[ CAS No. 6212-33-5 ] {[proInfo.proName]}

Name: 6212-33-5|2-Amino-2-(4-chlorophenyl)acetic acid|97%
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Quality Control of [ 6212-33-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6212-33-5 ]

SDS Specification

Alternatived Products of [ 6212-33-5 ]

Product Details of [ 6212-33-5 ]

CAS No. :	6212-33-5	MDL No. :	MFCD00049328
Formula :	C₈H₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QGJGBYXRJVIYGA-UHFFFAOYSA-N
M.W :	185.61	Pubchem ID :	587821
Synonyms :	2-Amino-2-(4-chlorophenyl)acetic acid	Chemical Name :	2-Amino-2-(4-chlorophenyl)acetic acid

Calculated chemistry of [ 6212-33-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.7
TPSA :	63.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.25
Log Po/w (XLOGP3) :	-1.07
Log Po/w (WLOGP) :	1.1
Log Po/w (MLOGP) :	-0.85
Log Po/w (SILICOS-IT) :	1.17
Consensus Log Po/w :	0.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.55
Solubility :	51.8 mg/ml ; 0.279 mol/l
Class :	Very soluble
Log S (Ali) :	0.23
Solubility :	315.0 mg/ml ; 1.7 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-2.08
Solubility :	1.55 mg/ml ; 0.00838 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 6212-33-5 ]

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 [ 6212-33-5 ]

* 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 [ 6212-33-5 ]
Downstream synthetic route of [ 6212-33-5 ]

[ 6212-33-5 ] Synthesis Path-Upstream 1~16

1
[ 104-88-1 ]
[ 6212-33-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	Stage #1: With water; ammonium chloride In methanol at 20℃; for 2 h; Stage #2: With hydrogenchloride In water; toluene for 24 h; Reflux	A solution of 4-chlorobenzaldehyde (4.79 g, 34.08 mmol) inmethanol (10 mL) was added dropwise under vigorous stirring to a solution of KCN (2.48 g, 38.08 mmol) and NH4Cl (2.04 g,38.08 mmol) in water (10 mL). The reaction mixture was vigorously stirred at room temperature for 2 h. Then, water (25 mL) was added and the resulting mixture was extracted with toluene (25 mL). The aqueous layer was discarded and the toluene phase was extracted with 6N aqueous HCl (3 × 10 mL). The combined aqueous phasewas refluxed for 24 h. After that, the reaction mixture was evaporated and the resulting residue was suspended in water. The pHwas adjusted to 6–7 by means of the addition of small portions ofNa2CO3to precipitate the amino acid. The (4-chlorophenyl)glycinewas filtered and dried (2.16 g, 11.62 mmol, 34percent yield) and used inthe next step without further purification. Thionyl chloride (1.79 mL, 24.59 mmol) was added dropwiseto an ice-cooled suspension of (4-chlorophenyl)glycine (2.16 g,11.62 mmol) in dry methanol (29 mL). The resulting solution wasstirred at room temperature for 24 h. Then, the solvent was con-centrated under vacuum and the residue was lyophilized to afforda white solid (2.55 g, 10.80 mmol, 93percent yield). Mp 196–198C (lit.194–197C [10]);1H NMR (D2O, 400 MHz) (, ppm) 7.54–7.50 (m,2H, C6H4), 7.46–7.41 (m, 2H, C6H4), 5.30 (s, 1H, CH), 3.81 (s, 3H,CH3);13C NMR (D2O, 100 MHz) (, ppm) 169.2 (C), 135.9 (C), 129.7(2 x CH), 129.6 (2 x CH), 129.5 (C), 55.7 (CH3), 53.9 (CH); HRMS (ESI-TOF) calc. for [C9H11ClNO2]+requires 200.0473, found 200.0464.

