[ CAS No. 4499-07-4 ] {[proInfo.proName]}

Name: 4499-07-4|2-(1H-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride|99%
Brand: Ambeed
SKU: A377466
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Quality Control of [ 4499-07-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4499-07-4 ]

Product Details of [ 4499-07-4 ]

CAS No. :	4499-07-4	MDL No. :	MFCD01325081
Formula :	C₉H₁₃Cl₂N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LKFGBWROFLZYQJ-UHFFFAOYSA-N
M.W :	234.13	Pubchem ID :	2788071
Synonyms :

Calculated chemistry of [ 4499-07-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	62.5
TPSA :	54.7 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.54
Log Po/w (WLOGP) :	2.67
Log Po/w (MLOGP) :	1.35
Log Po/w (SILICOS-IT) :	1.93
Consensus Log Po/w :	1.7

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.136 mg/ml ; 0.000581 mol/l
Class :	Soluble
Log S (Ali) :	-3.34
Solubility :	0.108 mg/ml ; 0.000462 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.35
Solubility :	0.105 mg/ml ; 0.000447 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 4499-07-4 ]

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

Application In Synthesis of [ 4499-07-4 ]

* 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 [ 4499-07-4 ]
Downstream synthetic route of [ 4499-07-4 ]

[ 4499-07-4 ] Synthesis Path-Upstream 1~3

1
[ 4499-07-4 ]
[ 29518-68-1 ]

Reference： [1] Patent: EP1135374, 2006, B1, . Location in patent: Page/Page column 30

2
[ 189560-91-6 ]
[ 4499-07-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; water In ethyl acetate at 20℃;	Compound 3 (3 g) was dissolved in 3 N HCl/EtOAC (50 mL/25 mL) and stirred at room temperature overnight. The solvent was in vacuo and dried in high vacuum to give compound 4 as pink solid (2.4 g) at greater than 95percent yield. LC/MS (10-99percent) M+1/Z 162.4 retention time 0.62 min.

Reference： [1] Patent: WO2005/42497, 2005, A2, . Location in patent: Page/Page column 221

3
[ 95-54-5 ]
[ 107-95-9 ]
[ 4499-07-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1185 - 1208
[2] Patent: EP1135374, 2006, B1, . Location in patent: Page/Page column 29-30
[3] Journal of Molecular Structure, 2017, vol. 1148, p. 62 - 72

[ 4499-07-4 ] Synthesis Path-Downstream 1~59

1
[ 98-01-1 ]
[ 4499-07-4 ]
[ 26963-53-1 ]

Reference： [1]Indian journal of chemistry,1970,vol. 8,p. 126 - 129

2
[ 25109-26-6 ]
[ 4499-07-4 ]
[ 26963-54-2 ]

Reference： [1]Indian journal of chemistry,1970,vol. 8,p. 126 - 129

3
[ 75-15-0 ]
[ 4499-07-4 ]
[ 26963-59-7 ]

Reference： [1]Chemische Berichte,1984,vol. 117,p. 2597 - 2614

4
[ 2973-19-5 ]
[ 4499-07-4 ]
[ 155797-26-5 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1994,p. 1219 - 1226

5
[ 4499-07-4 ]
[ 100-52-7 ]
[ 26963-48-4 ]

Reference： [1]Chemische Berichte,1984,vol. 117,p. 2597 - 2614

6
[ 4499-07-4 ]
[ 79-04-9 ]
[ 80028-68-8 ]
[ 80028-70-2 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 582 - 585

7
[ 4499-07-4 ]
[ 10191-60-3 ]
[ 92095-33-5 ]

Reference： [1]Chemische Berichte,1984,vol. 117,p. 2597 - 2614

8
[ 4499-07-4 ]
[ 215050-13-8 ]
[ 215050-22-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1185 - 1208

