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[ CAS No. 6160-65-2 ] {[proInfo.proName]}

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Chemical Structure| 6160-65-2
Chemical Structure| 6160-65-2
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Quality Control of [ 6160-65-2 ]

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Product Details of [ 6160-65-2 ]

CAS No. :6160-65-2 MDL No. :MFCD00005289
Formula : C7H6N4S Boiling Point : -
Linear Structure Formula :SC(N2C3H3)2 InChI Key :RAFNCPHFRHZCPS-UHFFFAOYSA-N
M.W : 178.21 Pubchem ID :80264
Synonyms :

Calculated chemistry of [ 6160-65-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.85
TPSA : 67.73 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : 0.68
Log Po/w (WLOGP) : 0.76
Log Po/w (MLOGP) : -0.42
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 0.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 2.47 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (Ali) : -1.68
Solubility : 3.73 mg/ml ; 0.0209 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.09
Solubility : 14.5 mg/ml ; 0.0815 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.27

Safety of [ 6160-65-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P301+P312+P330-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364-P501 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6160-65-2 ]

* 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 [ 6160-65-2 ]

[ 6160-65-2 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 6160-65-2 ]
  • [ 105655-01-4 ]
  • [ 1000801-20-6 ]
YieldReaction ConditionsOperation in experiment
58% INTERMEDIATE 30; 6-Bromo-2,3-dihvdro-benzo[l,4]oxazine-4-carbothioic acid amide; A solution of Intermediate 13 (11.68 g, 54.6 mmol) in THF (120 mL) was added to thiocarbonyldiimidazole (19.45 g, 109.12 mmol) and the mixture divided between 8 microwave vials. The reactions were each heated to 12O0C under microwave irradiation for 15 minutes, then cooled to r.t., combined and poured into methanolic ammonia (10OmL of a 7M solution, 0.7 mol) and stirred at r.t. overnight. The mixture was concentrated in vacuo, and the residue partitioned between water (200 mL), 2M HCl (50 mL) and then hexane and ether. The resulting solid was collected by filtration and washed with methanol/water to give the title compound (8.72 g, 58%) as a brown solid. 5H (CDCl3) 4.33-4.40 (2H, m), 4.45-4.52 (2H, m), 6.41 (2H, br.s), 6.88 (IH, d, J 8.7 Hz), 7.25 (IH, dd, J 8.7, 2.1 Hz), 7.51 (IH, d, J 2.1 Hz). LCMS (ES+) 275 (M+H)+.; EXAMPLE 1 (METHOD A); 2-(6-Bromo-2.3-dihvdrobenzori,41oxazin-4-yl)-5,5-dimethyl-5,6-dihydro-4H- benzothiazol-7-one; Intermediate 13 (2 g, 9.4 mmol) and l,l'-thiocarbonyldiimidazole (3.3 g, 18.8 mmol) were combined in THF (16 ml) and heated to 125C under microwave irradiation <n="42"/>for 15 min. The mixture was cooled to r.t, reduced in vacuo, and ammonia (50 ml of a 7N solution in methanol, 0.35 mol) was added. It was stirred for 2 h, then concentrated in vacuo. The residue was partitioned between EtOAc (100 ml) and 2N HCl (100 ml). The organics were washed with brine (100 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with Et2O and heptane to give a yellow solid. Of this material, 0.5 g (1.8 mmol) was combined with Intermediate 1 (0.69 g, 3.1 mmol) and DIPEA (0.6 mL, 3.4 mmol) in THF (18 mL) and heated to 140C under microwave irradiation for 30 min. After cooling to r.t. the mixture was partitioned between EtOAc (130 mL) and water (130 mL). The organics were washed with water (150 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting crude material was purified by prep HPLC to yield the title compound as an off-white solid (166 mg, 23%). deltaH (CDCl3) 1.16 (6H, s), 2.44 (2H, s), 2.79 (2H, s), 4.07-4.17 (2H, m), 4.27- 4.38 (2H, m), 6.84 (IH, d, J 8.7 Hz), 7.17 (IH, dd, J 8.7, 2.3 Hz), 8.22 (IH, d, J2.3 Hz). LCMS (ES+) 393 (M+H)+.
