[ CAS No. 135-68-2 ]

Name: 135-68-2|4'-Chloro-[1,1'-biphenyl]-4-amine|98%
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Quality Control of [ 135-68-2 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 135-68-2 ]

Product Details of [ 135-68-2 ]

CAS No. :	135-68-2	MDL No. :	MFCD00477989
Formula :	C₁₂H₁₀ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	203.67 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 135-68-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	61.29
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	2.65
Log Po/w (WLOGP) :	3.6
Log Po/w (MLOGP) :	3.61
Log Po/w (SILICOS-IT) :	3.44
Consensus Log Po/w :	3.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.34
Solubility :	0.093 mg/ml ; 0.000457 mol/l
Class :	Soluble
Log S (Ali) :	-2.85
Solubility :	0.289 mg/ml ; 0.00142 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.18
Solubility :	0.00135 mg/ml ; 0.00000665 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.34

Safety of [ 135-68-2 ]

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

Application In Synthesis of [ 135-68-2 ]

* 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.

Downstream synthetic route of [ 135-68-2 ]

[ 135-68-2 ] Synthesis Path-Downstream 1~9

1
[ 6242-97-3 ]
[ 135-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum on activated charcoal; ethanol; hydrazine hydrate
	With hydrogenchloride; tin
	With hydrogenchloride; iron In ethanol

Reference： [1]Dewar; James [Journal of the Chemical Society, 1958, p. 4265,4269]
[2]Giovannini,E.; de Sousa,B.F.S.E. [Helvetica Chimica Acta, 1979, vol. 62, p. 185 - 197]
[3]Byron,D.J. et al. [Journal of the Chemical Society C: Organic, 1966, p. 840 - 845]

2
[ 1679-18-1 ]
[ 106-40-1 ]
[ 135-68-2 ]

Yield	Reaction Conditions	Operation in experiment
90.6%	With potassium carbonate In ethanol at 80℃; for 6h; Green chemistry;
88%	With potassium carbonate In ethanol; water at 65℃; for 4h;
88%	With sodium carbonate; triphenylphosphine In water at 80℃; for 18h; Schlenk technique;	Suzuki-Miyaura cross-coupling reaction General procedure: A mixture of aryl halide (0.25 mmol), phenylboronicacid (0.3 mmol), Na2CO3 (0.25 mmol), PPh3 (0.025 mmol)and Pd(at)PAAs-CD (0.5 mg, 0.2 mol% Pd per mol of arylhalide) were placed into a 10 mL Schlenck tube with1 mL H2O. The reaction mixture was reacted at 80 °C for18 h, and the reaction progress was monitored via gaschromatography mass spectrometry (GC-MS). The reactionmixture was allowed to cool to room temperature, andthen 3 mL water was added, and the product was extractedwith ethyl acetate (3 mL × 3). The organic layers werecombined and dried over anhydrous Na2SO4 and solventswere evaporated via rotary evaporator. The crude productwas purified by column chromatography (200-300 meshsilica) using a mixture of petroleum ether/ethyl acetate(10:1, v:v) as eluent. The structures of the products wereconfirmed by 1H NMR and 13C NMR spectroscopies.

61%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux;	General procedure for the synthesis of biphenyls 19a-c General procedure: To a stirred solution of 4-bromoaniline (2.0 mmol) in toluene (20 mL) was added Pd(Ph3P)4(0.14 mmol), a solution of sodium carbonate (12 mmol) in water (10 mL) and a solution ofphenylboronic acid (18a-c) (1.6 mmol) in ethanol (10 mL). All the solutions werepreviously degassed for 1 h under nitrogen atmosphere. The reaction was stirred andrefluxed overnight, under nitrogen atmosphere. The reaction mixture was poured into waterand extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 andconcentrated in vacuo, and then purified by column chromatography (SiO2,ciclohexane/ethyl acetate).4-Amino-4’-chlorobiphenyl (19a). Yield: 0.48 g, 61%. 1H NMR (500 MHz, CDCl3): δ 7.48- 7.42 (m, 2H), 7.40 - 7.32 (m, 4H), 6.77 - 6.73 (m, 2H), 3.74 (br s, 2H).
43%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene at 75℃; for 22h; Inert atmosphere;	(Synthesis of Exemplified Compound 101) A 2 M aqueous solution of sodium carbonate (1.5 ml) was added to a solution of 4-bromoaniline (170 mg, 1.0 mmol) and Pd (PPh3) 4 (58 mg, 0.05 mmol) in toluene (2 ml). A solution of 4-chlorophenylboronic acid (258 mg, 1.5 mmol) in ethanol (2 ml) was slowly added to the reaction solution under argon flow, and stirred at 75 ° C. for 22 hours. After stirring, it was filtered through celite and the celite was washed with ether. The organic layer was washed sequentially with water and brine and dried over sodium sulfate. After filtration and evaporation, the residue was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1: 2) to give compound II-1 (88 mg, 43%).
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; benzene Heating;