9
[ 95-54-5 ]
[ 107-95-9 ]
[ 4499-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; for 25h;Heating / reflux;	Preparation 7; N3-[4-[2-(Benzimidazol-2-yl)ethyl]aminomethylbenzoyl)-N2-Cbz-L-2,3-diaminopropionic acid on 2-chlorotrityl resin; [Show Image] Step 1a; 2-[2-(Aminoethyl)]benzimidazole dihydrochloride; [Show Image] Combine o-phenylenediamine (10.8 g, 100 mmol) and beta-alanine (13.4 g, 150 mmol) in 6N HCl (100 mL). Heat at reflux 25 hours, allow to cool, and chill at -15C. Filter the solid and wash with cold 6N HCl, then cold EtOH. Dissolve the solid in 80% EtOH (125 mL), treat with decolorizing charcoal, and concentrate in vacuo to 40 g. Warm while adding EtOH (80 mL). Allow to cool, filter, and wash with EtOH to obtain the product as plates.
	With hydrogenchloride; In water; for 24h;Reflux;	2-Aminoethyl-1H-benzimidazole dihydrochloride and 2-aminopropyl-1H-benzimidazole dihydrochloride were prepared by the method reported by Cescon etal. [47]. A solution of 10.8g (0.1mol) of 7 o-phenylenediamine and 13.4g (0.15mol) of 8 beta-alanine in 100mL of 5.5mol·L-1 9 hydrochloric acid was refluxed for 24h. The solution was cooled overnight and the hydrochloride removed by filtration. It was recrystallized from 90% ethyl alcohol with the aid of decolorizing carbon. 10 2-Aminopropyl-1H-benzimidazole dihydrochloride was prepared by the same procedure as that of 2-Aminoethyl-1H-benzimidazole dihydrochloride, but using gamma-aminobutyric acid 10.3g (0.1mol) in place of p-alanine. All of the other reagents were of AR grade and were obtained from commercial sources and used without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1185 - 1208
[2]Patent: EP1135374,2006,B1 .Location in patent: Page/Page column 29-30
[3]Journal of Molecular Structure,2017,vol. 1148,p. 62 - 72

10
[ 4499-07-4 ]
N-perchloroethenylbenzimidoyl chloride [ No CAS ]
1-(dichloromethylene)-3-phenyl-1,4,5,6-tetrahydro[1,3,5]triazocino[1,8-a]benzimidazole [ No CAS ]

Reference： [1]Synthesis,2006,p. 2323 - 2326

11
[ 4499-07-4 ]
4-methyl-<i>N</i>-(1,2,2-trichloro-vinyl)-benzimidoyl chloride [ No CAS ]
1-(dichloromethylene)-3-(4-methylphenyl)-1,4,5,6-tetrahydro[1,3,5]triazocino[1,8-a]benzimidazole [ No CAS ]

Reference： [1]Synthesis,2006,p. 2323 - 2326

12
[ 4499-07-4 ]
2-benzenesulfonylamino-3-{4-[2-(1<i>H</i>-benzoimidazol-2-yl)-ethylamino]-3-nitro-benzoylamino}-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1185 - 1208

13
[ 4499-07-4 ]
[ 80028-69-9 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 582 - 585

14
[ 13335-73-4 ]
[ 4499-07-4 ]
C₂HF₃O₂*C₁₉H₂₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In acetonitrile; at 20℃;	To a solution of benzimidazole ethylene amine dihydrochloride (100 mg, 0.43 mmol), 3,4-dimethylphenoxyacetic acid (77 mg, 0.43 mmol), and BOP reagent (190 mg, 0.43 mmol) in acetonitrile (5 mL) was added triethylamine (0.23 mL, 1.72 mmol). After stirring at room temperature overnight, the solvent was removed under vacuum. The residue was taken up with water and saturated sodium bicarbonate (20 mL), extracted with dichloromethane (30 mL x 2), dried and removed the solvent. The crude mixture was purified by using Gilson HPLC to give white solid 5 as a TFA salt (170 mg) at 93 % yield. MUX LC/MS (10-99%) M+1/Z 324.163 retention time 2.62 min ; 1H NMR (DMSO) 8 2.12 (s, 3H), 8 2.15 (s, 3H), 8 2.99 (t, 2H, J = 5.88 Hz), 8 3.59 (m, 2H), 8 4.40 (s, 2H), 8 6.64 (dd, 1H, J = 2 Hz, 6.5 Hz), 8 6.75 (d, 1H, J = 1.8 Hz), 8 6.98 (8, 1H, J = 6.6 Hz), 8 7.12 (m, 2H), 7.40 (d, 1H, J = 5.76 Hz), 7.53 (m, 1H), 8.30 (t, 1H, J = 4.56 Hz), 12.24 (s, 1H) ; 13C NMR (DMSO) 8 18.4, 8 19. 57, 8 28.58, 8 36.74, 8 67.07, 8 110.8, 8 111.58, 8 116.13, 8 118.12, 8 120.86, 8 121.52, 8 128. 70, 8 130.12, 8 134.21, 8 137.25, 8 143. 24, 8 152. 74, 8 155.73, 8 167. 85.