23% INTERMEDIATE 136-Bromo-3,4-dihvdro-2H-benzo[l,41oxazine-4-carbothioic acid amideIntermediate 10 (1.7 g, 8.0 mmol) and l,r-thiocarbonyldiimidazole (2.84 g, 16 mmol) were combined in TetaF (15 mL) and heated to 1200C under microwave irradiation for 15 minutes. After cooling to r.t., NH3 (40 mL of a 7N solution in MeOH, 280 mmol) was added, and the mixture stirred at r.t. for 3 h. The reaction mixture was concentrated in vacuo and then partitioned between EtOAc (100 mL) and water (100 mL). The organic fraction was washed with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with ether and heptane to give the title compound (0.5 g, 23%) as a white solid. deltaH (DMSO-de) 8.20 (2H, br s), 7.60 (IH, d, J2.3 Hz), 7.21 (IH, dd, J 8.7, 2.3 Hz), 6.88 (IH, d, J 8.9 Hz), 4.30-4.16 (4H, m).
23% Intermediate 6 (1.7 g, 8 mmol) and lj'-thiocarbonyldiimidazole (2.84 g, 16 mmol) were combined in THF (15 mL) and heated to 12O0C under microwave irradiation for 15 minutes. After cooling to r.t., NH3 (40 mL, 7N solution in MeOH, 280 mmol) was added, and the mixture stirred at r.t. for 3 h. The reaction mixture was concentrated in vacuo and then partitioned between EtOAc (100 mL) and water (100 mL). The organic fraction was washed with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with Et2O and heptane to give the title compound (0.5 g, 23%) as a white solid. deltaH (DMSO-d6) 8.20 (2H, br. s), 7.60 (IH, d, J2.3 Hz), 7.21 (IH, dd, J 8.7 and 2.3 Hz), 6.88 (IH, d, J8.9 Hz), 4.30-4.16 (4H, m).
23% A solution of Intermediate 33 (1.7 g, 8 mmol) and l,r-thiocarbonyldiimidazole (2.84 g, 16 mmol) in TetaF (15 mL) was heated to 1200C under microwave irradiation, in a sealed tube, for 15 minutes. After cooling to r.t., NH3 (40 mL, 7N solution in MeOH, 280 mmol) was added. The reaction mixture was stirred at r.t. for 3 h, concentrated in vacuo, and then partitioned between EtOAc (100 mL) and water (100 mL). The organic fraction was washed with water (100 mL), then brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. Trituration with Et2O and heptane gave the title compound (0.5 g, 23%) as a white solid. deltaH (DMSO-d6) 8.20 (2H, br. s), 7.60 (IH, d, J 2.3 Hz), 7.21 (IH, dd, J 8.7 and 2.3 Hz), 6.88 (IH, d, J 8.9 Hz), 4.30-4.16 (4H, m).
INTERMEDIATE 312-(6-Bromo-2J-dihvdrobenzo("l,41oxazin-4-yl)-5,5-dimethyl-5,6-dihvdro-4H- benzothiazol-7-one Intermediate 10 (2.0 g, 9.4 mmol) and l,r-thiocarbonyldiimidazole (3.3 g, 18.8 mmol) were combined in TetaF (16 mL) and heated to 125C under microwave irradiation for 15 minutes. The mixture was cooled to r.t., concentrated in vacuo, and NH3 (50 mL of a 7N solution in methanol, 0.35 mol) was added. It was stirred for 2 h, then <n="109"/>concentrated in vacuo. The residue was partitioned between EtOAc (100 mL) and 2N HCl (IUO mL). The organic fraction was washed with brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with ether and heptane to give a yellow solid. Of this material, 0.5 g (1.8 mmol) was combined with Intermediate 5 (0.69 g, 3.1 mmol) and DIPEA (0.6 mL, 3.4 mmol) in THF (18 mL) and heated to 1400C under microwave irradiation for 30 minutes. After cooling to r.t. the mixture was partitioned between EtOAc (130 mL) and water (130 mL). The organic fraction was washed with water (150 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting crude material was purified by preparative HPLC (Method 6) to yield the title compound (166 mg, 23%) as an off-white solid. deltaH (CDCl3) 8.22 (IH, d, J2.3 Hz), 7.17 (IH, dd, J8.7, 2.3 Hz), 6.84 (IH, d, J8.7 Hz), 4.27-4.38 (2H, m), 4.07-4.17 (2H, m), 2.79 (2H, s), 2.44 (2H, s), 1.16 (6H, s).

  • 2
  • [ 1484-26-0 ]
  • [ 6160-65-2 ]
  • [ 206559-36-6 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; EXAMPLE 1. PREPARATION OF 1- (3-BENZYLOXY) PHENYLTHIOUREA (Compound 1); 1. I 02N X 1. 2. 1. TCD ., base >, I Compound 1 [0114] 3-Nitrophenol (X) is converted to ether (Y) by sequential treatment with sodium hydride and benzylbromide. Reduction of the aniline with tin chloride provides aniline (Z). In certain circumstances the reduction may be accomplished using a hydrogen/Pd catalyst system when the substituent on the aryl group does not include an aryl group. [0115] The final product, Compound 1 is obtained by treatment of Z with thiocarbonyl di- imidazole followed by ammonia. 3-Benzyloxyaniline (5 g, 25 mmol) is added dropwise over a one minute period to 4.94 g (27.6 mmol) thiocabonyl di-imidazole in methylene chloride (150 ml). The resulting mixture is stirred at room temperature overnight. An additional 400 mg thiocarbonyl di- imidazole (TCDI) is added and the reaction is continued for 2 hours more. The reaction is diluted with hexane and filtered through silica. Concentration provides 5.1 g of the desired 3- benzyloxyphenyl isothiocyanate. [0116] A portion of this isothiocyanate (50 mg, 0.21 mmol) in 1 ml methylene chloride is mixed with 0.5 ml of 2 M ammonia in methanol. After 30 minutes the reaction is concentrated to provide Compound 1 in quantitative yield. [0117] Alternatively thiocarbonyl di-imidazole (1.1 mmol, 196 mg) is added to a solution of 3-benzyloxyaniline (1 mmol, 199 mg) in dichloromethane (5 mL). The reaction is stirred at room temperature until the aniline is consumed, about 1 hour. A solution of methanolic ammonia (2 M, 2 mL) is added and the stirring continued for 2 hours. Solvent is evaporated and the residue purified by chromatography on silica gel to give 150 mg of (3-benzyloxyphenyl) thiourea. [0118] NMR (CDCI3) D : 5.08 (s, 2H), 6.03 (brs, 2H), 6.8 (M, 2H), 6.93 (m, 1H), 7. 3- 7. 47 (M, 6H), 7.82 (brs, 1H). MS (APCI) : M++1 = 259.
  • 3
  • [ 452-92-6 ]
  • [ 6160-65-2 ]
  • C10H6BrF2N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; for 16h; 2,4-Difluoro-5-bromoaniline (208 mg, 1.04 mmol) was added to a solution of thiocarbonyldiimidazole (185 mg 1.04 mmol) in DMF (10 mL) and the mixture was stirred for 16 h. 2-Hydrazino-N-(4-morpholin-4ylphenyl)-2 oxoacetamide (Intermediate 27, 211 mg, 0.8 mmol) was added and the mixture was stirred at 80C until a clear solution was obtained. EDAC (306 mg, 1.6 mmol) was added and stirring was continued for a further 1 h. The mixture was cooled then diluted with water (25 mL) and the resulting precipitate was filtered and dried to give the title compound the title compound (135 mg) as a solid; 1H NMR delta 11.09 (IH, s), 10.88 (IH, s), 8.45-8.33 (IH, m),7.74-7.57 (3H, m),6.95 (2H, d), 3.83-3.68 (5H, m), 3.15-2.99 (5H, m); MS m/e MH+ 482.
  • 4
  • [ 25475-67-6 ]
  • [ 6160-65-2 ]
  • [ 769960-94-3 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; N,N-dimethyl-formamide; at 65 - 70℃; for 1h; General Procedure A: Preparation of isothiocyanate 1,1 '-thiocarbonylimidazole (1.1 mmol) was added to a solution of amine (1 mmol) inTHF/DMF (2 mL, 1:1) and the reaction mixture was stirred at 65-70 0C for 1 h. The product thus formed, was used for further transformation without isolation.; Example 1; Synthesis of 2-(Isoquinolin-3-ylamino)-lH-benzimidazole-5-carboxylic acid benzothiazol-6- ylamide3-Isothiocyanatoisoquinoline was prepared from <strong>[25475-67-6]3-aminoisoquinoline</strong> (5 mmol) as described in general procedure A.The isothiocyanate from above was reacted with methyl 3,4-diaminobenzoate (5mmol) followed by cyclization using EDC as described in general procedure B to obtain 2- (Isoquinolin-3-ylamino)-lH-benzimidazole-5-carboxylic acid methyl ester. The ester was hydrolyzed to yield the corresponding carboxylic acid employing general procedure C. Benzothiazol-6-ylamine (0.25 mmol) was coupled with aforementioned carboxylic acid using HBTU employing general procedure D to provide 2-(Isoquinolm-3-ylammo)-lH- benzimidazole-5-carboxylic acid benzothiazol-6-ylamide. MS: m/z 437 (M+H)+.
  • 5
  • [ 6160-65-2 ]
  • [ 105655-01-4 ]
  • C12H10BrN3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 120℃; for 0.25h;Microwave irradiation; Intermediate 38 (1.7 g, 8 mmol) and l,l '-thiocarbonyldiimidazole (2.84 g, 16 mmol) were dissolved in THF (15 mL) and heated to 1200C under microwave irradiation for 15 minutes. After cooling to r.t., NH3 (40 mL, 7N solution in MeOH, 280 mmol) was added, and the mixture stirred at r.t. for 3 h. The reaction mixture was concentrated in vacuo and then partitioned between EtOAc (100 mL) and water (100 mL). The organic fraction was washed with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with Et2O and heptane to give the title compound (0.5 g, 23%) as a white solid. deltaH (DMSO-d6) 8.20 (2H, br. s), 7.60 (IH, d, J2.3 Hz), 7.21 (IH, dd, J 8.7 Hz and J2.3 Hz), 6.88 (IH, d, J 8.9 Hz), 4.30-4.16 (4H, m).
  • 6
  • [ 214750-74-0 ]
  • [ 29022-11-5 ]
  • [ 71989-31-6 ]
  • [ 35661-40-6 ]
  • [ 71989-33-8 ]
  • [ 47375-34-8 ]
  • [ 6160-65-2 ]
  • [ 1179539-48-0 ]
  • 7
  • [ 25475-67-6 ]
  • [ 6160-65-2 ]
  • [ 927902-45-2 ]
YieldReaction ConditionsOperation in experiment
76% 0.618 g (3.47 mmol) N,N'-thiocarbonyldiimidazole was dissolved in 20 mL acetonitrile, and 0.500 g (3.47 mmol) isoquinoline-3-amine in the form of a suspension in 15 mL acetonitrile was added dropwise in portions. The clear orange solution which formed was stirred for 12 hr, whereupon a reddish precipitate formed. The intermediate product was directly reacted, without workup, with 0.535 g (6.940 mmol) ammonium acetate for 25 min at 85° C. in a CEM microwave (100 watts). The solvent was removed under vacuum. The residue was stirred in water, and the resulting precipitate was suctioned off and washed with water. For further purification the solid was taken up in 5 mL acetonitrile and combined with 50 mL diisopropyl ether. The precipitate was filtered again and dried in a vacuum drying oven at 40° C., resulting in the isolation of 0.540 g (2.647 mmol, 76percent) purified N-isoquinolin-3-yl-thiourea.ESI-MS [M+H+]=204.15 Calculated for C10H9N3S=203.27
  • 8
  • [ 441713-62-8 ]
  • [ 443-86-7 ]
  • [ 6160-65-2 ]
  • methyl [2-(3-fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl]acetate [ No CAS ]
  • 9
  • [ 6160-65-2 ]
  • [ 15992-83-3 ]
  • C12H9N5S [ No CAS ]
  • 10
  • [ 33024-60-1 ]
  • [ 6160-65-2 ]
  • 4-isothiocyanatotetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h; Step 1 : TEA(1.1 g, 10.87 mmol, 3.00 equiv) was added into a solution of l ,l'-thiocarbonyldiimidazole (1.28 g, 7.18 mmol, 2.00 equiv) and 4-aminotetrahydropyran hydrochloride (500 mg, 3.63 mmol, 1.00 equiv) in DCM (5 mL) at 0 °C. The reaction mixture was warmed to RT and stirred for 2 h at this temperature. The resulting solution was then diluted with 20 mL of water and extracted with 3x100 mL of DCM. The combined organic layers were dried (Na2S04) and concentrated under vacuum. The residue was purified on an Si02 column with ethyl acetate/petroleum ether (1 :3) to give 200 mg (38percent) of 48 as colorless oil. 'H-NMR (300MHz, CDC13) 83.98-3.87 (m, 3H), 3.60-3.53 (m, 2H), 2.06-1.97 (m, 2H), 1.89-1.79 (m, 2H).
