[ CAS No. 42533-63-1 ] {[proInfo.proName]}

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Quality Control of [ 42533-63-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 42533-63-1 ]

Product Details of [ 42533-63-1 ]

CAS No. :	42533-63-1	MDL No. :	MFCD11847147
Formula :	C₇H₅BrClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	250.48	Pubchem ID :	-
Synonyms :

Safety of [ 42533-63-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501	UN#:	3261
Hazard Statements:	H302-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 42533-63-1 ]

* 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 [ 42533-63-1 ]
Downstream synthetic route of [ 42533-63-1 ]

[ 42533-63-1 ] Synthesis Path-Upstream 1~4

1
[ 42533-63-1 ]
[ 95-74-9 ]

Reference： [1] Chemische Berichte, 1892, vol. 25, p. 83

2
[ 42533-63-1 ]
[ 99-60-5 ]

Reference： [1] Chemische Berichte, 1891, vol. 24, p. 706

3
[ 42533-63-1 ]
[ 54439-75-7 ]

Reference： [1] Chemische Berichte, 1891, vol. 24, p. 706

4
[ 42533-63-1 ]
[ 2457-76-3 ]

Reference： [1] Chemische Berichte, 1891, vol. 24, p. 706

[ 42533-63-1 ] Synthesis Path-Downstream 1~11

1
[ 121-86-8 ]
[ 42533-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 20℃; for 12h;Heating / reflux;	A suspension of 2-chloro-4- nitrotoluene (10.0 g, 58.3 mmol), /V-bromosuccinimide (NBS, 10.9 g, 61.2 mmol), and 2,2'- azobis(2-methylpropionitrile) (AIBN, 0.29 g, 1.75 mmol) in 120 ml_ of CCU was heated at reflux under an atmosphere of N2 for 12 h. The reaction mixture was cooled to ambient temperature, and the solid was filtered and washed with EtOAc. The combined filtrate was washed with aq. NaHCO3, dried over Na2SO4, filtered, concentrated on rotovap, and further dried under vacuum. 1H NMR indicated the ratio of desired product to unreacted 2-chloro-4- nitrotoluene to be 50:50. This material was used directly in the next step.
	With N-Bromosuccinimide;dibenzoyl peroxide; In 1,2-dichloro-ethane; for 16h;Heating / reflux;	<strong>[121-86-8]2-Chloro-4-nitrotoluene</strong> (8.55 g, 50.0 mmol) is dissolved in 1,2-dichloroethane (120 mL). N-Bromosuccinimide (9.74 g, 55 mmol) and benzoyl peroxide (0.25 g, 1.03 mmol) are added, and the reaction mixture is stirred and heated to reflux for 16 h. The reaction is cooled to room temperature, and most of the solvent is evaporated in vacuo, leaving approximately 30 mL of dichloroethane. Hexanes (30 mL) and dichloromethane (30 mL) are added, and the precipitate that formed is filtered, and the filtrate washed with hexanes. The combined organic solution is evaporated in vacuo to afford benzyl bromide 38-B, which is used directly in the next step without further purification.
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux; UV-irradiation;	Description 102; 1-(Bromomethyl)-2-chloro-4-nitrobenzene (D102); A mixture of <strong>[121-86-8]2-chloro-4-nitrotoluene</strong> (0.20 g, 1.17 mmol), lambda/-bromosuccinimide (0.228 g, 1.28 mmol) and benzoyl peroxide (0.014 g, 0.058 mmol) in tetrachloromethane (7 ml.) was irradiated (500W lamp) at reflux overnight. The reaction mixture was concentrated to give a yellow oil/solid (0.391 g) which was used directly in the next step without further purification.

	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 12h;Reflux; Inert atmosphere;	1-(Bromomethyl)-2-chloro-4-nitro-benzene: A suspension of 2-chloro-4-nitrotol uene (10.0 g, 58.3 mmol), N-bromosuccinimide (NBS, 10.9 g, 61.2 mmol), and 2,2?-azobis(2- methylpropionitrile) (AIBN, 0.29 g, 1.75 mmol) in 120 mL of CC14 was heated at reflux under an atmosphere of N2 for 12 h. The reaction mixture was cooled to ambient temperature, and thesolid was filtered and washed with EtOAc. The combined filtrate was washed with aq. NaHCO3, dried over Na2SO4, filtered, concentrated on rotovap, and further dried under vacuum. ?H NMR indicated the ratio of desired product to unreacted <strong>[121-86-8]2-chloro-4-nitrotoluene</strong> to be 50:50. This material was used directly in the next step.
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chloroform; for 36h;	General procedure: To a solution of appropriate p-nitrotoluene derivatives (2.5 g,12.0 mmol) and 2, 2-azobisisobutyronitrile (AIBN, 34 mg,0.203 mmol) in chloroform (30 ml), N-bromosuccinimide (NBS,1.16 g, 6.5 mmol) was added in small batches, and the resultingmixture was stirred about 36 h at 56 C. The crude was filteredand washed with ethyl acetate. The filtrate was collected andwashed with saturated aqueous sodium bicarbonate and brine,and then dried over anhydrous sodium sulfate. After removingthe solvent under reduced pressure to give the crude product 6acand used in the next step without further purification.

Reference： [1]ACS Medicinal Chemistry Letters,2020,vol. 11,p. 491 - 496
[2]Chemische Berichte,1891,vol. 24,p. 706
[3]Journal of general chemistry of the USSR,1961,vol. 31,p. 3537 - 3540
Zhurnal Obshchei Khimii,1961,vol. 31,p. 3788 - 3793
[4]Medicinal Chemistry Research,1999,vol. 9,p. 149 - 161
[5]Journal of Medicinal Chemistry,2006,vol. 49,p. 4896 - 4911
[6]Patent: WO2007/75869,2007,A2 .Location in patent: Page/Page column 69
[7]Patent: US2007/275906,2007,A1 .Location in patent: Page/Page column 29-30
[8]Patent: WO2008/729,2008,A1 .Location in patent: Page/Page column 91
[9]Patent: WO2013/162727,2013,A1 .Location in patent: Page/Page column 71
[10]Bioorganic Chemistry,2016,vol. 68,p. 112 - 123

2
[ 121-86-8 ]
[ 7726-95-6 ]
[ 42533-63-1 ]

Reference： [1]Chemische Berichte,1891,vol. 24,p. 706

3
[ 1004-40-6 ]
[ 42533-63-1 ]
2-(2-chloro-4-nitrobenzylthio)-6-aminouracil [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 1425 - 1431

4
[ 1004-40-6 ]
[ 42533-63-1 ]
2-(2'-chloro-4'-nitrobenzyl)thio-1-(2'-chloro-4'-nitrobenzyl)-6-aminouracil [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 2263 - 2278

5
[ 960283-58-3 ]
[ 42533-63-1 ]
[ 1000813-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃; for 0.166667h;	Description 103; 1 ,1 -Dimethylethyl (2S)-4-[(2-chloro-4-nitrophenyl)methyl]-2-methyl-1 - piperazinecarboxylate (D103); A mixture of crude 1-(bromomethyl)-2-chloro-4-nitrobenzene (D102) (0.391 g), 1 ,1- dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate hydrochloride (0.407 g, 1.72 mmol) and Hunig's base (0.625 ml_, 3.59mmol) in dry DMF (3 mL) was stirred at room temperature for 10 minutes. The reaction mixture was concentrated to give an orange oil which was dissolved in DCM and washed with water (x2) and brine, then dried and concentrated to give an orange oil. Purification by column chromatography eluting with 0-30% EtOAc/pentane gave the title compound as a yellow oil (0.199 g). deltaH (CDCI3, 400MHz) 8.24 (1 H1 d), 8.12 (1 H, dd), 7.77 (1 H, d), 4.24 (1 H, br.s), 3.85 (1 H, d), 3.63 (2H, s), 3.14 (1 H, td), 2.76 (1 H, m), 2.59 (1H, m), 2.33 (1H, dd), 2.18 (1 H, m), 1.47 (9H1 s), 1.28 (3H1 d). MS (ES): MH+ 370/372,

Reference： [1]Patent: WO2008/729,2008,A1 .Location in patent: Page/Page column 92

6
[ 42533-63-1 ]
[ 54439-75-7 ]

Reference： [1]Chemische Berichte,1891,vol. 24,p. 706

7
[ 52301-88-9 ]
[ 42533-63-1 ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[52301-88-9](2-chloro-4-nitrophenyl)methanol</strong> (707 mg, 3.73 mmol) was dissolved in dichloromethane (15 mL) at 00C under nitrogen. Tribromophosphane (0.7 mL, 7.46 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by addition of 10% NaHCO3 solution (2 mL). After 10 minutes, Na2SO4 (15 g) was added. The solvent was filtered and evaporated to provide l-(bromomethyl)-2-chloro-4-nitrobenzene, which was used without further purification.

