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Quality Control of [ 196929-78-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 196929-78-9 ]

SDS Specification

Alternatived Products of [ 196929-78-9 ]

Product Details of [ 196929-78-9 ]

CAS No. :	196929-78-9	MDL No. :	MFCD05861479
Formula :	C₄H₁₁NOS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CESUXLKAADQNTB-SSDOTTSWSA-N
M.W :	121.20	Pubchem ID :	10964479
Synonyms :	(R)-2-Methylpropane-2-sulfinamide	Chemical Name :	(R)-2-Methyl-2-propanesulfinamide

Calculated chemistry of [ 196929-78-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	32.36
TPSA :	62.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.1
Log Po/w (XLOGP3) :	0.03
Log Po/w (WLOGP) :	1.27
Log Po/w (MLOGP) :	0.49
Log Po/w (SILICOS-IT) :	-1.04
Consensus Log Po/w :	0.37

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.54
Solubility :	34.6 mg/ml ; 0.286 mol/l
Class :	Very soluble
Log S (Ali) :	-0.89
Solubility :	15.6 mg/ml ; 0.129 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.7
Solubility :	24.1 mg/ml ; 0.199 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.64

Safety of [ 196929-78-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 196929-78-9 ]

* 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 [ 196929-78-9 ]

[ 196929-78-9 ] Synthesis Path-Downstream 1~22

1
[ 196929-78-9 ]
[ 1022-13-5 ]
[ 1217898-53-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2357 - 2368

2
[ 127413-59-6 ]
[ 196929-78-9 ]
[ 1262859-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) tetraethanolate; In tetrahydrofuran; for 2.5h;Reflux;	<strong>[127413-59-6]1-(3-Bromo-5-nitro-phenyl)-ethanone</strong> (11.6 g, 47.5 mmol), (R)-(+)-tert-butanesulfinamide (6.34 g, 52.3 mmol) and Ti(OEt)4 (24.64 ml, 119 mmol) were mixed in 62 ml THF and refluxed for 2.5 hrs. The reaction was cooled and carefully quenched by addition of ice and water. The white precipitate was filtered off and the aqueous mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as yellow oil. 1H-NMR (500 MHz, DMSO-d6): 8.58 (s, 1H), 8.55 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H), 1.24 (s, 9H); MS: 347 [(M+H)+]; [alpha]D=+54.5 (c=0.481% in chloroform).

Reference： [1]Patent: US2011/21520,2011,A1 .Location in patent: Page/Page column 49

3
[ 1260878-78-1 ]
[ 196929-78-9 ]
[ 1422510-26-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In dichloromethane; at 20℃; for 1h;	Intermediate 15 A. (5',E)-N-((4-Chloro-3-fluoropyridin-2-yl)methylene)-2- methylpropane-2-sulfinamide: A solution of (i?)-2-methylpropane-2-sulfinamide (0.540 g, 4.32 mmol), <strong>[1260878-78-1]4-chloro-3-fluoropicolinaldehyde</strong> (0.627 g, 3.93 mmol) and Cs2C03 (1.921 g, 5.89 mmol) in DCM (20 mL) was stirred for 1 h at rt. The reaction mixture was diluted with EtOAc and washed with brine (3x20 mL). The organic layer was dried over MgS04, filtered and concentrated in vacuo to provide the desired product (1.1 g, 100%). MS (ESI) m/z: 263.0 (M+H)+.

Reference： [1]Patent: WO2013/22814,2013,A1 .Location in patent: Paragraph 00316

4
[ 5780-66-5 ]
[ 196929-78-9 ]
[ 1421236-66-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 562 - 565

5
[ 27258-32-8 ]
[ 196929-78-9 ]
[ 1421236-70-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 562 - 565

6
(R)-4-chloro-2-((R)-1-(4-methylphenylsulfonamido)ethyl)phenyl 2-methylpropane-2-sulfinate [ No CAS ]
[ 1421840-44-9 ]
[ 196929-78-9 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6713 - 6717
Angew. Chem.,2013,vol. 125,p. 6845 - 6849,5