Reference： [1]Patent: WO2005/42497,2005,A2 .Location in patent: Page/Page column 221-222

15
[ 4499-07-4 ]
[ 19752-09-1 ]
C₂HF₃O₂*C₁₇H₁₆Cl₂N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; at 20℃;	Example 3:; This example teaches the preparation of 1- [2- (lH-benzoimidazol-2-yl)-ethyl]-3- (3, 4-dichloro- benzyl) -urea. To a solution of benzimidazole ethyl amine dihydrochloride (50 mg, 0.21 mmol) in pyridine (1.5 mL) was added 3, 4-dichlorobenzylisocyanate (43 ssL, 0.21 mmol). After stirring overnight at room temperature, the crude mixture was purified by Gilson HPLC to afford white solid (50 mg) as a TFA salt at 92% yield. LC/MS (10-99%) M+1/Z 324.2 retention time 2.97 min.

Reference： [1]Patent: WO2005/42497,2005,A2 .Location in patent: Page/Page column 223

16
[ 4499-07-4 ]
[ 19752-09-1 ]
C₂HF₃O₂*C₁₅H₁₃Cl₂N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; at 20℃;	Example 4:; This example teaches the preparation of N-[2-(lH-Benzoimidazol-2-yl)-ethyl]-3, 4-dichloro- benzenesulfonamide. To a solution of benzimidazole ethyl amine dihydrochloride (50 mg, 0.21 mmol) in pyridine (1.5 mL) was added 3,4-dichlorobenzyisocyanate (58 yL, 0.21 mmol). After stirring overnight at room temperature, the crude mixture was purified by Gilson HPLC to afford white solid (55 mg) as TFA salt at 92% yield.

Reference： [1]Patent: WO2005/42497,2005,A2 .Location in patent: Page/Page column 223

17
[ 189560-91-6 ]
[ 4499-07-4 ]

Yield	Reaction Conditions	Operation in experiment
> 95%	With hydrogenchloride; water; In ethyl acetate; at 20℃;	Compound 3 (3 g) was dissolved in 3 N HCl/EtOAC (50 mL/25 mL) and stirred at room temperature overnight. The solvent was in vacuo and dried in high vacuum to give compound 4 as pink solid (2.4 g) at greater than 95% yield. LC/MS (10-99%) M+1/Z 162.4 retention time 0.62 min.

Reference： [1]Patent: WO2005/42497,2005,A2 .Location in patent: Page/Page column 221

18
[ 85-44-9 ]
[ 4499-07-4 ]
[ 4667-71-4 ]

Reference： [1]Patent: EP1187812,2005,B1 .Location in patent: Page/Page column 23

19
[ 4499-07-4 ]
[ 29518-68-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; at 20℃; for 0.5h;	Step 1b; 2-[2-(Aminoethyl)]benzimidazole; [Show Image] Add the product (Preparation 7, Step 1a) (7.18 g) to a solution of potassium hydroxide (3.45 g) in methanol (120 mL). Stir the resulting mixture at room temperature for 30 minutes, filter, and concentrate the filtrate in vacuo. Extract with EtOAc (3 x 500 mL) and filter. Concentrate the filtrate in vacuo to give the title compound as a white solid (3.33 g).

Reference： [1]Patent: EP1135374,2006,B1 .Location in patent: Page/Page column 30

20
2-adamantyloxycarbonyl-α-methyl-DL-tryptophan [ No CAS ]
[ 4499-07-4 ]
[ 191169-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	EXAMPLE 71 Tricyclo[3.3.1.13,7 ]dec-2-yl (+-)-[2-[[2-(1H-benzimidazol-2-yl)ethyl]amino]-1-(1H -indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate Following the procedure of Example 70, the title compound was prepared from 0.50 g (1.26 mmol) of 2-adamantyloxycarbonyl-alpha-methyl-DL-tryptophan and 0.33 g (1.41 mmol) of 1H-benzimidazole-2-ethanamine dihydrochloride with 0.5 mL of added triethylamine. The purified product after chromatography was obtained as a white foam, 0.38 g (56%); 1 H NMR (CDCl3) delta1.46-1.91 (17H, m), 3.01-3.16 (2H, m), 3.27 (1H, d, J 15 Hz), 3.43 (1H, d, J 15 Hz), 3.58 (2H, m), 4.80 (1H, br s), 5.23 (1H, s), 6.67 (1H, m), 6.89-7.72 (10H, m), 8.28 (1H, br s).