  • 11
  • [ 6160-65-2 ]
  • [ 851983-85-2 ]
  • 3β-(1H-imidazole-1-thiocarboxylate)-17-(1H-benzimidazol-1-yl)androsta-5,16-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.5% In dichloromethane; acetonitrile; for 5h;Reflux; A solution of 17-(lH-benzimidazol-l-yl)androsta-5,16-dien-3 -ol (VN/124-1) (0.2 g, 0.515 mmol), l,l'-thiocarbonyldiimidazole (0.18 g, 1.03 mmol) in anhydrous acetonitrile (2 mL) and DCM (1 mL) was refluxed for 5 h . The solvent evaporated, residue treated with water, and filtered. The crude brown solids obtained was purified by FCC using 1.7 percent ethanol in DCM in presence of traces of TEA (0.06percent) to give V PP397 (0.14 g, 54.5percent): mp 187-88 °C; IR (Neat) 1487, 1456, 1386, 1324, 1291, 1243, 1222, 1110, 986, 827, 743 cm"nH NMR (400 MHz, CDC13)? 1.03 (s, 3 H, 18-CH3), 1.14 (s, 3 H, I9-CH3), 5.31 - 5.42 (m, 1 H, 3a-H), 5.48 - 5.57 (m, 1 H, 6-H), 6.00 (br. s., 1 H, 16-H), 7.03 (s, 1 H, Ar-42 H), 7.28 - 7.35 (m, 2 H, Ar-51 and 61 Hs), 7.49 (d, J=5.14 Hz, 1 H, Ar-52 H), 7.64 (s, 1 H, Ar-41 H), 7.82 (d, J=7.58 Hz, 1 H, Ar-71 H), 7.96 (s, 1 H, Ar-21), 8.35 (s, 1 H, Ar-22 H); 13C NMR (400 MHz CDC13)? 183.3, 147.1, 143.3, 141.6, 139.0, 136.7, 130.7, 124.1, 123.4, 123.2, 122.5, 120.2, 117.9, 111.1, 83.3, 55.7, 50.3, 47.2, 37.2, 36.8, 36.6, 34.8, 31.1, 30.3, 30.2, 27.0, 20.6, 19.2, 16.0
  • 12
  • [ 2369-29-1 ]
  • [ 6160-65-2 ]
  • 2-mercapto-4,6-difluorobenzimidazole [ No CAS ]
  • 13
  • [ 54396-44-0 ]
  • [ 6160-65-2 ]
  • 1-[2-methyl-3-(trifluoromethyl)phenyl]thiourea [ No CAS ]
  • 14
  • [ 1123-93-9 ]
  • [ 6160-65-2 ]
  • C11H8N4S2 [ No CAS ]
  • 15
  • [ 6160-65-2 ]
  • [ 6294-52-6 ]
  • C13H12N4O2S2 [ No CAS ]
  • 16
  • [ 23687-26-5 ]
  • [ 6160-65-2 ]
  • 6-isothiocyanatoisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.06 g With triethylamine; In tetrahydrofuran; at 20℃; for 4h; 1.81 g <strong>[23687-26-5]isoquinolin-6-amine</strong>, 2.46 g TCDI and 2 eq Et3N in 8 ml THF were stirred at room temperature for 4 hours. After removing THF by vacuum, the residue was purified by a column (EA/Hexane=1:1) to give 1.06 g of product. The NMR spectral data of the compound is listed below:1H NMR (500 MHz DMSO d-6): delta 7.67 (d, 1H), 7.81 (d, 1H), 8.04 (s, 1H), 8.21 (d, 1H), 8.54 (d, 1H), 9.33 (s, 1H).
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; ;