[ CAS No. 213133-77-8 ] {[proInfo.proName]}

Name: 213133-77-8|2-(3,4-Dichlorobenzyl)-1H-benzo[d]imidazole|97%
Brand: Ambeed
SKU: A273012
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3d Animation Molecule Structure of 213133-77-8

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Quality Control of [ 213133-77-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 213133-77-8 ]

Product Details of [ 213133-77-8 ]

CAS No. :	213133-77-8	MDL No. :	MFCD09743967
Formula :	C₁₄H₁₀Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XPFCXIKQEQOMMW-UHFFFAOYSA-N
M.W :	277.15	Pubchem ID :	19063344
Synonyms :

Calculated chemistry of [ 213133-77-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.07
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	75.57
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	4.7
Log Po/w (WLOGP) :	4.46
Log Po/w (MLOGP) :	3.85
Log Po/w (SILICOS-IT) :	5.15
Consensus Log Po/w :	4.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.0
Solubility :	0.00275 mg/ml ; 0.00000991 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.03
Solubility :	0.00258 mg/ml ; 0.00000932 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.06
Solubility :	0.000024 mg/ml ; 0.0000000865 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 213133-77-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 213133-77-8 ]

* 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 [ 213133-77-8 ]
Downstream synthetic route of [ 213133-77-8 ]

[ 213133-77-8 ] Synthesis Path-Upstream 1~4

1
[ 1004177-28-9 ]
[ 213133-77-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: With ammonium hydroxide; copper(l) iodide; <i>L</i>-proline; sodium hydroxide In water; dimethyl sulfoxide at 20℃; for 3 h; Inert atmosphere Stage #2: With acetic acid In water; dimethyl sulfoxide at 80℃; for 7 h; Inert atmosphere	General procedure: To a stirred solution of N-(2-iodophenyl)benzamide 4a (50 mg, 0.15 mmol), CuI (2.9 mg, 0.02 mmol), L-proline (3 mg, 0.03 mmol), and NaOH (9 mg, 0.22 mmol) in DMSO (1 mL) was added 30percent aqueous NH₄OH (14.3 μL, 0.22 mmol) dropwise. After stirring at room temperature for 3 h, acetic acid (1 mL) was added dropwise. Then, the reaction mixture was heated to 80 °C for 7 h. After cooling to room temperature, the reaction mixture was extracted with EtOAc (3 ~ 20 mL) and washed with 5percent aqueous solution of NaHCO₃ (~ 20 mL). The organic layer was dried over anhydrous Na₂SO₄, and concentrated in vacuo. The residue was purified by column chromatography (SiO_2,n-hexane/EtOAc 2/1) to yield the title product 7a (18 mg, 60percent).

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1172 - 1192

2
[ 5807-30-7 ]
[ 95-54-5 ]
[ 213133-77-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With boric acid In 5,5-dimethyl-1,3-cyclohexadiene for 16 h; Reflux	General procedure: To a stirred solution of benzene-1,2-diamine 1 (1.85 mmol)in xylenes (10 mL) were added carboxylic acid 2 (2.77 mmol)and boric acid (0.185 mmol). The resulting solution wasrefluxed for 16 h. After cooling to room temperature, the reactionwas concentrated under reduced pressure and diluted withEtOAc (50 mL). The organic phase was washed with saturatedNaHCO3 solution (2 50 mL), dried over anhydrous Na2SO4and then concentrated under reduced pressure. The residuewas purified by silica gel flash column chromatography (elutingwith 10–15percent Ethyl acetate in hexanes) to afford the title compounds3a–y and 5.6.2.8 2-(3,4-Dichlorobenzyl)-1H-benzo[d]imidazole (3h) Yield 65percent; Off white solid; mp 189-191 °C; IR (KBr) 2851, 2758, 1508, 1451, 1410, 1241, 1183, 1027, 754 cm^-1; ¹H NMR (400 MHz, DMSO-d₆) δ 12.30 (br s, 1H), 7.64 (d, J = 2.20 Hz, 1H), 7.59 (d, J = 8.05 Hz, 1H), 7.48-7.56 (m, 1H), 7.39-7.48 (m, 1H), 7.33 (dd, J = 2.19, 8.29 Hz, 1H), 7.08-7.18 (m, 2H), 4.21 (s, 2H); ¹³C NMR (100 MHz, DMSO-d₆) δ 152.7, 138.8, 131.0, 130.7, 129.5, 129.4, 121.5, 33.7; HRMS calcd for C₁₄H₁₀Cl₂N₂ m/z 276.0225, found 276.0221.

