[ CAS No. 64205-92-1 ] {[proInfo.proName]}

Name: 64205-92-1|4,5-Dihydro-1H-imidazole-2-sulfonic acid|98%
Brand: Ambeed
SKU: A856898
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Quality Control of [ 64205-92-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 64205-92-1 ]

Product Details of [ 64205-92-1 ]

CAS No. :	64205-92-1	MDL No. :	MFCD03426388
Formula :	C₃H₆N₂O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JTRHTNVGGLWMFV-UHFFFAOYSA-N
M.W :	150.16	Pubchem ID :	274561
Synonyms :

Calculated chemistry of [ 64205-92-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	38.68
TPSA :	87.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.73
Log Po/w (XLOGP3) :	-1.6
Log Po/w (WLOGP) :	-0.85
Log Po/w (MLOGP) :	-1.5
Log Po/w (SILICOS-IT) :	-0.19
Consensus Log Po/w :	-0.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	0.3
Solubility :	302.0 mg/ml ; 2.01 mol/l
Class :	Highly soluble
Log S (Ali) :	0.28
Solubility :	286.0 mg/ml ; 1.9 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.13
Solubility :	112.0 mg/ml ; 0.746 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.49

Safety of [ 64205-92-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 64205-92-1 ]

* 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 [ 64205-92-1 ]
Downstream synthetic route of [ 64205-92-1 ]

[ 64205-92-1 ] Synthesis Path-Upstream 1~4

1
[ 96-45-7 ]
[ 7732-18-5 ]
[ 64205-92-1 ]

Reference： [1] Patent: US5373010, 1994, A,
[2] Patent: US5231096, 1993, A,
[3] Patent: US5112822, 1992, A,
[4] Patent: US5130441, 1992, A,

2
[ 96-45-7 ]
[ 64205-92-1 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 17, p. 3241 - 3251
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3533 - 3538
[3] Helvetica Chimica Acta, 1996, vol. 79, # 7, p. 1967 - 1979
[4] Angewandte Chemie, 1996, vol. 108, # 18, p. 2263 - 2265

3
[ 82358-16-5 ]
[ 64205-92-1 ]

Yield	Reaction Conditions	Operation in experiment
21 mmol, 32%	With dihydrogen peroxide; sodium chloride In water	2-Imidazoline-2-sulfonic acid (ISA). ISA was prepared according to the procedure described in literature (Gluchowski, C. U.S. Pat. No. 5,130,441, 1992). To a solution of 2-imidazolinethione (6.6 g, 65 mmol), sodium molybdate(IV) dihydrate (0.5 g, 2.1 mmol) and NaCl (1.5 g) in 150 ml of distilled water was added 30percent of H₂O₂ (50 ml, 450 mmol) for 1 h at -10° C. The reaction mixture was stored at -20° C. for 12 h and then reaction temperature was slowly warmed up to 25° C. The white crystal obtained was filtered and dried in vacuo to provide 2.8 g (21 mmol, 32percent) of the acid. The compound was used in the examples noted below.

Reference： [1] Patent: US6316637, 2001, B1,

4
[ 96-45-7 ]
[ 504-75-6 ]
[ 120-93-4 ]
[ 64205-92-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 1995, vol. 43, # 9, p. 2530 - 2535

[ 64205-92-1 ] Synthesis Path-Downstream 1~71

1
[ 96-45-7 ]
[ 504-75-6 ]
[ 120-93-4 ]
[ 64205-92-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1995,vol. 43,p. 2530 - 2535

2
[ 96-45-7 ]
[ 64205-92-1 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 3241 - 3251
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 3533 - 3538
[3]Helvetica Chimica Acta,1996,vol. 79,p. 1967 - 1979
[4]Angewandte Chemie,1996,vol. 108,p. 2263 - 2265

3
[ 141068-94-2 ]
[ 64205-92-1 ]
[ 179863-46-8 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3533 - 3538
[2]Patent: WO2003/99289,2003,A2 .Location in patent: Page 61

4
[ 88-89-1 ]
(S)-2-{11-[3,5-Bis-(tert-butoxycarbonylamino-methyl)-benzoylamino]-undecanoylamino}-5-guanidino-pentanoic acid methyl ester; compound with acetic acid [ No CAS ]
[ 64205-92-1 ]
(S)-2-(11-{3,5-Bis-[(4,5-dihydro-1H-imidazol-2-ylamino)-methyl]-benzoylamino}-undecanoylamino)-5-guanidino-pentanoic acid methyl ester; compound with picric acid [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1996,vol. 79,p. 1967 - 1979

5
2-(2,6-Bis-aminomethyl-phenoxy)-ethanol [ No CAS ]
[ 64205-92-1 ]
2-{2,6-Bis-[(4,5-dihydro-1H-imidazol-2-ylamino)-methyl]-phenoxy}-ethanol [ No CAS ]