7
[ 34595-26-1 ]
[ 196929-78-9 ]
2-methylpropane-2-sulfinic acid [1-(2-piperidin-1-ylphenyl)methylidene]amide [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2013,vol. 25,p. 9345 - 9350

8
[ 18925-10-5 ]
[ 146137-72-6 ]
[ 196929-78-9 ]
[ 1560811-17-7 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1224 - 1227

9
[ 37687-18-6 ]
[ 196929-78-9 ]
(R)-2-methyl-N-[1-(1-methyl-1H-pyrazol-4-yl)ethylidene]-2-propanesulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With titanium(IV) isopropylate; at 85℃; for 24h;Inert atmosphere; Microwave irradiation; Sealed tube;	1-(1-Methyl-1H-pyrazol-4-yl)-1-ethanone (1.05 g, 8.46 mmol), (R)-2-methyl-2-propanesulfinamide (0.96 g, 7.9 mmol) and Ti(OiPr)4 (9.1 g, 9.57 mL, 32 mmol) were mixed in a high pressure tube, sealed and irradiated in a microwave reactor at 85 C (50 W) for 24 h. The progress of the reaction was monitored by 1H NMR. After disappearance of the sulfinamide signals, the reaction mixture was diluted with THF (30 mL) and poured into water (70 mL). After 20 min of stirring, the suspension was filtered through a pad of Super Cel, and the precipitate was washed two times with DCM. The filtrate was diluted with water (100 mL) and extracted with DCM (20 mL * 3). The combined extracts were dried over K2CO3 and evaporated under reduced pressure. The residue was recrystallized from diethyl ether to afford 2e (1.59 g, 88%) as a beige crystalline solid. Rf: 0.26 (EtOAc). = -73.7 (c 1, CHCl3). Mp 88-89 C (Et2O). 1H NMR (400 MHz, CDCl3): delta 7.84 (s, 1H, CHpyr), 7.81 (s, 1H, CHpyr), 3.93 (s, 3H, NMe), 2.60 (s, 3H, MeC=N), 1.27 (s, 9H, tBu). 13C NMR (100 MHz, CDCl3): delta 171.19, 139.40, 130.98, 124.47, 56.74, 39.36, 22.26 3C, 20.87. MS (70 eV, EI): m/z (%) = 228 (12) [MH]+, 211 (2), 172 (12), 171 (100), 170 (12), 130 (51), 123 (36), 108 (72), 107 (18), 89 (12), 82 (34), 81 (10). C10H17N3OS (227.3): calcd C 52.83, H 7.54, N 18.48, S 14.11; found C 52.80, H 7.55, N 18.35, S 13.97.

Reference： [1]Tetrahedron Asymmetry,2014,vol. 25,p. 667 - 676

10
[ 357405-75-5 ]
[ 196929-78-9 ]
(R,E)-N-(4-bromo-2,5-difluorobenzylidene)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(II) sulfate; In 1,2-dichloro-ethane; at 60℃; for 18h;	StepiTo a round bottom flask with stir bar was added <strong>[357405-75-5]4-bromo-2,5-difluorobenzaldehyde</strong> (5.3 g, 24.0 mmol), (R)-2-methylpropane-2-sulfinamide (3.2 g, 26.4 mmol) and DOE (80 mL). To this mixture was then added copper (II) sulfate (5.74 g, 36.0 mmol). The reaction mixture was heated in a preheated oil bath at 60 00 for i8 hours. The reaction mixture was filtered througha pad celite, washing the solids with DOE. The filtrate was concentrated to afford a viscous green oil of (R,E)-N-(4-bromo-2,5-difluorobenzylidene)-2-methylpropane-2-sulfinamide (7.2 g,22.2 mmol, 93 percent yield). Material was taken onto next step without further purification. LOMS m/z 326.0 (M + H), Rt i .04 mm.
93%	With copper(II) sulfate; at 60℃; for 18h;	StepiTo a round bottom flask with stir bar was added <strong>[357405-75-5]4-bromo-2,5-difluorobenzaldehyde</strong> (5.3 g, 24.0 mmol), (R)-2-methylpropane-2-sulfinamide (3.2 g, 26.4 mmol) and DOE (80 mL). To this mixture was then added copper (II) sulfate (5.74 g, 36.0 mmol). The reaction mixture was heated in a preheated oil bath at 60 00 for i8 hours. The reaction mixture was filtered througha pad celite, washing the solids with DOE. The filtrate was concentrated to afford a viscous green oil of (R,E)-N-(4-bromo-2,5-difluorobenzylidene)-2-methylpropane-2-sulfinamide (7.2 g,22.2 mmol, 93 percent yield). Material was taken onto next step without further purification. LOMS m/z 326.0 (M + H), Rt 1.04 mm.

