[ CAS No. 22002-44-4 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 22002-44-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 22002-44-4 ]

Product Details of [ 22002-44-4 ]

CAS No. :	22002-44-4	MDL No. :	MFCD00060649
Formula :	C₈H₉ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	156.61	Pubchem ID :	-
Synonyms :

Safety of [ 22002-44-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22002-44-4 ]

* 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.

Upstream synthesis route of [ 22002-44-4 ]
Downstream synthetic route of [ 22002-44-4 ]

[ 22002-44-4 ] Synthesis Path-Upstream 1~5

1
[ 22002-44-4 ]
[ 6640-27-3 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 10, p. 1162 - 1166

2
[ 22002-44-4 ]
[ 30435-35-9 ]
[ 6640-27-3 ]
[ 60468-61-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 75 - 82
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 75 - 82
[3] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 75 - 82

3
[ 104-93-8 ]
[ 22002-44-4 ]
[ 56180-49-5 ]
[ 6640-27-3 ]
[ 32133-80-5 ]
[ 54788-38-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 385 - 392

4
[ 104-93-8 ]
[ 22002-44-4 ]
[ 56180-49-5 ]
[ 6640-27-3 ]
[ 32133-80-5 ]
[ 54788-38-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 385 - 392

5
[ 22002-44-4 ]
[ 320407-92-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With azobisisobutyronitrile In N-Bromosuccinimide; water	3-Chloro-4-methoxytoluene 8 (2.6 mL, 19.2 mmol) was dissolved in dichlomethane (30 mL) and N-bromosuccinimide (3.75 g, 21.1 mmol) was added followed by AIBN (36.0 mg). The reaction was heated to reflux for 19 hrs., then cooled to room temperature and the precipitate was filtered off. The filtrate was diluted with dichloromethane and washed with 0.5 M aqueous sodium bicarbonate, followed by water. The organic mixture was dried over sodium sulfate, filtered and concentrated under vacuum to yield 9 (4.73 g, 82percent). The benzyl bromide was used as the crude material without further purification. ¹H NMR (400 MHz, CDCl₃): δ 7.42 (d, 1H, J=2.4 Hz), 7.26 (dd, 1H, J=2.4 Hz, J=8.4 Hz), 6.88 (d, 1H, J=8.4 Hz), 4.44 (s, 2H), 3.90 (s, 3H).
58%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4.5 h; Reflux	Preparation 594-(Bromomethyl)-2-chloro-1 -methoxybenzeneTo a solution of 2-chloro-1 -methoxy-4-methylbenzene (300 mg, 1 .92 mmol) in carbon tetrachloride (1 0.0 ml_) was added N-bromosuccinimide (445 mg, 2.50 mmol) and benzoylperoxide (4.6 mg, 0.0192 mmol) and the reaction heated to reflux for 4.5 hours. The reaction mixture was allowed to cool to room temperature, diluted with DCM (20.0 ml_) and partitioned with a saturated aqueous solution of sodium hydrogen peroxide (30.0 ml_). The organic layer was separated and the aqueous extracted with DCM (30 ml_). The combined organics were washed with brine (50.0 ml_), filtered through a phase separator cartridge and the solvent removed in vacuo to yield a yellow oil, which was purified by silica gel chromatography eluting with 50 percent heptane in DCM to yield the title compound (263 mg, 58percent).¹H NMR (400 MHz, CDCI₃): δ 3.90 (s, 3H), 4.44 (s, 2H), 7.25 (dd, 1 H), 7.41 (d, 1 H), 8.88 (d, 1 H).LCMS Rt = 3.29 minutes Molecular ion not observed

Reference： [1] Patent: US2002/169174, 2002, A1,
[2] European Journal of Organic Chemistry, 2005, # 2, p. 317 - 325
[3] Patent: WO2012/7868, 2012, A2, . Location in patent: Page/Page column 94-95
[4] Patent: US2007/88053, 2007, A1, . Location in patent: Page/Page column 19

