76350-90-8|(2-Methyl-[1,1'-biphenyl]-3-yl)methanol| Ambeed

Structure of 76350-90-8

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Quality Control of [ 76350-90-8 ] Purity: 97% SDS Specification

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Product Details of [ 76350-90-8 ]

CAS No. :	76350-90-8
Formula :	C₁₄H₁₄O
M.W :	198.26
SMILES Code :	OCC1=C(C)C(C2=CC=CC=C2)=CC=C1
MDL No. :	MFCD00134200
Boiling Point :	No data available
InChI Key :	BGTLHJPGBIVQLJ-UHFFFAOYSA-N
Pubchem ID :	596875

Safety of [ 76350-90-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 76350-90-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	12
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	62.97
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.49
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.0
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.34
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.15

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.44
Solubility	0.0723 mg/ml ; 0.000365 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.12
Solubility	0.15 mg/ml ; 0.000758 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.13
Solubility	0.00145 mg/ml ; 0.00000733 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.36 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.8

Application In Synthesis of [ 76350-90-8 ]

* 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.

Downstream synthetic route of [ 76350-90-8 ]

[ 76350-90-8 ] Synthesis Path-Downstream 1~42

1
[ 4489-12-7 ]
[ 76350-90-8 ]
[ 107686-57-7 ]

References: [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 4385 - 4394.

2
[ 76350-90-8 ]
5,7,7-Trichloro-8,8,8-trifluoro-4,4-dimethyl-2-oxo-octanenitrile [ No CAS ]
2-methyl-3-phenylbenzyl 3,3-dimethyl-4,6,6-trichloro-7,7,7-trifluoroheptanoate [ No CAS ]

References: [1]Chemistry Letters,1994,p. 703 - 706.

3
[ 76350-90-8 ]
3-(2,2-dichloro-3,3,3-trifluoropropyl)-2,2-dimethyl-1-(cyanohydroxymethyl)cyclopropane [ No CAS ]
2-methyl-3-phenylbenzyl trans-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate [ No CAS ]
2-methyl-3-phenylbenzyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate [ No CAS ]

References: [1]Chemistry Letters,1994,p. 703 - 706.

4
Bifenthrin [ No CAS ]
[ 76350-90-8 ]
[ 76023-99-9 ]

References: [1]Pesticide Science,1995,vol. 44,p. 269 - 276.

5
[ 75-77-4 ]
[ 76350-90-8 ]
[ 909792-54-7 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 3802 - 3803.

6
C₁₄H₁₂OLi^(1-)*Li⁽¹⁺⁾ [ No CAS ]
[ 76350-90-8 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 3379 - 3383.

7
4-bromo-1,3-dihydroisobenzofuran [ No CAS ]
[ 76350-90-8 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 3379 - 3383.

8
[ 576-23-8 ]
[ 76350-90-8 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 3379 - 3383.

9
[ 127168-82-5 ]
[ 76350-90-8 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 3379 - 3383.

10
[ 502483-86-5 ]
[ 76350-90-8 ]

References: [1]Tetrahedron,2008,vol. 64,p. 4275 - 4286.
[2]Tetrahedron Letters,2007,vol. 48,p. 3379 - 3383.

11
[ 76350-90-8 ]
[ 935740-92-4 ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 3802 - 3803.

12
[ 76350-90-8 ]
methyl 5-phenyl-1,2,3,4-tetrahydronaphthalene-2-carboxylate [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 3802 - 3803.

13
[ 76350-90-8 ]
trans-(2-methyl-3-phenylphenyl)methyl 3-formyl-2,2-dimethylcyclopropanecarboxylate [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 4385 - 4394.

14
[ 76350-90-8 ]
cis-(2-methyl-3-phenylphenyl)methyl 3-formyl-2,2-dimethylcyclopropanecarboxylate [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 4385 - 4394.

15
[ 76350-90-8 ]
bifenthrin [ No CAS ]

References: [1]Chemistry Letters,1994,p. 703 - 706.