Reference： [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 8, p. 1872 - 1878

3
[ 6831-55-6 ]
[ 213133-77-8 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1172 - 1192

4
[ 615-43-0 ]
[ 213133-77-8 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1172 - 1192

[ 213133-77-8 ] Synthesis Path-Downstream 1~11

1
[ 213133-77-8 ]
[ 1047731-79-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

2
[ 213133-77-8 ]
[ 1602747-55-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

3
[ 213133-77-8 ]
[ 1602747-50-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

4
[ 213133-77-8 ]
[ 96-32-2 ]
[ 1602748-35-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	General procedure: To a stirred solution of 2-phenyl-1H-benzo[d]imidazole 7a (50 mg, 0.26 mmol) and NaH (7 mg, 0.31 mmol) in DMF (0.5 mL) was added methyl bromoacetate (29 muL, 0.31 mmol) dropwise. After stirring at room temperature for 16 h, the reaction mixture was extracted with EtOAc (3 ~ 20 mL) and washed with H2O (~ 20 mL). The organic layer was dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, n-hexane/EtOAc 2/1) to yield the title product 8a (35 mg, 50%).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

Yield	Reaction Conditions	Operation in experiment
30%		General procedure: Example 2 2-phenyl-1H-benzo[d]imidazole To a round-bottom flask, N-(2-iodophenyl)benzamide (50 mg, 0.15 mmol), copper iodide (2.86 mg, 0.015 mmol), L-proline (3.45 mg, 0.03 mmol) and sodium hydroxide (9 mg, 0.225 mmol) are introduced and purging is carried out with nitrogen. Then, dimethyl sulfoxide (1 mL) is added thereto to dissolve the reaction mixture and 30% aqueous ammonia (14.3 muL, 0.225 mmol) is added dropwise thereto. The reaction mixture is agitated for 2-3 hours. The reaction progress and result are checked by TLC. Then, acetic acid (1 mL) is added dropwise thereto at room temperature and the reaction mixture is refluxed at 80 C. for 7 hours. The reaction progress and result are checked by TLC. After completing the reaction, the reaction mixture is extracted with ethyl acetate and water and aqueous solution of potassium carbonate is added dropwise thereto to perform neutralization, followed by extraction with ethyl acetate. The organic layer is dried with dry sodium sulfate, followed by filtering. The filtrate is concentrated under reduced pressure and the concentrate is purified by column chromatography (EA:n-hHex=1:2) to obtain 18 mg of the target compound (yield: 60%). 1H NMR (300 MHz, DMSO-d6) delta ppm 12.92 (br s, 1H) 8.18 (m, 2H) 7.52 (m, 5H) 7.21 (m, 2H)

