[ CAS No. 29682-39-1 ]

Name: 29682-39-1|1-Bromo-2-chloro-4-nitrobenzene|98%
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Quality Control of [ 29682-39-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 29682-39-1 ]

SDS Specification

Alternatived Products of [ 29682-39-1 ]

Product Details of [ 29682-39-1 ]

CAS No. :	29682-39-1	MDL No. :	MFCD00051514
Formula :	C₆H₃BrClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YKSXEJZFIQAUHJ-UHFFFAOYSA-N
M.W :	236.45	Pubchem ID :	34667
Synonyms :

Calculated chemistry of [ 29682-39-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.97
TPSA :	45.82 Å²

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) :	-5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.77
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	3.04
Log Po/w (SILICOS-IT) :	1.02
Consensus Log Po/w :	2.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.69
Solubility :	0.0482 mg/ml ; 0.000204 mol/l
Class :	Soluble
Log S (Ali) :	-3.89
Solubility :	0.0307 mg/ml ; 0.00013 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.25
Solubility :	0.132 mg/ml ; 0.000558 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.99

Safety of [ 29682-39-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 29682-39-1 ]

* 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 [ 29682-39-1 ]
Downstream synthetic route of [ 29682-39-1 ]

[ 29682-39-1 ] Synthesis Path-Upstream 1~9

1
[ 29682-39-1 ]
[ 21402-26-6 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 543,546
[2] Patent: WO2012/15723, 2012, A1, . Location in patent: Page/Page column 108

2
[ 29682-39-1 ]
[ 50638-46-5 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 543,546

3
[ 694-80-4 ]
[ 7697-37-2 ]
[ 16588-26-4 ]
[ 29682-39-1 ]

Reference： [1] American Chemical Journal, 1899, vol. 22, p. 273

4
[ 401631-87-6 ]
[ 121-73-3 ]
[ 29682-39-1 ]

Reference： [1] Synthesis, 2001, # 14, p. 2180 - 2190

5
[ 121-87-9 ]
[ 29682-39-1 ]

Reference： [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 I, p. 823[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1914, vol. <5> 23 I, p. 283 Anm.
[3] Synthesis, 2001, # 14, p. 2180 - 2190

6
[ 99-54-7 ]
[ 29682-39-1 ]

7
[ 694-80-4 ]
[ 7697-37-2 ]
[ 16588-26-4 ]
[ 29682-39-1 ]

Reference： [1] American Chemical Journal, 1899, vol. 22, p. 273

8
[ 29682-39-1 ]
[ 13631-21-5 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 543,546

9
[ 29682-39-1 ]
[ 1826-67-1 ]
[ 122531-09-3 ]

Yield	Reaction Conditions	Operation in experiment
15%	at -40℃; for 1 h; Inert atmosphere	under nitrogen gas, 1-bromo-2-chloro-4-nitrobenzene (57.4g, 0.243mol) dissolved in THF (500mL) and then , vinylmagnesium bromide (1M in THF, 728mL, 0.728mol) was slowly added dropwise in - 40 degree celcius followed by stirred at -40 degree celcius for 1 hour. Since, NH₄After completion of the reaction with Cl aqueous solution was raised to room temperature.Then, the ethyl acetate was extracted into the organic layer, MgSO₄to remove moisture in the organic layer, filtered and concentrated and purified by column chromatography using 5-bromo-6-chloro- 1H-indole (8.40g,Yield: 15percent) It was obtained.

Reference： [1] Patent: KR101601357, 2016, B1, . Location in patent: Paragraph 0285-0287

[ 29682-39-1 ] Synthesis Path-Downstream 1~68

1
[ 29682-39-1 ]
[ 21402-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With iron; ammonium chloride; In tetrahydrofuran; ethanol; water; at 60℃; for 3.5h;sealed tube;	To a solution of l-bromo-2-chloro-4-nitrobenzene (1.0 g, 4.23 mmol) in THF (7.24 mL) was added EtOH (7.24 mL) followed by ammonium chloride (0.339 g, 6.34 mmol) in water (7.23 mL, 401 mmol) and iron (0.945 g, 16.92 mmol). The reaction mixture was heated at 60 C in a sealed tube. After 3.5 hours, the reaction mixture was allowed to cool to room temperature and the heterogeneous mixture filtered through a disposable fritted funnel. The filter cake was washed with EtOAc. The solution was concentrated to half-volume, then diluted with EtOAc (10 mL) and 1 N NaOH (10 mL). Layers were separated. Aqueous phase was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford the title compounds as a tan solid. The crude material was used without further purification.

