[ CAS No. 67336-19-0 ] {[proInfo.proName]}

Name: 67336-19-0|H-Phg(4-Cl)-OH|98%
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SKU: A161500
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Quality Control of [ 67336-19-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 67336-19-0 ]

SDS Specification

Alternatived Products of [ 67336-19-0 ]

Product Details of [ 67336-19-0 ]

CAS No. :	67336-19-0	MDL No. :	MFCD03701467
Formula :	C₈H₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QGJGBYXRJVIYGA-ZETCQYMHSA-N
M.W :	185.61	Pubchem ID :	738019
Synonyms :	H-Phg(4-Cl)-OH;L-4-Chlorophenylglycine

Calculated chemistry of [ 67336-19-0 ]

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 [ 67336-19-0 ]

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

Application In Synthesis of [ 67336-19-0 ]

* 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 [ 67336-19-0 ]
Downstream synthetic route of [ 67336-19-0 ]

[ 67336-19-0 ] Synthesis Path-Upstream 1~17

1
[ 56464-72-3 ]
[ 67336-19-0 ]

Reference： [1] Tetrahedron Letters, 2001, vol. 42, # 39, p. 6925 - 6927
[2] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6542 - 6545

2
[ 144744-27-4 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6914 - 6920

3
[ 126402-96-8 ]
[ 67336-19-0 ]

Reference： [1] Synthesis, 1991, # 11, p. 1039 - 1042

4
[ 86169-29-1 ]
[ 67336-19-0 ]

Reference： [1] Chemistry - A European Journal, 1998, vol. 4, # 5, p. 935 - 941

5
[ 104-88-1 ]
[ 67336-19-0 ]

Reference： [1] Organic Preparations and Procedures International, 2005, vol. 37, # 1, p. 65 - 73
[2] Tetrahedron Letters, 1989, vol. 30, # 31, p. 4109 - 4110

6
[ 856214-68-1 ]
[ 67336-19-0 ]

Reference： [1] Organic Preparations and Procedures International, 2005, vol. 37, # 1, p. 65 - 73

7
[ 92303-74-7 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332

8
[ 126402-92-4 ]
[ 67336-19-0 ]

Reference： [1] Synthesis, 1991, # 11, p. 1039 - 1042
[2] Tetrahedron Letters, 1989, vol. 30, # 31, p. 4109 - 4110

9
[ 102333-75-5 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332

10
[ 104-88-1 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332

11
[ 67-66-3 ]
[ 104-88-1 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Synthetic Communications, 1988, vol. 18, # 14, p. 1685 - 1690

12
[ 144744-27-4 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6914 - 6920

13
[ 92303-74-7 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332

14
[ 102333-75-5 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332

15
[ 104-88-1 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332

16
[ 67-66-3 ]
[ 104-88-1 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1] Synthetic Communications, 1988, vol. 18, # 14, p. 1685 - 1690

17
[ 67336-19-0 ]
[ 191109-51-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: With borane-THF In tetrahydrofuran at 0 - 20℃; for 4.16667 h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 65℃; for 18 h;	To a solution of (iS)-2-amino-2-(4-chlorophenyl)acetic acid (10.0 g, 53.9 mmol) in THF (216 mL) was added 1.0 M borane tetrahydrofuran complex (216 mL, 216 mmol) via addition funnel over 45 min at 0 ⁰C. The ice-bath was removed and the reaction mixture was stirred for 3.25 h at room temperature. Water (6.79 mL, 377 mmol) was added followed by sodium hydroxide solution (40.4 mL, 202 mmol) (dropwise over 15 min). The reaction was heated to 65 ⁰C and stirred for 18 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (500 mL) and the organic phase was separated and washed with <n="56"/>water (200 mL). The aqueous phase was further extracted with DCM (2 x 250 mL). The organics were combined, dried over Na₂SO₄, and concentrated under reduced pressure to afford the title compound as a white solid (8.55 g, 92percent yield). Exact mass calculated for C₈H₁₀ClNO: 171.1, Found: LCMS m/z (percent) = 172.2 ([M+H]⁺, ³⁵Cl, 100), 174.2 ([M+H]⁺, ³⁷Cl, 33). ¹H NMR (400 MHz, Methanol-*/,) δ ppm 3.47 - 3.57 (m, 1 H), 3.59 - 3.69 (m, 1 H), 3.93 (dd, J= 7.58, 5.05 Hz, 1 H), 7.23 - 7.42 (m, 4 H).

