[ CAS No. 79562-49-5 ] {[proInfo.proName]}

Name: 79562-49-5|1,3-Difluoro-2-methyl-4-nitrobenzene|97%
Brand: Ambeed
SKU: A808733
Price: 7.0 USD
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Quality Control of [ 79562-49-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 79562-49-5 ]

SDS Specification

Alternatived Products of [ 79562-49-5 ]

Product Details of [ 79562-49-5 ]

CAS No. :	79562-49-5	MDL No. :	MFCD11519030
Formula :	C₇H₅F₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AVWNNVJXXMKAPB-UHFFFAOYSA-N
M.W :	173.12	Pubchem ID :	12795486
Synonyms :

Calculated chemistry of [ 79562-49-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.15
TPSA :	45.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.55
Log Po/w (XLOGP3) :	2.32
Log Po/w (WLOGP) :	3.02
Log Po/w (MLOGP) :	2.87
Log Po/w (SILICOS-IT) :	0.98
Consensus Log Po/w :	2.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.68
Solubility :	0.363 mg/ml ; 0.00209 mol/l
Class :	Soluble
Log S (Ali) :	-2.92
Solubility :	0.208 mg/ml ; 0.0012 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.33 mg/ml ; 0.00191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 79562-49-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P305+P351+P338-P311	UN#:	2811
Hazard Statements:	H302+H312-H315-H319-H331-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 79562-49-5 ]

* 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 [ 79562-49-5 ]
Downstream synthetic route of [ 79562-49-5 ]

[ 79562-49-5 ] Synthesis Path-Upstream 1~3

1
[ 79562-49-5 ]
[ 76350-70-4 ]

Reference： [1] Patent: US4327101, 1982, A,

2
[ 79562-49-5 ]
[ 76350-70-4 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 10, p. 3530 - 3543

3
[ 443-84-5 ]
[ 79562-49-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfuric acid; nitric acid In water at -10℃; for 0.5 h;	Example A36 A solution of 1,3-difluoro-2-methylbenzene (15 g, 0.12 mol) in H₂SO₄ (100 mL) was treated dropwise with HNO₃ (65percent, 11.4 g, 0.12 mol) at -10° C. The resultant mixture was stirred for about 30 min. The mixture was poured into ice-water and extracted with EtOAc (3*200 mL). The combined organics were washed with brine, dried (NaSO₄) and concentrated in vacuo to give 1,3-difluoro-2-methyl-4-nitrobenzene (16 g, 78percent yield). ¹H NMR (400 MHz, CDCl₃) δ 7.80 (m, 1H), 6.8-7.1 (m, 1H), 2.30 (s, 3H).
78%	at -10℃;	A solution of 1,3-difluoro-2-methyl-benzene (15 g, 0.12 mol) in H₂SO₄ (100 niL) was treated dropwise with 65percent HNO₃ (11.4 g, 0.12 mol) at -10 °C and the resultant mixture was stirred for about 30 min. The mixture was poured into ice- water and extracted with ethyl acetate (3 x 200 mL). The combined organic layers were washed with brine, dried (Na₂SO₄) and concentrated in vacuo to give 1,3- difluoro-2-methyl-4-nitro-benzene (16 g, 78percent yield). ¹H NMR (400MHz, CDC1₃): δ 7.80 (m, 1 H), 6.95 (m, 1 H), 2.30 (s, 3 H).
78%	at -10℃; for 0.5 h;	A solution of l ,3-difiuoro-2-methylbenzene (15 g, 0.12 mol) in H₂S0₄ (100 mL) was treated dropwise with HN0₃ (65 percent, 11.4 g, 0.12 mol) at -10 °C. The resultant mixture was stirred for about 30 min. The mixture was poured into ice- water and extracted with EtOAc (3 x 200 mL). The combined organics were washed with brine, dried (NaSO^ and concentrated in vacuo to give l,3-difluoro-2-methyl-4- nitrobenzene (16 g, 78percent yield). 'H NMR (400MHZ, CDCI3) δ 7.80 (m, 1 H), 6.8-7.1 (m, 1 H), 2.30 (s, 3 H).