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546
[2]Patent: WO2012/15723,2012,A1 .Location in patent: Page/Page column 108

2
[ 29682-39-1 ]
[ 15426-14-9 ]

Reference： [1]Journal of the Chemical Society,1963,p. 2385 - 2387

3
[ 29682-39-1 ]
C₁₇H₁₅Cl₂N₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3592 - 3595

4
[ 29682-39-1 ]
C₁₉H₁₉Cl₂N₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3592 - 3595

5
[ 29682-39-1 ]
C₃₉H₅₁Cl₂N₇O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3592 - 3595

6
[ 29682-39-1 ]
3-chloro-4-oxazol-4-yl-phenylamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2059 - 2063

7
[ 29682-39-1 ]
[ 13382-62-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2059 - 2063

8
[ 29682-39-1 ]
[ 87154-68-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2059 - 2063

9
2-chloro-4-nitrobenzenediazonium o-benzenedisulfonimide [ No CAS ]
[ 29682-39-1 ]

Reference： [1]Synthesis,2001,p. 2180 - 2190

10
[ 99-54-7 ]
[ 29682-39-1 ]

Reference： [1]Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1913,vol. <5> 22 I,p. 823
Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1914,vol. <5> 23 I,p. 283 Anm.

11
[ 29682-39-1 ]
[ 50638-46-5 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546

12
[ 29682-39-1 ]
[ 13631-21-5 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 543,546

13
[ 29682-39-1 ]
[ 36776-29-1 ]

Yield	Reaction Conditions	Operation in experiment
		2-chloro-4-nitro-bromobenzene (20 g) was dissolved in ethanol (160 ml), and an aqueous solution of sodium sulfate nanohydrate (15.2 g) and sulfur (2.0 g) in ethanol (200 ml) was added dropwise to the solution for 20 minutes under heat reflux. An aqueous solution of sodium hydroxide (5.1 g, 20.3 ml) was added dropwise to the solution for 20 minutes, and then, the mixture was cooled to room temperature, and ice-water was added thereto. The precipitates were filtered, and the pH of the filtrate was adjusted to about pH 5 with 6N hydrochloric acid, and the precipitates were collected by filtration and washed with water to give 2-chloro-4-nitrobenzenethiol (9.4 g). 1H-NMR (200 MHz, CDCl3) delta 4.28 (1H, s), 7.48 (1H, d, J = 8.8 Hz), 8.00 (1H, dd, J = 8.8, 2.2 Hz), 8.24 (1H, d, J = 2.6 Hz)

Reference： [1]Patent: EP1422228,2004,A1 .Location in patent: Page 205

14
[ 29682-39-1 ]
[ 7486-35-3 ]
[ 130546-37-1 ]

Yield	Reaction Conditions	Operation in experiment
	bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 150℃; for 0.25h;Microwave;	IntermediateExample I; EMI65.1Enant > omerically enriched-(trans)-ethyl-2-(4-amino*2-chlorophenyl) cyclopropanecarboxylate (111-1d) A mixture of<strong>[29682-39-1]1-bromo-2-chloro-4-nitrobenzene</strong> (IX-1 a) (0.800 g, 3.38mmol), dichlorobis (triphenylphosphine)palladium (II) (0. 238 g, 0.34mmol), and tributylvinyltin (1.60 g, 5.08mmol) in 10 mL of N,N-dimethylformamide, in two reaction tubes sealed with septa, was heated in a microwave synthesizer to 150 C for 15 minutes. The mixture was diluted with ethyl acetate and filtered through Celite. The filtrate was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. Chromatography on silica gel with hexane: ethyl acetate gave 0.43 g of a 70: 30 mixture of desired styrene product(IX-2a) and tributyltin bromide. The partially purified product (IX-2a) was dissolved in 3 mL of chloroform and added to a mixture of copper(I) trifluoromethanesulfonate-toluene complex (2: 1) (0.006 g, 0.012mmol) and(2R)-4-tert-Butyl-2- {1- [ (4R)-4-tert-butyl-4, 5-dihydro-1,3-oxazol-2-yl]- 1-methylethyl}-4, 5-dihydro-1, 3-oxazol(VIII-A) (0.007g, 0.024mmol) (prepared as described by Evans etal., J. Am. Chem. Soc. 1991,113, 726-728) which had been stirred at room temperature for one hour. Approximately 0.1 mL of a solution of ethyl diazoacetate (0.58 g, 5.18mmol) in 5 mL of chloroform was added and the mixture was carefully warmed with a heat gun until gas evolution and a color change from green to amber was observed. The rest of the ethyl diazoacetate solution was added dropwise over 1.5 hours. The solvent was evaporated and the residue subjected to chromatography on silica gel with hexane: ethyl acetate to give a mixture of desired product (IX-3a), diethyl fumarate and a small amount of cis isomer. Platinum oxide (0.014 g, 0.063mmol) was added to a solution of the partially purified product (IX-3a) in 10 mL of ethanol in a Fisher-Porter bottle. The mixture was degassed, flushed with nitrogen, degassed and filled with hydrogen (50 psi). After 45 minutes, the mixture was filtered throughCeiite. The filtrate was evaporated and the residue purified by chromatography on silica gel with hexane : ethyl acetate to give 0.198 g (24% yield over 3 steps)of enantiomerically enriched- (trans)-ethyl-2- (4-amino-2-chlorophenyl) cyclopropanecarboxylate (111-1d) as a yellow oil.1 HNMR (400 <Desc/Clms Page number 66>MHz,CDCI3)6 6.78 (d, J=8.24 Hz, 1 H), 6.68 (d, J=2.38 Hz, 1 H), 6.46 (dd, J=2.38 Hz, 8.24 Hz, 1 H), 4.16 (q, J=7.14 Hz, 2H), 3.67 (br s, 2H), 2.58 (m, 1 H), 1.68 (m, 1 H), 1.52 (m,1H), 1.27 (t, J=7.14 Hz, 3H), 1.22 (m, 1H).

