[ CAS No. 54624-57-6 ] {[proInfo.proName]}

Name: 54624-57-6|2-Bromobenzimidazole|98%
Brand: Ambeed
SKU: A103455
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Quality Control of [ 54624-57-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 54624-57-6 ]

SDS Specification

Alternatived Products of [ 54624-57-6 ]

Product Details of [ 54624-57-6 ]

CAS No. :	54624-57-6	MDL No. :	MFCD00160009
Formula :	C₇H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PHPYXVIHDRDPDI-UHFFFAOYSA-N
M.W :	197.03	Pubchem ID :	2776281
Synonyms :

Calculated chemistry of [ 54624-57-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.79
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.33
Log Po/w (XLOGP3) :	2.28
Log Po/w (WLOGP) :	2.33
Log Po/w (MLOGP) :	1.75
Log Po/w (SILICOS-IT) :	2.75
Consensus Log Po/w :	2.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.16
Solubility :	0.135 mg/ml ; 0.000685 mol/l
Class :	Soluble
Log S (Ali) :	-2.52
Solubility :	0.596 mg/ml ; 0.00302 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.0337 mg/ml ; 0.000171 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 54624-57-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 54624-57-6 ]

* 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 [ 54624-57-6 ]
Downstream synthetic route of [ 54624-57-6 ]

[ 54624-57-6 ] Synthesis Path-Upstream 1~8

1
[ 54624-57-6 ]
[ 15108-18-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	Reflux	The schematic representation of the synthesis of LHAc is given in Scheme 1. First, 2-bromobenzimidazole was obtained from 2-mercaptobenzimidazole by the reported method [13]. In the nextstep, 2-bromobenzimidazole (1.97 g, 0.01 mol) was refluxed in20 mL of 80percent hydrazine hydrate solution, to obtain 2-Hydrazinobenzimidazole (1.35 g, Yield: 91percent). Finally, diacetylmonoxime (1.01 g, 0.01 mol) was added to the 20 ml methanolicsolution of 2-hydrazinobenzimidazole (1.48 g, 0.01 mol) in presenceof 3 drops of glacial acetic acid. The resulting mixture wasrefluxed for 4 h. On cooling, the white crystals separated werefiltered and washed with cold methanol to get the desired product(1.6 g, yield: 55percent, M.P 240 C).
91%	for 4 h; Reflux	The schematic representation of the synthesis of ligand is given in Scheme 1 . First, 2-bromobenzimidazole was obtained from 2-mercaptobenzimidazole by the reported method [24]. In the next step, 2-bromobenzimidazole (1.97g, 10mmol) was refluxed in 20.0mL of 80percent hydrazine hydrate solution, to obtain 2-hydrazinobenzimidazole (1.35g, Yield: 91percent) [25]. Finally, to the magnetically stirred methanolic solution of 2-hydrazinobenzimidazole (1.65g, 10.0mmol), hydroxyacetone (0.740g, 10.0mmol) in methanol was added dropwise. The mixture was refluxed on a water bath for 1h. The progress of the reaction was monitored by TLC. The buff colored precipitate formed was filtered and washed with cold methanol. The solid product was dried in vacuo for 4h.

Reference： [1] Journal of Molecular Structure, 2017, vol. 1133, p. 546 - 556
[2] Polyhedron, 2017, vol. 127, p. 225 - 237

2
[ 54624-57-6 ]
[ 2620-76-0 ]

Reference： [1] Patent: CN106967052, 2017, A,
[2] Patent: CN106946853, 2017, A,
[3] Patent: CN107417668, 2017, A,

3
[ 134469-07-1 ]
[ 54624-57-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 52, p. 15859 - 15862[2] Angew. Chem., 2015, vol. 127, # 52, p. 16085 - 16088,3
[3] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 22, p. 2509 - 2512
[4] Journal of Molecular Structure, 2017, vol. 1133, p. 546 - 556
[5] Polyhedron, 2017, vol. 127, p. 225 - 237
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 4, p. 705 - 716
[7] Synthetic Communications, 2013, vol. 43, # 14, p. 1882 - 1895
[8] Chemistry - An Asian Journal, 2014, vol. 9, # 9, p. 2542 - 2547,6
[9] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 3997 - 4002

