Home Cart 0 Sign in  
X

[ CAS No. 54730-35-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 54730-35-7
Chemical Structure| 54730-35-7
Chemical Structure| 54730-35-7
Structure of 54730-35-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 54730-35-7 ]

Related Doc. of [ 54730-35-7 ]

Alternatived Products of [ 54730-35-7 ]

Product Details of [ 54730-35-7 ]

CAS No. :54730-35-7 MDL No. :MFCD00266300
Formula : C7H7Cl2N Boiling Point : -
Linear Structure Formula :- InChI Key :GTEUMCIATAHZFK-UHFFFAOYSA-N
M.W :176.04 Pubchem ID :641154
Synonyms :

Calculated chemistry of [ 54730-35-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.83
TPSA : 26.02 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) : -5.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 2.7

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.117 mg/ml ; 0.000665 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.151 mg/ml ; 0.00086 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.65
Solubility : 0.039 mg/ml ; 0.000222 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 54730-35-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54730-35-7 ]

* 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 [ 54730-35-7 ]
  • Downstream synthetic route of [ 54730-35-7 ]

[ 54730-35-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 7149-69-1 ]
  • [ 54730-35-7 ]
YieldReaction ConditionsOperation in experiment
80% With tin(ll) chloride In N,N-dimethyl-formamide for 1 h; Preparation 1; 3 ,5 -dichloro-4-methylaniline; Dissolve 1, 3 -dichloro-2-methyl-5 -nitrobenzene (0.50 g, 2.43 mmol) in DMF and treat with tin (II) chloride dihydrate (2.74 g, 12.1 mmol) in a single portion. Stir the reaction for 1 hour and dilute with ethyl acetate and filter through celite. Wash the filtrate four times with water and twice with brine, dry over MgSO4, filter and concentrate to a dark oil. Purify the residue by silica gel chromatography eluting with a gradient of 5percent to 10percent ethyl acetate in hexanes to give 342 mg (80percent) of the titled product as white flakes.
80% With tin(ll) chloride In N,N-dimethyl-formamide for 1 h; Preparation 8; 3 ,5 -dichloro-4-methylaniline; Dissolve l,3-dichloro-2-methyl-5-nitrobenzene (0.50 g, 2.43 mmol) in DMF and treat with tin (II) chloride dihydrate (2.74 g, 12.1 mmol) in a single portion. Stir the reaction for 1 hour, dilute with ethyl acetate, and filter through celite. Wash the filtrate four times with water and twice with brine, dry over MgSO4, filter and concentrate to a dark oil. Purify the residue by silica gel chromatography eluting with a gradient of 5percent to 10percent ethyl acetate in hexanes to give 342 mg (80percent) of the titled product as white flakes.
0.28 g With iron; ammonium chloride In methanol; water at 20℃; Inert atmosphere; Reflux Purged a 50-mL round-bottomed flask with argon. Charged l,3-dichloro-2-methyl-5- nitrobenzene (500 mg, 2.43 mmol, Eq: 1.00; from Maybridge), iron (678 mg, 12.1 mmol, Eq: 5.0), ammonium chloride (1.3 g, 24.3 mmol, Eq: 10.0), methanol (10 mL), and water (5 mL) while purging with argon. Fitted the reaction flask with a condenser, then sealed under a positive pressure of argon. Heated at reflux for 2 h, then cooled to room temperature. Stirred over weekend at room temperature. HPLC showed the reaction was complete. Filtered the reaction mixture through a bed of celite, rinsing with methanol. Concentrated filtrate. Added water and ethyl acetate, then added solid sodium bicarbonate. Transferred the mixture to a separatory funnel and added more ethyl acetate. Split layers and washed the organic layer with saturated sodium chloride solution. Dried over magnesium sulfate, filtered, and concentrated. Obtained 0.28 g (65.5percent) of 3,5-dichloro-4-methylaniline as a yellow solid. The FontWeight="Bold" FontSize="10" H NMR showed a second, unknown component. Carried to the isothiocyanate
Reference: [1] Gazzetta Chimica Italiana, 1996, vol. 126, # 3, p. 179 - 185
[2] Tetrahedron, 1998, vol. 54, # 12, p. 2953 - 2966
[3] Patent: WO2007/127763, 2007, A2, . Location in patent: Page/Page column 37
[4] Patent: WO2007/127726, 2007, A2, . Location in patent: Page/Page column 40
[5] Journal of the Chemical Society, 1931, p. 79,81
[6] Journal of the Chemical Society, 1922, vol. 121, p. 814
[7] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 94
[8] Patent: WO2014/6066, 2014, A1, . Location in patent: Paragraph 0256
  • 2
  • [ 121-86-8 ]
  • [ 54730-35-7 ]
Reference: [1] Journal of the Chemical Society, 1922, vol. 121, p. 814
  • 3
  • [ 99-99-0 ]
  • [ 54730-35-7 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 79,81
  • 4
  • [ 54730-35-7 ]
  • [ 204930-37-0 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: With hydrogen bromide In water at 0 - 20℃; Heating / reflux
Stage #2: With sodium nitrite In water at 0℃; for 0.25 h;
Stage #3: With hydrogen bromide; copper(I) bromide In water at 50℃; for 1 h;
Preparation 2; 5-bromo- 1 ,3-dichloro-2-methylbenzene; Suspend the 3,5-dichloro-4-methylaniline in 48percent HBr (5 mL) and water (5 mL) and heat with a heat gun until the mixture is near the boiling point. Cool the slurry to room temperature and then cool to 00C with an ice/brine bath. Add a solution of sodium nitrite (109 mg, 1.58 mmol) in water (2 mL) dropwise. After the addition is complete, stir <n="39"/>the reaction an additional 15 min in the cold bath. Add a solution of CuBr (1.08 g, 7.53 mmol) in 48percent HBr (2 mL) and heat the rapidly stirring reaction to 500C for 1 hour. Cool the reaction to room temperature, dilute the reaction with ethyl acetate and discard the aqueous layer. Wash the organic layer with water and brine, dry with MgSO4, filter through celite and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 164 mg (45percent) of the product as a yellow solid.
45%
Stage #1: With hydrogen bromide In waterHeating / reflux
Stage #2: With sodium nitrite In water at 0℃; for 0.25 h;
Stage #3: With hydrogen bromide; copper(I) bromide In water at 50℃; for 1 h;
Preparation 9; 5-bromo-l,3-dichloro-2-methylbenzene; Suspend 3, 5 -dichloro-4-methylaniline in 48percent HBr (5 mL) and water (5 mL) and heat with a heat gun until the mixture is near the boiling point. Cool the slurry to room temperature and then cool to 00C with an ice/brine bath. Add dropwise a solution of sodium nitrite (109 mg, 1.58 mmol) in water (2 mL). After the addition is complete, stir the reaction an additional 15 min in the cold bath. Add a solution of CuBr (1.08 g, 7.53 mmol) in 48percent HBr (2 mL) and heat the rapidly stirring reaction to 500C for 1 hour. Cool the reaction to room temperature, dilute with EtOAc and discard the aqueous layer. Wash the organic layer with water and brine, dry with MgSO4, filter through celite and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 164 mg (45percent) of the product as a yellow solid.
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 4, p. 871 - 877
[2] Patent: WO2007/127763, 2007, A2, . Location in patent: Page/Page column 37-38
[3] Patent: WO2007/127726, 2007, A2, . Location in patent: Page/Page column 40
[4] Tetrahedron, 1998, vol. 54, # 12, p. 2953 - 2966
[5] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 94
  • 5
  • [ 54730-35-7 ]
  • [ 111829-72-2 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 4, p. 871 - 877
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 54730-35-7 ]

