6397-33-7|2-(Isopropylthio)aniline| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 6397-33-7 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 6397-33-7 ]

CAS No. :	6397-33-7
Formula :	C₉H₁₃NS
M.W :	167.27
SMILES Code :	NC1=CC=CC=C1SC(C)C
MDL No. :	MFCD08691961
InChI Key :	BZPPEJDGWPFYAL-UHFFFAOYSA-N
Pubchem ID :	13852720

Safety of [ 6397-33-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 6397-33-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	2
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	52.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	51.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.17
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.0
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.78
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.72
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.15
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.37

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.41
Solubility	0.653 mg/ml ; 0.0039 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.7
Solubility	0.33 mg/ml ; 0.00198 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.96
Solubility	0.182 mg/ml ; 0.00109 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.9 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.68

Application In Synthesis of [ 6397-33-7 ]

* 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 [ 6397-33-7 ]

[ 6397-33-7 ] Synthesis Path-Downstream 1~35

1
[ 6397-33-7 ]
[ 137-07-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1885 - 1890.

2
[ 6397-33-7 ]
[ 106-95-6 ]
[ 102968-92-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 1885 - 1890.

3
[ 1551-21-9 ]
[ 622-37-7 ]
[ 6397-33-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 521 - 528.

5
[ 6397-33-7 ]
[ 13338-49-3 ]
2'-isopropylthio-2-(anilinomethyl)imidazoline [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 2229 - 2239.

6
[ 75-30-9 ]
[ 137-07-5 ]
[ 6397-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In ethanol; at 0 - 20℃; for 4h;Inert atmosphere;	6. Preparation of 2- (isopropylthio) aniline (Compound 9) Under the protection of nitrogen, compound 2-amino-thiophenol (12.52 g, 0.1 mol), 2-iodopropane (18.71 g, 0.11 mol) and ethanol (130 mL) was successively added to a flask. Under stirring, potassium tert-butoxide (14.61 g, 0.13 mol) was slowly added under 0 C. The reaction was warmed to room temperature and conducted for 4 hours, and the reaction was monitored as being substantially completed by HPLC. The reaction mixture was filtered through Celite, the filter cake was washed with ethanol and the combined filtrate was concentrated in vacuo by rotary evaporator. The residue was dissolved in ethyl acetate (200mL), washed with water and brine successively. It was dried over anhydrous sodium sulfate, filtered and concentrated by a rotary evaporator under vacuo to give a crude product. The crude product was purified by silica gel column chromatography to give the desired product as yellowish oil. MS Calcd.: 167; MS Found: 168(M+H) +.

References: [1]European Journal of Organic Chemistry,2020,vol. 2020,p. 937 - 943.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 2229 - 2239.
[3]Patent: EP2990405,2016,A1 .Location in patent: Paragraph 0084; 0090.

7
[ 6397-33-7 ]
[ 862699-08-9 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 7672 - 7678.

8
[ 868961-34-6 ]
[ 6397-33-7 ]
[ 951695-89-9 ]

References: [1]Tetrahedron,2007,vol. 63,p. 9393 - 9400.

9
2-((2,6-diisopropylphenyl)amino)-2-oxoacetyl chloride [ No CAS ]
[ 6397-33-7 ]
[ 951695-92-4 ]

References: [1]Tetrahedron,2007,vol. 63,p. 9393 - 9400.

10
[ 6397-33-7 ]
[ 862699-09-0 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 7672 - 7678.

11
[ 6397-33-7 ]
2-(1-iodo-1-methylethylsulfonyl)-biphenyl [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 7672 - 7678.

12
[ 6397-33-7 ]
[ 862699-12-5 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 7672 - 7678.

13
[ 6397-33-7 ]
[ 862699-10-3 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 7672 - 7678.

14
[ 6397-33-7 ]
[ 179104-32-6 ]

Yield	Reaction Conditions	Operation in experiment
99%		Only 0.2% of 2-aminophenylisopropylsulfane (formed by dehalogenation) was found as an impurity. Pure, colorless 2-amino-6-chlorophenyl-isopropylsulfane with a content of more than 99% was obtained by distillation at a boiling point of 144 C. at 11 mbar.

References: [1]Patent: US5872300,1999,A .

15
copper(II) chloride dihydrate [ No CAS ]
[ 6397-33-7 ]
[ 80383-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sulfur dioxide; ammonia; In tetrahydrofuran; water; acetic acid;	EXAMPLE 2 2-(1-Methylethylthio)benzenesulfonamide To a solution of 2-(1-methylethylthio)benzenamine (200 g, 1.20 mol) in a mixture of concentrated hydrochloric acid (420 ml) and glacial acetic acid (120 ml) was added a solution of sodium nitrile (91.2 g, 1.32 mol) in water (180 ml) at -5 to 0. The solution was stirred at 0 for 1/2 hour and then poured, in several portions, into a mixture of cupric chloride dihydrate (24 g) and liquid sulfur dioxide (370 ml, 8.28 mol), in glacial acetic acid (1200 ml) at 0. The resulting solution was stirred at 0 for one hour and then allowed to warm to room temperature. After several hours, ether (1000 ml) was added, and the reaction mixture was stirred overnight and then poured into ice-water. The resulting oil was extracted into dichloromethane. The organic extracts were washed with water and 5% aqueous sodium bicarbonate (until neutral), dried (MgSO4) and concentrated in vacuo to give an oil. The crude sulfonyl chloride was dissolved in dry THF (2000 ml) and treated with anhydrous liquid ammonia (50 ml, 2.3 mol) at 0. The solution was stirred at 0 for one hour, allowed to warm to room temperature, and stirred an additional 2.5 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with water (1000 ml) and extracted with dichloromethane. The extracts were washed with water, dried (MgSO4) and concentrated to yield the crude product. The oil was dissolved in hot (60) hexane/n-butyl chloride (5/2). Upon cooling, 2-(1-methylethylthio)benzenesulfonamide settled out as a dark oil. NMR (CDCl3)delta: 1.30 (d, --CH3); 3.60 (hept. --CH--); 5.75 (broad s, --NH2); 7.0-8.2 (m, Ar--H). IR (Nujol): 3200-3300 doublet); 1300 and 1150 cm-1.

References: [1]Patent: US4818277,1989,A .

16
[ 137-07-5 ]
[ 75-26-3 ]
[ 6397-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol;	EXAMPLE 1 2-(1-Methylethylthio)benzenamine To a solution of 2-aminothiophenol (90%, 100 g, 0.72 mol) and sodium hydroxide (31.7 g, 0.792 mol) in 90% aqueous ethanol (500 ml) was added dropwise 2-bromopropane (89 g, 0.72 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 3 hours, cooled to room temperature, and then concentrated in vacuo. The residue was diluted with water (300 ml) and extracted with ether (3*500 ml). The ether extracts were washed with water and brine, dried with MgSO4 and concentrated in vacuo to yield the crude product. Distillation through a Vigreaux column gave 2-(1-methylethylthio)benzenamine: bp 94 (2.2-2.4 mm). NMR (CDCl3)delta: 1.25 (d, 6H, --CH3), 3.15 (hept., 1H, --CH--); 4.25 (broad s, 2H, --NH2); 6.40-7.40 (m, 4H, Ar--H).
	With triethylamine; In acetonitrile; at 25℃; for 6h;Reflux;	A solution of 2-aminothiophenol (125 g), acetonitrile (4 L), triethylamine (242.4 g) at 25 C was added bromoisopropane (123 g), and the mixture was refluxed at reflux for 6 hours. Cooling to room temperature, Dropping 2,4,5-trichloropyrimidine (180g), heated to reflux for 12h, The reaction is complete, cool down to 25 C, Add sodium phosphotungstic acid (4g), add 30% hydrogen peroxide (700ml), the temperature to 60 C, the reaction 2 hours, the reaction is completed, Add 10L of water, precipitation of solid, filtration, water and ethanol mixture (1/1) leaching, drying product 302g, purity 98.9%, yield: 87.2%.

References: [1]Patent: US4818277,1989,A .
[2]Patent: CN106854182,2017,A .Location in patent: Paragraph 0020; 0021; 0022.