Yield	Reaction Conditions	Operation in experiment
87%	With calcium hypochlorite In water; acetic acid; acetone at 0℃; for 1h;
87%	With bis[1-methyl-3-(3-sulfopropyl)imidazolium] hexafluorotitanate; dihydrogen peroxide; sodium chloride In water at 60℃; for 3h; Green chemistry;	2.3 General procedures for bromination of arenes using NaBr and H₂O₂ catalyzed by 1 General procedure: For the typical experiment, to 3 mL of water, anisole (or the other substrate, 5 mmol), NaBr (10 mmol), 1 (2.0 mmol), and 30% aqueous solution of H2O2 (10 mmol) were mixed sequentially in a single addition. The obtained mixture was stirred vigorously at room temperature. Upon completion of the reaction, the upper organic phase was separated by decantation and the left mixture was extracted by diethyl ether repeatedly (2 mL × 3 mL). The combined organic phase was analyzed by GC and GC-MS. The conversion of anisole was based on GC analysis with n-dodecane as the internal standard. The selectivity of the product was based on GC analysis using the normalization method. The GC yield was obtained on the basis of conversion × selectivity. The products were further identified by GC-MS. (0011) The left mixtures, containing the aqueous phase and the precipitated yellow solids, were added with the saturated Na2SO3 solution gradually to destroy the unreacted H2O2 until the KI-starch test paper changed to blue color. Afterwards, the obtained mixtures were recharged with anisole (5 mmol), NaBr (5 mmol), H2O2 (10 mmol), and H2SO4 (2.5 mmol) if required, for next run.
87%	With chloro-trimethyl-silane; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 18h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
82%	With azobisisobutyronitrile; In N-Bromosuccinimide; water;	3-Chloro-4-methoxytoluene 8 (2.6 mL, 19.2 mmol) was dissolved in dichlomethane (30 mL) and N-bromosuccinimide (3.75 g, 21.1 mmol) was added followed by AIBN (36.0 mg). The reaction was heated to reflux for 19 hrs., then cooled to room temperature and the precipitate was filtered off. The filtrate was diluted with dichloromethane and washed with 0.5 M aqueous sodium bicarbonate, followed by water. The organic mixture was dried over sodium sulfate, filtered and concentrated under vacuum to yield 9 (4.73 g, 82%). The benzyl bromide was used as the crude material without further purification. 1H NMR (400 MHz, CDCl3): delta 7.42 (d, 1H, J=2.4 Hz), 7.26 (dd, 1H, J=2.4 Hz, J=8.4 Hz), 6.88 (d, 1H, J=8.4 Hz), 4.44 (s, 2H), 3.90 (s, 3H).
58%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4.5h;Reflux;	Preparation 594-(Bromomethyl)-2-chloro-1 -methoxybenzeneTo a solution of 2-chloro-1 -methoxy-4-methylbenzene (300 mg, 1 .92 mmol) in carbon tetrachloride (1 0.0 ml_) was added N-bromosuccinimide (445 mg, 2.50 mmol) and benzoylperoxide (4.6 mg, 0.0192 mmol) and the reaction heated to reflux for 4.5 hours. The reaction mixture was allowed to cool to room temperature, diluted with DCM (20.0 ml_) and partitioned with a saturated aqueous solution of sodium hydrogen peroxide (30.0 ml_). The organic layer was separated and the aqueous extracted with DCM (30 ml_). The combined organics were washed with brine (50.0 ml_), filtered through a phase separator cartridge and the solvent removed in vacuo to yield a yellow oil, which was purified by silica gel chromatography eluting with 50 % heptane in DCM to yield the title compound (263 mg, 58%).1H NMR (400 MHz, CDCI3): delta 3.90 (s, 3H), 4.44 (s, 2H), 7.25 (dd, 1 H), 7.41 (d, 1 H), 8.88 (d, 1 H).LCMS Rt = 3.29 minutes Molecular ion not observed
	With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane; for 3h;Heating / reflux;	A solution of 4-chloro-3-methoxy-toluene (30a; 0.5 g; 3.2 mmol), NBS (0.57 g; 3.2 mmol) and benzoyl peroxide (0.031 g; 0.13 mmol) and 32 mL of DCE were heated at reflux for 3 h. The reaction mixture was cooled, diluted with DCM and washed with water and brine. The organic extract was dried, filtered and evaporated to yield the bromomethyl compound 30b which was used without further purification.

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 2 h / 0 °C 2: trifluoroacetic acid / 1 h / 20 °C

Yield	Reaction Conditions	Operation in experiment
60%	With tetradecyl(tributyl)phosphonium methanesulfonate at 20℃; for 18h; Inert atmosphere; Electrolysis; Sealed tube; Green chemistry;

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86%	With N-chloro-succinimide; iron(III) chloride In acetonitrile for 0.5h;
81%	With ammonium iodide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium chloride In tetrahydrofuran at 20℃; for 12h; Green chemistry; regioselective reaction;	NH₄I catalytic chlorination of electron-rich aromatic compounds;typical procedure General procedure: Anisole (0.5 mmol), TsOH∘H2O (0.6 mmol), mCPBA (75%, 0.6 mmol), NH4I (0.05 mmol) and LiCl (1.0 mmol) were added to THF (5 mL). The mixture was stirred at r.t. for 12 h. Then H2O (10 mL), sat. aq Na2S2O3(4 mL), and sat. aq Na2CO3 (4 mL) were added. The mixture was extracted with CH2Cl2 (3 × 10 mL) and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified on a silica gel plate (20 : 1hexane-EtOAc) to afford a yellow oil product of 4-chloroanisole 64 mg(91%).
73%	With benzyltrimethylazanium tetrachloro-λ³-iodanuide In acetic acid at 70℃; for 20h;
60%	With Oxone; potassium chloride In water; acetonitrile at 20℃;
	With sulfuryl dichloride
	With sulfuryl dichloride In tetrachloromethane Irradiation;
63 %Chromat.	With iodobenzene; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium chloride In tetrahydrofuran at 20℃; for 24h; regioselective reaction;	A typical procedure for the catalytic chlorination of electron-rich aromatic compounds: General procedure: To THF (4mL), anisole (0.3mmol, 32mg), TsOH·H2O (0.3mmol, 57.1mg), mCPBA (75%, 0.3mmol, 69mg), PhI (0.12mmol, 25mg) and LiCl (0.36mmol, 16mg) were added. The mixture was stirred at r.t. for 24h. Then H2O (10mL), sat.aq. Na2S2O3 (4mL), and sat. aq. Na2CO3 (4mL) were added. The mixture was extracted with CH2Cl2 (3×10mL) and the combined organic layer was dried over anhydried Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel plate (hexane/EtOAc=20/1) to give the yellow oil product of 4-chloroanisole 35mg (90%).
	With N-chloro-succinimide
71 %Spectr.	With Oxone; sodium chloride In 2,2,2-trifluoroethanol; water at 20℃; for 8h; Sealed tube;

Physical hazards
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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
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H220	Extremely flammable gas
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H260	In contact with water releases flammable gases which may ignite spontaneously
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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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
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H361d	Suspected of damaging the unborn child
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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
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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

[ CAS No. 22002-44-4 ] {[proInfo.proName]}

Quality Control of [ 22002-44-4 ]

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Application In Synthesis of [ 22002-44-4 ]

[ 22002-44-4 ] Synthesis Path-Upstream 1~5

[ 22002-44-4 ] Synthesis Path-Downstream 1~11

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