[ CAS No. 3584-66-5 ] {[proInfo.proName]}

Name: 3584-66-5|5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole|95%
Brand: Ambeed
SKU: A323296
Price: 14.0 USD
Availability: InStock
Rating: 96 (25 reviews)

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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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Quality Control of [ 3584-66-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3584-66-5 ]

SDS Specification

Alternatived Products of [ 3584-66-5 ]

Product Details of [ 3584-66-5 ]

CAS No. :	3584-66-5	MDL No. :	MFCD00005595
Formula :	C₈H₄Cl₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SIZGSKQSWJIWFP-UHFFFAOYSA-N
M.W :	269.94	Pubchem ID :	77134
Synonyms :

Calculated chemistry of [ 3584-66-5 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	60.34
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.98
Log Po/w (XLOGP3) :	4.22
Log Po/w (WLOGP) :	3.93
Log Po/w (MLOGP) :	3.05
Log Po/w (SILICOS-IT) :	4.28
Consensus Log Po/w :	3.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.58
Solubility :	0.00707 mg/ml ; 0.0000262 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.53
Solubility :	0.00792 mg/ml ; 0.0000293 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.42
Solubility :	0.00102 mg/ml ; 0.00000377 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 3584-66-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338-P311	UN#:	2811
Hazard Statements:	H301+H311+H331-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 3584-66-5 ]

* 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 [ 3584-66-5 ]

[ 3584-66-5 ] Synthesis Path-Downstream 1~23

3
[ 95-83-0 ]
[ 2533-69-9 ]
[ 3584-66-5 ]

Reference： [1]Archiv der Pharmazie,2000,vol. 333,p. 123 - 129

4
[ 95-83-0 ]
[ 2533-69-9 ]
[ 3584-66-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With acetic acid; at 20℃; for 1.16667h;Cooling;	(i) Methyl 2,2,2-trichloroacetimidate (480 muL, 3.86 mmol) was added dropwise to a cooled solution of 4-chloro-benzene-1,2-diamine (500 mg, 3.51 mmol) in acetic acid (20 mL). At the end of the addition (10 min), the reaction mixture was kept at room temperature for 1 h. The reaction mixture was extracted with CH2Cl2, washed with water, dried with anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to provide 5-chloro-2-trichloromethyl-1H-benzimidazole (805 mg, 85%). LRMS (ESI) m/z 269 [M + H]+.
82%	With acetic acid; at 0 - 20℃; for 2.5h;	24. 55 mmol of PHENYLENEDIAMINE 1a-k, 1M, In were dissolved in 50 ml of acetic acid, AND 27 MMOL of methy 2, 2, 2-TRICHFOROACETIMIDATE 2 WERE added at 0C over the course of 0.5 hour under an N2 atmosphere. When the addition was complete, the reaction mixture was slowly warmed to room temperature and stirred at this temperature for 2 hours. The reaction mixture was poured into ice-water, and the resulting precipitate was filtered off with suction, washed with a little water and dried at 40C under reduced pressure. 3a: R = 5-Cl ; brown solid, yield : 82%

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 58,p. 624 - 639
[2]Patent: WO2005/4863,2005,A1 .Location in patent: Page/Page column 134
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5251 - 5256
[4]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1156 - 1159
[5]Indian Journal of Heterocyclic Chemistry,2014,vol. 24,p. 87 - 92

5
[ 3584-66-5 ]
[ 39811-14-8 ]

Yield	Reaction Conditions	Operation in experiment
97%		0.5 g of 2-trichloromethylbenzimidazole 3a-m was introduced in portions at 0C into 30 ml of 2N NaOH solution. The resulting solution was acidified (pH 3) using 2N HCI solution and stirred for 1 hour. The mixture was cooled, and the resulting precipitate was filtered off with suction and washed 2 x with WATER/ACETONITRILE (3: 1) and 2 x with diethyl ether. 4a: R = 5-Cl ; brown solid, yield: 97%
95%	With sodium hydroxide;Cooling;	(ii) 5-Chloro-2-trichloromethyl-1H-benzimidazole (700 mg, 2.61 mmol) was added to a cooled solution of sodium hydroxide (60 mL, 1 N). The resulting solution was filtered and the filtrate was acidified with hydrochloric acid (1 N) to pH 4. The precipitate was filtered off, washed twice with a solution of water and acetonitrile (ratio 3:1) and twice with ether. After drying, this led to 5-chloro-1H-benzimidazole-2-carboxylic acid (484 mg, 95%). LRMS (ESI) m/z 195 [M - H]-. (