17
[ 32333-53-2 ]
[ 6397-33-7 ]
4-Chloro-3-trifluoromethyl-2-isopropylthiobenzensulfonanilide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 12 4-Chloro-3-trifluoromethyl-2--isopropylthiobenzensulfonanilide (Compound No. 66) The procedure of Example 10 was repeated using 16.7 g of <strong>[6397-33-7]2-isopropylthioaniline</strong> and 27.9 g of 4-chloro-3-trifluoromethylbenzenesulfonyl chloride to yield 37.7 g of the title compound as a brown oil. Purification by silicagel-colum chromatography gave a colorless oil, n [23/D ] =1.5518.

References: [1]Patent: EP306222,1989,A3 .

18
[ 6397-33-7 ]
[ 79-03-8 ]
[ 1215018-77-1 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 3965 - 3972.

19
[ 6397-33-7 ]
[ 761440-16-8 ]

References: [1]Patent: US2014/128387,2014,A1 .
[2]Patent: EP2990405,2016,A1 .
[3]Patent: CN105622520,2016,A .
[4]Patent: CN105646333,2016,A .
[5]Patent: WO2017/41771,2017,A1 .
[6]Patent: CN108383799,2018,A .

20
[ 1190399-72-4 ]
[ 6397-33-7 ]
[ 1609171-11-0 ]

Yield	Reaction Conditions	Operation in experiment
1.30 g		N-(2-(isopropylthio)phenyl)-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (A-5) A mixture of 4-chloro-3-methyl-6-methylmercaptopyrazolo[3,4-d]pyrimidine (A-3) (1.21 g, 5.63 mmol) and <strong>[6397-33-7]2-(isopropylthio)aniline</strong> (A-4) (1.42 g, 8.50 mmol) in isopropanol (56 mL) was stirred at reflux for 3 h. After cooling down to ambient temperature, TEA (0.78 mL, 5.66 mmol) was added to the mixture, and the solution was again heated to reflux for 0.5 h. After cooling down to ambient temperature, the mixture was filtered to give the title compound (A-5) as white solid (1.30 g, 3.77 mmol). MS-ESI (m/z): 346 (M+H)+.

References: [1]Patent: US2014/128387,2014,A1 .Location in patent: Paragraph 0619; 0620.

21
[ 6397-33-7 ]
[ 1609170-60-6 ]

References: [1]Patent: US2014/128387,2014,A1 .

22
[ 6397-33-7 ]
[ 1609170-61-7 ]

References: [1]Patent: US2014/128387,2014,A1 .

23
[ 6397-33-7 ]
[ 76697-50-2 ]

References: [1]Patent: US2014/128387,2014,A1 .

24
[ 24424-99-5 ]
[ 6397-33-7 ]
C₁₉H₂₉NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In acetonitrile; at 20℃; for 12h;	2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine (B) To a mixture of <strong>[6397-33-7]2-(isopropylthio)aniline</strong> (23 g, 0.14 mol) in acetonitrile (250 mL) at RT was added DMAP (8.5 g, 70 mmol) and (Boc)2O (150 g, 688 mmol). After stirred at ambient temperature for 12 h, the solution was concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1) to give the title compound (B-1). To a mixture of (B-1) (54 g, 0.14 mol) in DCM (500 mL) at 0 C. was added m-CPBA (101 g. 0.44 mol). After stirred at ambient temperature for 12 h, the solution was washed with saturated NaHSO3, brine, dried with Na2SO4 and concentrated to give the compound (B-2) as a solid.

References: [1]Patent: US2014/128387,2014,A1 .Location in patent: Paragraph 0623; 0624.

25
[ 24424-99-5 ]
[ 6397-33-7 ]
C₁₉H₂₉NO₆S [ No CAS ]

References: [1]Patent: US2014/128387,2014,A1 .

26
[ 6397-33-7 ]
5-chloro-N2-(2-(2-d-prop-2-yloxyl)-5-methyl-4-(2,2,6,6-tetrafluoropiperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine [ No CAS ]