24167-56-4|4-Fluoro-N,N-dimethylbenzamide| Ambeed

CAS No. :	24167-56-4
Formula :	C₉H₁₀FNO
M.W :	167.18
SMILES Code :	O=C(N(C)C)C1=CC=C(F)C=C1
MDL No. :	MFCD01214152
InChI Key :	NUOGEPIJFRZXIN-UHFFFAOYSA-N
Pubchem ID :	141077

Safety of [ 24167-56-4 ]

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

Computational Chemistry of [ 24167-56-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	44.3
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.31 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.05
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	1.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.95
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.	2.27
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	1.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.81

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.8
Solubility	2.64 mg/ml ; 0.0158 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.	-1.11
Solubility	13.0 mg/ml ; 0.0778 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	-2.73
Solubility	0.313 mg/ml ; 0.00187 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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.55 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	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)	1.0

Application In Synthesis of [ 24167-56-4 ]

* 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 [ 24167-56-4 ]

[ 24167-56-4 ] Synthesis Path-Downstream 1~55

1
[ 403-43-0 ]
[ 124-40-3 ]
[ 24167-56-4 ]

References: [1]Tetrahedron,1970,vol. 26,p. 2007 - 2026.

2
[ 53391-61-0 ]
[ 24167-56-4 ]
[ 80965-01-1 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 1682 - 1688.

3
[ 421-20-5 ]
[ 24167-56-4 ]
C₁₀H₁₃FNO⁽¹⁺⁾*FO₃S^(1-) [ No CAS ]

References: [1]Chemische Berichte,1985,vol. 118,p. 620 - 633.

4
[ 368-39-8 ]
[ 24167-56-4 ]
N-<Ethoxy(4-fluorphenyl)methylen>-N-methylmethanaminium-tetrafluoroborat [ No CAS ]

References: [1]Chemische Berichte,1985,vol. 118,p. 620 - 633.

5
[ 54075-76-2 ]
[ 24167-56-4 ]
C₁₀H₁₃FNO⁽¹⁺⁾*Cl₆Sb^(1-) [ No CAS ]

References: [1]Chemische Berichte,1985,vol. 118,p. 620 - 633.

6
[ 24167-56-4 ]
[ 68204-67-1 ]
[ 66635-94-7 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 820 - 823.

7
[ 24167-56-4 ]
[ 12116-05-1 ]
[ 96660-75-2 ]

References: [1]Chemische Berichte,1985,vol. 118,p. 620 - 633.

8
[ 24167-56-4 ]
[ 66635-71-0 ]
[ 66635-82-3 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1037 - 1049.

9
[ 24167-56-4 ]
[ 83820-99-9 ]
[ 96327-71-8 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1037 - 1049.

10
[ 24167-56-4 ]
[ 83820-76-2 ]
[ 107115-66-2 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 820 - 823.

11
[ 24167-56-4 ]
[ 121192-98-1 ]
[ 121193-00-8 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1202 - 1207.

12
[ 24167-56-4 ]
[ 186752-37-4 ]
4-chloro-2-(4-fluorophenyl)-5,6-dihydrobenzo[h]quinazoline [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 1663 - 1669.

13
[ 24167-56-4 ]
[ 134330-67-9 ]
N¹,N¹-dimethyl-N²-(5,6-dihydro<1>benzothiepino<5,4-d>pyrimidin-4-yl)-4-fluorobenzamidine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 787 - 791.

Yield	Reaction Conditions	Operation in experiment
70%	With 1-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate; (tBuCN)2Cu*OTf; silver fluoride; In tetrahydrofuran; at 80℃; for 18h;Inert atmosphere;	General procedure: To an oven-dried 4 mL vial was added AgF (25 mg, 0.2 mmol, 2.0 equiv), ('BuCN^CuOTf (76 mg, 0.2 mmol, 2.0 equiv), [Me3pyF]PF6 (86 mg, 0.3 mmol, 3.0 equiv) and THF (2.0 mL). The aryl boronate ester (0.1 mmol, 1.0 equiv) was added (solid aryl boronate esters were weighed in the vial prior to adding THF, and liquid aryl boronate esters were added neat by syringe after the addition of THF). The vial was sealed with a Teflon- lined cap and heated at 50 C with vigorous stirring for 18 h. The solution was allowed to cool to room temperature, and 11.0 mu^ (0.1 mmol, 1.0 equiv) of 1 -bromo-4-fluorobenzene was added as an internal standard. The crude reaction mixture was analyzed by 19F NMR spectroscopy to determine the yield of aryl fluoride. 19F NMR chemical shifts were compared to authentic samples of the aryl fluoride product to confirm the identity of the product, and the identities of the products were further assessed by GC/MS.; cReactions were conducted at 80 C.
		The procedure of Example IA is followed substituting the following N,N-dimethyl aryl carboxamides for 4-methyl-N,N-dimethylbenzamide: 4-chloro-N,N-dimethylbenzamide; N,n-dimethyl-4-fluorobenzamide; N,n-dimethyl-4-methoxybenzamide; N,n-dimethyl-4-trifluoromethyl benzamide; N,n-dimethyl-2-thienylcarboxamide.