Reference： [1]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 91

8
[ 1082827-81-3 ]
[ 42533-63-1 ]
[ 1391467-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 50 h / 20 - 60 °C 2: hydrogen / Raney nickel / methanol / 12 h / 20 °C / 2585.81 Torr

Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2012/101043, 2012, A1

9
[ 1082827-81-3 ]
[ 42533-63-1 ]
[ 1391467-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 20 - 60℃; for 50h;	A.5.a To a solution of (3,5-dimethyl-1 H-pyrazol-4-yl)-acetic acid tert-butyl ester (2.6 g, 12.4 mmol, preparation according to WO2007/141267 by using 2,4-pentanedione instead of 3,5- heptanedione) and 2-chloro-4-nitrobenzyl bromide (3.11 g, 12.4 mmol) in acetonitrile (30 mL) is added K2C03 (2.575 g, 18.6 mmol) and the mixture is stirred for 48 hours at room temperature and after that 2 hours at 60°C. The solid is filtered off and the solvent is removed by evaporation. The residue is dissolved in dichloromethane/water. After extraction with dichloromethane the organic layer is dried over MgS04 and evaporated under reduced pressure to yield 4.4 g of [3,5-dimethyl-1-(2-chloro-4-nitrobenzyl)-1 H-pyrazol-4-yl]acetic acid tert-butyl ester (ESI mass spectrum: [M+H]+ = 380).
4.4 g	With potassium carbonate In acetonitrile at 20 - 60℃; for 50h;	A.5.a 5.) [1-(4-Amino-2-chloro-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid tert-butyl ester a) To a solution of (3,5-dimethyl-1H-pyrazol-4-yl)-acetic acid tert-butyl ester (2.6 g, 12.4 mmol, preparation according to WO2007/141267 by using 2,4-pentanedione instead of 3,5-heptanedione) and 2-chloro-4-nitrobenzyl bromide (3.11 g, 12.4 mmol) in acetonitrile (30 mL) is added K2CO3 (2.575 g, 18.6 mmol) and the mixture is stirred for 48 hours at room temperature and after that 2 hours at 60° C. The solid is filtered off and the solvent is removed by evaporation. The residue is dissolved in dichloromethane/water. After extraction with dichloromethane the organic layer is dried over MgSO4 and evaporated under reduced pressure to yield 4.4 g of [3,5-dimethyl-1-(2-chloro-4-nitrobenzyl)-1H-pyrazol-4-yl]acetic acid tert-butyl ester (ESI mass spectrum: [M+H]+=380).

Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2012/101043, 2012, A1 Location in patent: Page/Page column 42
[2]Current Patent Assignee: GOSSAMER BIO INC - US2013/23576, 2013, A1 Location in patent: Paragraph 0185

10
[ 42533-63-1 ]
[ 28163-00-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With ammonium hydroxide; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide at 20℃; for 1.5h; Green chemistry;

Reference： [1]Azarifar, Davood; Najminejad, Zohreh [Journal of the Iranian Chemical Society, 2015, vol. 12, # 1, p. 107 - 111]

11
[ 2032-33-9 ]
[ 42533-63-1 ]
benzyl[(2-chloro-4-nitrophenyl)methyl]propylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.2%	In acetonitrile; for 4h;Reflux;	N-Benzylpropyl-1-amine (700 mg, 3.98 mmol) was added sequentially to a 50 mL single-necked flask.1-(Bromomethyl)-2-chloro-4-nitrobenzene (1.0 g, 4.65 mmol),Anhydrous potassium carbonate (1.6 g, 9.52 mmol), acetonitrile 20 mL,Heated back to reflux for 4 hours.The reaction was completed by TLC. Spin the solvent,Wash with saturated saline solution,Dry over anhydrous sodium sulfate and purify petroleum ether by column chromatography:Ethyl acetate 50:1,Obtained a white solid 800mg,The yield was 63.2%.

Reference： [1]Patent: CN109206346,2019,A .Location in patent: Paragraph 0320; 0326; 0327; 0328

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[ CAS No. 42533-63-1 ] {[proInfo.proName]}

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Safety of [ 42533-63-1 ]

Application In Synthesis of [ 42533-63-1 ]

[ 42533-63-1 ] Synthesis Path-Upstream 1~4

[ 42533-63-1 ] Synthesis Path-Downstream 1~11

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry