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Chemical Structure| 2687-25-4 Chemical Structure| 2687-25-4

Structure of 2687-25-4

Chemical Structure| 2687-25-4

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Product Details of [ 2687-25-4 ]

CAS No. :2687-25-4
Formula : C7H10N2
M.W : 122.17
SMILES Code : NC1=CC=CC(C)=C1N
MDL No. :MFCD00011589
InChI Key :AXNUJYHFQHQZBE-UHFFFAOYSA-N
Pubchem ID :17593

Safety of [ 2687-25-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H312-H315-H319-H341
Precautionary Statements:P501-P270-P202-P201-P264-P280-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P302+P352+P312-P405
Class:6.1
UN#:2811
Packing Group:

Computational Chemistry of [ 2687-25-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 2.0
Molar Refractivity 40.22
TPSA ?

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

52.04 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.24
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

0.92
Log Po/w (WLOGP)?

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

1.18
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.

1.15
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

0.87
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.07

Water Solubility

Log S (ESOL):?

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

-1.67
Solubility 2.61 mg/ml ; 0.0214 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.6
Solubility 3.08 mg/ml ; 0.0252 mol/l
Class?

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

Very 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

-2.02
Solubility 1.17 mg/ml ; 0.00955 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

Yes
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

No
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

Yes
Log Kp (skin permeation)?

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

-6.39 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

1.0
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

1.0 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)

1.0

Application In Synthesis of [ 2687-25-4 ]

* 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 [ 2687-25-4 ]