Reference： [1]Le, Xuanduong; Dong, Zhengping; Liu, Yansheng; Jin, Zhicheng; Huy, Thanh-Do; Le, Minhdong; Ma, Jiantai [Journal of Materials Chemistry A, 2014, vol. 2, # 46, p. 19696 - 19706]
[2]Tong, Jinhui; Wang, Haiyan; Cai, Xiaodong; Zhang, Qianping; Ma, Hengchang; Lei, Ziqiang [Applied Organometallic Chemistry, 2014, vol. 28, # 2, p. 95 - 100]
[3]Zhang, Wei; Yao, Zi-Jian; Deng, Wei [Journal of the Brazilian Chemical Society, 2019, vol. 30, # 8, p. 1667 - 1677]
[4]Acosta Dávila, John Alejandro; Adler, Natalia S.; Aucar, Maria G.; Battini, Leandro; Bollini, Mariela; Cavasotto, Claudio N.; Cordo, Sandra M.; Fernández, Gabriela A.; Gamarnik, Andrea V.; García, Cybele C.; Gebhard, Leopoldo G.; Hernández de los Ríos, Alejandro; Leal, Emilse S.; Monge, María Eugenia; Morell, María L.; Videla, Mariela [European Journal of Medicinal Chemistry, 2019, vol. 182]
[5]Current Patent Assignee: TOKYO MEDICAL AND DENTAL UNIVERSITY - JP2019/89720, 2019, A Location in patent: Paragraph 0089; 0092
[6]Ren; McClelland [Canadian Journal of Chemistry, 1998, vol. 76, # 1, p. 78 - 84]

3
[ 100-65-2 ]
[ 108-90-7 ]
[ 135-68-2 ]
[ 1205-71-6 ]
[ 1203-43-6 ]
[ 1204-42-8 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 295 - 300

4
[ 62-53-3 ]
[ 1073-69-4 ]
[ 135-68-2 ]
[ 1204-44-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 41% 2: 13%	With manganese(IV) oxide In acetonitrile at 20℃; Overall yield = 54 %; regioselective reaction;

Reference： [1]Jasch, Hannelore; Scheumann, Julia; Heinrich, Markus R. [Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10699 - 10706]

5
[ 135-68-2 ]
[ 85118-24-7 ]
N-(2-bromo-4-(trifluoromethyl)benzyl)-4'-chloro-[1,1'-biphenyl]-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 16h;	Solid NaBH(OAc)3 (1.4 g, 6.8 mmol) was added to a DCE solution (10 mL) of <strong>[85118-24-7]2-bromo-4-(trifluoromethyl)benzaldehyde</strong> (860 mg, 3.4 mmol), 4'-chloro-[1,1'-biphenyl]-4-amine (761 mg, 3.7 mmol), and AcOH (0.78 mL, 13.6 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Reference： [1]Patent: US2012/302610,2012,A1 .Location in patent: Page/Page column 43

6
[ 135-68-2 ]
[ 42860-02-6 ]
[ 1415130-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	Neat i-Pr2NEt (0.21 mL, 1.19 mmol) was added to a DCM mixture (5 mL) of <strong>[42860-02-6]3-bromo-5-chlorobenzoic acid</strong> (140 mg, 0.60 mmol), 4'-chloro-[1,1'-biphenyl]-4-amine (145 mg, 0.71 mmol), HOBt (92 mg, 0.60 mmol) and EDCI (114 mg, 0.60 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting precipitate was filtered off, washed with water and MeOH, and dried in vacuo to yield the title compound.

Reference： [1]Patent: US2012/302610,2012,A1 .Location in patent: Page/Page column 105