16
[ 76350-90-8 ]
[ 4445-49-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; cetyltrimethylammonim bromide; In water; at 0 - 70℃; for 64h;	15 g of 2-methyl-3-biphenylmethanol and 75 mg cetyltrimethylammonium bromide were added to 150 ml of water, and the resultant mixture was cooled to 0 C. in an ice bath. 48 g of potassium permanganate was added to the cold mixture and reaction was stirred at 0 C. for 10 min., at room temperature for 16 h, then at 70 C. for 48 h. The clear solution containing black solid was filtered through a pad of celite, and washed with 100 ml of dichloromethane. The aqueous solution was then acidified to pH 3 with 6 N aqueous hydrochloric acid and extracted four times with 150 ml portions of ethyl acetate. The combined organic fractions were dried over anhydrous sodium sulfate, and concentrated to 12.9 g of product; 1H NMR (d6-DMSO): delta=7.28-7.46 (m, 5 H), 7.51-7.61 (m, 2 H), 7.84-7.89 (dd, 1H), 13.0 (s, 2H).

References: [1]Patent: US2004/254215,2004,A1 .Location in patent: Page 61-62.

Yield	Reaction Conditions	Operation in experiment
		Examples of the substituted or unsubstituted aralkyl alcohol include; benzyl alcohol, 2-methyl-3 -phenylbenzyl alcohol, 2,3,4,5,6-pentafluorobenzyl alcohol, 2,3,5,6-tetrafluoro-4-(methoxyinthyl)benzyl alcohol, 2,3,5,6-tetrafluoro-4-methoxybenzyl alcohol, 2,3,5,6-tetrafluoro-4-chlorobenzyl alcohol, 2,3,5,6-tetrafluoro-4-bromobenzyl alcohol, 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl alcohol, 2,3,5,6-tetrafluoro-4-difluoromethylbenzyl alcohol, 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol, ...
		Specific insecticidally useful compounds according to the invention include the esters derived from each of: ... 4-fluoro-3-phenoxybenzyl alcohol alpha-cyano-4-fluoro-3-phenoxybenzyl alcohol 5-benzyl-3-furylmethanol 2-allyl-3-methyl-4-hydroxycyclopent-2-enone 2-methyl-3-phenylbenzyl alcohol
		Method G 2-Methyl[1,1'-biphenyl]-3-methanol was prepared as follows: To 100 ml of stirred 50% aqueous ethanol was added 2-methyl-3-nitrobenzyl alcohol (41.8 g, 0.25 mole) and 85.0 grams of iron powder. The mixture was brought to reflux, and 5.2 ml of concentrated hydrochloric acid was slowly added. Upon complete addition, the reaction mixture was stirred under reflux for 2 hours. The reaction mixture was then made just basic with ethanolic 15% potassium hydroxide. The hot mixture was filtered through diactomaceous earth to remove the iron. The filter cake was washed with ethanol. The filtrate was acidified with hydrogen chloride, then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure. Hexane was added to the residue, and the water-hexane azeotrope was removed by distillation. The addition of hexane and the subsequent removal of the water-hexane azeotrope by distillation was repeated three times. The 3-hydroxymethyl-2-methylaniline hydrochloride residue thus obtained was used as follows. A stirred solution of 3-hydroxymethyl-2-methylaniline hydrochloride (43.4 g, 0.25 mole) and 17.2 ml of concentrated sulfuric acid in ice-water was cooled to 0, and a solution of sodium nitrite (17.3 g, 0.25 mole) in water was added dropwise. Upon complete addition, the reaction mixture was stirred for an additional 0.5 hour, then an additional 8 ml of concentrated sulfuric acid was added dropwise. With the temperature maintained at 0, a solution of potassium iodide (49.8 g, 0.30 mole) in water was added dropwise to the reaction mixture, followed by the addition of 0.1 gram of copper powder. The reaction mixture was slowly warmed to 70 where it stirred for 1 hour. The reaction mixture was then allowed to stand for 18 hours while cooling to room temperature. The reaction mixture was then taken up in water and extracted with chloroform. The chloroform extract was washed with an aqueous saturated solution of sodium bisulfite, then with water. The chloroform layer was dried and filtered. The filtrate was evaporated under reduced pressure to give 3-iodo-2-methylbenzyl alcohol (15.2 g) as a dark solid. In a photoreactor was placed 3-iodo-2-methylbenzyl alcohol (5.0 g, 0.02 mole) and 800 ml of benzene. To this was added sodium thiosulfate (5.0 g, 0.04 mole) in 15 ml of water. The mixture was purged with argon for 30 minutes, then irradiated with a 200 watt medium pressure ultraviolet lamp for 36.5 hours. The reaction mixture was then transferred to a separatory funnel. The photoreactor was washed with approximately 20 ml each of water, chloroform, and acetone. These washes were added to the separatory funnel. The organic layer was washed with aqueous 0.5 M sodium thiosulfate, then with an aqueous solution saturated with sodium chloride. The organic layer was then dried and filtered. The filtrate was evaporated under reduced pressure to an oily residue. The residue was purified by column chromatography on silica gel, elution with 1:1 hexane:chloroform, to give 2-methyl[1,1'-biphenyl]-3-methanol (2.4 g). The nmr and ir spectra were consistent with that expected for the named compound.

