[ CAS No. 74257-00-4 ] {[proInfo.proName]}

Name: 74257-00-4|1-(Mesitylsulfonyl)-3-nitro-1H-1,2,4-triazole|97%
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SKU: A204347
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2D 3D

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Quality Control of [ 74257-00-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 74257-00-4 ]

Product Details of [ 74257-00-4 ]

CAS No. :	74257-00-4	MDL No. :	MFCD00009754
Formula :	C₁₁H₁₂N₄O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SFYDWLYPIXHPML-UHFFFAOYSA-N
M.W :	296.30	Pubchem ID :	716901
Synonyms :

Calculated chemistry of [ 74257-00-4 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.27
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.81
TPSA :	119.05 Å²

Pharmacokinetics

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

Lipophilicity

Log Po/w (iLOGP) :	1.89
Log Po/w (XLOGP3) :	2.49
Log Po/w (WLOGP) :	2.43
Log Po/w (MLOGP) :	2.6
Log Po/w (SILICOS-IT) :	-0.95
Consensus Log Po/w :	1.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.45
Solubility :	0.104 mg/ml ; 0.000351 mol/l
Class :	Soluble
Log S (Ali) :	-4.64
Solubility :	0.00686 mg/ml ; 0.0000232 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.01
Solubility :	0.288 mg/ml ; 0.000971 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.33

Safety of [ 74257-00-4 ]

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

Application In Synthesis of [ 74257-00-4 ]

* 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.

Upstream synthesis route of [ 74257-00-4 ]
Downstream synthetic route of [ 74257-00-4 ]

[ 74257-00-4 ] Synthesis Path-Upstream 1~1

1
[ 773-64-8 ]
[ 24807-55-4 ]
[ 74257-00-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With triethylamine In 1,4-dioxane for 1.5 h; Cooling with ice	An oven dried 1.0 l round-bottomedflask containing a magnetic stir bar was equipped with a Claisen adapter. 3-Nitro-1,2,4-triazole (19.5 g, 0.171 mol), dry dioxane (200 ml) and triethylamine (1.0 equiv., 17.3 g,0.171 mol) was transferred to the reaction flask and the solution was cooled in an ice-bathwith magnetic stirring.47 The Claisen adapter was fitted with a 200 ml pressure-equalizingaddition funnel, containing a dioxane solution (150 ml) of mesitylenesulfonyl chloride(37.4 g, 0.171 mol). The solution of mesitylenesulfonyl chloride was added dropwise overa period of approx. 0.5 h and the final suspension was stirred for an additional 1 h andthen warmed to rt. After removal of the precipitated Et3N·HCl by filtration, the filtratewas concentrated in vacuo to give a yellow solid, which was dissolved in dichloromethane(150 ml) and the solution was washed with water (150 ml).48 The organic layer was driedover anhydrous Na2SO4 and evaporated in vacuo to give a yellow solid. Recrystallizationfrom boiling toluene (20–30 ml) followed by washing with ice-cold toluene and dryingovernight at 1.9 mmHg, provided 24–25 g (46percent–48percent) of the title compound as light yellow solid,49 mp. 131C–133C (lit.37 130C–132C). Rf = 0.23 (20percent hexane in CH2Cl2, UV);1H NMR (300 MHz, CDCl3): δ 8.84 (s, 1H), 7.07 (s, 2H), 2.69 (s, 6H), 2.34 (s, 3H);13C NMR (75 MHz, CDCl3): δ 162.9, 147.5, 145.2, 142.5, 133.0, 127.9, 23.2, 21.3; IR(solid): 3126, 2983, 2947, 1597.Anal. Calcd. for C11H12N4O4S: C, 44.59; H, 4.08; N, 18.91. Found: C, 44.69; H,3.88; N, 18.72. The purity of the product (96percent) established by RP-HPLC, tR = 8.41 min(254 nm).

Reference： [1] Organic Preparations and Procedures International, 2014, vol. 46, # 3, p. 267 - 271
[2] Tetrahedron Letters, 1986, vol. 27, # 45, p. 5529 - 5532

[ 74257-00-4 ] Synthesis Path-Downstream 1~18

1
[ 28288-50-8 ]
[ 74257-00-4 ]
[ 76991-94-1 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2265 - 2268

3
[ 21090-30-2 ]
[ 74257-00-4 ]
[ 76859-60-4 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 5529 - 5532

4
[ 123027-47-4 ]
[ 74257-00-4 ]
[ 132885-40-6 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1394 - 1399

5
[ 123027-51-0 ]
[ 74257-00-4 ]
[ 132885-38-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1394 - 1399

6
[ 74257-00-4 ]
[ 76887-38-2 ]
[ 76887-39-3 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2265 - 2268

7
[ 74257-00-4 ]
[ 110434-97-4 ]
[ 110434-90-7 ]
[ 110507-86-3 ]
[ 110507-85-2 ]

Reference： [1]Liebigs Annalen der Chemie,1987,p. 1065 - 1072

8
[ 74257-00-4 ]
[ 110434-95-2 ]
[ 110434-88-3 ]
[ 110507-86-3 ]

Reference： [1]Liebigs Annalen der Chemie,1987,p. 1065 - 1072

9
[ 128110-25-8 ]
[ 74257-00-4 ]
[ 127940-28-7 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 5353 - 5356

10
[ 773-64-8 ]
[ 24807-55-4 ]
[ 74257-00-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With triethylamine; In 1,4-dioxane; for 1.5h;Cooling with ice;	An oven dried 1.0 l round-bottomedflask containing a magnetic stir bar was equipped with a Claisen adapter. 3-Nitro-1,2,4-triazole (19.5 g, 0.171 mol), dry dioxane (200 ml) and triethylamine (1.0 equiv., 17.3 g,0.171 mol) was transferred to the reaction flask and the solution was cooled in an ice-bathwith magnetic stirring.47 The Claisen adapter was fitted with a 200 ml pressure-equalizingaddition funnel, containing a dioxane solution (150 ml) of mesitylenesulfonyl chloride(37.4 g, 0.171 mol). The solution of mesitylenesulfonyl chloride was added dropwise overa period of approx. 0.5 h and the final suspension was stirred for an additional 1 h andthen warmed to rt. After removal of the precipitated Et3N·HCl by filtration, the filtratewas concentrated in vacuo to give a yellow solid, which was dissolved in dichloromethane(150 ml) and the solution was washed with water (150 ml).48 The organic layer was driedover anhydrous Na2SO4 and evaporated in vacuo to give a yellow solid. Recrystallizationfrom boiling toluene (20?30 ml) followed by washing with ice-cold toluene and dryingovernight at 1.9 mmHg, provided 24?25 g (46percent?48percent) of the title compound as light yellow solid,49 mp. 131C?133C (lit.37 130C?132C). Rf = 0.23 (20percent hexane in CH2Cl2, UV);1H NMR (300 MHz, CDCl3): delta 8.84 (s, 1H), 7.07 (s, 2H), 2.69 (s, 6H), 2.34 (s, 3H);13C NMR (75 MHz, CDCl3): delta 162.9, 147.5, 145.2, 142.5, 133.0, 127.9, 23.2, 21.3; IR(solid): 3126, 2983, 2947, 1597.Anal. Calcd. for C11H12N4O4S: C, 44.59; H, 4.08; N, 18.91. Found: C, 44.69; H,3.88; N, 18.72. The purity of the product (96percent) established by RP-HPLC, tR = 8.41 min(254 nm).

Reference： [1]Organic Preparations and Procedures International,2014,vol. 46,p. 267 - 271
[2]Tetrahedron Letters,1986,vol. 27,p. 5529 - 5532

11
[ 74257-00-4 ]
[ 4105-38-8 ]
[ 76887-37-1 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2265 - 2268

12
[ 74257-00-4 ]
[ 191086-83-6 ]
[ 191086-85-8 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 4635 - 4642

13
[ 74257-00-4 ]
[ 191086-82-5 ]
[ 191086-84-7 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 4635 - 4642

14
[ 74257-00-4 ]
[ 40615-39-2 ]
triethylammonium dimethyl boranophosphate [ No CAS ]
2,4,6-Trimethyl-benzenesulfonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
5`-O-(dimethoxytrityl)thymidin-3'-yl dimethyl boranophosphate [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 4137 - 4140