Reference： [1]Angewandte Chemie,1996,vol. 108,p. 2263 - 2265

6
[ 178322-43-5 ]
[ 64205-92-1 ]
2-[N-(7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)amino]imidazoline sulfate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 3515 - 3529

7
(3S,7S)-3,7-Diamino-5-ethyl-[1,5]diazocan-2-one; hydrochloride [ No CAS ]
[ 64205-92-1 ]
(3S,7R)-Bis(4,5-dihydro-1H-imidazol-2-ylamino)-5-ethyl-2-keto-1,5-diazacyclooctane [ No CAS ]

Reference： [1]Synlett,1999,p. 1875 - 1878

Yield	Reaction Conditions	Operation in experiment
52.3%		Preparation of imidazoline-2-sulfonic acid 2-Imidazolidinethione (Compound 8, Aldrich, 66.3 g, 650 mmol), Na2 MoO4 (5g, 227 mmol) and NaCl (15 g. 256 mmol) were added to 300 ml H2 O. Although some dissolution occurred, a solid residue remained in the liquid of the mixture. The mixture was cooled to -10° C. using an immersion cooler. 500 ml of a 30percent (w/v) aqueous H2 O2 solution was placed in a jacketed controlled drop rate addition funnel and cooled to 0° C. using an ice/H2 O bath. The aqueous H2 O2 solution was added to the mixture at a rate of 60 drops/min. The mixture was stirred for 16 hours at -10° C. During this time, the mixture changed from a white suspension to a dark blue solution to a light blue suspension. At the end of 16 hours, a solid filtered from the suspension and dried in vacuo. No further purification was needed. Yield: 57.8 g (a yield of 52.3percent) of the title compound as a white solid mp 157°-159° C.; 1 H NMR (300 MHz, DMSO d6) and 10.38 (br, 2H); 3.85 (s, 4H). This solid was stable when stored in the dark at 0° C. for at least 6 months.
52.3%		EXAMPLE 99 Imidazoline-2-sulfonic acid 2-Imidazolidinethione (Aldrich, 66.3 g, 650 mmol), Na2 MoO4 (5 g, 227 mmol) and NaCl (15 g. 256 mmol) were added to 300 ml H2 O. Although some dissolution occurred, a solid residue remained in the liquid of the mixture. The mixture was cooled to -10° C. using an immersion cooler. 500 ml of a 30percent (w/v) aqueous H2 O2 solution was placed in a jacketed controlled drop rate addition funnel and cooled to 0° C. using an ice/H2 O bath. The aqueous H2 O2 solution was added to the mixture at a rate of 60 drops/min. The mixture was stirred for 16 hours at -10° C. During this time, the mixture changed from a white suspension to a dark blue solution to a light blue suspension. At the end of 16 hours, a solid was filtered from the suspension and dried in vacuo. NO further purification was needed. Yield: 57.8 g (a yield of 52.3percent) of the title compound as a white solid mp 157°-159° C.; H NMR (300 MHz, DMSO d6) delta 10.38 (br, 2H); 3.85 (s, 4H). solid was stable when stored in the dark at 0° C. for at least 6 months.
		Step 1 Synthesis of imidazoline-2-sulfonic acid: 3.32 g (32.5 mmol) of 2-imidazolinethion, 250 mg (1.03 mmol) of sodium molybdate dihydrate and 750 mg of sodium chloride were stirred in 15 ml of water under cooling with ice. 25 ml of 30 percent aqueous hydrogen peroxide solution was slowly dropped into the resultant mixture while the inner temperature is kept at 4°C or below. After the completion of the dropping, the reaction mixture was stirred under cooling with ice for 2 hours. The reaction liquid was filtered to obtain the precipitate, which was washed with cold water and then dried in vacuo to obtain the title compound. Yield: 1.47 g (9.81 mniol) (30 percent) 1 H-NMR (DMSO-d6) delta: 3.85 (4H, s), 10.35 (1H, br)

10
[ 263382-27-0 ]
[ 64205-92-1 ]
2-([5-Methoxycarbonyl-1H-pyrrol-2-yl]methyl}amino)-4,5-dihydro-1H-imidazole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2000,vol. 6,p. 709 - 718

11
(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-(4-trifluoromethyl-phenylcarbamoyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester; compound with acetic acid [ No CAS ]
[ 64205-92-1 ]
methyl 3α-(4,5-dihydro-1H-imidazol-3-ium-2-yl)-7α,12α-bis[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-olate chloride [ No CAS ]

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 2931 - 2936

12
[ 64205-92-1 ]
(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-(4-trifluoromethyl-phenylcarbamoyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester; compound with acetic acid [ No CAS ]
eicosyl 3α-(4,5-dihydro-1H-imidazol-3-ium-2-yl)-7α,12α-bis[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate chloride [ No CAS ]