		Method G 2-Methyl[1,1'-biphenyl]-3-methanol was prepared as follows: To 100 ml of stirred 50% aqueous ethanol was added 2-methyl-3-nitrobenzyl alcohol (41.8 g, 0.25 mole) and 85.0 grams of iron powder. The mixture was brought to reflux, and 5.2 ml of concentrated hydrochloric acid was slowly added. Upon complete addition, the reaction mixture was stirred under reflux for 2 hours. The reaction mixture was then made just basic with ethanolic 15% potassium hydroxide. The hot mixture was filtered through diatomaceous earth to remove the iron. The filter cake was washed with ethanol. The filtrate was acidified with hydrogen chloride, then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure. Hexane was added to the residue, and the water-hexane azeotrope was removed by distillation. The addition of hexane and the subsequent removal of the water-hexane azeotrope by distillation was repeated three times. The 3-hydroxymethyl-2-methylaniline hydrochloride residue thus obtained was used as follows. A stirred solution of 3-hydroxymethyl-2-methylaniline hydrochloride (43.4 g, 0.25 mole) and 17.2 ml of concentrated sulfuric acid in ice-water was cooled to 0, and a solution of sodium nitrate (17.3 g, 0.25 mole) in water was added dropwise. Upon complete addition, the reaction mixture was stirred for an additional 0.5 hour, then an additional 8 ml of concentrated sulfuric acid was added dropwise. With the temperature maintained at 0, a solution of potassium iodide (49.8 g, 0.30 mole) in water was added dropwise to the reaction mixture, followed by the addition of 0.1 gram of copper powder. The reaction mixture was slowly warmed to 70 where it stirred for 1 hour. The reaction mixture was then allowed to stand for 18 hours while cooling to room temperature. The reaction mixture was then taken up in water and extracted with chloroform. The chloroform extract was washed with an aqueous saturated solution of sodium bisulfite, then with water. The chloroform layer was dried and filtered. The filtrate was evaporated under reduced pressure to give 3-iodo-2-methylbenzyl alcohol (15.2 g) as a dark solid. In a photoreactor was placed 3-iodo-2-methylbenzyl alcohol (5.0 g, 0.02 mole) and 800 ml of benzene. To this was added sodium thiosulfate (5.0 g, 0.04 mole) in 15 ml of water. The mixture was purged with argon for 30 minutes, then irradiated with a 200 watt medium pressure ultraviolet lamp for 36.5 hours. The reaction mixture was then transferred to a separatory funnel. The photoreactor was washed with approximately 20 ml each of water, chloroform, and acetone. These washes were added to the separatory funnel. The organic layer was washed with aqueous 0.5 M sodium thiosulfate, then with an aqueous solution saturated with sodium chloride. The organic layer was then dried and filtered. The filtrate was evaporated under reduced pressure to an oily residue. The residue was purified by column chromatography on silica gel, elution with 1:1 hexane:chloroform, to give 2-methyl[1,1'-biphenyl]-3-methanol (2.4 g). The nmr and ir spectra were consistent with that expected for the named compound.
		Method G 2-Methyl[1,1'-biphenyl]-3-methanol was prepared as follows: To 100 ml of stirred 50% aqueous ethanol was added 2-methyl-3-nitrobenzyl alcohol (41.8 g, 0.25 mole) and 85.0 grams of iron powder. The mixture was brought to reflux, and 5.2 ml of concentrated hydrochloric acid was slowly added. Upon complete addition, the reaction mixture was stirred under reflux for 2 hours. The reaction mixture was then made just basic with ethanolic 15% potassium hydroxide. The hot mixture was filtered through diatomaceous earth to remove the iron. The filter cake was washed with ethanol. The filtrate was acidified with hydrogen chloride, then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure. Hexane was added to the residue, and the water-hexane azeotrope was removed by distillation. The addition of hexane and the subsequent removal of the water-hexane azeotrope by distillation was repeated three times. The 3-hydroxymethyl-2-methylaniline hydrochloride residue thus obtained was used as follows. A stirred solution of 3-hydroxymethyl-2-methylaniline hydrochloride (43.4 g, 0.25 mole) and 17.2 ml of concentrated sulfuric acid in ice-water was cooled to 0, and a solution of sodium nitrite (17.3 g, 0.25 mole) in water was added dropwise. Upon complete addition, the reaction mixture was stirred for an additional 0.5 hour, then an additional 8 ml of concentrated sulfuric acid was added dropwise. With the temperature maintained at 0, a solution of potassium iodide (49.8 g, 0.30 mole) in water was added dropwise to the reaction mixture, followed by the addition of 0.1 gram of copper powder. The reaction mixture was slowly warmed to 70 where it stirred for 1 hour. The reaction mixture was then allowed to stand for 18 hours while cooling to room temperature. The reaction mixture was then taken up in water and extracted with chloroform. The chloroform extract was washed with an aqueous saturated solution of sodium bisulfite, then with water. The chloroform layer was dried and filtered. The filtrate was evaporated under reduced pressure to give 3iodo-2-methylbenzyl alcohol (15.2 g) as a dark solid. In a photoreactor was placed 3-iodo-2-methylbenzyl alcohol (5.0 g, 0.02 mole) and 800 ml of benzene. To this was added sodium thiosulfate (5.0 g, 0.04 mole) in 15 ml of water. The mixture was purged with argon for 30 minutes, then irradiated with a 200 watt medium pressure ultraviolet lamp for 36.5 hours. The reaction mixture was then transferred to a separatory funnel. The photoreactor was washed with approximately 20 ml each of water, chloroform, and acetone. These washes were added to the separatory funnel. The organic layer was washed with aqueous 0.5 M sodium thiosulfate, then with an aqueous solution saturated with sodium chloride. The organic layer was then dried and filtered. The filtrate was evaporated under reduced pressure to an oily residue. The residue was purified by column chromatography on silica gel, elution with 1:1 hexane:chloroform, to give 2-methyl[1,1'-biphenyl]-3-methanol (2.4 g).

18
[ 60310-81-8 ]
[ 76350-90-8 ]
(2-methyl[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 3 By the method of Example 2, (2-methyl[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate (Compound 3) was prepared from trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride and 2-methyl-[1,1'-biphenyl]-3-methanol; yield 0.98 g as an oil. NMR (CDCl3, ppm): 1.15(s,3H); 1.27(s,3H); 1.53(d,J=5 Hz,1H); 1.93-2.18(m,1H); 2.22(s,3H); 4.02(ddd,J=3,8, 25 Hz,1H); 5.22(s,2H), 7.20-7.45(m,8H).

References: [1]Patent: US4552892,1985,A .

19
(1R)-trans-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride [ No CAS ]
[ 76350-90-8 ]
(2-methyl-[1,1'-biphenyl]-3-yl)-methyl 1R-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydrogenchloride; In toluene;	(c) Synthesis of (2-methyl-[1,1'-biphenyl]-3-yl)methyl 1R-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate To a stirred mixture of 0.8 gram (0.004 mole) of (2-methyl-[1,1'-biphenyl]-3-methanol and 0.3 ml of pyridine was added 1.0 gram (0.004 mole) of 1R-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride in 25 ml of toluene. A solid precipitate formed immediately. The reaction mixture was stirred at ambient temperature for 16 hours, then poured into 50 ml of 2 N hydrochloric acid. The mixture was shaken and the organic layer separated. The organic layer was washed with one portion of 25 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was placed on a column of 100 grams of silica gel. Elution was accomplished with toluene. The appropriate fraction was concentrated under reduced pressure to give 1.11 grams of (2-methyl-[1,1'-biphenyl]-3-yl)methyl 1R-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. Gas chromatographic analysis indicated >98% purity. The ir spectrum was consistent with the proposed structure. nmr (CCl4): 1.32 (6H,2), 2.12 (2H,m), 2.21 (3H,s), 5.17 (2H,s), 6.95 (1H,d).

References: [1]Patent: US4395567,1983,A .