7
[ 2028-74-2 ]
[ 62-53-3 ]
[ 135-68-2 ]
[ 1204-44-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 44% 2: 12%	With sodium hydroxide In water at 75℃;	II.13 II.13 4′-Chlorobiphenyl-2-amine and 4′-chlorobiphenyl-4-amine 0344] 4′-Chlorobiphenyl-2-amine and 4′-chlorobiphenyl-4-amine were synthesized from aniline (20.0 mmol, 2.33 g) and 4-chlorophenyldiazonium chloride (2.00 mmol, 5.00 ml of the 0.4 M aryldiazonium chloride solution prepared by general method GM 1) analogously to general method GM 3 at 75° C. Diethyl ether was used for extraction. Excess aniline was removed by means of vacuum distillation. The two regioisomers were separated by means of column chromatography (silica gel, hexane/EtOAc=4:1). 4′-Chlorobiphenyl-2-amine (0.88 mmol, 179 mg, 44%) and 4′-chlorobiphenyl-4-amine (0.24 mmol, 49 mg, 12%) were obtained. RRN 65 4′-Chlorobiphenyl-2-amine [0345] Rf 0.6 (hexane/EtOAc=4:1) [UV] [0346] 1H NMR (360 MHz, CDCl3): δ=6.76 (dd, J=0.9 Hz, J=8.0 Hz, 1H), 6.82 (dt, J=1.1 Hz, J=7.47 Hz, 1H), 7.09 (dd, J=1.4 Hz, J=7.6 Hz, 1H), 7.16 (ddd, J=1.6 Hz, J=7.4 Hz, J=8.0 Hz, 1H), 7.37-7.45 (m, 4H). [0347] 13C NMR (90.6 MHz, CDCl3): δ=115.7 (CH), 118.8 (CH), 126.3 (Cq), 128.8 (CH), 129.0 (2×CH), 130.3 (CH), 130.4 (2×CH), 133.1 (Cq), 137.9 (Cq), 143.4 (Cq). [0348] MS (EI) m/z (%): 205 (29) [37Cl-M+], 204 (10), 203 (100) [35Cl-M+], 202 (12), 169 (17), 168 (56), 167 (37), 166 (14), 83 (29). [0349] HRMS (EI) calculated for C12H10ClN [M+]: 203.0502. found: 203.0502. RRN 66 4′-Chlorobiphenyl-4-amine [0350] Rf 0.3 (hexane/EtOAc=4:1) [UV] [0351] 1H NMR (600 MHz, CDCl3): δ=6.75 (d, J=8.6 Hz, 2H), 7.35 (d, J=8.6 Hz, 2H), 7.37 (d, J=8.6 Hz, 2H), 7.45 (d, J=8.5 Hz, 2H). [0352] 13C NMR (151 MHz, CDCl3): δ=115.4 (2×CH), 127.5 (2×CH), 127.8 (2×CH), 128.7 (2×CH), 130.2 (Cq), 132.1 (Cq), 139.6 (Cq), 146.1 (Cq). [0353] MS (EI) m/z (%): 205 (32) [37Cl-M+], 204 (18), 203 (100) [35Cl-M+], 169 (12), 168 (9), 167 (24), 139 (10), 101 (11), 83 (21). [0354] HRMS (EI) calculated for C12H10ClN [M+]: 203.0502. found: 203.0502.

Reference： [1]Current Patent Assignee: BASF SE - US2013/338369, 2013, A1 Location in patent: Paragraph 0243; 0244; 0343; 0344; 0345; 0346; 0347-0349

8
[ 1073-70-7 ]
[ 62-53-3 ]
[ 135-68-2 ]
[ 1204-44-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 51% 2: 9%	With oxygen; sodium hydroxide In water at 60℃; for 33h; regioselective reaction;

Reference： [1]Hofmann, Josefa; Jasch, Hannelore; Heinrich, Markus R. [Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2314 - 2320]

9
[ 637-87-6 ]
[ 89415-43-0 ]
[ 135-68-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 1h;	3. General procedure for Suzuki-Miyaura coupling: General procedure: To a mixture of aryl halide (1 mmol), arylboronic acid (1.2 mmol), Pd-AcAc-Am-Fe3O4/SiO2 (30 mg ), and K2CO3 (3 mmol), DMF: water (8:2, 5 mL) was added and stirred at 80 °C under aerobic conditions. After completion of reaction, monitored by TLC, the reaction mixture was cooled. The catalyst was separated by using external magnet. The product was extracted with ethylacetate (2×10 mL) The organic layer was dried with Na2SO4 and then concentrated on a rotary evaporator afforded corresponding biaryls in excellent yield. The crude products were then purified by column chromatography (2 % ethyl acetate). All synthesized products were confirmed from physical constant IR, 1H and 13C NMR.

Reference： [1]Vibhute, Sandip P.; Mhaldar, Pradeep M.; Shejwal, Rajendra V.; Pore, Dattaprasad M. [Tetrahedron Letters, 2020, vol. 61, # 11]

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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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
Environmental hazards
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. 135-68-2 ]

Quality Control of [ 135-68-2 ]

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[ 135-68-2 ] Synthesis Path-Downstream 1~9

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