[ 2687-25-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 517-21-5 ]
  • [ 2687-25-4 ]
  • [ 13708-12-8 ]
  • 2
  • [ 2687-25-4 ]
  • [ 1457-92-7 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; thionyl chloride; In pyridine; 4-Methyl-2,1,3-benzothiadiazole Thionyl chloride (166 g, 1.4 mol) was added to a solution of 2,3-diaminotoluene (71 g, 0.58 mol) in pyridine (430 mL) dropwise at a temperature below 45 C. Concentrated HCl (300 mL) was then added dropwise while care was taken to ensure that the reaction temperature did not exceed 65 C. After cooling to room temperature, the reaction mixture was subjected to a steam distillation. The light-yellow oil suspension in the water layer was extracted with diethyl ether. The combined extracts were washed with brine and dried over Na2SO4. After removal of the solvent by rotary evaporation, 4-methyl-2,1,3-benzothiadiazole was obtained as a light-yellow liquid in 92% (80.6 g) of yield. Rf=0.62 (hexane/ethyl acetate=3:1); 1H NMR (200 MHz, CDCl3) δ2.74 (s, 3H), 7.34 (m, 1H), 7.48 (d,J1=8.7 Hz, J2=6.7 Hz, 1H), 7.83 (m, 1H).
89% Combine 3-methyl-1,2-phenylenediamine (30.53g, 249.87mmol, 1.0 equivalent), triethylamine (138.92mL, 999.47mmol, 4.0 equivalent) and dichloromethane (300mL) Add a dry three-necked flask equipped with magnetic stirring and place in an ice bath.The mixture was stirred for more than 1 hour, and then thionyl chloride (36.25 mL, 499.74 mmol, 2.0 equivalents) and dichloromethane (100 mL) were slowly added dropwise. The mixture was stirred at this temperature for 1 hour and then the mixture was placed in an oil bath. After stirring for 20 hours at 40C, the reaction was monitored by thin layer chromatography until the reaction was completed.The reaction was stopped and the resulting mixture was cooled to room temperature and quenched by adding water.The mixture was extracted three times with ethyl acetate.The combined organic phase was washed with water, dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1-4:1) to obtain 33.40 g of a colorless liquid with a yield of 89%.
77% With thionyl chloride; triethylamine; In dichloromethane; at 45℃; for 7h;Cooling with ice; Take compound XD-1 (2.26g) and dissolve it in DCM (60mL),Add triethylamine (Et3N, 10.3mL),Stir at room temperature until the solid is completely dissolved,Slowly drip thionyl chloride (SOCl2, 2.7mL) under ice bath,Heat in an oil bath at 45C for 7 hours and stop heating.The solvent was evaporated under reduced pressure, water (70mL) was added,Adjust the pH to 1 with 1N hydrochloric acid, and extract with ethyl acetate (30mL x 3),Dry with anhydrous sodium sulfate.The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 10:1).Compound XD-2 (2.1 g) was obtained as a yellow oil.
63% With pyridine; thionyl chloride; at 30℃;Cooling with ice; Inert atmosphere; To the 500 mL two-necked flask to which the dropping funnel was attached, 12 g (98 mmol) of the above compound (1-e) and 100 mL of pyridine were added, and the mixture was stirred under ice cooling under an argon atmosphere.Thionyl chloride 16.4 mL (240 mmol) was slowly added dropwise so that the liquid temperature did not exceed 30 C. Next, 48 mL of concentrated HCl was slowly added dropwise so that the liquid temperature did not exceed 60 C, and the mixture was stirred at room temperature. Water was added to the reaction liquid, and the mixture was extracted with ether to give the compound (1-f) (yield: 9.3 g, yield: 63%) as a brown oily liquid.
44% With pyridine; thionyl chloride; at 60℃; for 9h;Reflux; To a stirredsolution of 3-Methylbenzene-1,2-diamine (15; 5 g , 41 mmol) in 20 mL of pyridine,thionyl chloride was added very slowly (8.2 mL, 110 mmol,2.7 eq.), while the temperature was kept at 60C. After that, theresulting slurry was heated to reflux for 9 h. The dark reaction mixturewas allowed to cool to room temperature and hydrolyzed with water verycarefully. After adding 1 L of water the mixture was steam distilled. Thedistillation was stopped, after 800 mL of steam; the aqueous phase wassaturated with NaCl and extracted four times with diethyl ether. Thecombined organic layers were dried over Na2SO4 andevaporated to dryness to afford the oily product (2.7 g, 13 mmol,44%). 1H-NMR (300 MHz, Acetone): δ = 7.81 (d, J = 8.8Hz, 1H), 7.59 - 7.49 (m, 1H), 7.41 (d, J = 6.7 Hz, 1H), 2.67 (s,3H) ppm. 13C-NMR (75 MHz, Acetone): δ = 156.15, 155.74,132.29, 130.63, 128.90, 119.58, 17.80 ppm. MS (EI): m/z = 150 [M+].EA calc. for C7H6N2S: C, 55.97; H, 4.03; N,18.65; found: C, 56.20; H, 4.13; N, 18.41.
With thionyl chloride; In pyridine; water; A. 4-Methyl-benzo[1,2,5]thiadiazole (839A) To a solution of 2,3-diaminotoluene (5.0 g, 40.9 mmol) in pyridine (40 mL) at 0 C. was added thionyl chloride (7.0 mL, 98.2 mmol) dropwise. The reaction mixture was stirred at 0 C. for 30 mins, then water (200 mL) was added. The solution was extracted with dicholomethane (2*250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give compound 839A (5.57 g) as a dark brown liquid.

  • 3
  • [ 131543-46-9 ]
  • [ 2687-25-4 ]
  • [ 13708-12-8 ]
YieldReaction ConditionsOperation in experiment
98% With 10 wtpercent sulfated polyborate; In neat (no solvent); at 100℃; for 0.05h;Green chemistry; General procedure: To a mixture of substituted o-phenylenediamines derivative(2.0 mmol) and 1,2-diketone / alpha-hydroxy ketone (2.0 mmol),was added sulfated polyborate (10 wt%). The reaction mixture was stirred at 100 C in an oil bath. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and quenched by water. The resultant product was filtered/extracted with EtOAc to get the product. Crude products were either recrystallized from ethanol or purified by column chromatography using silica as the stationary phase and EtOAc: pet. ether as mobile phase. The products obtained were known compounds and were identified by melting point and 1H and 13C NMR spectroscopy. The spectral data were compared with the literature values.
  • 4
  • [ 1457-92-7 ]
  • [ 2687-25-4 ]
  • 5
  • [ 530-62-1 ]
  • [ 2687-25-4 ]
  • [ 15965-57-8 ]
 

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Technical Information

Categories

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