20
[ 76350-90-8 ]
[ 115363-11-6 ]

Yield	Reaction Conditions	Operation in experiment
28 g	With Jones reagent; In acetone; at 25℃; for 6h;	Pour 40 g of CrO3 into a volumetric flask containing 120 mL of water, add 34.5 mL of concentrated H2SO4, shake well, and dilute to 150 mL with water to obtain Jones reagent.30 g of <strong>[76350-90-8]2-methyl-3-phenylbenzyl alcohol</strong> were added to the three-necked flask,32mL water, 200mL acetone, ice water bath, drop 90mL Jones reagent, control reaction temperature is 25 C, reaction 6 h,The reaction was followed by thin layer chromatography, and dichloromethane was used as a developing solvent. After the substrate point disappeared and the aldehyde point disappeared, the reaction was stopped, and the reaction took 6 h.The acetone was removed under reduced pressure, a large amount of precipitate was produced, suction filtration, and the filter cake was washed with water to whiteness, and dried to obtain a crude product of 30 g yield 99%.The crude product was dissolved in ethanol (the amount of ethanol was twice the mass of the product) and heated at 60 C.All were dissolved, filtered, and the filtrate was cooled to -10 C under electric stirring, and then the crystals were suction filtered, dried to obtain 28 g, and the melting point was measured at a melting point of 151-153 C.

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 12904 - 12905.
[2]Patent: CN108947866,2018,A .Location in patent: Paragraph 0009.

21
[ 999-97-3 ]
[ 76350-90-8 ]
[ 1316808-61-3 ]

References: [1]Applied Organometallic Chemistry,2011,vol. 25,p. 608 - 615.

22
bifenthrin [ No CAS ]
[ 74609-46-4 ]
[ 76350-90-8 ]

References: [1]Journal of Molecular Catalysis B: Enzymatic,2013,vol. 97,p. 225 - 232.

23
[ 83647-43-2 ]
[ 98-80-6 ]
[ 76350-90-8 ]

Yield	Reaction Conditions	Operation in experiment
74.62%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 12h;Inert atmosphere;	To a solution of 20.00 g (99.47 mmol, 1.0 eq) of (3-bromo-2-methyl-phenyl)methanol 1A and 24.26 g (198.94 mmol, 2.0 eq) of phenylboronic acid in 156 mL of toluene and 52mL of EtOH, were added 812.3 mg (0.995 mmol, 0.01 eq) of Pd(dppf)Cl2.CH2Cl2 and 25.07g (2 M, 149.21 mL, 3.0 eq) of NaHCC under nitrogen gas. The mixture was stirred at 80C for 12 hours. The mixture was separated, and the aqueous phase was extracted with 2 x 400 mL of ethyl acetate (EtOAc). The combined organic phase was washed with 2 x 200 mL of brine, dried over Na2SC>4, filtered and the solvent was concentrated. The residue was purified by column eluted with petroleum ether/ethyl acetate = 25/1-10/1 to give crude product (25 g) as a yellow solid. The solid was smashed in 100 mL of petroleum ether, and the suspension was filtered to give 15.00 g (74.62%) of (2-methyl-[l,l'-biphenyl]-3-yl)methanol as a white solid. lH NMR (400 MHz, CDC13): delta 7.40-7.31 (m, 4H) 7.25-7.22 (m, 3H) 4.75-4.74 (m, 2H) 2.21 (m, 3H) 1.62~1.59(m, 1H).
73%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; water; toluene; at 80℃; for 12h;Inert atmosphere; Sealed tube;	To a stirred solution of (3-bromo-2-methylphenyl)methanol (4, 1 g, 5 mmol), phenyl boronic acid (5, 1.4 g, 10 mmol) in toulene (12 mL) and EtOH (4 mL) were added PdCl2(dppf).DCM (0.04 g, 0.05 mmol) and 2M aqueous NaHC03 solution (4 mL), the reaction mixture was degasified with nitrogen gas for 10 min. The reaction mixture was then heated in a seal tube at 80 C for 12 h. The reaction mixture was filtered through celite; the filtrate was diluted with water and extracted with ethyl acetate (2 x 100 mL). The organic layer was then dried over sodium sulfate, evaporated and the crude was purified on combiflash MPLC using 20% ethyl acetate in hexanes as eluent to afford (2-methyl-[l, l'-biphenyl]-3-yl)methanol as off-white solid (6, Yield: 0.81 g, 73%). LCMS (ES) m/z = 199.1 [M+H]+
68.9%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;Inert atmosphere;	The compound I-1C (2 g, 10 mmol) obtained in the previous step was dissolved in dioxane (30 ml).Add 2N aqueous potassium carbonate solution (10 ml),Then, phenylboric acid (1.46 g, 12 mmol) and tetrakistriphenylphosphine palladium (150 mg, 0.12 mmol) were added, and the obtained reaction solution was replaced with nitrogen three times.The reaction was carried out at 100 C for 3 hours under a nitrogen atmosphere, and TLC showed the reaction was completed.After the methanol was rotated under reduced pressure, a saturated ammonium chloride solution (250 ml) was added.The mixture was extracted with ethyl acetate (150 mL×3), and then evaporated. Ethyl acetate = 10/1 (volume ratio V / V)),Compound I-1D (1.36 g, pale yellow solid) was obtained.Yield: 68.9%.

