[ CAS No. 556-97-8 ] {[proInfo.proName]}

Name: 556-97-8|5-Chloro-m-xylene|97%
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Quality Control of [ 556-97-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 556-97-8 ]

CAS No. :	556-97-8	MDL No. :	MFCD00060273
Formula :	C₈H₉Cl	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FKKLHLZFSZGXBN-UHFFFAOYSA-N
M.W :	140.61	Pubchem ID :	32887
Synonyms :

Calculated chemistry of [ 556-97-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.38
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-4.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.4
Log Po/w (XLOGP3) :	3.88
Log Po/w (WLOGP) :	2.96
Log Po/w (MLOGP) :	3.53
Log Po/w (SILICOS-IT) :	3.41
Consensus Log Po/w :	3.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.65
Solubility :	0.0315 mg/ml ; 0.000224 mol/l
Class :	Soluble
Log S (Ali) :	-3.58
Solubility :	0.0372 mg/ml ; 0.000265 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.76
Solubility :	0.0244 mg/ml ; 0.000174 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 556-97-8 ]

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

Application In Synthesis of [ 556-97-8 ]

* 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 [ 556-97-8 ]
Downstream synthetic route of [ 556-97-8 ]

[ 556-97-8 ] Synthesis Path-Upstream 1~4

1
[ 556-97-8 ]
[ 75-65-0 ]
[ 89-20-3 ]
[ 2157-39-3 ]

Reference： [1] Patent: US5254584, 1993, A,

2
[ 556-97-8 ]
[ 461-97-2 ]

Reference： [1] Patent: CN105399632, 2016, A,

3
[ 95-47-6 ]
[ 95-66-9 ]
[ 556-97-8 ]
[ 95-72-7 ]
[ 6781-98-2 ]
[ 615-60-1 ]
[ 608-23-1 ]
[ 20824-80-0 ]
[ 68266-67-1 ]
[ 34060-72-5 ]
[ 52331-02-9 ]
[ 70172-92-8 ]
[ 552-45-4 ]
[ 55676-90-9 ]

Reference： [1] Patent: EP1508557, 2005, A1, . Location in patent: Page/Page column 23-24
[2] Patent: EP1508557, 2005, A1, . Location in patent: Page/Page column 24

4
[ 79-46-9 ]
[ 556-97-8 ]
[ 62358-81-0 ]
[ 67-68-5 ]
[ 103426-20-6 ]
[ 56961-33-2 ]

Reference： [1] Patent: US4563465, 1986, A,
[2] Patent: US4585866, 1986, A,

[ 556-97-8 ] Synthesis Path-Downstream 1~78

1
[ 75-77-4 ]
[ 556-97-8 ]
[ 17961-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium

Reference： [1]Eaborn; Moore [Journal of the Chemical Society, 1959, p. 3640]

2
[ 556-97-8 ]
[ 13289-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid

Reference： [1]Klages [Chemische Berichte, 1896, vol. 29, p. 311]

3
[ 108-69-0 ]
[ 556-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride Diazotization_.Behandlung der Diazoniumsalz-Loesung mit CuCl;
	Multi-step reaction with 2 steps 1: 1) conc. HCl, NaNO₂, 2) 1M KOH / 1) water, 10 min, ice bath, 2) 30 min, ice bath 2: CuCl, HCl / triazene moiety as protecting group for aromatic amines; var. triazenes

Reference： [1]Kohlrausch; Pongratz [Monatshefte fur Chemie, 1934, vol. 64, p. 361,364, 365][Monatshefte fuer Chemie, 1935, vol. 65, p. 6,14]
[2]Klages [Chemische Berichte, 1896, vol. 29, p. 311]
[3]Gross, Margaret L.; Blank, David H.; Welch, Willard M. [Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2104 - 2109]

4
[ 556-97-8 ]
[ 67-63-0 ]
[ 31364-24-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid

Reference： [1]Mannschreck,A.; Ernst,L. [Chemische Berichte, 1971, vol. 104, p. 228 - 247]

5
<(3,5-Dimethylphenyl)azo>pyrrolidine [ No CAS ]
[ 556-97-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	With hydrogenchloride; copper(l) chloride
	With hydrogenchloride; copper(l) chloride triazene moiety as protecting group for aromatic amines; var. triazenes;

Reference： [1]Gross, Margaret L.; Blank, David H.; Welch, Willard M. [Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2104 - 2109]
[2]Gross, Margaret L.; Blank, David H.; Welch, Willard M. [Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2104 - 2109]