4
[ 95-54-5 ]
[ 54624-57-6 ]

Reference： [1] Journal of the Korean Chemical Society, 2010, vol. 54, # 5, p. 589 - 593
[2] Journal of the Chilean Chemical Society, 2012, vol. 57, # 2, p. 1122 - 1125,4

5
[ 51-17-2 ]
[ 54624-57-6 ]

Reference： [1] Tetrahedron Letters, 1986, vol. 27, # 9, p. 1051 - 1054

6
[ 934-32-7 ]
[ 54624-57-6 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 10, p. 2518 - 2521

7
[ 583-39-1 ]
[ 54624-57-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 5, p. 1918 - 1924

8
[ 95-54-5 ]
[ 54624-57-6 ]

Reference： [1] Synthetic Communications, 2013, vol. 43, # 14, p. 1882 - 1895

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[ 54624-57-6 ]

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Yield	Reaction Conditions	Operation in experiment
74%	With pyridine; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere;	Step 1: Preparation of intermediate benzyl <strong>[54624-57-6]2-bromo-1H-1,3-benzodiazole</strong>-1-carboxylate (7a) Under nitrogen atmosphere, benzyl chloroformate (0.174 mL, 1.218 mmol) was added to a solution of <strong>[54624-57-6]2-bromo-1H-1,3-benzodiazole</strong> (200 mg, 1.015 mmol) and pyridine (0.123 mL, 1.523 mmol) in anhydrous dichloromethane (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 hours, then cooled to 0° C. Water (5 mL) was added, and once at room temperature, the aqueous layer was extracted with dichloromethane (2*7 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate: 80/20) to provide benzyl <strong>[54624-57-6]2-bromo-1H-1,3-benzodiazole</strong>-1-carboxylate (7a) (250 mg, 0.755 mmol, 74percent). 1H NMR (400 MHz, CDCl3) delta 5.54 (s, 2H), 7.30-7.37 (m, 2H), 7.39-7.48 (m, 3H), 7.50-7.55 (m, 2H), 7.64-7.71 (m, 1H), 7.85-7.92 (m, 1H).
	With pyridine; In dichloromethane; water;	Step 1: Preparation of intermediate benzyl <strong>[54624-57-6]2-bromo-1H-1,3-benzodiazole</strong>-1-carboxylate (7a) Under nitrogen atmosphere, benzyl chloroformate (0.174 mL, 1.218 mmol) was added to a solution of <strong>[54624-57-6]2-bromo-1H-1,3-benzodiazole</strong> (200 mg, 1.015 mmol) and pyridine (0.123 mL, 1.523 mmol) in anhydrous dichloromethane (4 mL) at 0°C. The reaction mixture was stirred at room temperature for 3 hours, then cooled to 0°C. Water (5 mL) was added, and once at room temperature, the aqueous layer was extracted with dichloromethane (2 x 7 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate: 80/20) to provide benzyl <strong>[54624-57-6]2-bromo-1H-1,3-benzodiazole</strong>-1-carboxylate (7a) (250 mg, 0.755 mmol, 74percent). 1H NMR (400 MHz, CDCl3) d 5.54 (s, 2H), 7.30-7.37 (m, 2H), 7.39-7.48 (m, 3H), 7.50-7.55 (m, 2H), 7.64-7.71 (m, 1 H), 7.85-7.92 (m, 1H).

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
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. 54624-57-6 ] {[proInfo.proName]}

Quality Control of [ 54624-57-6 ]

Related Doc. of [ 54624-57-6 ]

Product Details of [ 54624-57-6 ]

Calculated chemistry of [ 54624-57-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 54624-57-6 ]

Application In Synthesis of [ 54624-57-6 ]

[ 54624-57-6 ] Synthesis Path-Upstream 1~8

[ 54624-57-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 54624-57-6 ]

Bromides

Related Parent Nucleus of [ 54624-57-6 ]

Benzimidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 54624-57-6 ]

Related Parent Nucleus of
[ 54624-57-6 ]