Aryls

Chemical Structure| 17601-75-1

[ 17601-75-1 ]

2,4-Dichloro-5-methylaniline

Similarity: 0.91

Chemical Structure| 7149-75-9

[ 7149-75-9 ]

4-Chloro-3-methylaniline

Similarity: 0.90

Chemical Structure| 95-74-9

[ 95-74-9 ]

2-Chloro-4-aminotoluene

Similarity: 0.88

Chemical Structure| 861519-29-1

[ 861519-29-1 ]

5-Chloro-4-methylbenzene-1,3-diamine

Similarity: 0.87

Chemical Structure| 29027-20-1

[ 29027-20-1 ]

3-Chloro-5-methylaniline

Similarity: 0.84

Chlorides

Chemical Structure| 17601-75-1

[ 17601-75-1 ]

2,4-Dichloro-5-methylaniline

Similarity: 0.91

Chemical Structure| 7149-75-9

[ 7149-75-9 ]

4-Chloro-3-methylaniline

Similarity: 0.90

Chemical Structure| 95-74-9

[ 95-74-9 ]

2-Chloro-4-aminotoluene

Similarity: 0.88

Chemical Structure| 861519-29-1

[ 861519-29-1 ]

5-Chloro-4-methylbenzene-1,3-diamine

Similarity: 0.87

Chemical Structure| 29027-20-1

[ 29027-20-1 ]

3-Chloro-5-methylaniline

Similarity: 0.84

Amines

Chemical Structure| 17601-75-1

[ 17601-75-1 ]

2,4-Dichloro-5-methylaniline

Similarity: 0.91

Chemical Structure| 7149-75-9

[ 7149-75-9 ]

4-Chloro-3-methylaniline

Similarity: 0.90

Chemical Structure| 95-74-9

[ 95-74-9 ]

2-Chloro-4-aminotoluene

Similarity: 0.88

Chemical Structure| 861519-29-1

[ 861519-29-1 ]

5-Chloro-4-methylbenzene-1,3-diamine

Similarity: 0.87

Chemical Structure| 29027-20-1

[ 29027-20-1 ]

3-Chloro-5-methylaniline

Similarity: 0.84