[ CAS No. 69605-90-9 ] {[proInfo.proName]}

Name: 69605-90-9|[1,1'-Biphenyl]-3-ylmethanol|98%
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SKU: A198425
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Quality Control of [ 69605-90-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 69605-90-9 ]

CAS No. :	69605-90-9	MDL No. :	MFCD08703631
Formula :	C₁₃H₁₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WGUZZTGZDPJWSG-UHFFFAOYSA-N
M.W :	184.23	Pubchem ID :	603556
Synonyms :

Calculated chemistry of [ 69605-90-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	58.01
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.34
Log Po/w (XLOGP3) :	3.32
Log Po/w (WLOGP) :	2.69
Log Po/w (MLOGP) :	3.08
Log Po/w (SILICOS-IT) :	3.42
Consensus Log Po/w :	2.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.58
Solubility :	0.0489 mg/ml ; 0.000265 mol/l
Class :	Soluble
Log S (Ali) :	-3.42
Solubility :	0.0699 mg/ml ; 0.000379 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.74
Solubility :	0.00332 mg/ml ; 0.000018 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.57

Safety of [ 69605-90-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 69605-90-9 ]

* 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 [ 69605-90-9 ]
Downstream synthetic route of [ 69605-90-9 ]

[ 69605-90-9 ] Synthesis Path-Upstream 1~2

1
[ 69605-90-9 ]
[ 14704-31-5 ]

Reference： [1] Patent: US5521192, 1996, A,

2
[ 69605-90-9 ]
[ 7789-60-8 ]
[ 14704-31-5 ]

Reference： [1] Patent: US6489487, 2002, B1,

[ 69605-90-9 ] Synthesis Path-Downstream 1~85

1
[ 716-76-7 ]
[ 69605-90-9 ]

Yield	Reaction Conditions	Operation in experiment
95%		Biphenyl-3-carboxylic acid (217.0 mg, 1.09 mmol) in THF was added to LiAlH4 (1.0 M in THF) (1.64 ml) at 00C under N2 during 15 min. The mixture was then stirred at r.t. for 2.5 h. H2O was carefully added to the mixture at 00C. NaOH (1.0 M) was added. The product was extracted wit EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated yielding the title compound as a yellow oil (95%).1H NMR (CD3OD) delta 7.61-7.59 (m, 3H), 7.52-7.49 (m, IH), 7.45-7.38 (m, 3H), 7.35-7.30 (m, 2H), 4.67 (s, 2H).
95%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2.75h;Inert atmosphere;	Biphenyl-3-ylmethanol Biphenyl-3-carboxylic acid (217.0 mg, 1.09 mmol) in THF was added to LiAlH4 (1.0 M in THF) (1.64 ml) at 0 C. under N2 during 15 min. The mixture was then stirred at r.t. for 2.5 h. H2O was carefully added to the mixture at 0 C. NaOH (1.0 M) was added. The product was extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated yielding the title compound as a yellow oil (95%). 1H NMR (CD3OD) delta 7.61-7.59 (m, 3H), 7.52-7.49 (m, 1H), 7.45-7.38 (m, 3H), 7.35-7.30 (m, 2H), 4.67 (s, 2H).
		EXAMPLE III STR20 To a suspension of 100 mg of lithium aluminum hydride in 20 mL of ether was added 500 mg 3-phenylbenzoic acid. The reaction mixture was stirred at room temperature overnight. After any excess lithium aluminum hydride was destroyed with water, the organic layer was washed successively with 25 mL aliquots of dilute hydrochloric acid, dilute sodium hydroxide and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent removed by evaporation under reduced pressure to yield 360 mg of 3-hydroxymethylbiphenyl as a crystalline solid.

Reference： [1]Patent: WO2010/97410,2010,A1 .Location in patent: Page/Page column 135
[2]Patent: US2012/40942,2012,A1 .Location in patent: Page/Page column 63-64
[3]Medicinal Chemistry Research,1996,vol. 6,p. 69 - 80
[4]ChemMedChem,2015,vol. 10,p. 380 - 395
[5]Bulletin of the Chemical Society of Japan,1959,vol. 32,p. 955,958
[6]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7288 - 7300
[7]Patent: US5594141,1997,A

2
[ 2567-29-5 ]
[ 69605-90-9 ]

Reference： [1]Annales de Chimie (Cachan, France),1888,vol. <6> 15,p. 242
Bulletin de la Societe Chimique de France,1888,vol. <2> 49,p. 98

3
[ 2928-43-0 ]
[ 69605-90-9 ]

Reference： [1]Journal of the American Chemical Society,1991,vol. 113,p. 7676 - 7684
[2]Journal of the American Chemical Society,1989,vol. 111,p. 4887 - 4895

4
[ 69605-90-9 ]
[ 1204-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	With iodosylbenzene; In acetonitrile; at 60℃; for 2h;	General procedure: Oxidation of alcohols was typically carried out as follows: a suspension with 5 mg of the synthesized catalyst in acetonitrile (2 mL) was magnetically stirred, and the substrate namely alcohols (0.1 mmol) and PhIO (2.5 equiv.) was then added. The resulting mixture was kept at 60 C with magnetical stirring for a set time. The selectivity and conversion were determined by GC analysis.

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1204 - 1208
[2]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7288 - 7300
[3]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 4839 - 4853
[4]Catalysis Communications,2015,vol. 65,p. 34 - 40

5
[ 1016160-90-9 ]
[ 69605-90-9 ]

Reference： [1]Journal of the American Chemical Society,1984,vol. 106,p. 4987 - 5000

6
[ 103668-94-6 ]
[ 69605-90-9 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3878 - 3881

7
[ 82804-36-2 ]
[ 69605-90-9 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1204 - 1208

8
[ 208941-39-3 ]
[ 98-80-6 ]
[ 69605-90-9 ]

Reference： [1]Synlett,1998,p. 671 - 675

9
[ 69605-90-9 ]
[ 38580-82-4 ]

Yield	Reaction Conditions	Operation in experiment
	In thionyl chloride;	A solution of 50 mg of <strong>[69605-90-9]3-hydroxymethylbiphenyl</strong> in 1.5 mL thionyl chloride was heated at reflux temperature for 4 hr, cooled to room temperature and the solvent removed by evaporation under reduced pressure to yield 45 mg of 3-chloromethylbiphenyl which was used in the next step without further purification or characterization.

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 293 - 306
[2]Medicinal Chemistry Research,1996,vol. 6,p. 69 - 80
[3]Patent: US5594141,1997,A
[4]Advanced synthesis and catalysis,2012,vol. 354,p. 2465 - 2472,8
[5]Chemical Communications,2014,vol. 50,p. 11060 - 11062

11
[ 69605-90-9 ]
[ 545-06-2 ]
2,2,2-trichloro-acetimidic acid biphenyl-3-ylmethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587

12
[ 19926-50-2 ]
[ 69605-90-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 293 - 306

13
[ 69605-90-9 ]
C₆H₁₀N₂(CH₂C₆H₄C₆H₅)2 [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 293 - 306

14
[ 69605-90-9 ]
(1R,2R,3R,5R,6R)-2-Amino-3-(biphenyl-3-ylmethoxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587

15
[ 69605-90-9 ]
(1R,2R,3R,5R,6R)-2-Amino-3-(biphenyl-3-ylmethoxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587

16
[ 69605-90-9 ]
(1R,2R,3R,5R,6R)-2-Azido-3-(biphenyl-3-ylmethoxy)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4570 - 4587

17
[ 69605-90-9 ]
N-benzyl-N-methyl-(3-phenyl)benzylamine [ No CAS ]