian G.; Willis, Colin R. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1231 - 1234]

9
[ 80-39-7 ]
N-fluoro-N-ethyl-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With sodium hydride In dichloromethane; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: With N-fluorobis(benzenesulfon)imide In dichloromethane; mineral oil at 20℃; for 6h; Inert atmosphere;
34%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With potassium hydride In dichloromethane at 24℃; for 0.5h; Stage #2: With N-fluorobis(benzenesulfon)imide In dichloromethane at 24℃; for 6h;
	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With sodium hydride In dichloromethane at 0℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: With N-fluorobis(benzenesulfon)imide In dichloromethane at 0 - 20℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Wang, Dinghai; Wu, Lianqian; Wang, Fei; Wan, Xiaolong; Chen, Pinhong; Lin, Zhenyang; Liu, Guosheng [Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 6811 - 6814]
[2]Taylor, Dawne M.; Meier, G. Patrick [Tetrahedron Letters, 2000, vol. 41, # 18, p. 3291 - 3294]
[3]Ji, Yun-Xing; Li, Jinxia; Li, Chun-Min; Qu, Shuanglin; Zhang, Bo [Organic Letters, 2021, vol. 23, # 1, p. 207 - 212]

10
[ 80-39-7 ]
(S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane [ No CAS ]
[ 259656-68-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With 15-crown-5; sodium hydride; sodium iodide In N,N-dimethyl-formamide at 0 - 80℃; Stage #2: (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane In N,N-dimethyl-formamide at 80℃; for 70h; Further stages.;

Reference： [1]Bergeron, Raymond J.; Müller, Ralf; Bussenius, Jörg; McManis, James S.; Merriman, Ronald L.; Smith, Richard E.; Yao, Hua; Weimar, William R. [Journal of Medicinal Chemistry, 2000, vol. 43, # 2, p. 224 - 235]

11
[ 80-39-7 ]
[ 62871-09-4 ]
[ 309974-76-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With magnesium bromide In tetrahydrofuran at -78℃; for 0.5h; Stage #3: 10-bromodec-1-ene In tetrahydrofuran at -78 - 20℃;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]

12
[ 80-39-7 ]
[ 70-55-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 30 - 40℃; for 6h; Irradiation;
50%	With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 30 - 40℃; for 6h; ultrasonic irradiation;

Reference： [1]Katohgi, Masashi; Yokoyama, Masataka; Togo, Hideo [Synlett, 2000, # 7, p. 1055 - 1057]
[2]Katohgi, Masashi; Togo, Hideo [Tetrahedron, 2001, vol. 57, # 35, p. 7481 - 7486]

13
[ 80-39-7 ]
[ 224619-59-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With iodine In tetrahydrofuran at -78℃; for 0.5h;
78%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; Further stages.;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]
[2]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

14
[ 80-39-7 ]
[ 309974-83-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 0.5h; Stage #3: With dihydrogen peroxide In tetrahydrofuran at 0 - 20℃; for 16h;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]

15
[ 80-39-7 ]
[ 106-95-6 ]
[ 309974-75-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With magnesium bromide In tetrahydrofuran at -78℃; for 0.5h; Stage #3: allyl bromide In tetrahydrofuran at -78 - 20℃;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]

16
[ 75-77-4 ]
[ 80-39-7 ]
N-ethyl-4-trimethylsilylmethylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - 20℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 1h; Further stages.;