Reference： [1] Patent: WO2009/58300, 2009, A1, . Location in patent: Page/Page column 53-54

[ 67336-19-0 ] Synthesis Path-Downstream 1~26

1
[ 67-66-3 ]
[ 104-88-1 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 1685 - 1690

2
C₁₂H₁₇ClN₂O*H⁽¹⁺⁾ [ No CAS ]
[ 67336-19-0 ]

Reference： [1]Tetrahedron Letters,1989,vol. 30,p. 4109 - 4110

3
[ 126402-96-8 ]
[ 67336-19-0 ]

Reference： [1]Synthesis,1991,p. 1039 - 1042

4
[ 144744-27-4 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6914 - 6920

5
[ 86169-29-1 ]
[ 67336-19-0 ]

Reference： [1]Chemistry - A European Journal,1998,vol. 4,p. 935 - 941

6
[ 56464-72-3 ]
[ 67336-19-0 ]
D-(-)-4-chlorophenylglycine amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6925 - 6927
[2]Journal of Organic Chemistry,2002,vol. 67,p. 6542 - 6545

7
4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)phenylglycinonitrile [ No CAS ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1]Organic Preparations and Procedures International,2005,vol. 37,p. 65 - 73

8
[ 104-88-1 ]
[ 67336-19-0 ]

Reference： [1]Organic Preparations and Procedures International,2005,vol. 37,p. 65 - 73
[2]Tetrahedron Letters,1989,vol. 30,p. 4109 - 4110

9
[ 856214-68-1 ]
[ 67336-19-0 ]

Reference： [1]Organic Preparations and Procedures International,2005,vol. 37,p. 65 - 73

10
[ 104-88-1 ]
resin-bound p-methylphenylboronic acid [ No CAS ]
[ 67336-19-0 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 6925 - 6927

11
[ 104-88-1 ]
benzoquinone-(1.4)-bis-<2.5-diamino-anil> [ No CAS ]
[ 67336-19-0 ]

Reference： [1]Chemistry - A European Journal,1998,vol. 4,p. 935 - 941

12
[ 126402-92-4 ]
[ 67336-19-0 ]

Reference： [1]Synthesis,1991,p. 1039 - 1042
[2]Tetrahedron Letters,1989,vol. 30,p. 4109 - 4110

13
[ 67336-19-0 ]
[ 191109-51-0 ]

Yield	Reaction Conditions	Operation in experiment
92%		To a solution of (iS)-2-amino-2-(4-chlorophenyl)acetic acid (10.0 g, 53.9 mmol) in THF (216 mL) was added 1.0 M borane tetrahydrofuran complex (216 mL, 216 mmol) via addition funnel over 45 min at 0 0C. The ice-bath was removed and the reaction mixture was stirred for 3.25 h at room temperature. Water (6.79 mL, 377 mmol) was added followed by sodium hydroxide solution (40.4 mL, 202 mmol) (dropwise over 15 min). The reaction was heated to 65 0C and stirred for 18 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (500 mL) and the organic phase was separated and washed with <n="56"/>water (200 mL). The aqueous phase was further extracted with DCM (2 x 250 mL). The organics were combined, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a white solid (8.55 g, 92% yield). Exact mass calculated for C8H10ClNO: 171.1, Found: LCMS m/z (%) = 172.2 ([M+H]+, 35Cl, 100), 174.2 ([M+H]+, 37Cl, 33). 1H NMR (400 MHz, Methanol-*/,) delta ppm 3.47 - 3.57 (m, 1 H), 3.59 - 3.69 (m, 1 H), 3.93 (dd, J= 7.58, 5.05 Hz, 1 H), 7.23 - 7.42 (m, 4 H).

Reference： [1]Patent: WO2009/58300,2009,A1 .Location in patent: Page/Page column 53-54
[2]Journal of the American Chemical Society,2019,vol. 141,p. 5135 - 5138

14
[ 102333-75-5 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3327 - 3332

15
[ 104-88-1 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3327 - 3332

16
[ 92303-74-7 ]
[ 67336-19-0 ]
[ 43189-37-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3327 - 3332
[2]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3327 - 3332

17
[ 67336-19-0 ]
[ 1391628-35-5 ]