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 407 - 418

2
[ 32549-33-0 ]
[ 6212-33-5 ]

Reference： [1] Patent: CN106380415, 2017, A, . Location in patent: Paragraph 0037; 0038

3
[ 1353886-52-8 ]
[ 6212-33-5 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 3, p. 663 - 670
[2] Synthetic Communications, 2012, vol. 42, # 17, p. 2540 - 2554

4
[ 7099-88-9 ]
[ 6212-33-5 ]

Reference： [1] Chemistry - A European Journal, 2014, vol. 20, # 1, p. 245 - 252

5
[ 6212-32-4 ]
[ 6212-33-5 ]

Reference： [1] European Journal of Medicinal Chemistry, 1995, vol. 30, # 6, p. 515 - 520
[2] Journal of the Chemical Society, 1962, p. 1440 - 1444
[3] Pharmazie, 1990, vol. 45, # 7, p. 529 - 530

6
[ 24091-92-7 ]
[ 6212-33-5 ]

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 1, p. 420 - 423

7
[ 39546-47-9 ]
[ 6212-33-5 ]

Reference： [1] Journal of Organic Chemistry, 1973, vol. 38, p. 2094 - 2096

8
[ 104-88-1 ]
[ 6212-33-5 ]

Reference： [1] Science China Chemistry, 2013, vol. 56, # 1, p. 117 - 123

9
[ 39533-35-2 ]
[ 6212-33-5 ]

Reference： [1] Journal of Organic Chemistry, 1973, vol. 38, p. 2094 - 2096

10
[ 140-53-4 ]
[ 6212-33-5 ]

Reference： [1] Journal of Organic Chemistry, 1966, vol. 31, p. 3708 - 3711

11
[ 43189-37-3 ]
[ 6212-33-5 ]

Reference： [1] Journal of Organic Chemistry, 1983, vol. 48, # 5, p. 627 - 634

12
[ 6212-33-5 ]
[ 43189-20-4 ]

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 407 - 418

13
[ 67-56-1 ]
[ 6212-33-5 ]
[ 43189-20-4 ]

Reference： [1] Journal of the Chemical Society. Perkin transactions 1, 1976, # 5, p. 475 - 481

14
[ 6212-33-5 ]
[ 43189-37-3 ]

Reference： [1] Journal of the Chemical Society. Perkin transactions 1, 1976, # 5, p. 475 - 481

15
[ 6212-33-5 ]
[ 74590-69-5 ]

Reference： [1] Journal of Fluorine Chemistry, 1991, vol. 55, # 2, p. 131 - 136
[2] Journal of Chemical Research, Miniprint, 1995, # 8, p. 1933 - 1945

16
[ 24424-99-5 ]
[ 6212-33-5 ]
[ 147353-95-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 2059 - 2073

[ 6212-33-5 ] Synthesis Path-Downstream 1~20

1
[ 67-56-1 ]
[ 6212-33-5 ]
[ 43189-20-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1976,p. 475 - 481

2
[ 6212-33-5 ]
[ 74590-69-5 ]

Reference： [1]Journal of Fluorine Chemistry,1991,vol. 55,p. 131 - 136
[2]Journal of Chemical Research, Miniprint,1995,p. 1933 - 1945

3
[ 43189-37-3 ]
[ 6212-33-5 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 627 - 634

4
[ 24091-92-7 ]
[ 6212-33-5 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 420 - 423

5
[ 6212-33-5 ]
[ 43189-37-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1976,p. 475 - 481

6
[ 67-56-1 ]
[ 6212-33-5 ]
[ 42718-19-4 ]