Reference： [1]Patent: US5631281,1997,A

21
13-cyclohexyl-6-[[4-(4-morpholinyl)-1-piperidinyl]carbonyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid [ No CAS ]
[ 4499-07-4 ]
N-[2-(1H-benzimidazol-2-yl)ethyl]-13-cyclohexyl-6-[[4-(4-morpholinyl)-1-piperidinyl]carbonyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	N-[2-(]H-benzimidazol-2-yl)ethyl]-13-cyclohexyl-6-[[4-(4-morpholinyl)-1-piperidinyl]carbonyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxamide; A solution of 13-cyclohexyl-6-[[4-(4-morpholinyl)-1-piperidinyl]carbonyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (47 mg, 0.085 mmol), N,N-diisopropylethylamine (60 muL, 0.34 mmol), 2-(2-aminoethyl)benzimidazole dihydrochloride (23 mg, 0.1 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (23 mg, 0.12 mmol), and 1-hydroxybenzotriazole (16 mg, 0.12 mmol) in CH2Cl2 (3.1 mL) was stirred at r.t. overnight, then introduced directly to silica gel. Elution (gradient: 0%?5% MeOH in CH2C12) gave the title compound as a yellow powder (20 mg, 34% yield). LC/MS (ESI) retention time: 1.57 min, m/z 697 (MH+); 1H NMR (400 MHz, CDCl3) delta 1.09-1.21 (m, 1 H) 1.22-1.37 (m, 3 H) 1.38-1.48 (m, 1 H) 1.58-1.68 (m, 1 H) 1.69-1.76 (m, 2 H) 1.87 (t, 1 H) 1.97 (t, 2 H) 2.27 (t, J=10.95 Hz, 1 H) 2.39 (s, 3 H) 2.61-2.72 (m, 1 H) 2.72-2.82 (m, 1 H) 3.26 (t, J=6.04 Hz, 2 H) 3.61-3.70 (m, 4 H) 3.98 (s, 2 H) 4.18 (s, 1 H) 4.86 (s, 1 H) 6.80 (s, 1 H) 7.13 (dd, J=6.04, 3.27 Hz, 2 H) 7.33-7.38 (m, 2 H) 7.40-7.46 (m, 2 H) 7.46-7.53 (m, 3 H) 7.73 (d, J=8.56 Hz, 1 H) 7.77-7.85 (m, 1 H) 8.04 (s, 1 H).

Reference： [1]Patent: US2007/78122,2007,A1 .Location in patent: Page/Page column 238

22
[ 4499-07-4 ]
4-sulfonic acid-1,8-naphthalic anhydride potassium salt [ No CAS ]
N-[2-(2-benzimidazoyl)ethyl]-4-sulfonato-1,8-naphthalimide potassium salt [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 2635 - 2637

23
[ 4499-07-4 ]
[ 121633-88-3 ]
[ 1258439-32-5 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1403 - 1408

24
[ 4499-07-4 ]
[ 871268-56-3 ]
[ 1258439-38-1 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1403 - 1408

25
[ 4499-07-4 ]
[ 262428-61-5 ]
[ 1258439-37-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1403 - 1408

26
[ 1226971-98-7 ]
[ 4499-07-4 ]
[ 1323980-60-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 6900 - 6905

27
[ 1226972-00-4 ]
[ 4499-07-4 ]
[ 1323980-59-1 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 6900 - 6905

28
[ 1226972-03-7 ]
[ 4499-07-4 ]
[ 1323980-61-5 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 6900 - 6905

29
[ 1323980-43-3 ]
[ 4499-07-4 ]
[ 1323980-58-0 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 6900 - 6905

30
[ 4499-07-4 ]
[ 708-06-5 ]
[ 1442646-79-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol;	3.1.1 [C20H17N3O] (L) The Schiff base was synthesized as reported earlier [14a]. 2-Aminoethyl benzimidazolyl dihydrochloride (AB.2HCl) was neutralized by adding requisite amount of aqueous K2CO3. A stirred methanolic solution of 2-hydroxy-1-naphthaldehyde was added slowly to the above solution. After about 1/2h a yellow solid separated out. The solid was dried over P2O5 and finally recrystallized from acetonitrile. Melting Point 213C, m/z 316 (M+1).

Reference： [1]Dalton Transactions,2013,vol. 42,p. 8553 - 8557
[2]Inorganica Chimica Acta,2016,vol. 450,p. 279 - 284

31
[ 4499-07-4 ]
N-hydroxysuccinimidyl (1-oxynaphthyl)acetate [ No CAS ]
N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)-2-(naphthalen-1-yloxy)acetamide [ No CAS ]