Reference： [1]Patent: WO2014/141153,2014,A1 .Location in patent: Page/Page column 54
[2]Patent: WO2014/141104,2014,A1 .Location in patent: Page/Page column 132

11
[ 54221-96-4 ]
[ 196929-78-9 ]
(R,E)-N-((6-methoxypyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate; In dichloromethane; at 20℃; for 5h;	To a stirred suspension of (R)-2-methylpropane-2-sulfinamide (l.Og, 8.25 mmol) and Cs2C03 (4.03 g, 12.38 mmol) in DCM (15 mL) was added a solution of 6- methoxypicolinaldehyde (1.092 mL, 9.08 mmol) in DCM (2 mL) dropwise. The solution was then stirred at rt for 5 h. The solid was filtered and solvent was removed. The crude product was purified by normal phase chromatography to provide VI-3a as clear colorless oil (1.91 g, 96percent). LC-MS (ESI) m/z: 241.0 [M+H]+; 'H NMR (400MHZ, CDCI3) delta 8.59 (s, 1H), 7.72 - 7.58 (m, 2H), 6.85 (dd, J=7.9, 1.1 Hz, 1H), 3.99 (s, 3H), 1.29 (s, 9H).

Reference： [1]Patent: WO2015/2915,2015,A1 .Location in patent: Page/Page column 224-225

12
[ 54221-96-4 ]
[ 196929-78-9 ]
(R)-N-((6-methoxypyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate; In dichloromethane; at 20℃; for 5h;	To a stirred suspension of (R)-2-methylpropane-2-sulfinamide (1.0 g, 8.3 mmol) and CS2CO3 (4.0 g, 12 mmol) in DCM (15 mL), was added a solution of 6- methoxypicolinaldehyde in DCM (1.1 mL, 9.1 mmol, in 3 mL DCM) dropwise. The solution was then stirred at rt for 5 h. The solid was filtered off, and the solvent was removed. The crude product was purified by normal phase chromatography to afford Intermediate 11A (1.9 g, 96percent) as a clear colorless oil. LC-MS (ESI) m/z: 241.0 [M+H]+; XH NMR (400MHz, CDC13) delta 8.59 (s, 1H), 7.72 - 7.58 (m, 2H), 6.85 (dd, J= 7.9, 1.1 Hz, 1H), 3.99 (s, 3H), 1.29 (s, 9H).

Reference： [1]Patent: WO2015/2915,2015,A1 .Location in patent: Page/Page column 107

13
[ 118289-17-1 ]
[ 196929-78-9 ]
(R)-N-[(1E)-(2-bromopyridin-4-yl)methylidene]-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With caesium carbonate; In dichloromethane; at 20℃; for 18.5h;	To a stirred suspension of(R)-2-methylpropane-2-sulfinamide (13.03 g, 108 mmol) and Cs2CO3 (52.5 g, 161 mmol) in DCM (400 ml) was added 2-bromopyridine-4- carbaldehyde (20 g, 108 mmol) over 10 mm. The reaction mixture was then stirred for 18.5 h at rt. The reaction mixture was concentrated and the residue was diluted with EtOAc (50 ml) and washed with brine (3 x 20 ml). The organic layer was dried overMgSO4, filtered and the filtrate concentrated. The residue was purified by normal phase chromatography using hexanes and EtOAc as eluents to afford (R)-N-[(1E)-(2- bromopyridin-4-yl)methylidene]-2-methylpropane-2-sulfinamide (27.2 g, 87percent) as a white solid. MS(ESI) m/z: 289-291.0 (M+H).
87%	With caesium carbonate; In dichloromethane; at 20℃; for 18.5h;	To a stirred suspension of (R)-2-methylpropane-2-sulfinamide (13.03 g, 108 mmol) and CS2CO3 (52.5 g, 161 mmol) in DCM (400 ml) was added 2-bromopyridine-4- carbaldehyde (20 g, 108 mmol) over 10 min. The reaction mixture was then stirred for 18.5 h at rt. The reaction mixture was concentrated and the residue was diluted with EtOAc (50 ml) and washed with brine (3 x 20 ml). The organic layer was dried over MgS04 and filtered and then the filtrate was concentrated. The residue was purified by normal phase chromatography using hexanes and EtOAc as eluents to afford (27.2 g, 87percent) of (R)-N-[(lE)-(2-bromopyridin-4-yl)methylidene]-2-methylpropane-2-sulfinamide as a white solid. MS(ESI) m/z: 289-291.0 (M+H)+.
59%	With titanium(IV) tetraethanolate; In dichloromethane; at 20℃;Inert atmosphere;	To a solution of 2?bromopyridine?4?carbaldehyde (7e, 1g,5.38 mmol) and Ti(OEt)4 (5.64 mL, 26.9 mmol) in CH2Cl2(10.75 mL) was added (R)-2-methylpropane-2-sulfinamide(0.717 g, 5.91 mmol). The reaction was stirred overnight at rt.The reaction mixture was poured into a rapidly stirred mixtureof brine. The resulting suspension was filtered through a plug ofCelite and the filter cake was washed with CH2Cl2 to give a biphasicfiltrate. The layers were separated. The organic layer waswashed with brine, dried over MgSO4, filtered and concentrated.Column chromatography on silica gel (gradient elution 0?30percent EtOAc/Hex) gave 0.92 g (59percent yield) of (R)?N?[(1E)?(2?bromopyridin?4?yl)methylidene]?2?methylpropane?2?sulfinamide as a yellowoil. LCMS: 288.9 (M+H)+ and 290.9 (M+2+H)+. 1H NMR(400 MHz, CDCl3) d: 8.56?8.52 (m, 2H), 7.89 (s, 1H), 7.64 (dd,J = 4.9, 1.6 Hz, 1H), 1.29 (s, 9H).

Reference： [1]Patent: WO2015/116886,2015,A1 .Location in patent: Page/Page column 191
[2]Patent: WO2015/116882,2015,A1 .Location in patent: Page/Page column 180; 181
[3]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2257 - 2272