6
[ 5807-30-7 ]
[ 95-54-5 ]
[ 213133-77-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With Zn/Al2O3; In 5,5-dimethyl-1,3-cyclohexadiene; at 130℃; for 6.08333h;	10.8 g of o-phenylenediamine and 24.6 g of 3,4-chlorophenylacetic acid were placed in a 250 ml three-neck round bottom flask.Add 100 ml of xylene and stir for 5 minutes.Add 1.2 g of Zn/Al2O3 catalyst and connect the water separator.The mixture was heated to reflux at 130 C for 6 hours, and the solvent was recovered by using a distillation recovery device. When about 80 ml of xylene was recovered, the mixture was distilled under reduced pressure.Stop the vacuum distillation when the xylene recovery is 90 ml.Add 150 ml of ethanol and add 10 ml of ammonia water.0.5 g of activated carbon, stirred and dissolved for 30 minutes,Filter the activated carbon and slowly add 50 ml of pure water to the filtrate.Stir while stirring, product precipitation, filtration, hot water wash twice,Filtration and drying gave 22.2 g of 2-(3,4-chlorobenzyl)benzimidazole, the yield was 80%, and the product color was good.
65%	With boric acid; In 5,5-dimethyl-1,3-cyclohexadiene; for 16h;Reflux;	General procedure: To a stirred solution of benzene-1,2-diamine 1 (1.85 mmol)in xylenes (10 mL) were added carboxylic acid 2 (2.77 mmol)and boric acid (0.185 mmol). The resulting solution wasrefluxed for 16 h. After cooling to room temperature, the reactionwas concentrated under reduced pressure and diluted withEtOAc (50 mL). The organic phase was washed with saturatedNaHCO3 solution (2 50 mL), dried over anhydrous Na2SO4and then concentrated under reduced pressure. The residuewas purified by silica gel flash column chromatography (elutingwith 10-15% Ethyl acetate in hexanes) to afford the title compounds3a-y and 5.6.2.8 2-(3,4-Dichlorobenzyl)-1H-benzo[d]imidazole (3h) Yield 65%; Off white solid; mp 189-191 C; IR (KBr) 2851, 2758, 1508, 1451, 1410, 1241, 1183, 1027, 754 cm-1; 1H NMR (400 MHz, DMSO-d6) delta 12.30 (br s, 1H), 7.64 (d, J = 2.20 Hz, 1H), 7.59 (d, J = 8.05 Hz, 1H), 7.48-7.56 (m, 1H), 7.39-7.48 (m, 1H), 7.33 (dd, J = 2.19, 8.29 Hz, 1H), 7.08-7.18 (m, 2H), 4.21 (s, 2H); 13C NMR (100 MHz, DMSO-d6) delta 152.7, 138.8, 131.0, 130.7, 129.5, 129.4, 121.5, 33.7; HRMS calcd for C14H10Cl2N2 m/z 276.0225, found 276.0221.

Reference： [1]Patent: CN109535080,2019,A .Location in patent: Paragraph 0033
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 1872 - 1878

7
[ 1004177-28-9 ]
[ 213133-77-8 ]

Yield	Reaction Conditions	Operation in experiment
40%		General procedure: To a stirred solution of N-(2-iodophenyl)benzamide 4a (50 mg, 0.15 mmol), CuI (2.9 mg, 0.02 mmol), L-proline (3 mg, 0.03 mmol), and NaOH (9 mg, 0.22 mmol) in DMSO (1 mL) was added 30% aqueous NH4OH (14.3 muL, 0.22 mmol) dropwise. After stirring at room temperature for 3 h, acetic acid (1 mL) was added dropwise. Then, the reaction mixture was heated to 80 C for 7 h. After cooling to room temperature, the reaction mixture was extracted with EtOAc (3 ~ 20 mL) and washed with 5% aqueous solution of NaHCO3 (~ 20 mL). The organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, n-hexane/EtOAc 2/1) to yield the title product 7a (18 mg, 60%).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

8
[ 6831-55-6 ]
[ 213133-77-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

9
[ 615-43-0 ]
[ 213133-77-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

10
[ 4856-97-7 ]
[ 95-50-1 ]
[ 213133-77-8 ]
2-(2,3-dichlorobenzyl)-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%Spectr.; 31%Spectr.	With trifluorormethanesulfonic acid; at 140℃; for 2.5h;	General procedure: Solution ofbenzimidazole (0.1 mmol) in TfOH (1 mL) and arene (0.1 mL) was magnetically stirred at 140 Cin glass high pressure tube for 2.5 h, then poured into water (50 mL). After extraction with CH2Cl2(3 × 30 mL), the combined extracts were consequently washed with water (50 mL), saturatedaqueous solution of Na2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporatedin vacuo to give crude products, which were subjected to chromatographic separation on silica gelusing petroleum ether/diethyl ether as an eluent.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1962 - 1973

11
[ 95-54-5 ]
[ 213133-77-8 ]
2-(2,3-dichlorobenzyl)-1H-benzimidazole [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1962 - 1973

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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. 213133-77-8 ] {[proInfo.proName]}

Quality Control of [ 213133-77-8 ]

Related Doc. of [ 213133-77-8 ]

Product Details of [ 213133-77-8 ]

Calculated chemistry of [ 213133-77-8 ]

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Application In Synthesis of [ 213133-77-8 ]

[ 213133-77-8 ] Synthesis Path-Upstream 1~4

[ 213133-77-8 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 213133-77-8 ]

Aryls

Chlorides

Related Parent Nucleus of [ 213133-77-8 ]

Benzimidazoles

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[ 213133-77-8 ]

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[ 213133-77-8 ]