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 2931 - 2936

13
[ 4097-89-6 ]
[ 88-89-1 ]
[ 64205-92-1 ]
tris{2-[(4,5-dihydro-1H-imidazol-2-yl)amino]ethyl}amine tris(2,4,6-trinitrophenol) salt [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2003,vol. 86,p. 3740 - 3752

14
[ 64205-92-1 ]
[ 775278-53-0 ]
1-[(4,5-dihydro-1H-imidazol-2-yl)aminomethyl]-3-(2-pyridylaminomethyl)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 2211 - 2217

15
[ 64205-92-1 ]
(3-aminomethyl-benzyl)-(1<i>H</i>-benzoimidazol-2-yl)-amine [ No CAS ]
1-[N-(benzimidazol-2-yl)aminomethyl]-3-[(4,5-dihydro-1H-imidazol-2-yl)aminomethyl]benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 2211 - 2217

16
[ 1007884-34-5 ]
[ 64205-92-1 ]
(S)-tert-butyl 2-(5-(4'-(2-((S)-1-((S)-3-methyl-2-(3,4-dihydroimidazol-2-ylamino)butanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol; at 100℃; for 12.0h;	A mixture of (S)-tert-butyl 2-(5-(4'-(2-((S)-1-((S)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (cj-2) (0.298 g, 0.480 mmol), <strong>[64205-92-1]4,5-dihydro-1H-imidazole-2-sulfonic acid</strong> (AstaTech) (0.090 g, 0.60 mmol) and iPr2NEt (0.083 mL, 0.48 mmol) in EtOH (4 mL) was heated at 100° C. for 12 h. The cooled mixture was evaporated to dryness and the residue was purified by prep HPLC (Luna 5u C18/MeCN-H2O-TFA, .x.2) to afford the TFA salt of the title compound (0.390 g, 73percent) as a light yellow solid.1HNMR (400 MHz, DMSO-d6) delta 14.66 (br s, 2H), 8.51 (br s, 1H), 8.20 (d, J=10.1 Hz, 2H), 8.10 (br s, 1H), 7.82-7.91 (m, 7H), 7.30 (br s, 1H), 5.12 (t, J=7.1 Hz, 1H), 4.97-5.05 (m, 2H), 4.37 (dd, J=4.3, 10.1 Hz, 2H), 3.82-3.86 (m, 2H), 3.73-3.77 (m, 2H), 3.59 (s, 4H), 3.39-3.48 (m, 2H), 2.15-2.25 (m, 2H), 1.93-2.07 (m, 5H), 1.40 (s, 4H), 1.17 (s, 5H), 0.93 (d, J=6.6 Hz, 3H), 0.69 (br s, 3H).LCMS: Anal. Calcd. for C39H49N9O3: 691; found: 692 (M+H)+.
	With N-ethyl-N,N-diisopropylamine; In ethanol; at 100℃; for 12.0h;	Preparation of (S)-tert-Butyl 2-(5-(4'-(2-((S)-1-((S)-3-methyl-2-(3,4-dihydroimidazol-2-ylamino)butanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (cj-8) A mixture of (S)-tert-butyl 2-(5-(4'-(2-((S)-1-((S)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (cj-2) (0.298 g, 0.480 mmol), <strong>[64205-92-1]4,5-dihydro-1H-imidazole-2-sulfonic acid</strong> (AstaTech) (0.090 g, 0.60 mmol) and iPr2NEt (0.083 mL, 0.48 mmol) in EtOH (4 mL) was heated at 100° C. for 12 h. The cooled mixture was evaporated to dryness and the residue was purified by prep HPLC (Luna 5u C18/MeCN-H2O-TFA, *2) to afford the TFA salt of the title compound (0.390 g, 73percent) as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6) delta 14.66 (br s, 2H), 8.51 (br s, 1H), 8.20 (d, J=10.1 Hz, 2H), 8.10 (br s, 1H), 7.82-7.91 (m, 7H), 7.30 (br s, 1H), 5.12 (t, J=7.1 Hz, 1H), 4.97-5.05 (m, 2H), 4.37 (dd, J=4.3, 10.1 Hz, 2H), 3.82-3.86 (m, 2H), 3.73-3.77 (m, 2H), 3.59 (s, 4H), 3.39-3.48 (m, 2H), 2.15-2.25 (m, 2H), 1.93-2.07 (m, 5H), 1.40 (s, 4H), 1.17 (s, 5H), 0.93 (d, J=6.6 Hz, 3H), 0.69 (br s, 3H). LCMS: Anal. Calcd. for C39H49N9O3: 691; found: 692 (M+H)+.

Reference： [1]Patent: US2008/44379,2008,A1 .Location in patent: Page/Page column 139
[2]Patent: US2008/44380,2008,A1 .Location in patent: Page/Page column 136-137

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[ 14150-94-8 ]
[ 110-17-8 ]
[ 10458-14-7 ]
[ 64205-92-1 ]
[ 214698-69-8 ]