14
[ 191805-29-5 ]
[ 196929-78-9 ]
(R,E)-tert-butyl 1-((tert-butylsulfinyl)imino)-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.7%	With titanium(IV) tetraethanolate; at 105℃; for 4h;Inert atmosphere;	Step b: A flask containing tert-butyl 1 -oxo-8-azaspiro [4.Sjdecane-8- carboxylate (238 g, 939 mmol) was charged with (R)-(+)-2-methyl-2-propanesulfinamide (171 g, 1409 mmol) under N2 atmosphere. Titanium(IV)ethoxide (985 mL, 4.70 mol) was added and the mixture was then heated to 105 C for 4 h. The heating mantle was removed and the mixture was vacuum transferred, under a stream of N2, with EtOAc (6 L) via a FEP tubing cannula to a 10 L, 4-necked flask equipped with a mechanical overhead stirrer and a 250 mL addition funnel with an N2 inlet adapter that was cooled in a cold water bath. Water (288 mL) was added dropwise via theaddition funnel over 30-45 mm, resulting in the precipitation of a large volume of light yellow salts. The suspension was aged for 15 minutes with the bath removed before filtering the entire mixture through Celite, washing with EtOAc (2 x 1 L). The filtrate was then washed with water (3 x 1 L) and concentrated under reduced pressure. Upon concentration and back-addition of heptane (2 L), the water was azeotroped off, which led to the precipitation of a cloudy, white film of salts on the interior wall of the flask. The light brown mixture was filtered through a medium sintered glass funnel (rinsed with EtOAc and heptane). The filtrate was further concentrated until most of the EtOAc was removed, and additional heptane was added (1 L). The mixture was concentrated further under reduced pressure to produce a precipitate, and additional heptane (500 mL) was added to keep the mixture mobile. The mixture was stirred at RT, then cooled with an ice bath before isolating the solids by vacuum filtration. The solid was washed three times with ice-cold heptane. The solid was dried under reduced pressure to give (R,E)-tert-butyl 1-((tert- butylsulfinyl)imino)-8-azaspiro[4.Sjdecane-8-carboxylate as a cream solid (408.9 g, 66.7% yield). ?H NMR (400 MHz, Chloroform-d) oe ppm 3.93 (m, 2 H), 3.05 (m, 3 H), 2.71 (dt, J=19.6, 7.2 Hz, 1 H), 1.96-1.71 (m, 6 H), 1.49 (s, 9 H), 1.42 (m, 2 H), 1.27 (s, 9 H).
66.7%	With titanium(IV) tetraethanolate; at 105℃; for 4h;Inert atmosphere;	Step b: A flask containing ferf-butyl l-oxo-8-azaspiro[4.5]decane-8- carboxylate (238 g, 939 mmol) was charged with (R)-(+)-2-methyl-2-propanesulfinamide (171 g, 1409 mmol) under N2 atmosphere. Titanium(IV)ethoxide (985 mL, 4.70 mol) was added and the mixture was then heated to 105 C for 4 h. The heating mantle was removed and the mixture was vacuum transferred, under a stream of N2j with EtOAc (6 L) via a FEP tubing cannula to a 10 L, 4-necked flask equipped with a mechanical overhead stirrer and a 250 mL addition funnel with an N2 inlet adapter that was cooled in a cold water bath. Water (288 mL) was added dropwise via the addition funnel over 30-45 min, resulting in the precipitation of a large volume of light yellow salts. The suspension was aged for 15 minutes with the bath removed before filtering the entire mixture through Celite, washing with EtOAc (2 x 1 L). The filtrate was then washed with water (3 x 1 L) and concentrated under reduced pressure. Upon concentration and back-addition of heptane (2 L), the water was azeotroped off, which led to the precipitation of a cloudy, white film of salts on the interior wall of the flask. The light brown mixture was filtered through a medium sintered glass funnel (rinsed with EtOAc and heptane). The filtrate was further concentrated until most of the EtOAc was removed, and additional heptane was added (1 L). The mixture was concentrated further under reduced pressure to produce a precipitate, and additional heptane (500 mL) was added to keep the mixture mobile. The mixture was stirred at RT, then cooled with an ice bath before isolating the solids by vacuum filtration. The solid was washed three times with ice-cold heptane. The solid was dried under reduced pressure to give (R,E)-tert-butyl l-((tert- butylsulfinyl)imino)-8-azaspiro[4.5]decane-8-carboxylate as a cream solid (408.9 g, 66.7% yield). NMR (400 MHz, Chloroform- ) delta ppm 3.93 (m, 2 H), 3.05 (m, 3 H), 2.71 (dt, 7=19.6, 7.2 Hz, 1 H), 1.96-1.71 (m, 6 H), 1.49 (s, 9 H), 1.42 (m, 2 H), 1.27 (s, 9 H).

Reference： [1]Patent: WO2016/203405,2016,A1 .Location in patent: Paragraph 00367
[2]Patent: WO2016/203406,2016,A1 .Location in patent: Paragraph 00368
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 1781 - 1792