Yield	Reaction Conditions	Operation in experiment
100%		Description 1; To ice-chilled methanol (300ml) under argon was carefully added dropwise thionyl chloride (15.44ml; 0.217mol) over 45min. 4-Chlorophenylglycine (26.26g; 0.141 mol) was added, ice cooling removed and the reaction mixture warmed to 400C; the reaction was stirred at 400C for 48h. After cooling to room temperature, the reaction was evaporated under reduced pressure. Re-evaporation from methanol afforded a white solid which was triturated with diethyl ether (ca. 700ml) and then stored at ca. 40C for 64h, filtered, washed with diethyl ether and dried in vacuo to afford the title product as the hydrochloride salt (33.4Og; 100%). 1H NMR (d6-DMSO) delta: 3.72 (3H, s), 5.36 (1 H, s), 7.53 - 7.58 (4H, m), 9.07 (3H, s). Mass Spectrum (Electrospray LC/MS): Found 200 (MH+). C9H1035CINO2 requires 199. Ret. time 1.32 min.
100%		Description 1; To ice-chilled methanol (300ml) under argon was carefully added dropwise thionyl chloride (15.44ml; 0.217mol) over 45min. 4-Chlorophenylglycine (26.26g; 0.141 mol) was added, ice cooling removed and the reaction mixture warmed to 400C; the reaction was stirred at 400C for 48h. After cooling to room temperature, the reaction was evaporated under reduced pressure. Re-evaporation from methanol afforded a white solid which was triturated with diethyl ether (ca. 700ml) and then stored at ca. 40C for 64h, filtered, washed with diethyl ether and dried in vacuo to afford the title product as the hydrochloride salt (33.4Og; 100%). 1H NMR (de-DMSO) delta: 3.72 (3H, s), 5.36 (1 H, s), 7.53 - 7.58 (4H, m), 9.07 (3H, s). Mass Spectrum (Electrospray LC/MS): Found 200 (MH+). C9H1035CINO2 requires 199. Ret. time 1.32 min.
100%		Description 1 : Methyl amino(4-chlorophenyl)acetate; To ice-chilled methanol (300ml) under argon was carefully added dropwise thionyl chloride (15.44ml; 0.217mol) over 45min. 4-Chlorophenylglycine (26.26g; 0.141 mol) was added, ice cooling removed and the reaction mixture warmed to 400C. The reaction was stirred at 400C for 48h. After cooling to room temperature, the reaction was evaporated under reduced pressure. Re-evaporation from methanol afforded a white solid which was triturated with diethyl ether (ca. 700ml) and then stored at ca. 40C for 64h, filtered, washed with diethyl ether and dried in vacuo to afford the title product as the hydrochloride salt (33.4Og; 100%). 1H NMR (d6-DMSO) delta: 3.72 (3H, s), 5.36 (1 H, s), 7.53 - 7.58 (4H, m), 9.07 (3H, s). Mass Spectrum (Electrospray LC/MS): Found 200 (MH+). C9H1035CINO2 requires 199. Ret. time 1.32 min.

100%		Description 1 : Methyl amino(4-chlorophenyl)acetate; To ice-chilled methanol (300ml) under argon was carefully added dropwise thionyl chloride (15.44ml; 0.217mol) over 45min. 4-Chlorophenylglycine (26.26g; 0.141 mol) was added, ice cooling removed and the reaction mixture warmed to 400C. The reaction was stirred at 400C for 48h. After cooling to room temperature, the reaction was evaporated under reduced pressure. Re-evaporation from methanol afforded a white solid which was triturated with diethyl ether (ca. 700ml) and then stored at ca. 40C for 64h, filtered, washed with diethyl ether and dried in vacuo to afford the title product as the hydrochloride salt (33.4Og; 100%). 1H NMR (d6-DMSO) delta: 3.72 (3H, s), 5.36 (1 H, s), 7.53 - 7.58 (4H, m), 9.07 (3H, s). Mass Spectrum (Electrospray LC/MS): Found 200 (MH+). C9H1035CINO2 requires 199. Ret. time 1.32 min.
100%		To ice-chilled methanol (300 ml) under argon was carefully added dropwise thionyl chloride (15.44 ml; 0.217 mol) over 45 min. 4-Chlorophenylglycine (26.26 g; 0.141 mol) was added, ice cooling removed and the reaction mixture warmed to 40 C.; the reaction was stirred at 40 C. for 48 h. After cooling to room temperature, the reaction was evaporated under reduced pressure. Re-evaporation from methanol afforded a white solid which was triturated with diethyl ether (ca. 700 ml) and then stored at ca. 4 C. for 64 h, filtered, washed with diethyl ether and dried in vacuo to afford the title product as the hydrochloride salt (33.40 g; 100%). 1H NMR (d6-DMSO) delta: 3.72 (3H, s), 5.36 (1H, s), 7.53-7.58 (4H, m), 9.07 (3H, s). Mass Spectrum (Electrospray LC/MS): Found 200 (MH+). C9H1035ClNO2 requires 199. Ret. time 1.32 min.
93%	With thionyl chloride; at 20℃; for 24h;Cooling with ice;	A solution of 4-chlorobenzaldehyde (4.79 g, 34.08 mmol) inmethanol (10 mL) was added dropwise under vigorous stirring to a solution of KCN (2.48 g, 38.08 mmol) and NH4Cl (2.04 g,38.08 mmol) in water (10 mL). The reaction mixture was vigorously stirred at room temperature for 2 h. Then, water (25 mL) was added and the resulting mixture was extracted with toluene (25 mL). The aqueous layer was discarded and the toluene phase was extracted with 6N aqueous HCl (3 × 10 mL). The combined aqueous phasewas refluxed for 24 h. After that, the reaction mixture was evaporated and the resulting residue was suspended in water. The pHwas adjusted to 6-7 by means of the addition of small portions ofNa2CO3to precipitate the amino acid. The (4-chlorophenyl)glycinewas filtered and dried (2.16 g, 11.62 mmol, 34% yield) and used inthe next step without further purification. Thionyl chloride (1.79 mL, 24.59 mmol) was added dropwiseto an ice-cooled suspension of (4-chlorophenyl)glycine (2.16 g,11.62 mmol) in dry methanol (29 mL). The resulting solution wasstirred at room temperature for 24 h. Then, the solvent was con-centrated under vacuum and the residue was lyophilized to afforda white solid (2.55 g, 10.80 mmol, 93% yield). Mp 196-198C (lit.194-197C [10]);1H NMR (D2O, 400 MHz) (, ppm) 7.54-7.50 (m,2H, C6H4), 7.46-7.41 (m, 2H, C6H4), 5.30 (s, 1H, CH), 3.81 (s, 3H,CH3);13C NMR (D2O, 100 MHz) (, ppm) 169.2 (C), 135.9 (C), 129.7(2 x CH), 129.6 (2 x CH), 129.5 (C), 55.7 (CH3), 53.9 (CH); HRMS (ESI-TOF) calc. for [C9H11ClNO2]+requires 200.0473, found 200.0464.
	With hydrogenchloride; for 6.5h;Heating / reflux;	4-Chlorophenylglycine (225 mg) was dissolved in 10% hydrogen chloride-methanol solution (3 ml) and heated under reflux for 6.5 hours. The reaction liquid was cooled and condensed under reduced pressure. The resulting residue was dried to provide methyl 2-amino-2-(4-chlorophenyl)acetate hydrochloride (282 mg) as a white solid.

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 130 - 137
[2]Patent: WO2008/92874,2008,A1 .Location in patent: Page/Page column 31
[3]Patent: WO2008/92876,2008,A1 .Location in patent: Page/Page column 29
[4]Patent: WO2008/92877,2008,A2 .Location in patent: Page/Page column 30
[5]Patent: WO2008/92879,2008,A1 .Location in patent: Page/Page column 33
[6]Patent: US2008/221185,2008,A1 .Location in patent: Page/Page column 25
[7]Organic Letters,2018,vol. 20,p. 7239 - 7244
[8]Journal of Molecular Catalysis A: Chemical,2017,vol. 426,p. 407 - 418
[9]Patent: EP1595867,2005,A1 .Location in patent: Page/Page column 28

7
[ 6212-33-5 ]
[ 42718-19-4 ]

Yield	Reaction Conditions	Operation in experiment
100%		Description 1 : Methyl amino(4-chlorophenyl)acetateTo ice-chilled methanol (300ml) under argon was carefully added dropwise thionyl chloride (15.44ml; 0.217mol) over 45min. 4-Chlorophenylglycine (26.26g; 0.141 mol) was added, ice cooling removed and the reaction mixture warmed to 400C; the reaction was stirred at 400C for 48h. After cooling to room temperature, the reaction was evaporated under reduced pressure. Re-evaporation from methanol afforded a white solid which was triturated with diethyl ether (ca. 700ml) and then stored at ca. 40C for 64h, filtered, washed with diethyl ether and dried in vacuo to afford the title product as the hydrochloride salt (33.4Og; 100%). 1H NMR (d6-DMSO) delta: 3.72 (3H, s), 5.36 (1 H, s), 7.53 - 7.58 (4H, m), 9.07 (3H, s). Mass Spectrum (Electrospray LC/MS): Found 200 (MH+). C9H1035CINO2 requires 199. Ret. time 1.32 min.
100%		Description 1 : Methyl amino(4-chlorophenyl)acetate hydrochlorideTo ice-chilled methanol (300ml) under argon was carefully added dropwise thionyl chloride (15.44ml; 0.217mol) over 45min. 4-Chlorophenylglycine (26.26g; 0.141 mol) was added, ice cooling removed and the reaction mixture warmed to 400C; the reaction was stirred at 400C for 48h. After cooling to room temperature, the reaction was evaporated under reduced pressure. Re-evaporation from methanol afforded a white solid which was triturated with diethyl ether (ca. 700ml) and then stored at ca. 40C for 64h, filtered, washed with diethyl ether and dried in vacuo to afford the title product as the hydrochloride salt(33.4Og; 100%). 1H NMR (d6-DMSO) delta: 3.72 (3H, s), 5.36 (1 H, s), 7.53 - 7.58 (4H, m), <n="33"/>9.07 (3H, s). Mass Spectrum (Electrospray LC/MS): Found 200 (MH+). C9H10^CINO2 requires 199. Ret. time 1.32 min.

Reference： [1]Patent: WO2007/104776,2007,A1 .Location in patent: Page/Page column 33
[2]Patent: WO2007/116061,2007,A1 .Location in patent: Page/Page column 31-32

8
[ 24424-99-5 ]
[ 6212-33-5 ]
[ 147353-95-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2059 - 2073

9
[ 24424-99-5 ]
[ 6212-33-5 ]
[ 917027-02-2 ]
[ 53994-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(4-Chlorophenyl)glycine With sodium hydroxide In 1,4-dioxane; water for 0.0833333h; Stage #2: di-<i>tert</i>-butyl dicarbonate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 24h;	A Step A. (R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid and (S)-2- ((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid Step A. (R)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid and (S)-2- ((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid To a stirred solution of racemic 2-amino-2-(4-chlorophenyl)acetic acid (20 g, 108 mmol) in dioxane:water (200 mL: 100 mL) at 0 °C was added sodium hydroxide (IN aqueous solution, 100 mL, 100 mmol). The reaction was stirred for 5 minutes and then di-tert-butyl dicarbonate (35 g, 162 mmol) and sodium hydrogen carbonate (9.08 g, 108 mmol) were added in one portion. The reaction was stirred at r.t. for 24 hours. After this time the reaction was evaporated under a vacuum and then acidified to a pH of about 4 with saturated aqueous KHSO4 solution. The separated organic layer was extracted with EtOAc (300 mL), dried over MgSC>4, filtered and the filtrate was evaporated under reduced pressure to give the title compound. Mass Spectrum (ESI) m/z = 229.9 (M- iBu+H).