Reference： [1]Patent: WO2005/4863,2005,A1 .Location in patent: Page/Page column 135
[2]European Journal of Medicinal Chemistry,2012,vol. 58,p. 624 - 639
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5251 - 5256
[4]Indian Journal of Heterocyclic Chemistry,2014,vol. 24,p. 87 - 92

6
[ 109-01-3 ]
[ 3584-66-5 ]
(5-chloro-1H-benzoimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 8289 - 8298

7
[ 3584-66-5 ]
5-chloro-1H-benzoimidazole-2-carboxylic acid (2-dimethylamino-ethyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5251 - 5256

8
[ 3584-66-5 ]
5-chloro-1H-benzoimidazole-2-carboxylic acid (2-dimethylamino-ethyl)-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5251 - 5256

9
[ 3584-66-5 ]
(5-chloro-1H-benzoimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5251 - 5256
[2]Indian Journal of Heterocyclic Chemistry,2014,vol. 24,p. 87 - 92

10
[ 3584-66-5 ]
5-chloro-1H-benzoimidazole-2-carboxylic acid (4-methyl-piperazin-1-yl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5251 - 5256

11
[ 109-01-3 ]
[ 3584-66-5 ]
[ 673487-12-2 ]

Yield	Reaction Conditions	Operation in experiment
22%	With ammonium acetate; In acetonitrile; for 18h;	To a suspension [OF 5-CHLORO-2-TRICHLOROMETHYL-1H-BENZOIMIDAZOLE] (100 mg, 0.37 mmol) in acetonitrile (4 mL) was added N-methylpiperazine (0.04 mL, 0.4 [MMOL).] The mixture was stirred for 10 min then ammonium acetate (29 mg, 0.38 [MMOL)] was added. After 18 h the reaction mixture was diluted with satd aq [NAHCO3] (10 mL), and then extracted with [DICHLOROMETHANE] [(3 X 10] mL). The combined extracts were dried [(NA2SO4)] and then concentrated under reduced pressure. The crude product was purified on silica gel (10 g; 0-10% methanol (2 M NH3)/dichloromethane) to afford 23 mg (22%) of the title compound. MS [(ESI)] : mass calculated for [C13H16N40,] 277.11 ; [M/Z] found, 278.2 [M+H] [+. 1H] NMR (400 MHz, CD30D) : 7.79-7. 74 [(M,] 2H), 7.45 (dd, [J =] 8.6, 2.0 Hz, [1H),] 4.23-4. 17 (m, 4H), 3.63-3. 58 (m, 4H), 3.01 (s, 3H).

Reference： [1]Patent: WO2004/22060,2004,A2 .Location in patent: Page/Page column 48

12
cis-octahydro-pyrrolo[3,4-b]pyridine [ No CAS ]
[ 3584-66-5 ]
cis-(5-chloro-1H-benzoimidazol-2-yl)-(octahydro-pyrrolo[3,4-b]pyridin-6-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate; In water; acetonitrile; at 100℃; for 1h;	To a suspension of <strong>[3584-66-5]5-chloro-2-trichloromethyl-1H-benzoimidazole</strong> (30 mg, 0.11 mmol) and K2CO3 (46 mg, 0.33 mmol) in CH3CN/H2O (10:1, 3 mL) was added cis-octahydro-pyrrolo[3,4-b]pyridine (28 mg, 0.22 mmol). After 1 h at 100 C., the mixture was filtered and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated to give a yellow oil, which was purified by FCC to give a brown solid (14 mg, 40%). MS (ESI): mass calcd. for C15H17ClN4O, 304.11; m/z found, 305.4 [M+H]+. 1H NMR (mixture of rotamers; MeOD): 7.70-7.58 (m, 2H), 7.35-7.25 (m, 1H), 4.43-4.28 (m, 0.6H), 4.19-4.09 (m, 0.6H), 3.77-3.69 (m, 1H), 3.46-3.40 (m, 0.3H), 3.38-3.33 (m, 0.3H), 3.33-3.28 (m, 2H), 3.04-2.82 (m, 1.5H), 2.71-2.53 (m, 1H), 2.50-2.31 (m, 1.5H), 1.95-1.43 (m, 4H).

Reference： [1]Patent: US2007/238771,2007,A1 .Location in patent: Page/Page column 11-12

13
[ 172739-03-6 ]
[ 3584-66-5 ]
5-Chloro-2-[(3aR,6aS)-5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]carbonyl}-1H-benzimidazole [ No CAS ]