15
[ 196929-78-9 ]
[ 208264-53-3 ]
N-[1-(4-bromo-1,3-thiazol-2-yl)ethylidene]-(R)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With titanium(IV) tetraethanolate; In tetrahydrofuran; at 75℃; for 16h;	This experiment was carried out in two identical batches. Titanium(IV) ethoxide (321 g, 1 .41 mol) was added in one portion to a room temperature (-15 C) solution of 1 -(4-bromo-1 ,3-thiazol-2-yl)ethanone (145 g, 704 mmol) and (f?)-2-methylpropane-2- sulfinamide (128 g, 1 .06 mol) in tetrahydrofuran (2.0 L), and the reaction mixture was heated at 75 C for 16 hours. It was then cooled to room temperature (-15 C), quenched with water (500 mL), and filtered. The filter cake was washed with ethyl acetate (4 x 500 mL), and the combined filtrates were concentrated in vacuo. The residues from the two batches were combined and purified via silica gel chromatography (Gradient: 5% to 25% ethyl acetate in petroleum ether), providing the product as a yellow solid. Yield: 340 g, 1.10 mol, 78%.1H NMR (400 MHz, CDCI3) delta 7.42 (s, 1 H), 2.85 (s, 3H), 1.32 (s, 9H).

Reference： [1]Patent: WO2017/51294,2017,A1 .Location in patent: Page/Page column 40; 41

16
[ 37687-18-6 ]
[ 196929-78-9 ]
(R,Z)-2-methyl-N-(1-(1-methyl-1H-pyrazol-4-yl)ethylidene)propane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With titanium(IV) isopropylate; In toluene; at 110℃; for 16h;Inert atmosphere;	To a mixture of (R)-2-methylpropane-2-sulfinamide (2.58 g, 21.27 mmol) and <strong>[37687-18-6]1-(1-methyl-1H-pyrazol-4-yl)ethanone</strong> (2.2 g, 17.72 mmol) in toluene (35 mL) was added titanium(IV) isopropoxide (10.49 mL, 35.44 mmol) under a nitrogen atmosphere. The reaction mixture was heated to 110 C for 16 h. Sat. aq. NaHCO3 (10 mL) was added and filtered through a short pad of anhydrous Na2SO4, washed with EtOAc (20 mL x 3). The combined organic layers were concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc =2 : 3) to give the title compound (2.5 g, 62%) as a yellow solid. 1H NMR(400 MHz, CDCl3) delta 7.85 (s, 1H), 7.81 (s, 1H), 3.93 (s, 3H), 2.61 (s, 3H), 1.27 (s, 9H).

Reference： [1]Patent: WO2017/58821,2017,A1 .Location in patent: Page/Page column 327; 328

17
[ 61563-28-8 ]
[ 196929-78-9 ]
(R)-N-(2-chloro-4-methylbenzylidene)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
442 mg	With caesium carbonate; In dichloromethane; at 45℃;	To a stirred solution of 2-chloro-3-methyl-benzaldehyde (327 mg, 2.12 mmol) in dichloromethane (10 mL) was added (R)-(+)-2-methyl-2-propanesulfinidine (308 mg, 2.54 mmol) and cesium carbonate (993 mg, 3.05 mmol) at RT. The resulting mixture was stirred overnight at 45 C. The reaction mixture was filtered through celite bed and the bed was washedwith dichloromethane (5 mL x 2). The combined filtrates were concentrated and the residue thus obtained was purified by silica gel column chromatography to yield 442 mg of the titled compound. ?H NMR (300 MHz, CDC13) oe 1.27 (s, 9H), 1.41 (s, 1H), 2.39 (s, 3H), 7.15 (d, J = 8.4 Hz, 2H), 7.95 (d, J = 7.8 Hz, 1H), 8.99 (s, 1H); ESI-MS (m/z) 258 (M+H)+

Reference： [1]Patent: WO2017/199103,2017,A1 .Location in patent: Page/Page column 44