16
[ 24167-56-4 ]
[ 54246-93-4 ]
N'-(5,6-dihydro-benzo[h]quinazolin-4-yl)-4-fluoro-N,N-dimethyl-benzamidine [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1999,p. 548 - 558.

17
[ 24167-56-4 ]
[ 134722-24-0 ]
N,N-dimethyl-N'-(5,6-dihydro[1]benzoxepino[5,4-d]pyrimidin-4-yl)-4-fluorobenzamidine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 425 - 429.

18
[ 57330-47-9 ]
[ 24167-56-4 ]
(4-fluoro-phenyl)-(2-methyl-6-methylsulfanyl-1H-indol-3-yl)-methanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4741 - 4745.

19
[ 24167-56-4 ]
[ 6142-73-0 ]
methylenecyclopropyl(4-fluorophenyl) ketone [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9645 - 9660.

20
[ 24167-56-4 ]
N,N,N',N'-tetramethyl-1,2-bis(4-fluorophenyl)ethylenediamine [ No CAS ]
N,N,N',N'-tetramethyl-1,2-bis(4-fluorophenyl)ethylenediamine [ No CAS ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 6843 - 6850.

21
[ 1624-01-7 ]
[ 459-57-4 ]
[ 24167-56-4 ]

References: [1]Organic Letters,2007,vol. 9,p. 3429 - 3432.

22
[ 4375-83-1 ]
[ 459-57-4 ]
[ 24167-56-4 ]

References: [1]Organic Letters,2007,vol. 9,p. 3429 - 3432.

23
[ 24167-56-4 ]
2-(4'-fluorophenyl)-4-methylfuran [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9645 - 9660.

24
[ 24167-56-4 ]
N-[4-(3-(4-fluorophenyl)[1,2,4]oxadiazol-5-yl)-2,3-dihydro[1]benzoxepin-5-yl]formamide oxime [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 425 - 429.

25
[ 24167-56-4 ]
C₁₉H₁₅FN₄O₂ [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1999,p. 548 - 558.

26
[ 24167-56-4 ]
N-<4-(3-(4-fluorophenyl)<1,2,4>oxadiazol-5-yl)-2,3-dihydro<1>benzothiepin-5-yl>formamide oxime [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 787 - 791.

27
[ 24167-56-4 ]
[ 66635-90-3 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1037 - 1049.
[2]Journal of Organic Chemistry,1982,vol. 47,p. 1682 - 1688.

28
[ 24167-56-4 ]
[ 107115-74-2 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 820 - 823.

29
[ 24167-56-4 ]
[ 83073-37-4 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 820 - 823.

30
[ 24167-56-4 ]
[ 83727-10-0 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 1682 - 1688.

31
[ 24167-56-4 ]
[ 80965-10-2 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 1682 - 1688.

32
[ 24167-56-4 ]
[ 80965-16-8 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 1682 - 1688.

33
[ 24167-56-4 ]
[ 83727-09-7 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 1682 - 1688.

34
[ 24167-56-4 ]
[ 80965-06-6 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 1682 - 1688.