2 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 0.5h;Inert atmosphere;	A mixture of (3-bromo-2-methylphenyl)methanol (2.071 g, 10.3 mmol), phenylboronic acid (2.51 g, 20.60 mmol) and [l,l'-bis(diphenylphosphino)ferrocene] dichloropalladium (II) dichloromethane complex (0.084 g, 0.103 mmol) in toluene (15.45 ml) and ethanol (5.15 ml) was placed under argon. To this solution was added sodium bicarbonate, 2M (15.45 ml, 30.9 mmol) and the mixture was heated at 80 C for 30 min. The reaction mixture was diluted with 20 mL ethyl acetate and 5 mL water. The organic portion was concentrated by rotatory evaporation. The crude product was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford 2 g of an off-white solid. 1H NMR (400MHz, CHLOROFORM-d) delta 7.47-7.29 (m, 7H), 7.23 (s, 1H), 4.80 (d, J=5.6 Hz, 2H), 2.27 (s, 3H), 1.63-1.59 (m, 1H).
2 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 0.5h;Inert atmosphere;	A mixture of (3-bromo-2-methylphenyl)methanol (2.071 g, 10.3 mmol), phenylboronic acid (2.51 g, 20.60 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (0.084 g, 0.103 mmol) in toluene (15.45 mL) and ethanol (5.15 mL) was placed under argon. To this solution was added sodium bicarbonate, 2M (15.45 mL, 30.9 mmol) and the mixture was heated at 80 C. for 30 minutes. The reaction mixture was diluted with 20 mL ethyl acetate and 5 mL water. The organic portion was concentrated by rotatory evaporation. The crude product was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford 2 g of an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta 7.47-7.29 (m, 7H), 7.23 (s, 1H), 4.80 (d, J=5.6 Hz, 2H), 2.27 (s, 3H), 1.63-1.59 (m, 1H).
4.58 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In ethanol; toluene; at 80℃; for 0.5h;Inert atmosphere;	A mixture of compound 2 (4.6 g, 22.8 mmol), phenylboronic acid 3 (5.65 g, 46.3 mmol) and [ 1 , 1 ' -bis (diphenylphosphino) - ferrocene ] dichloropalladium ( I I ) dichloromethane complex (0.188 g, 0.103 mmol) in toluene (34.5 mL) and ethanol (11.3 mL) was placed under argon. To this solution sodium bicarbonate, 2M (34.5 mL, 69.0 mmol) was added and the mixture was heated at 80 C for 30 min. Ethyl acetate (44 mL) and (11 mL) water were added to the reaction mixture. The organic extract was concentrated by rotatory evaporation. The crude product was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford 4.58 g of an off-white solid, mp: 58.0- 59.5 C; 1H NMR (600 MHz, CDC13) delta [ppm] : 7.43-7.40 (m, 3H) , 7.35 (m, 1H) , 7.31-7.29 (m, 2H) , 1H) , 7.26 (t, J=7.6 Hz, 1H) , 7.20 (dd, Jl=7.6 Hz, J2=1.3 Hz, 1H) , 4.78 (s, 2H) , 2.25 (s, 3H) ; 13C NMR (151MHz, DMSO-d6) delta [ppm]: 143.0, 142.2, 140.0, 133.8, 129.7, 129.5, 128.2, 127.0, 126.9, 125.7, 64.2, 16.0; IR V (ATR cm-1) : 3365, 3054, 1601, 1469, 1047, 757.

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5857 - 5867.
[2]Patent: WO2018/200571,2018,A1 .Location in patent: Page/Page column 44-45.
[3]Patent: WO2019/87214,2019,A1 .Location in patent: Paragraph 000121.
[4]Patent: CN110092740,2019,A .Location in patent: Paragraph 0115; 0120-0121; 0128-0130.
[5]Patent: WO2015/34820,2015,A1 .Location in patent: Page/Page column 42.
[6]Patent: US2015/291549,2015,A1 .Location in patent: Paragraph 0210; 0211.
[7]Patent: WO2017/118762,2017,A1 .Location in patent: Page/Page column 39; 40.

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3-{2-[({2,6-dimethoxy-4-[(2-methyl-3-phenylphenyl)methoxy]phenyl}methyl)(methyl)amino]ethyl}-1-phenylurea [ No CAS ]