18
[ 351410-62-3 ]
[ 196929-78-9 ]
(R,E)-N-((5-fluoro-2-methoxypyridin-3-yl) methylene)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In dichloromethane; at 20℃;Inert atmosphere;	A flask (equipped with a nitrogen inlet, overhead stirring, and thermocouple) was charged with DCM (3 L, 10 vol). The mixture was agitated, and the mixture was deoxygenated with subsurface nitrogen for 1 h. Next 5-fluoro-2- methoxynicotinaldehyde (1) (300 g, 1934 mmol) and (R)-2-methylpropane-2-sulfinamide (246 g, 2031 mmol) were charged. The CS2CO3 (441 g, 1354 mmol) was charged in portions, with agitation, over several minutes . The reaction was agitated overnight at ambient temperature under nitrogen. The reaction was sampled and analyzed by HPLC for reaction completion. A 15 wt% solution of the citric acid (in water) was prepared (using 1.5 eq of citric acid based on the CS2CO3 input). This solution was charged into the reactor with the reaction mixture, using an addition funnel. The charge was done in portions. The biphasic mixture was transferred to a separatory funnel, and the lower DCM layer was removed. The upper aqueous layer was removed and discarded. The DCM layer was transferred back into the separatory funnel, and washed with saturated brine (2 L). Again, the lower DCM layer was removed, and the upper aqueous layer was discarded. The DCM layer was concentrated under vacuum (rotovap) to give the desired product.
	With caesium carbonate; In dichloromethane; at 20℃;Inert atmosphere;	A flask (equipped with a nitrogen inlet, overhead stirring, and thermocouple) was charged with DCM (3 L, 10 vol). The mixture was agitated, and the mixture was deoxygenated with subsurface nitrogen for 1 h. Next 5-fluoro-2- methoxynicotinaldehyde (1) (300 g, 1934 mmol) and (R)-2-methylpropane-2-sulfinamide (246 g, 2031 mmol) were charged. The CS2CO3 (441 g, 1354 mmol) was charged in portions, with agitation, over several minutes. The reaction was agitated overnight at ambient temperature under nitrogen. The reaction was sampled and analyzed by HPLC for reaction completion. A 15 wt% solution of the citric acid (in water) was prepared (using 1.5 eq of citric acid based on the CS2CO3 input). This solution was charged into the reactor with the reaction mixture, using an addition funnel. The charge was done in portions. The biphasic mixture was transferred to a separatory funnel, and the lower DCM layer was removed. The upper aqueous layer was removed and discarded. The DCM layer was transferred back into the separatory funnel, and washed with saturated brine (2 L). Again, the lower DCM layer was removed, and the upper aqueous layer was discarded. The DCM layer was concentrated under vacuum (rotovap) to give the desired product.

Reference： [1]Patent: WO2018/81417,2018,A2 .Location in patent: Page/Page column 159
[2]Patent: WO2019/84285,2019,A1 .Location in patent: Page/Page column 202; 203

19
[ 19832-98-5 ]
[ 196929-78-9 ]
(R<SUB>S</SUB>)-N-(tert-butanesulfinyl)-4-methyl-3,4-dihydronaphthalen-1(2H)-imine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 2219 - 2233

20
[ 2840-44-0 ]
[ 196929-78-9 ]
(R<SUB>S</SUB>)-N-(tert-butanesulfinyl)-7-fluoro-3,4-dihydronaphthalen-1(2H)-imine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 2219 - 2233

21
[ 137890-05-2 ]
[ 196929-78-9 ]
C₁₀H₁₇N₃OS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4091 - 4109

22
[ 351410-62-3 ]
[ 196929-78-9 ]
(R)-N-((5-fluoro-2-methoxypyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.5 g	With caesium carbonate; In dichloromethane; at 30℃; for 4h;Inert atmosphere;	Dissolve 5-fluoro-2-methoxypyridine-3-formaldehyde 4a (10.00 g, 64.5 mmol) in dichloromethane (120 mL), Add cesium carbonate (42.00 g, 129.00 mmol) and (R)-2-methylpropane-2-sulfinamide (8.26 g, 67.70 mmol) in this order, and react at 30 C for 4 hours after the addition. After the reaction, the solution was filtered, and the filtrate was directly spin-dried to obtain (R)-N-((5-fluoro-2-methoxypyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide 4b. (17.50 g, yellow oil), directly into the next step without further purification;

Reference： [1]Patent: CN110627812,2019,A .Location in patent: Paragraph 0074; 0086

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[ 196929-78-9 ]

A812105[ 907200-18-4 ]

(R)-2-Methylpropane-2-sulfinamide-15N

Reason: Stable Isotope

Ghs Precautionary Statements

Precautionary Statements-General
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P304	IF INHALED:
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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
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P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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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. 196929-78-9 ] {[proInfo.proName]}

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[ 196929-78-9 ] Synthesis Path-Downstream 1~22

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