Home Cart Sign in  
Chemical Structure| 2407-11-6 Chemical Structure| 2407-11-6

Structure of 2407-11-6

Chemical Structure| 2407-11-6

2-Chloro-6-nitrobenzo[d]thiazole

CAS No.: 2407-11-6

4.5 *For Research Use Only !

Cat. No.: A542206 Purity: 97%

Change View

Size Price

US Stock

Global Stock

In Stock
250mg łÇʶÊÊ Inquiry Inquiry
1g łÇÿ¶ÊÊ Inquiry Inquiry
5g łÍÿ¶ÊÊ Inquiry Inquiry
10g łďÿ¶ÊÊ Inquiry Inquiry
25g łÇÿʶÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • 250mg

    łÇʶÊÊ

  • 1g

    łÇÿ¶ÊÊ

  • 5g

    łÍÿ¶ÊÊ

  • 10g

    łďÿ¶ÊÊ

  • 25g

    łÇÿʶÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 2407-11-6 ]

CAS No. :2407-11-6
Formula : C7H3ClN2O2S
M.W : 214.63
SMILES Code : O=[N+](C1=CC=C2N=C(Cl)SC2=C1)[O-]
MDL No. :MFCD00022852
InChI Key :KUCSJGBXJBQHNI-UHFFFAOYSA-N
Pubchem ID :75476

Safety of [ 2407-11-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2407-11-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 53.45
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

86.95 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.47
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.42
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.86
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.73
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.59
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.21

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.77
Solubility 0.0363 mg/ml ; 0.000169 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.93
Solubility 0.00254 mg/ml ; 0.0000119 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.97
Solubility 0.228 mg/ml ; 0.00106 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.18 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.54

Application In Synthesis of [ 2407-11-6 ]

* 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.

  • Downstream synthetic route of [ 2407-11-6 ]

[ 2407-11-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2407-11-6 ]
  • [ 2406-90-8 ]
YieldReaction ConditionsOperation in experiment
83% To a solution of 2-CHLOROBENZOTHIAZOLE (12.0 g, 70.7 MMOL) in concentrated H2SO4 (60 mL) was added HN03 (69% solution, 6 mL) dropwise at 0C for 20 min. The mixture was stirred at 5C for 3h, poured into ice-water (150 mL). The precipitate was collected and washed with 5% sodium bicarbonate and water, dried in VACUO.'H NMR analysis showed the mixture contained 78% 6-nitro-2-chlorobenzothiazole and 8% 5-nitro-2- chlorobenzothiazole. Recrystallization from ethanol gave 6-nitro-2-chlorobenzothiazole as white crystalline solid (11 g, 72%). 3.5 g of the solid was dissolved in refluxing ethanol-acetic acid (150: 15 mL), Iron powder was added in one portion.. The mixture was refluxed for 1.5h, filtered. The filtrate was concentrated in vacuo to half volume and neutralized with 10% NaOH to pH 7.5, extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to give a residue, which was RECRYSTALLIZED from ethanol. Light purple crystals (2.5 g, 83%) were obtained. Mp 160-164C ; TLC single spot at Rf 0.27 (30% EtOAc/hexane) ;'HNMR (270 MHz, DMSO-d6) 5 7.58 (1H, d, J = 9.0 Hz, 4-H), 7.03 (1H, d, J = 2.0 Hz, 7-H), 6.77 (1 H, dd, J = 9.0, 2. 0 Hz, 5-H), 5.55 (2H, s, NH2). The mother liquor from the RECRYSTALLIZATION of nitration product was evaporated and subjected to iron powder reduction as described above. The crude product was purified with flash chromatography (ethyl acetate-DCM gradient elution) to give 2-CHLORO- benzothiazol-5-yl-amine as yellow solid. Mp 146-149C ; TLC single spot at Rf 0.52 (10% EtOAc/DCM) ;'HNMR (270 MHZ, DMSO-d6) 8 7.63 (1 H, d, J = 8. 6 HZ, 7-H), 7.05 (1 H, d, J = 2.3 Hz, 4-H), 6.78 (1 H, dd, J = 8.6, 2.3 Hz, 6-H), 5.40 (2H, s, NH2).
61% (B) Synthesis of 2-chloro-6-aminobenzothiazole (3) Compound 2 (1.96 g, 9.14 mmol) was dissolved in ethanol (150 mL) and purified water (100 mL), and the solution was added with anhydrous tin(II) chloride (20.7 g, 91.7 mmol). The mixture was added with 4.8 mol/L hydrochloric acid (20 mL, 96 mmol) and refluxed at 120 C. After disappearance of the starting materials was confirmed by thin layer chromatography (developing solvent: dichloromethane), the mixture was basified with aqueous sodium hydroxide. The precipitates were removed by filtration, After, ethanol was evaporated, the residue was extracted three times with ethyl acetate. Then organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/1) to obtain Compound 3 as white solid (1.02 g, 61% yield). 1H-NMR (300 MHz, CDCl3) delta 3.85 (br, 2H), 6.81 (dd, 1H, J=2.4, 8.7 Hz), 6.99 (d, 1H, J=2.4 Hz), 7.70 (d, 1H, J=8.7 Hz). MS (ESI+) 185.0, [M+H]+.
33% With iron; acetic acid; at 40℃; for 5h; Suspend 2-Chloro-6-nitro-benzothiazole (21.43 g, 99.8 mmol) in glacial acetic acid (30OmL). Add elemental iron (12.9 g, 231 mmol) and stir at 40 0C for 5 h. Filter the reaction mixture through Celite, concentrate in vacuo, and adsorb onto silica gel. Subject the residue to silica gel flash column chromatography in two portions [(120 g column, 0-10% CH3OH/CH2CI2), (120 g column, 0-5% CH3OHZCH2Cl2)] to yield the desired product (6.17 g, 33%). mass spectrum (m/e): 185.0 (M+l).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 2407-11-6 ]

Chlorides

Chemical Structure| 3622-38-6

A166200 [3622-38-6]

2-Chloro-5-nitrobenzo[d]thiazole

Similarity: 0.98

Chemical Structure| 2942-22-5

A104300 [2942-22-5]

2-Chloro-7-nitrobenzo[d]thiazole

Similarity: 0.88

Chemical Structure| 2406-90-8

A272625 [2406-90-8]

2-Chlorobenzo[d]thiazol-6-amine

Similarity: 0.84

Chemical Structure| 2941-48-2

A185058 [2941-48-2]

2,5-Dichlorobenzothiazole

Similarity: 0.75

Chemical Structure| 1261737-67-0

A128161 [1261737-67-0]

2-Chlorobenzo[d]thiazol-5-ol

Similarity: 0.73

Nitroes

Chemical Structure| 3622-38-6

A166200 [3622-38-6]

2-Chloro-5-nitrobenzo[d]thiazole

Similarity: 0.98

Chemical Structure| 2942-22-5

A104300 [2942-22-5]

2-Chloro-7-nitrobenzo[d]thiazole

Similarity: 0.88

Chemical Structure| 2942-06-5

A116868 [2942-06-5]

6-Nitrobenzothiazole

Similarity: 0.87

Chemical Structure| 2942-07-6

A130140 [2942-07-6]

5-Nitrobenzo[d]thiazole

Similarity: 0.85

Chemical Structure| 58759-63-0

A144185 [58759-63-0]

5-Nitrobenzothiazole-2-thiol

Similarity: 0.79