Home Cart 0 Sign in  
X

[ CAS No. 6953-65-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 6953-65-7
Chemical Structure| 6953-65-7
Chemical Structure| 6953-65-7
Structure of 6953-65-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 6953-65-7 ]

Related Doc. of [ 6953-65-7 ]

Alternatived Products of [ 6953-65-7 ]

Product Details of [ 6953-65-7 ]

CAS No. :6953-65-7 MDL No. :MFCD09971879
Formula : C8H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :NIWRFQPRPJVQLO-UHFFFAOYSA-N
M.W :182.61 Pubchem ID :23383
Synonyms :

Calculated chemistry of [ 6953-65-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.23
TPSA : 48.91 Ų

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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 1.71
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 2.48
Consensus Log Po/w : 1.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.529 mg/ml ; 0.00289 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 0.81 mg/ml ; 0.00444 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.36
Solubility : 0.0804 mg/ml ; 0.000441 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 6953-65-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6953-65-7 ]

* 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 [ 6953-65-7 ]
  • Downstream synthetic route of [ 6953-65-7 ]

[ 6953-65-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 79-14-1 ]
  • [ 95-83-0 ]
  • [ 6953-65-7 ]
YieldReaction ConditionsOperation in experiment
82% at 150℃; for 4 h; 21 a)A mixture of 4-chlorobenzene-1,2-diamine (105 g, 736 mmoles, 1 eq.) andhydroxyacetic acid (112 g, 2 eq.) in xylene (1500 mL) was stirred at 150 °C for 4 hours. The mixture was then cooled to 60 °C and treated with 3N HC1 (480 ml), then basified to pH=7-8 by the addition of aqueous ammonia. The mixture was filtered and the solid was collected, washed with H20 and tert-butyl methyl ether to give 123 g (82percent yield) of (5 -chloro- 1 H-benzo [d]imidazo l-2-yl)methano 1 21 a.
82% at 150℃; for 4 h; A mixture of 4-chlorobenzene-1,2-diamine (105 g, 736 mmoles, 1 eq.) and hydroxyacetic acid (112 g, 2 eq.) in xylene (1500 mL) was stirred at 150°C for 4 hours. The mixture was then cooled to 60°C and treated with 3N HC1 (480 ml), then basified to pH = 7-8 by the addition of aqueous ammonia. The mixture was filtered and the solid was collected, washed with H20 and tert-butyl methyl ether to give 123 g (82percent yield) of (5 -chloro- 1 H-benzo [d]imidazol-2-yl)methanol (7a).
Reference: [1] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223
[2] Patent: WO2014/60411, 2014, A1, . Location in patent: Page/Page column 58
[3] Patent: WO2015/158653, 2015, A1, . Location in patent: Page/Page column 37; 38
[4] Annales Pharmaceutiques Francaises, 2003, vol. 61, # 1, p. 57 - 61
[5] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1272 - 1274
[6] Chemische Berichte, 1951, vol. 84, p. 719,727
[7] Journal of the Chemical Society, 1949, p. 1260,1268
[8] Journal of the Chemical Society, 1950, p. 1515,1516
[9] Patent: WO2004/22060, 2004, A2, . Location in patent: Page/Page column 24
[10] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 933 - 936
[11] MedChemComm, 2018, vol. 9, # 7, p. 1194 - 1205
  • 2
  • [ 6953-65-7 ]
  • [ 74-88-4 ]
  • [ 380177-22-0 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: With sodium hydroxide In acetone for 0.5 h;
Stage #2: for 24 h;
N-Methyl-2-methanol-5-chlorobenzimidazole 49 was prepared according to using the procedure by Harisha et al. [28] A solution of 5-chloro-(1H-benzimidazole-2-yl)-methanol 28 (1.50 g, 8.20 mmol), and sodium hydroxide (0.33 g, 8.2 mmol) were stirred in dry acetone (30 mL) for 30 min. Then, iodomethane (1.41 g, 8.20 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50percent HCl to neutralize the excess potassium carbonate. The solid was washed with cold water (100 mL) and aqueous ethanol. The product was purified by column chromatography (9:1 chloroform/ethanol) to give the desired product 38 as bright orange crystals Yield 9percent.
Reference: [1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1272 - 1274
[2] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 933 - 936
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 6953-65-7 ]

Chlorides

Chemical Structure| 6478-79-1

[ 6478-79-1 ]

5,6-Dichloro-2-methylbenzimidazole

Similarity: 0.86

Chemical Structure| 34569-15-8

[ 34569-15-8 ]

6-Chloro-2-ethyl-1H-benzo[d]imidazole

Similarity: 0.83

Chemical Structure| 4887-91-6

[ 4887-91-6 ]

6-Chloro-2-propyl-1H-benzo[d]imidazole

Similarity: 0.81

Chemical Structure| 4886-29-7

[ 4886-29-7 ]

6-Chloro-2-isopropyl-1H-benzo[d]imidazole

Similarity: 0.80

Chemical Structure| 4887-82-5

[ 4887-82-5 ]

6-Chloro-1H-benzo[d]imidazole

Similarity: 0.76

Alcohols

Chemical Structure| 20034-02-0

[ 20034-02-0 ]

(6-Methyl-1H-benzo[d]imidazol-2-yl)methanol

Similarity: 0.78

Chemical Structure| 540516-28-7

[ 540516-28-7 ]

2-(Hydroxymethyl)-5-bromobenzimidazole

Similarity: 0.74

Chemical Structure| 4856-97-7

[ 4856-97-7 ]

(1H-Benzoimidazol-2-yl)methanol

Similarity: 0.74

Chemical Structure| 4589-66-6

[ 4589-66-6 ]

(1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol

Similarity: 0.65

Chemical Structure| 39811-07-9

[ 39811-07-9 ]

(5-Fluoro-1H-benzo[d]imidazol-2-yl)methanol

Similarity: 0.64

Related Parent Nucleus of
[ 6953-65-7 ]

Benzimidazoles

Chemical Structure| 6478-79-1

[ 6478-79-1 ]

5,6-Dichloro-2-methylbenzimidazole

Similarity: 0.86

Chemical Structure| 34569-15-8

[ 34569-15-8 ]

6-Chloro-2-ethyl-1H-benzo[d]imidazole

Similarity: 0.83

Chemical Structure| 4887-91-6

[ 4887-91-6 ]

6-Chloro-2-propyl-1H-benzo[d]imidazole

Similarity: 0.81

Chemical Structure| 4886-29-7

[ 4886-29-7 ]

6-Chloro-2-isopropyl-1H-benzo[d]imidazole

Similarity: 0.80

Chemical Structure| 20034-02-0

[ 20034-02-0 ]

(6-Methyl-1H-benzo[d]imidazol-2-yl)methanol

Similarity: 0.78