78%	at -10℃; for 0.5 h;	A solution of 1,3-difluoro-2-methyl-benzene (15 g, 0.12 mol) in H₂SO₄ (100 mL) was treated drop-wise with 65percent HNO₃ (11.4 g, 0.12 mol) at -10° C. and the resultant mixture was stirred for 30 min. The mixture was poured into ice-water and extracted with EtOAc (3*). The combined organic layers were washed with brine, dried over Na₂SO₄ and concentrated in vacuo to give 1,3-difluoro-2-methyl-4-nitro-benzene (16 g, 78percent). ¹H NMR (400 MHz, CDCl₃): δ 7.80 (m, 1H), 6.95 (m, 1H), 2.30 (s, 3H).
66%	With nitric acid In ice-water; sulfuric acid	(1) 10.25 g of 2,6-difluorotoluene are suspended in 13 ml of conc. sulfuric acid, and 4.1 ml of fuming nitric acid are added dropwise thereto at 20° to 25° C. for about 30 minutes. The mixture is stirred at the same temperature for 1.5 hours. The reaction mixture is poured into 200 g of ice-water. The precipitates are collected by filtration, washed with water and then dried. The brown solid product (13.5 g) thus obtained is distilled under reduced pressure, whereby 9.20 g of 2,4-difluoro-3-methyl-nitrobenzene are obtained. Yield: 66percent B.p. 78°-80° C. (4 mm Hg) M.p. 35°-38° C.
49%	at 15 - 30℃;	A. Preparation of 1,3-difluoro-2-methyl-4-nitro-benzene (1) 24.6 mL, (0.60 mol) of fuming nitric acid was slowly added over 45 minutes to 61.5 g (0.48 mol) of 1,3-difluoro-2-methyl-benzene in 78 mL (1.463 mol) concentrated sulfuric acid in a partial ice bath at 15-20° C., and maintaining the reaction temperature, upon addition, between 25-30° C. The reaction mixture was then allowed to stir for an additional 1 h at r.t. and subsequently poured into 1 L ice water, filtered, washed with 3*300 mL water, and dried in vacuo to yield 49.93 g crude product as a white solid. The crude product was then crystallized from 60 mL hexane, filtered, and solvent removed in vacuo to yield 41.260 g (49percent) product as a yellow crystalline solid and a further 7.58 g product was isolated from the mother liquor.

Reference： [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 10, p. 3530 - 3543
[2] Patent: US2008/90856, 2008, A1, . Location in patent: Page/Page column 40
[3] Patent: WO2010/51373, 2010, A1, . Location in patent: Page/Page column 64
[4] Patent: WO2013/36232, 2013, A2, . Location in patent: Paragraph 00273
[5] Patent: US2014/315917, 2014, A1, . Location in patent: Paragraph 0506
[6] Patent: US4327101, 1982, A,
[7] Patent: US2009/197933, 2009, A1, . Location in patent: Page/Page column 5

[ 79562-49-5 ] Synthesis Path-Downstream 1~31

1
[ 443-84-5 ]
[ 79562-49-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfuric acid; nitric acid; In water; at -10℃; for 0.5h;	Example A36 A solution of <strong>[443-84-5]1,3-difluoro-2-methylbenzene</strong> (15 g, 0.12 mol) in H2SO4 (100 mL) was treated dropwise with HNO3 (65%, 11.4 g, 0.12 mol) at -10 C. The resultant mixture was stirred for about 30 min. The mixture was poured into ice-water and extracted with EtOAc (3*200 mL). The combined organics were washed with brine, dried (NaSO4) and concentrated in vacuo to give 1,3-difluoro-2-methyl-4-nitrobenzene (16 g, 78% yield). 1H NMR (400 MHz, CDCl3) delta 7.80 (m, 1H), 6.8-7.1 (m, 1H), 2.30 (s, 3H).
78%	With sulfuric acid; nitric acid; at -10℃;	A solution of <strong>[443-84-5]1,3-difluoro-2-methyl-benzene</strong> (15 g, 0.12 mol) in H2SO4 (100 niL) was treated dropwise with 65% HNO3 (11.4 g, 0.12 mol) at -10 C and the resultant mixture was stirred for about 30 min. The mixture was poured into ice- water and extracted with ethyl acetate (3 x 200 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to give 1,3- difluoro-2-methyl-4-nitro-benzene (16 g, 78% yield). 1H NMR (400MHz, CDC13): delta 7.80 (m, 1 H), 6.95 (m, 1 H), 2.30 (s, 3 H).
78%	With sulfuric acid; nitric acid; at -10℃; for 0.5h;	A solution of l ,3-difiuoro-2-methylbenzene (15 g, 0.12 mol) in H2S04 (100 mL) was treated dropwise with HN03 (65 %, 11.4 g, 0.12 mol) at -10 C. The resultant mixture was stirred for about 30 min. The mixture was poured into ice- water and extracted with EtOAc (3 x 200 mL). The combined organics were washed with brine, dried (NaSO^ and concentrated in vacuo to give l,3-difluoro-2-methyl-4- nitrobenzene (16 g, 78% yield). 'H NMR (400MHZ, CDCI3) delta 7.80 (m, 1 H), 6.8-7.1 (m, 1 H), 2.30 (s, 3 H).