15
[ 39096-01-0 ]
C₂₀H₁₈NO₄P [ No CAS ]
[ 74257-00-4 ]
(naphthalen-1-yl-styrylcarbamoyl-methyl)-phosphonic acid didiethylcarbamoylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; at 20.0℃; for 3.5h;	Example 47 (Naphthalen-1-yl-styrylcarbamoyl-methyl)-phosphonic acid didiethylcarbamoylmethyl ester, Cpd 180 To a solution of Compound 37 (0.21 g, 0.53 mmol) and N,N-diethyl-2-hydroxyacetamide (0.15 g, 1.17 mmol) in pyridine (5 mL) was added 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT; 0.47 g, 1.59 mmol) and the mixture was stirred at rt for 3.5 h. The reaction was concentrated under reduced pressure, and the residue taken up in EtOAc. The solution was washed sequentially with 1N KHSO4 (aq), saturated NaHCO3 (aq), and brine, then dried (Na2SO4), and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica, 0-30percent acetone/heptane) to yield 0.07 g of Compound 180 as a yellow solid: HPLC: 3.88 min; MS (ES) m/z 594 (MH+).

Reference： [1]Patent: US2005/176769,2005,A1 .Location in patent: Page/Page column 73

16
N,N-bis(2-chloroethyl)-P-[N'-(t-Boc)-2-aminoethyl]phosphonamidic acid [ No CAS ]
[ 74257-00-4 ]
N,N-bis(2-chloroethyl)-P-[N'-(t-Boc)-2-aminoethyl]phosphonic diamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; ethyl acetate;	N,N-Bis(2-chloroethyl)-P-[N'-t-Boc)-2-aminoethyl]phosphonic diamide 41 1.75 g of N,N-bis(2-chloroethyl)-P-[N'-(t-Boc)-2-aminoethyl]phosphonamidic acid 40 is dissolved in dry pyridine (50 mL) and concentrated in vacuo. This process is repeated once more with more pyridine (50 mL). The residue is dissolved in dry pyridine (25 mL) and 2.96 g of 1-(2-mesitylenesulfonyl)-3-nitro-1,2,4-triazole is added. Ammonia gas is bubbled through for 60 minutes. The reaction mixture is concentrated in vacuo, redissolved in ethyl acetate (100 mL) and washed with saturated NaHCO3 (2*100 mL) and saturated NaCl (75 mL). The organic phase is dried over anhydrous MgSO4, concentrated in vacuo and purified by flash chromatography to yield N,N-bis(2-chloroethyl)-P-[N'-(t-Boc)-2-aminoethyl]phosphonic diamide 41.

Reference： [1]Patent: US6258360,2001,B1

17
N1,N1-diisopropyl-N2-(4-methylbenzene-1-sulfonyl)-3-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)propanamidine [ No CAS ]
[ 74257-00-4 ]
N1,N1-diisopropyl-N2-(4-metylbenzenesulfonyl)-3-(4-(3-nitro-1h-1,2,4-triazole-1-yl)-2-oxo-3,4-dihydropyrimidine-1(2H)-yl)propionamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With pyridine; diphenyl hydrogen phosphate; at 25.0℃; for 48.0h;Inert atmosphere;	To a stirred mixture of uracil derivative 15 (105.1 mg, 0.25mmol) in pyridine (1 mL) under argon, 1-(mesitylsulfonyl)-3-nitro-1H-1,2,4-triazole) (MSNT) (265 mg, 1.14 mmol) anddiphenylphosphate (30 mg, 0.12 mmol) were added. Afterstirring the reaction mixture for 48 hours at roomtemperature, the pyridine was evaporated and methanol(10 mL) was added. The product 30 precipitates frommethanol as white crystals: 112 mg (86 percent); Rf = 0.76 (CH2Cl2 /MeOH = 20 : 1); 1H NMR (600 MHz, DMSO-d6) delta / ppm: 9.74(s, 1H, CH-triazole), 8.42 (d, 1H, J6',5' = 7.0 Hz, H-6'), 7.67 (d,2H, J = 8.0 Hz, Ar), 7.33 (d, 2H, J = 8.0 Hz, Ar), 7.08 (d, 1H,J5',6' = 7.0 Hz, H-5'), 4.37 (m, 1H, CH-(CH3)), 4.24 (t, 2H, J3,2 =7.5 Hz, CH2-3), 3.70 (brs, 1H, CH-(CH3)2), 3.34 (t, 2H, J2,3= 7.5Hz, CH2-2), 2.36 (s, 3H, CH3-Ts), 1.24 (dd, 12H, J = 6.4 Hz, J =3.3 Hz, 2×CH-(CH3)2); 13C-NMR (150 MHz, DMSO-d6) delta /ppm: 163.1 (s, C-4'), 161.5 (s, C-1), 158.2 (s, triazole), 154.3(d, C-6'), 154.1 (s, C-2'), 145.9 (s, triazole), 141.5 (s, Ar),141.3 (s, Ar), 129.2 (d, Ar), 125.5 (d, Ar), 94.2 (d, C-5'), 50.3(d, CH-(CH3)2), 48.2 (t, CH2-3), 47.4 (d, CH-(CH3)2), 31.1 (t,CH2-2), 20.9 (q, CH3-Ts), 20.1 (q, CH-(CH3)2), 19.6 (q, CH-(CH3)2).

Reference： [1]Croatica Chemica Acta,2017,vol. 90,p. 625 - 636

18
N1-cyclopentyl-N2-(4-methylbenzene-1-sulfonyl)-3-(2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)propanamidine [ No CAS ]
[ 74257-00-4 ]
N1-cyclopentyl-N2-(4-metylbenzenesulfonyl)-3-(4-(3-nitro-1h-1,2,4-triazole-1-yl)-2-oxo-3,4-dihydropyrimidine-1(2H)-yl)propionamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With pyridine; diphenyl hydrogen phosphate; at 25.0℃; for 48.0h;Inert atmosphere;	To a stirred mixture of uracil derivative 18 (100 mg,0.25 mmol) in pyridine (1 mL) under argon,1-(mesitylsulfonyl)-3-nitro-1H-1,2,4-triazole) (MSNT)(265 mg, 1.14 mmol) and diphenylphosphate (30 mg,0.12 mmol) were added. After stirring the reaction mixturefor 48 hours at room temperature, the pyridine wasevaporated and methanol (10 mL) was added. Productprecipitates from methanol as white crystals 67 mg (56 percent):Rf = 0.52 (CH2Cl2 / MeOH 20 : 1); 1H NMR (300 MHz, DMSOd6)delta / ppm: 9.75 (s, 1H, CH-triazole), 8.76 (d, 1H, J = 6.9 Hz,NH-cyclopentyl), 8.34 (d, 1H, J6',5' = 7.0 Hz, H-6'), 7.70 (d, 2H,J = 7.0 Hz, Ar), 7.32 (d, 2H, J = 7.4 Hz, Ar), 7.01 (d, 1H, J5',6'= 7.0 Hz, H-5'), 4.31 (t, 2H, J3,2 = 6.0 Hz, CH2-3), 4.00 (m, 1H,CH-cyclopentyl), 3.06 (t, 2H, J2,3= 6.0 Hz, CH2-2), 2.35 (s, 3H,CH3-Ts), 1.76 (m, 2H, CH2-cyclopentyl), 1.54 (m, 2H, CH2-cyclopentyl), 1.45 (m, 2H, CH2-cyclopentyl), 1.38 (m, 2H,CH2-cyclopentyl); 13C-NMR (150 MHz, DMSO-d6) delta / ppm:163.9 (s, C-4'), 163.2 (s, C-1), 158.0 (s, triazole), 154.4 (d, C-6'), 153.8 (s, C-2'), 145.8 (s, triazole), 141.5 (s, Ar), 141.4 (s,Ar), 129.2 (d, Ar), 125.6 (d, Ar), 93.5 (d, C-5'), 52.9 (d, CHcyclopentyl)48.9 (t, CH2-3), 32.5 (t, CH2-2), 31.6 (t, CH2-cyclopentyl), 23.5 (t, CH2-cyclopentyl), 20.9 (q, CH3-Ts).

Reference： [1]Croatica Chemica Acta,2017,vol. 90,p. 625 - 636

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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
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. 74257-00-4 ] {[proInfo.proName]}

Quality Control of [ 74257-00-4 ]

Related Doc. of [ 74257-00-4 ]

Product Details of [ 74257-00-4 ]

Calculated chemistry of [ 74257-00-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 74257-00-4 ]

Application In Synthesis of [ 74257-00-4 ]

[ 74257-00-4 ] Synthesis Path-Upstream 1~1

[ 74257-00-4 ] Synthesis Path-Downstream 1~18

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry