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2,5-Dibromo-1,3-dimethylbenzene,2,5-Dibromo-1,3-dimethylbenzene

2,5-Dibromo-1,3-dimethylbenzene,2,5-Dibromo-1,3-dimethylbenzene

2,5-Dibromo-1,3-dimethylbenzene,2,5-Dibromo-1,3-dimethylbenzene

CAS No.: 100189-84-2,CAS No.: 100189-84-2

Category Products

Cat.NO.:A1481647,A183233,A1481647,A183233 Purity:98+%,98%,98+%,98%

Product Details of [ 100189-84-2 ]

CAS No. :	100189-84-2
Formula :	C₈H₈Br₂
M.W :	263.96
SMILES Code :	CC1=CC(Br)=CC(C)=C1Br
MDL No. :	MFCD00079745
Boiling Point :	No data available
InChI Key :	XXFGKGMZLZIPCN-UHFFFAOYSA-N
Pubchem ID :	2758047

Safety of [ 100189-84-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 100189-84-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	51.77
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.75
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	4.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.83
Log P_o/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.	4.39
Log P_o/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	4.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.94
Solubility	0.00304 mg/ml ; 0.0000115 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.52
Solubility	0.00794 mg/ml ; 0.0000301 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	-4.88
Solubility	0.0035 mg/ml ; 0.0000132 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
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	Yes
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	Yes
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.	-4.51 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	1.0
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	0.0 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)	1.52

Application In Synthesis of [ 100189-84-2 ]

* 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 [ 100189-84-2 ]

[ 100189-84-2 ] Synthesis Path-Downstream 1~35

1
[ 24596-19-8 ]
[ 100189-84-2 ]

Yield	Reaction Conditions	Operation in experiment
72%		4-Bromo-2,6-dimethylaniline (6.00 g, 30 mmol) was suspended in 48% HBr aqueous solution (20 mL), NaNO 2 (2.28 g, 33 mmol) dissolved in water at -10 C. was added and stirred for 1 hour And sulfamic acid (0.58 g, 6 mmol) was added. This was treated with FeSO 4 .7H 2 O (4.17 g, 15 mmol) in 48% HBr aqueous solution (20 mL) and heated gradually to 80 C., and the mixture was stirred at 80 C. for 1 hour. Water was added to the mixture, the mixture was extracted with hexane, and the organic phase was dried with anhydrous Na 2 SO 4, then the solvent was removed under reduced pressure. Purification with medium pressure (silica gel, hexane) gave 2,5-dibromo-m-xylene (6.19 g, 72% yield).
72%		4-Bromo-2,6-dimethylaniline (6.00 g, 30 mmol) was suspended in 48% HBr aqueous solution (20 mL), NaNO 2 (2.28 g, 33 mmol) dissolved in water at -10 C. was added and stirred for 1 hour And sulfamic acid (0.58 g, 6 mmol) was added. This was treated with FeSO 4 .7H 2 O (4.17 g, 15 mmol) in 48% HBr aqueous solution (20 mL) and heated gradually to 80 C., and the mixture was stirred at 80 C. for 1 hour. Water was added to the mixture, the mixture was extracted with hexane, and the organic phase was dried with anhydrous Na 2 SO 4, then the solvent was removed under reduced pressure. Purification with medium pressure (silica gel, hexane) gave 2,5-dibromo-m-xylene (6.19 g, 72% yield).

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 5925 – 5933.
[2]Patent: JP2018/90535,2018,A .Location in patent: Paragraph 0072; 0073; 0082; 0083.
[3]Patent: JP2018/90536,2018,A .Location in patent: Paragraph 0098; 0099; 0100; 0101.
[4]Chemistry – An Asian Journal,2020,vol. 15,p. 524 – 530.
[5]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 804 – 814.
[6]Journal of Organic Chemistry,2012,vol. 77,p. 2074 – 2079.
[7]Recueil des Travaux Chimiques des Pays-Bas,1906,vol. 25,p. 175.

Recueil des Travaux Chimiques des Pays-Bas,1909,vol. 28,p. 93.
[8]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 2248 – 2253.

2
[ 100189-84-2 ]
1,4-dibromo-2,6-dimethyl-3,5-dinitro-benzene [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1906,vol. 25,p. 175.

Recueil des Travaux Chimiques des Pays-Bas,1909,vol. 28,p. 93.

3
[ 124-38-9 ]
[ 100189-84-2 ]
[ 7697-32-7 ]

References: [1]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 804 – 814.
[2]Journal of Organic Chemistry,1971,vol. 36,p. 544 – 549.

4
[ 100189-84-2 ]
[ 107-30-2 ]
[ 33641-91-7 ]

References: [1]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 2248 – 2253.

5
[ 100189-84-2 ]
[ 100189-85-3 ]

References: [1]Journal of the American Chemical Society,1986,vol. 108,p. 1415 – 1418.

6
[ 7664-93-9 ]
[ 100189-84-2 ]
[ 7697-37-2 ]
1,4-dibromo-2,6-dimethyl-3,5-dinitro-benzene [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1906,vol. 25,p. 175.

Recueil des Travaux Chimiques des Pays-Bas,1909,vol. 28,p. 93.

7
[ 100189-84-2 ]
CuCN [ No CAS ]
[ 95216-09-4 ]

References: [1]Bulletin de la Societe Chimique de France,1958,p. 310,313.

8
[ 100189-84-2 ]
[ 68-12-2 ]
[ 400822-47-1 ]

Yield	Reaction Conditions	Operation in experiment
47%		Step 1: A solution of <strong>[100189-84-2]2,5-dibromoxylene</strong> (2.0 g, 7.6 mmol) in DCM (20 ml) was treated with n-BuLi (2.5 M solution in hexane, 3 ml, 1.0 equiv.) at -78C. After stirring for 1h, DMF (1.8 ml, 23 mmol, 3 eq.) was added and the solution was allowed to warm to room temperature. It was acidified to pH 2 with 5% hydrochloric acid and extracted with diethyl ether (3×50 ml). The combined organic phase was dried and evaporated and the residue was purified by column chromatography using PE:EA = 10:1 as eluent to give 4-bromo-3,5-dimethylbenzaldehyde (0.76 g, yield: 47%).
		A solution of <strong>[100189-84-2]2,5-dibromoxylene</strong> (8.0 g, 30.3 mmol) in diethyl ether (120 mL) is cooled to -78 C. and then treated with n-buthyllithium (20 mL, 1.6 M in hexane). After stirring for 40 min, DMF (6 mL) is slowly added. The mixture is warmed to rt and stirred for 1 h. The mixture is cooled again to -78 C. before another portion of n-butyllithium (5 mL) is added. The reaction mixture is allowed to warm to rt and stirred for another hour. The reaction is quenched by adding 5% aq. HCl. The mixture is extracted with EA, and the extract is concentrated in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 4-bromo-3,5-dimethyl-benzaldehyde (8.2 g) as a white soft solid.
		A solution of <strong>[100189-84-2]2,5-dibromoxylene</strong> (8.0 g, 30.3 mmol) in diethyl ether (120 ml_) is cooled to -78C and then treated with n-buthyllithium (20 ml_, 1.6 M in hexane). After stirring for 40 min, DMF (6 ml_) is slowly added. The mixture is warmed to rt and stirred for 1 h. The mixture is cooled again to -78C before another portion of n- butyllithium (5 ml_) is added. The reaction mixture is allowed to warm to rt and stirred for another hour. The reaction is quenched by adding 5% aq. HCI. The mixture is extracted with EA, and the extract is concentrated in vacuo. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 4-bromo- 3,5-dimethyl-benzaldehyde (8.2 g) as a white soft solid.

References: [2]Patent: EP2128158,2009,A1 .Location in patent: Page/Page column 21.
[3]Patent: US2008/194670,2008,A1 .Location in patent: Page/Page column 49.
[4]Patent: WO2006/100631,2006,A1 .Location in patent: Page/Page column 132.
[5]Dyes and Pigments,2018,vol. 155,p. 323 – 331.

9
[ 59557-90-3 ]
[ 100189-84-2 ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 5065 – 5070.

10
[ 100189-84-2 ]
[ 689260-65-9 ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 5065 – 5070.

11
[ 100189-84-2 ]
[ 86-74-8 ]
[ 883550-98-9 ]

References: [1]Chemistry – A European Journal,2006,vol. 12,p. 2358 – 2370.
[2]Angewandte Chemie – International Edition,2020,vol. 59,p. 3156 – 3160.

Angew. Chem.,2020,vol. 132,p. 3181 – 3185,5.

12
[ 100189-84-2 ]
9-{4-[bis(2,4,6-trimethylphenyl)boryl]-3,5-dimethylphenyl}-9H-carbazole [ No CAS ]

References: [1]Chemistry – A European Journal,2006,vol. 12,p. 2358 – 2370.

13
[ 100189-84-2 ]
9,9′,9”-[borylidynetris(3,5-dimethyl-1,4-phenylene)]tris-9H-carbazole [ No CAS ]

References: [1]Chemistry – A European Journal,20

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