35
[ 53391-61-0 ]
ethyl acetate n-hexane [ No CAS ]
[ 24167-56-4 ]
[ 80965-01-1 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium acetate; trichlorophosphate; In water; 1,2-dichloro-ethane;	EXAMPLE 10 Preparation of 2-(methylthio)-5-(4-fluorobenzoyl)pyrrole (Step 2) A solution of <strong>[24167-56-4]N,N-dimethyl-4-fluorobenzamide</strong> (8.4 g, 0.05 moles) in anhydrous 1,2-dichloroethane (170 ml) containing phosphorous oxychloride (7.7 g, 0.05 moles) was heated at reflux temperature for 1 hour. At the end of this time 2-methylthiopyrrole (2.82 g, 0.025 moles) was added and heating was continued for an additional 0.5 hour. The solution was cooled to room temperature, and to the cooled solution was cautiously added, with good agitation, a solution of sodium acetate (12.3 g, 0.15 moles) in water (50 ml) and the mixture was then boiled under reflux for 1 hour. The organic phase was separated, washed with water, dried, and evaporated. The residue was subjected to column chromatography on silica gel using ethyl acetate-hexane (1:9) as the eluding solvent. A yellow colored solid 2-(methylthio)-5-(4-fluorobenzoyl)pyrrole (3.2 g, 54%) was obtained which after crystallization from ether-hexane had m.p. 112-113 C. UV: (MeOH) 218.5, 248, 343 nm(epsilon9770, 8510, 13,800). IR: (CHCl3) 3440, 3250, 1610 cm-1.
54%	With sodium acetate; trichlorophosphate; In water; 1,2-dichloro-ethane;	EXAMPLE 10 Preparation of 2-(methylthio)-5-(4-fluorobenzoyl)pyrrole (Step 2) A solution of <strong>[24167-56-4]N,N-dimethyl-4-fluorobenzamide</strong> (8.4 g, 0.05 moles) in anhydrous 1,2-dichloroethane (170 ml) containing phosphorus oxychloride (7.7 g, 0.05 moles) was heated at reflux temperature for 1 hour. At the end of this time 2-methylthiopyrrole (2.82 g, 0.025 moles) was added and heating was continued for an additional 0.5 hour. The solution was cooled to room temperature, and to the cooled solution was cautiously added, with good agitation, a solution of sodium acetate (12.3 g, 0.15 moles) in water (50 ml) and the mixture was then boiled under reflux for 1 hour. The organic phase was separated, washed with water, dried, and evaporated. The residue was subjected to column chromatography on silica gel suing ethyl acetate-hexane (1:9) as the eluding solvent. A yellow colored solid 2-(methylthio)-5-(4-fluorobenzoyl)pyrrole (3.2 g, 54%) was obtained which after crystallization from ether-hexane had m.p. 112-113 C. UV: (MeOH) 218.5, 248, 343 nm (epsilon 9770, 8510, 13,800). IR: (CHCl3) 3440, 3250, 1610 cm-1. NMR: (CDCl3) 2.48 (s, 3H); 6.25 (q, 1H; J=2.5, 4 Hz); 6.80 (q, 1H; J=2.5, 4 Hz); 7.12 (q, 2H; J=8, 8); 7.92 (q, 2H; J=5.5, 8); 10.67 (s, 1H, WH=22). Calcd. for C12 H10 FNOS: C, 61.24; H, 4.28. Found: C, 61.01; H, 4.21.

References: [1]Patent: US4347186,1982,A .
[2]Patent: US4347187,1982,A .

36
[ 24167-56-4 ]
[ 83820-84-2 ]
[ 88777-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate trihydrate; trichlorophosphate; In hexane; water; ethyl acetate; 1,2-dichloro-ethane;	EXAMPLE 7 A solution of 758 mg. of <strong>[24167-56-4]N,N-dimethyl-4-fluorobenzamide</strong> and 0.44 ml. of phosphorous oxychloride in 50 ml. of 1,2-dichloroethane is refluxed for one hour. To this solution is added a solution of 500 mg. of isopropyl 5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in 10 ml. 1,2-dichloroethane. The reaction mixture is refluxed for 3 hours. A solution of 3.3 g. sodium acetate trihydrate in 9 ml water is added and refluxed for a further 10 hours. The organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue is purified by preparative t.l.c. using hexane:ethyl acetate (90:10). Crystallization from dichloromethane-hexane yields isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate (XI, R=H, L=p-F, R2 =iC3 H7, n=1), m.p. 92 C.

References: [1]Patent: US4410534,1983,A .

37
[ 1271-54-1 ]
[ 24167-56-4 ]
[ 89252-46-0 ]
[ 89252-45-9 ]

References: [1]Chemische Berichte,1984,vol. 117,p. 23 - 41.

38
copper(II) perchlorate hydrate [ No CAS ]
[ 24167-56-4 ]
[Cu(p-fluoro-N,N-dimethylbenzamide)4](ClO₄)2 [ No CAS ]

References: [1]Inorganica Chimica Acta,1981,vol. 53,p. L253 - L256.

39
[ 15018-66-3 ]
[ 24167-56-4 ]
[ 457072-63-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,2010,vol. 58,p. 369 - 374.

40
[ 200412-97-1 ]
[ 24167-56-4 ]
[ 457072-46-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,2010,vol. 58,p. 369 - 374.

41
[ 26979-06-6 ]
[ 24167-56-4 ]
[ 457072-56-9 ]

References: [1]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 715 - 719.

42
[ 26979-06-6 ]
[ 24167-56-4 ]
[ 457072-23-0 ]

References: [1]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 715 - 719.

43
[ 20876-99-7 ]
[ 24167-56-4 ]

References: [1]Organic Letters,2015,vol. 17,p. 544 - 547.
[2]Journal of the American Chemical Society,2011,vol. 133,p. 11482 - 11484.
[3]Journal of the American Chemical Society,2017,vol. 139,p. 1452 - 1455.

44
[ 459-57-4 ]
[ 68-12-2 ]
[ 24167-56-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium iodide; In dimethyl sulfoxide; at 20℃;Electrochemical reaction;	General procedure: In a typical experiment, DMSO (8 mL), ketones (1 mmol), formamides (5 mmol) and NaI (4 mmol)were added to the undivided cell. The electrosynthesis was carried out in the undivided cell fitted with a Ni sheet cathode (2 cm × 2.5 cm× 0.02 cm) and a graphite rod anode at a constant current (50 mA) at room temperature under magnetic stirring. The electrolysis was ended when ketone had been completely consumed(monitored by GC-MS). After the electrolysis, the electrolyte solution was decolorized with Na2S2O3, and then washed with distilled water (50 mL) and extracted with ethyl acetate (10 mL × 3). The solvent was removed under reduced pressure, and the crude product was purified by column chromatography on silica gel using petroleum ether-ethyl acetate(5:1) as eluent.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 7156 - 7159.
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 3231 - 3235.
[3]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2855 - 2861.
[4]ACS Catalysis,2015,vol. 5,p. 884 - 891.
[5]New Journal of Chemistry,2017,vol. 41,p. 15268 - 15276.

45
[ 459-57-4 ]
[ 124-40-3 ]
[ 24167-56-4 ]

References: [1]Synlett,2012,vol. 23,p. 1175 - 1180.

46
[ 459-56-3 ]
[ 68-12-2 ]
[ 24167-56-4 ]

Yield	Reaction Conditions	Operation in experiment
72%Chromat.		General procedure: Various N,N-dimethyl benzamides were obtained followinga simple procedure which involves charging the reactionmixture containing benzyl alcohols (1mmol), catalyst(20wt%) and DMF (5mL) into a two necked 50mL roundbottom flask (RBF) and stirred for 10min at RT and then70% aqueous TBHP (5mmol) was introduced dropwiseto the mixture under continuous stirring at RT. The RBFwas fitted with a water condenser and heated for 24h at100C. After 24h, the reaction mixture was cooled to RTand catalyst was then separated by filtration. The reactionmixture was diluted with 100mL of DW and extractedusing ethyl acetate (2 × 60mL). The combined organiclayer was dried using Na2SO4and concentrated underrotatory evaporator. The crude products were purified bychromatography using silica gel, hexane and ethyl acetate.Similarly a range of N,N-substituted benzamides werealso obtained by taking the stoichiometric amount of variousN-substituted formamides in 5mL of toluene keepingother parameters constant.

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 9793 - 9797.
[2]Catalysis Letters,2018,vol. 148,p. 3102 - 3111.

47
[ 24167-56-4 ]
[ 49679-19-8 ]
[ 1402062-69-4 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 755 - 762.

48
[ 24167-56-4 ]
[ 49679-19-8 ]
[ 1402062-53-6 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 755 - 762.

49
[ 24167-56-4 ]
[ 41873-39-6 ]
[ 1402062-77-4 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 755 - 762.

50
[ 24167-56-4 ]
[ 41873-39-6 ]
[ 1402062-85-4 ]

References: [1]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 755 - 762.

51
[ 400727-57-3 ]
[ 24167-56-4 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 2552 - 2559.

52
[ 456-22-4 ]
[ 68-12-2 ]
[ 24167-56-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With di-tert-butyl peroxide; copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 130℃; for 12h;Sealed tube;	General procedure: A 50 mL sealed tube (with a Teflon high pressure valve) equipped with a magnetic stir bar was charged with Cu(OTf)2 (0.05 mmol), followed by carboxylic acid (0.5 mmol), formamide (2.0 mmol), tert-butyl peroxide (DTBP, 1 mmol), and DCE (1 mL). After the reaction mixture was stirred at 130 C for 12 h, it was allowed to cool to ambient temperature. The reaction mixture was diluted with ethyl acetate, and then filtered through a small pad of Celite. The filtrate was washed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL, twice). The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel preparative TLC to give the corresponding product.

References: [1]Chinese Chemical Letters,2015,vol. 26,p. 11 - 14.
[2]European Journal of Organic Chemistry,2013,p. 1218 - 1222.

53
[ 598-32-3 ]
[ 24167-56-4 ]
4-fluoro-N,N-dimethyl-2-(3-oxobutyl)benzamide [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 8009 - 8013.
[2]Chemical Science,2013,vol. 4,p. 2665 - 2669.

54
[ 24167-56-4 ]
[ 459-57-4 ]

Yield	Reaction Conditions	Operation in experiment
99%Chromat.	With lithium diisobutylmorpholinoaluminum hydride; In tetrahydrofuran; hexane; at 0℃; for 0.5h;	General procedure: The following procedure for reduction of N,N-dimethylbenzamide with LDBMOA is representative. To a solution of N,N-dimethylbenzamide (0.149 g, 1.0 mmol) in THF (10.0 mL) containing naphthalene as an internal standard was added LDBMOA (2.4 mL, 0.5 M in THF-hexanes, 1.2 mmol) at 0 C. After 30 min, the reaction mixture was hydrolyzed with 1 N aq HCl (10 mL) and extracted with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate, and filtered. After the removal of solvents in vacuum and purification of residue by column chromatography on silica gel gave benzaldehyde (0.103 g, 97%).
> 99%Chromat.	With C11H25AlNO4(1-)*Na(1+); In tetrahydrofuran; toluene; at 0 - 20℃; for 0.5h;	General procedure: The following experimental procedure describes a representative example of the partial reduction of N,N-dimethylbenzamide to benzaldehyde. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum,was charged with N,N-dimethylbenzamide (0.07 mL,0.5 mmol) and THF (5 mL). After cooling to 0 C, piperidine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at room temperature. The reaction was quenched with 1 N aqueous HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The organic layer was dried over anhydrous magnesium sulfate. GC analysis showed quantitative conversion to benzaldehyde. All products listed in Table 2 were confirmed through comparison with the GC data of authentic samples.
92%Chromat.	With benzoic acid ethyl ester; copper diisobutyl-t-butoxyaluminum hydride; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere;	General procedure: The following experimental procedure for the chemoselective partial reduction of ethyl benzoate and N,N-dimethyl 3-toluamide is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with ethyl benzoate (0.07mL, 0.5mmol), N,N-dimethyl 3-toluamide (0.08mL, 0.5mmol) and 5mL THF. After CDBBA (9.01mL, 0.44M soln. 4.0mmol) was slowly added and stirred for 12h at room temperature. The reaction was quenched by aqueous 1N HCl (10mL) and extracted with diethyl ether (2×10mL). The combined organic layers were dried over MgSO4. GC analysis showed a 97% recovery yield of ethyl benzoate and 95% yield of 3-methylbenzaldehyde. All products in Table 2 were confirmed through comparison with GC data of authentic sample.

References: [1]Helvetica Chimica Acta,2018,vol. 101.
[2]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 4194 - 4196.
[3]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 1919 - 1921.
[4]Tetrahedron Letters,2018,vol. 59,p. 2335 - 2340.

55
[ 1122-40-3 ]
[ 24167-56-4 ]
[ 1083428-66-3 ]

References: [1]Organic Process Research and Development,2008,vol. 12,p. 1044 - 1059.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Friedel-Crafts Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction • Vilsmeier-Haack Reaction

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[ 24167-56-4 ]

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P337	If eye irritation persists:
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H226	Flammable liquid and vapour
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H228	Flammable solid
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 24167-56-4

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CAS No.: 24167-56-4

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[ 24167-56-4 ] Synthesis Path-Downstream 1~55

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[ 24167-56-4 ]

Fluorinated Building Blocks

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CAS No.: 24167-56-4

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CAS No.: 24167-56-4

Alternative Products

Product Details of [ 24167-56-4 ]

Safety of [ 24167-56-4 ]

Computational Chemistry of [ 24167-56-4 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 24167-56-4 ]

[ 24167-56-4 ] Synthesis Path-Downstream 1~55

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 24167-56-4 ]

Fluorinated Building Blocks

Aryls

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

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Related Functional Groups of
[ 24167-56-4 ]