6
[ 556-97-8 ]
[ 62358-81-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethane	V.i (i) (i) 3-Chloro-5-methylbenzyl Bromide A solution of 5-chloro-m-xylene (14.06 g; 0.1 mol), NBS (17.8 g; 0.1 mol) and AIBN (1.1 g; 6.7 mmol) in CCl4 was refluxed for two hours. The resultant mixture was cooled, and the solid material formed was removed by filtration. Concentration yielded the sub-title compound (17.9 g; 80%). 1H-NMR (400 MHz; CDCl3): δ 7.20 (s, 1H); 7.11 (s, 1H); 7.09 (s, 1H); 4.41 (s, 2H); 2.34 (s, 3H).
68%	With N-Bromosuccinimide In tetrachloromethane for 3h; Heating / reflux; UV-irradiation;	K Example K 1-Bromomethyl-3-chloro-5-methyl-benzene (46): The mixture of 1-Chloro-3,5-dimethyl-benzene (32 g, 0.23 mol) and N-bromosuccinimide (40.5 g, 0.23M) in carbon tetrachloride (400 ml) was refluxed for 3 hr under a light of 500 W tungsten light. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, hexane) to afford 33 g (68%) of a white solid. 1H NMR (200 MHz, CDCl3) δ: 2.32 (3H, s), 4.39 (2H, s), 7.10 (2H, s), 7.18 (1H, s).
60%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 0.333333h; Heating / reflux;	A [00326] To a solution of m-chloroxylene (0.96g, 6.8mmol) in carbon tetrachloride at reflux was added N-bromosuccinmide (1.4g, 7.5 mmol) followed by benzoyl peroxide (1.6g, 6.8 mmol). The reaction was allowed to stir for 20 minutes and cooled to room temperature, filtered off precipitate and the filtrate was concentrated under reduced pressure and the EPO resulting residue was purified via silica gel chromatography using petroleum ether as eluant to give 0.89g of l-(bromomethyl)-3-chloro-5-methylbenzene (60%). NMR (CDCl3): 2.31 (s,3H) 4.37 (s,2H) 7.09 (s,lH) 7.12 (s,lH) 7.20 (s,lH).

60%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane	V Preparation of 1-(bromomethyl)-3-chloro-5-methylbenzene Preparation of 1-(bromomethyl)-3-chloro-5-methylbenzene To a solution of m-chloroxylene (0.96 g, 6.8 mmol) in carbon tetrachloride at reflux was added N-bromosuccinimide (1.4 g, 7.5 mmol) followed by benzoyl peroxide (1.6 g, 6.8 mmol). The reaction was allowed to stir for 20 minutes and cooled to room temperature, filtered off precipitate and the filtrate was concentrated under reduced pressure and the resulting residue was purified via silica gel chromatography using petroleum ether as eluant to give 0.89 g of 1-(bromomethyl)-3-chloro-5-methylbenzene (60%). NMR (CDCl3): 2.31 (s, 3H) 4.37 (s, 2H) 7.09 (s, 1H) 7.12 (s, 1H) 7.20 (s, 1H).
	With N-Bromosuccinimide; dibenzoyl peroxide
	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 20℃; for 0.333333h; Heating / reflux;	A [0362] To a solution of m-chloroxylene (0.96g, 6.8mmol) in carbon tetrachloride at reflux was added N-bromosuccinmide (1.4g, 7.5 mmol) followed by benzoyl peroxide (1.6g, 6.8 mmol). The reaction was allowed to stir for 20 minutes and cooled to room temperature, filtered off precipitate and the filtrate was concentrated under reduced pressure and the resulting residue was purified via silica gel chromatography using petroleum ether as eluant to give 0.89g of l-(bromomethyl)-3-chloro-5-methylbenzene. NMR (CDCl3): 2.31 (s,3H) 4.37 (s,2H) 7.09 (s,lH) 7.12 (s,lH) 7.20 (s,lH).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US6255301, 2001, B1
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2008/70920, 2008, A1 Location in patent: Page/Page column 40-41
[3]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2007/25307, 2007, A2 Location in patent: Page/Page column 306 - 307
[4]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2010/272681, 2010, A1
[5]Newman,M.S.; Landers,J.O. [Journal of Organic Chemistry, 1977, vol. 42, # 15, p. 2556 - 2559]
[6]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2008/106139, 2008, A1 Location in patent: Page/Page column 476

7
[ 110-91-8 ]
[ 556-97-8 ]
[ 16800-77-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium t-butanolate In toluene at 105℃; for 1h;

Reference： [1]Bei; Guram; Turner; Weinberg [Tetrahedron Letters, 1999, vol. 40, # 7, p. 1237 - 1240]

8
[ 556-97-8 ]
[ 36343-05-2 ]
(3,5-dimethyl-phenyl)-heptyl-methyl-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1237 - 1240

9
[ 556-97-8 ]
[ 98-80-6 ]
[ 17057-88-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With cesium fluoride In toluene	9 Example 9 Example 9 This is an example of Pd/ligand 2-catalyzed Suzuki reaction for biaryl synthesis. 3,5-Dimethylbiphenyl A reaction mixture of phenylboronic acid (190 mg, 1.56 mmol), CsF (474 mg, 3.12 mmol), Pd(dba)2 (6 mg, 10 μmol), ligand 2 (10 mg, 29 μmol), and 5-chloro-m-xylene (0.14 mL, 1.0 mmol) in toluene (4 mL) was heated at reflux and monitored by GC-MS. After 5 h, GC-MS analysis showed a >98% GC yield of the desired product 3,5-dimethylbiphenyl. TON=100 and TOF=20.
98%	With potassium phosphate; C₇₅H₅₈Cl₂N₄Pd In water; isopropyl alcohol at 25℃; for 4.5h; Schlenk technique;
95%	With potassium phosphate; C₂₀H₂₈Br₂N₂Pd In water; isopropyl alcohol at 25℃; for 7.5h;

94%	With Pd(dba)2*o-C6H4-<P(cyclohex)2>-<C(Me)(-OCH2CH2O-)>; cesium fluoride In 1,4-dioxane at 100 - 110℃;
94%	With cesium fluoride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; 2’-(dicyclohexylphosphino)acetophenone ethylene ketal In toluene at 105℃; for 3h;
90%	With tetrabutyl ammonium fluoride; tricyclohexylphosphine at 85 - 90℃; for 5h;
90%	With potassium carbonate In water; isopropyl alcohol at 90℃; for 8h;
64%	With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 19h;
44%	With orotic acid; caesium carbonate In acetone at 80℃; for 18h; Inert atmosphere;
41%	With cetyltrimethylammonim bromide; sodium hydroxide In water at 30℃; for 48h; Irradiation;	2.3. Photocatalytic reactions General procedure: The reactions were conducted under an air atmosphere with apressure of 1 atm. When aryl bromides were used as substrates,the reactant mixture consisted of 1 mmol of aryl bromide, 2 mmolof phenylboronic acid, 3 mmol of Cs2CO3, 50 mg of Pd(at)NiO80/SiC,7 mL of dimethylformamide (DMF) and 3 mL of H2O. When arylchlorides were used as substrates, the reactant mixture consistedof 1 mmol of aryl chloride, 2 mmol of phenylboronic acid, 3 mmolof NaOH, 2 mmol of cetyltrimethylammonium bromide (CTAB),100 mg of Pd(at)NiO80/SiC and 10 mL of H2O. The reaction temperaturewas set at 30 °C and controlled by a circulating water bath.The mixture was stirred at 500 rpm using a magnetic stirrer during the reaction and was exposed to a xenon lamp. A low-pass optical filter was employed to block light with k < 400 nm. The light intensity was maintained at 0.35 W/cm2 for both aryl bromides and arylchlorides. The effect of the wavelength of light on catalytic performance was investigated using various light-emitting diode (LED)lamps with different wavelengths.After reaction, the reaction mixture was diluted with dichloromethane(DCM, 10 mL). The organic phase was extracted and filtered through a millipore filter (pore size: 0.22 lm). Then,0.5 mmol of n-dodecane was added as an internal standard. The product yield was determined by gas chromatography-mass spectrometry(GC-MS, BRUKER SCION SQ 456 GC-MS) using ndodecaneas the internal calibration standard. The values givenare the average of two experiments. The yields were calculated based on the amount of aryl halide. The residue was purified bycolumn chromatography on silica gel (silica: 200-300; eluant: hexane/ethyl acetate) to isolate the desired product.
65%Chromat.	With bis(1-glycyl-3-methyl imidazolium chloride)palladium(II); triethylamine at 25℃; for 5h; Ionic liquid; Green chemistry;	1.3. General experimental procedure for the Suzuki-Miyaurareaction General procedure: In a conical flask (50mL), a mixture of aryl halide (1 mmol), phenyl boronic acid (1.2 mmol),triethylamine (1 mmol), [Aemim]Br (1ml) and [Gmim]Cl-Pd (II) (0.1mol%, 5 mg)was added and stirred at 25OC for a period as indicated in Table 5(The reaction was monitored by HPLC and TLC). The resulting heterogeneousmixture was extracted with ethyl acetate or diethyl ether (3x 5 mL). Theorganic phase was separated and dried over anhydrous Na2SO4and evaporated. Evaporation of the solvent gave the crud product residue whichwas further purified by flash chromatography using n-hexane/EtOAc to give thedesired coupling product in 82-94% isolated yields.

Reference： [1]Current Patent Assignee: FREESLATE, INC. - US6268513, 2001, B1
[2]Han, Fangwai; Xu, Ying; Zhu, Rongjiao; Liu, Guiyan; Chen, Chen; Wang, Jianhui [New Journal of Chemistry, 2018, vol. 42, # 9, p. 7422 - 7427]
[3]Liu, Guiyan; Han, Fangwai; Liu, Chengxin; Wu, Hongli; Zeng, Yongfei; Zhu, Rongjiao; Yu, Xia; Rao, Shuang; Huang, Genping; Wang, Jianhui [Organometallics, 2019, vol. 38, # 7, p. 1459 - 1467]
[4]Bei, Xiaohong; Crevier, Thomas; Guram, Anil S.; Jandeleit, Bernd; Powers, Timothy S.; et al. [Tetrahedron Letters, 1999, vol. 40, # 20, p. 3855 - 3858]
[5]Bei, Xiaohong; Turner, Howard W.; Weinberg, W. Henry; Guram, Anil S.; Petersen, Jeffrey L. [Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6797 - 6803]
[6]Li, Jin-Heng; Deng, Chen-Liang; Xie, Ye-Xiang [Synthetic Communications, 2007, vol. 37, # 14, p. 2433 - 2448]
[7]Burange, Anand S.; Luque, Rafael; Rajabi, Fatemeh; Voskressensky, Leonid G. [Molecular catalysis, 2021, vol. 515]
[8]Li, Jin-Heng; Zhu, Qi-Ming; Xie, Ye-Xiang [Tetrahedron, 2006, vol. 62, # 47, p. 10888 - 10895]
[9]Zhang, Hong-Ping; Dai, You-Zhi; Zhou, Xi; Yu, Huang [Synlett, 2012, vol. 23, # 8, p. 1221 - 1224]
[10]Braunschweig, Holger; Guo, Xiang-Yun; Guo, Xiao-Ning; Hao, Cai-Hong; Jiao, Zhi-Feng; Marder, Todd B.; Qiao, Yan; Qin, Yong; Radius, Udo; Tian, Ya-Ming; Wang, Ying-Xiong; Zhang, Bin [Journal of Catalysis, 2020, vol. 389, p. 517 - 524]
[11]Karthikeyan, Parasuraman; Vanitha, Arumugam; Radhika, Pachaiappan; Suresh, Kannan; Sugumaran, Arunachalam [Tetrahedron Letters, 2013, vol. 54, # 52, p. 7193 - 7197]

Yield	Reaction Conditions	Operation in experiment
	Protonier. in HF-SbF5-Gemisch. --> 5-Chlor-1.3-dimethyl-benzolium-kation;

Yield	Reaction Conditions	Operation in experiment
	/BRN= 165422/ (V δ), 6percent - waessr. KOH (24h, Raumtemperatur);
	/BRN= 166863/ (V Γ), 6percent - waessr. KOH (24h, Raumtemperatur);

Yield	Reaction Conditions	Operation in experiment
	With quinoline

13
[ 556-97-8 ]
[ 960-16-7 ]
[ 17057-88-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium fluoride; tetrabutylammomium bromide; tris-(o-tolyl)phosphine at 125 - 130℃; for 72h;
44%	With palladium diacetate; orotic acid; cesium fluoride In 1,4-dioxane at 100℃; for 22h; Sealed tube; Inert atmosphere; Schlenk technique;

Reference： [1]Li, Jin-Heng; Tang, Bo-Xiao; Tao, Li-Ming; Xie, Ye-Xiang; Liang, Yun; Zhang, Man-Bo [Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7488 - 7490]
[2]Zhang, Hong-Ping; Li, Xiao-Fang; Li, Hong-Yan [Journal of Chemical Research, 2013, vol. 37, # 4, p. 219 - 222]

14
[ 58-08-2 ]
[ 556-97-8 ]
8-[3,5-dimethylphenyl]-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium phosphate In 1-methyl-pyrrolidin-2-one at 125℃; for 24h;

Reference： [1]Chiong, Hendrich A.; Daugulis, Olafs [Organic Letters, 2007, vol. 9, # 8, p. 1449 - 1451]

15
[ 556-97-8 ]
[ 947-84-2 ]
2-(3,5-dimethylphenyl)-6-phenylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With 3 A molecular sieve; caesium carbonate In N,N-dimethyl-formamide at 20 - 145℃; for 26h;

Reference： [1]Chiong, Hendrich A.; Pham, Quynh-Nhu; Daugulis, Olafs [Journal of the American Chemical Society, 2007, vol. 129, # 32, p. 9879 - 9884]

16
[ 556-97-8 ]
[ 62358-64-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NBS, (PhCO)2O₂ 2: NaOMe 3: LiAlH₄