Reference： [1]Current Patent Assignee: AMGEN INC - WO2013/49250, 2013, A1 Location in patent: Page/Page column 88

10
[ 7099-88-9 ]
[ 6212-33-5 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 245 - 252

11
[ 26830-95-5 ]
[ 6212-33-5 ]
[ 1361458-09-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2862 - 2868

12
[ 2112-22-3 ]
[ 6212-33-5 ]
5,6-dichloro-2-(4-chlorophenyl)quinazolin-4(3H)-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2862 - 2868

13
[ 6575-07-1 ]
[ 6212-33-5 ]
5-chloro-2-(4-chlorophenyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With iron(III) chloride; potassium carbonate In toluene at 120℃; for 16h;

Reference： [1]Kumar, Manoranjan; Richa; Sharma, Sushila; Bhatt, Vinod; Kumar, Neeraj [Advanced Synthesis and Catalysis, 2015, vol. 357, # 13, p. 2862 - 2868]

14
[ 6212-33-5 ]
[ 38469-83-9 ]
[ 860192-88-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2862 - 2868

15
[ 91-02-1 ]
[ 6212-33-5 ]
3-(4-chlorophenyl)-1-phenylimidazo[1,5-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With di-tert-butyl peroxide; iodine In toluene at 120℃; for 12h; Sealed tube;	24 4.3. General procedure for the heterogeneous copper(II)-catalyzedsynthesis of 1,3-disubstituted imidazo[1,5-a]pyridines General procedure: To a 10mL reaction tube were added L-Proline-MCM-41-Cu(OTf)2 (71mg, 0.045mmol), 2-benzoylpyridine 1 (0.3mmol), amino acid 2(0.9mmol), molecular iodine (0.045mmol), DTBP (0.75mmol), and toluene (2mL). The reaction tube was sealed and placed in an oil bath at room temperature. The reaction mixture was stirred at 120 °C for 12 h. After being cooled to room temperature, the reaction mixture was diluted with 15 mL of EtOAc, and filtered. The L-Proline-MCM-41-Cu(OTf)2 complex was washed with EtOAc (25mL) and ethanol (2 5mL), and reused in the next run. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (petroleum ether: EtOAc 15:1-20:1) to provide the desired product 3.
81%	With di-tert-butyl peroxide; iodine; copper(II) bis(trifluoromethanesulfonate) In toluene at 120℃; for 10h; Sealed tube;

Reference： [1]Liao, Yang; Yan, Chenyu; Zhang, Rongli; Cai, Mingzhong [Journal of Organometallic Chemistry, 2019, vol. 881, p. 1 - 12]
[2]Wang, Huiqiao; Xu, Wentao; Xin, Lilan; Liu, Wenmin; Wang, Zhiqiang; Xu, Kun [Journal of Organic Chemistry, 2016, vol. 81, # 9, p. 3681 - 3687]

16
[ 6212-33-5 ]
[ 88-75-5 ]
[ 1141-35-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In toluene at 130℃; for 24h; Schlenk technique; Sealed tube;	7 Embodiment 7 In a clean dry 10 ml Schlenk reaction tube, are sequentially added ortho-nitro phenol 35 mg, the chlorobenzene gly 139 mg, potassium carbonate 69 mg, in order to 1 ml of toluene as a solvent, the reaction tube seal, in 130 °C reaction under 24 hours. After the reaction, the reaction mixture directly by rotating the evaporimeter turns on lathe does, then the volume ratio of 30:1 of petroleum ether and ethyl acetate as the eluant, by separating by silica gel column, to obtain 52 mg white solid, yield 90%.
	Multi-step reaction with 2 steps 1: potassium carbonate / toluene; water / 20 h / 150 °C / Schlenk technique; Inert atmosphere 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / toluene; water / 8 h / 150 °C / Schlenk technique