Reference： [1]Patent: WO2005/51890,2005,A1 .Location in patent: Page/Page column 65-66

15
[ 29682-39-1 ]
[ 107-19-7 ]
[ 689300-56-9 ]

Reference： [1]Patent: WO2004/39764,2004,A1 .Location in patent: Page/Page column 121

16
[ 4079-68-9 ]
[ 29682-39-1 ]
[ 689300-03-6 ]

Reference： [1]Patent: WO2004/39764,2004,A1 .Location in patent: Page/Page column 90-91

17
copper-(I) chloride [ No CAS ]
[ 29682-39-1 ]
[ 17734-85-9 ]
[ 62322-92-3 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; sodium carbonate; In nitrobenzene;	EXAMPLE 11 12.65 parts of 1-amino-5-methoxyanthraquinone, 15.3 parts of <strong>[29682-39-1]1-bromo-2-chloro-4-nitrobenzene</strong>, 5 parts of sodium carbonate and 1 part of copper-(I) chloride in 120 parts of nitrobenzene are stirred for 3 hours at 170. To remove the water formed during the reaction, a stream of nitrogen is passed through the apparatus during the reaction. After cooling the reaction mixture to 25, the 1-(2'-chloro-4'-nitroanilino)-5-methoxyanthraquinone formed is filtered off, washed with nitrobenzene, ethanol and hot water and extracted by boiling with 5% strength hydrochloric acid. The colorant is obtained in a yield of 19.5 parts, that is to say 95% of theory. It bulk-dyes polyester in an orange-coloured shade having excellent fastness properties. Analysis: Calculated: C, 61.70; H, 3.21; N, 6.85%. Found: C, 61.4; H, 3.1; N, 6.8%.

Reference： [1]Patent: US4082778,1978,A

18
[ 29682-39-1 ]
[ 89694-48-4 ]
C₁₃H₉Cl₂NO₃ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 2951 - 2954

19
[ 29682-39-1 ]
[ 197958-29-5 ]
[ 4420-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;S-Phos; In N,N-dimethyl-formamide; at 100℃; for 18h;	[0361] Experimental Details: To a stirred and degassed mixture of compound 1 (5.9 g, 25 mmol) and compound 2 (3.3 g, 27 mmol) in DMF (50 mL) and aqueous Na2CO3 (20 mL, 2 M) was added Pd2(dbbf)3 (26 mg, 0.028 mmol) under N2 atmosphere and stirred at 100 C for 18 h. After cooling to room temperature and filtrating off the solid, the filtrate was extracted with EA (200 mL). The organic layer was concentrated to give the crude product 3 which is done next step without purification.
	With sodium carbonate;tris-(dibenzylideneacetone)dipalladium(0); In water; N,N-dimethyl-formamide; at 100℃; for 18h;Inert atmosphere;	Example 9 Experimental Details: To a stirred and degassed mixture of compound 1 (5.9 g, 25 mmol) and compound 2 (3.3 g, 27 mmol) in DMF (50 mL) and aqueous Na2CO3 (20 mL, 2 M) was added Pd2(dbbf)3 (26 mg, 0.028 mmol) under N2 atmosphere and stirred at 100 C. for 18 h. After cooling to room temperature and filtrating off the solid, the filtrate was extracted with EA (200 mL). The organic layer was concentrated to give the crude product 3 which is done next step without purification.

Reference： [1]Patent: WO2008/91681,2008,A2 .Location in patent: Page/Page column 209
[2]Patent: US2010/16298,2010,A1 .Location in patent: Page/Page column 176

20
[ 280-57-9 ]
[ 29682-39-1 ]
[ 127-08-2 ]
[ 1173174-00-9 ]