78%	With sulfuric acid; nitric acid; at -10℃; for 0.5h;	A solution of <strong>[443-84-5]1,3-difluoro-2-methyl-benzene</strong> (15 g, 0.12 mol) in H2SO4 (100 mL) was treated drop-wise with 65% HNO3 (11.4 g, 0.12 mol) at -10 C. and the resultant mixture was stirred for 30 min. The mixture was poured into ice-water and extracted with EtOAc (3*). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 1,3-difluoro-2-methyl-4-nitro-benzene (16 g, 78%). 1H NMR (400 MHz, CDCl3): delta 7.80 (m, 1H), 6.95 (m, 1H), 2.30 (s, 3H).
66%	With nitric acid; In ice-water; sulfuric acid;	(1) 10.25 g of <strong>[443-84-5]2,6-difluorotoluene</strong> are suspended in 13 ml of conc. sulfuric acid, and 4.1 ml of fuming nitric acid are added dropwise thereto at 20 to 25 C. for about 30 minutes. The mixture is stirred at the same temperature for 1.5 hours. The reaction mixture is poured into 200 g of ice-water. The precipitates are collected by filtration, washed with water and then dried. The brown solid product (13.5 g) thus obtained is distilled under reduced pressure, whereby 9.20 g of 2,4-difluoro-3-methyl-nitrobenzene are obtained. Yield: 66% B.p. 78-80 C. (4 mm Hg) M.p. 35-38 C.
49%	With sulfuric acid; nitric acid; at 15 - 30℃;	A. Preparation of 1,3-difluoro-2-methyl-4-nitro-benzene (1) 24.6 mL, (0.60 mol) of fuming nitric acid was slowly added over 45 minutes to 61.5 g (0.48 mol) of <strong>[443-84-5]1,3-difluoro-2-methyl-benzene</strong> in 78 mL (1.463 mol) concentrated sulfuric acid in a partial ice bath at 15-20 C., and maintaining the reaction temperature, upon addition, between 25-30 C. The reaction mixture was then allowed to stir for an additional 1 h at r.t. and subsequently poured into 1 L ice water, filtered, washed with 3*300 mL water, and dried in vacuo to yield 49.93 g crude product as a white solid. The crude product was then crystallized from 60 mL hexane, filtered, and solvent removed in vacuo to yield 41.260 g (49%) product as a yellow crystalline solid and a further 7.58 g product was isolated from the mother liquor.

Reference： [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 3530 - 3543
[2]Patent: US2008/90856,2008,A1 .Location in patent: Page/Page column 40
[3]Patent: WO2010/51373,2010,A1 .Location in patent: Page/Page column 64
[4]Patent: WO2013/36232,2013,A2 .Location in patent: Paragraph 00273
[5]Patent: US2014/315917,2014,A1 .Location in patent: Paragraph 0506
[6]Patent: US4327101,1982,A
[7]Patent: US2009/197933,2009,A1 .Location in patent: Page/Page column 5

2
[ 79562-49-5 ]
[ 76350-70-4 ]