Reference： [1]Current Patent Assignee: XINYANG NORMAL UNIVERSITY - CN105777662, 2016, A Location in patent: Paragraph 0075; 0076; 0077
[2]Tang, Lin; Yang, Zhen; Sun, Tian; Zhang, Di; Ma, Xiantao; Rao, Weihao; Zhou, Yuqiang [Advanced Synthesis and Catalysis, 2018, vol. 360, # 16, p. 3055 - 3062]

17
[ 6212-33-5 ]
[ 43189-20-4 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2017,vol. 426,p. 407 - 418

18
[ 6212-33-5 ]
[ 3381-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(4-Chlorophenyl)glycine With hydrogen bromide In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0 - 20℃; for 3.5h;	4.1.2.1. 2-Bromo-4-(methylthio)butanoic acid (35c). General procedure: To a solution ofDL-methionine (3.0 g, 20.1 mmol) in H2O (50 mL) was added 30% HBr (20 mL). The reaction mixture was stirred at 0 C for 10 min. A solution of sodium nitrite (1.7 g, 24 mmol) in H2O (50 mL) was added. The reaction mixture was stirred at 0 C for 30 min and thenwarmed to rt for 3 h. The reaction mixture was extracted withEtOAc (100 mL 3). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure to give 3.6 g of intermediate 35c (83% yield).

Reference： [1]Xue, Xiaoqian; Zhang, Yan; Wang, Chao; Zhang, Maofeng; Xiang, Qiuping; Wang, Junjian; Wang, Anhui; Li, Chenchang; Zhang, Cheng; Zou, Lingjiao; Wang, Rui; Wu, Shuang; Lu, Yongzhi; Chen, Hongwu; Ding, Ke; Li, Guohui; Xu, Yong [European Journal of Medicinal Chemistry, 2018, vol. 152, p. 542 - 559]

19
[ 119-33-5 ]
[ 6212-33-5 ]
[ 35875-75-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / toluene; water / 20 h / 150 °C / Schlenk technique; Inert atmosphere 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / toluene; water / 8 h / 150 °C / Schlenk technique

Reference： [1]Tang, Lin; Yang, Zhen; Sun, Tian; Zhang, Di; Ma, Xiantao; Rao, Weihao; Zhou, Yuqiang [Advanced Synthesis and Catalysis, 2018, vol. 360, # 16, p. 3055 - 3062]

20
[ 6212-33-5 ]
[ 122453-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine; trichlorophosphate / 5 h / 65 °C 2.1: 20 °C / Reflux 3.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 4.1: sodium hydroxide / 0.33 h / 20 °C 4.2: 2 h / 60 °C
	Multi-step reaction with 4 steps 1.1: triethylamine; trichlorophosphate / 5 h / 65 °C 2.1: 20 °C / Reflux 3.1: acetic acid; sodium acetate; bromine / 2.17 h / 90 - 110 °C 4.1: trichlorophosphate / toluene / 0.5 h / 97 °C 4.2: 5 h / 97 °C

Reference： [1]Current Patent Assignee: JIANGSU INST PARASITIC DISEASES - CN109006823, 2018, A Current Patent Assignee: JIANGSU INST PARASITIC DISEASES - CN109006824, 2018, A
[2]Current Patent Assignee: JIANGSU INST PARASITIC DISEASES - CN109006823, 2018, A Current Patent Assignee: JIANGSU INST PARASITIC DISEASES - CN109006824, 2018, A

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P270	Do not eat, drink or smoke when using this product.
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P281	Use personal protective equipment as required.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P320
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P321
P322
P330	Rinse mouth.
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
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P501	Dispose of contents/container to ...
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Physical hazards
Code	Phrase
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
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
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
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
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. 6212-33-5 ] {[proInfo.proName]}

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Medicinal Chemistry

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[ 6212-33-5 ] Synthesis Path-Upstream 1~16

[ 6212-33-5 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 6212-33-5 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

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Physical hazards

Health hazards

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[ 6212-33-5 ]