[ CAS No. 3101-60-8 ] {[proInfo.proName]}

Name: 3101-60-8|4-tert-Butylphenyl glycidyl ether|98%
Brand: Ambeed
SKU: A728193
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Quality Control of [ 3101-60-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 3101-60-8 ]

CAS No. :	3101-60-8	MDL No. :	MFCD00005136
Formula :	C₁₃H₁₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HHRACYLRBOUBKM-UHFFFAOYSA-N
M.W :	206.28	Pubchem ID :	18360
Synonyms :

Calculated chemistry of [ 3101-60-8 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.79
TPSA :	21.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.1
Log Po/w (XLOGP3) :	3.26
Log Po/w (WLOGP) :	2.76
Log Po/w (MLOGP) :	2.28
Log Po/w (SILICOS-IT) :	3.6
Consensus Log Po/w :	3.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.2
Solubility :	0.129 mg/ml ; 0.000624 mol/l
Class :	Soluble
Log S (Ali) :	-3.39
Solubility :	0.0838 mg/ml ; 0.000406 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.82
Solubility :	0.0313 mg/ml ; 0.000152 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.37

Safety of [ 3101-60-8 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P201-P202-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P308+P313-P405-P501	UN#:	2810
Hazard Statements:	H315-H319-H340	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 3101-60-8 ]

* 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 [ 3101-60-8 ]

[ 3101-60-8 ] Synthesis Path-Downstream 1~87

1
[ 582-33-2 ]
[ 3101-60-8 ]
[ 60377-65-3 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

2
[ 120-47-8 ]
[ 3101-60-8 ]
[ 70193-83-8 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

3
[ 94-13-3 ]
[ 3101-60-8 ]
[ 60377-15-3 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

4
[ 18982-18-8 ]
[ 3101-60-8 ]
[ 70193-85-0 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

5
[ 18982-18-8 ]
[ 3101-60-8 ]
[ 60377-14-2 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

6
[ 19438-10-9 ]
[ 3101-60-8 ]
[ 60377-17-5 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

7
[ 3943-97-3 ]
[ 3101-60-8 ]
[ 70193-89-4 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

8
[ 3943-97-3 ]
[ 3101-60-8 ]
[ 60377-18-6 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

9
[ 5597-50-2 ]
[ 3101-60-8 ]
[ 70192-90-4 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

10
[ 5597-50-2 ]
[ 3101-60-8 ]
[ 60377-56-2 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

11
[ 2563-97-5 ]
[ 3101-60-8 ]
[ 5255-96-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1966,vol. 39,p. 2490 - 2494

12
[ 84697-08-5 ]
[ 3101-60-8 ]
[ 70193-88-3 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

13
[ 3943-95-1 ]
[ 3101-60-8 ]
[ 60377-21-1 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

14
[ 61389-68-2 ]
[ 3101-60-8 ]
[ 60377-58-4 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

15
[ 99-76-3 ]
[ 3101-60-8 ]
[ 70193-82-7 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

16
[ 99-76-3 ]
[ 3101-60-8 ]
[ 60377-13-1 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

17
prop-2-yn-1-yl 4-hydroxybenzoate [ No CAS ]
[ 3101-60-8 ]
[ 70193-86-1 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

18
methoxymethyl 4-hydroxybenzoate [ No CAS ]
[ 3101-60-8 ]
[ 70193-87-2 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

19
(E)-3-(4-Hydroxy-phenyl)-acrylic acid 2-methoxy-ethyl ester [ No CAS ]
[ 3101-60-8 ]
[ 70193-90-7 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

20
[ 116144-68-4 ]
[ 3101-60-8 ]
[ 70193-91-8 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

21
[ 208932-51-8 ]
[ 3101-60-8 ]
[ 70193-92-9 ]

Reference： [1]Patent: DE2735856,1979,
Chem.Abstr.,1979,vol. 91

22
1-(6-Amino-hexylamino)-3-(4-tert-butyl-phenoxy)-propan-2-ol [ No CAS ]
[ 3101-60-8 ]
1-(4-tert-Butyl-phenoxy)-3-{6-[3-(4-tert-butyl-phenoxy)-2-hydroxy-propylamino]-hexylamino}-propan-2-ol [ No CAS ]

Reference： [1]Patent: CH599924,1978,
Patent: DE2260444,1974,
Chem.Abstr.,1974,vol. 81

23
[ 94530-69-5 ]
[ 3101-60-8 ]
[ 60377-20-0 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

24
[ 3101-60-8 ]
[ 619-45-4 ]
[ 66876-35-5 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

25
[ 65659-36-1 ]
[ 3101-60-8 ]
[ 119319-37-8 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 765 - 771

26
[ 3101-60-8 ]
[ 3210-65-9 ]

Reference： [1]Journal of Sulfur Chemistry,2012,vol. 33,p. 351 - 361
[2]Journal of Organic Chemistry,2003,vol. 68,p. 2525 - 2527
[3]Heteroatom Chemistry,2008,vol. 19,p. 97 - 99
[4]Journal of Organic Chemistry,1980,vol. 45,p. 4254 - 4255

27
[ 3101-60-8 ]
[ 28713-50-0 ]
1-(4-tert-Butyl-phenoxy)-3-[3-(4-tert-butyl-phenoxy)-2-hydroxy-propylsulfanyl]-propan-2-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3363 - 3366

28
[ 3101-60-8 ]
1-(4-tert-Butyl-phenoxy)-3-mercapto-propan-2-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 3363 - 3366

29
[ 3101-60-8 ]
1-Bromo-3-(4-tert-butyl-phenoxy)-propan-2-ol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 1680 - 1686

30
[ 75-91-2 ]
[ 3101-60-8 ]
1-tert.-Butylperoxy-3-(4-tert.-butylphenoxy)-2-hydroxypropan [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1985,p. 2948 - 2962

31
[ 527-73-1 ]
[ 3101-60-8 ]
[ 188264-54-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 591 - 599

32
[ 3101-60-8 ]
[ 191084-13-6 ]
1-(4-tert-Butyl-phenoxy)-3-[(4-fluoro-benzyl)-(2-phenyl-propyl)-amino]-propan-2-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 3357 - 3360

33
[ 3101-60-8 ]
[ 191084-12-5 ]
1-(4-tert-Butyl-phenoxy)-3-[(3,3-diphenyl-propyl)-(4-methyl-benzyl)-amino]-propan-2-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 3357 - 3360

34
[ 959701-71-4 ]
[ 3101-60-8 ]
1'-[3-(4-tert-butylphenoxy)-2-hydroxypropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With lithium perchlorate; In acetonitrile; at 80℃; for 16h;	To a mixture of spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione (0.15 g, 0.5 mmol) in acetonitrile (3.0 mL) was added 2-[(4-tert-butylphenoxy)methyl]oxathiine (0.11 g, 0.55 mmol) followed by lithium perchlorate (0.058 g, 0.55 mmol). The reaction mixture was stirred at 80° C. for 16 hours. The solvent was removed under vacuum. The crude product was purified by flash column chromatography (SiO2, 100percent EtOAc to 2percent methanol in EtOAc) to give the desired product as a purple solid (0.072 g, 29percent). M.p.=137-140° C.; 400 MHz 1H NMR (CDCl3) delta: 8.05 (d, 1H), 7.75 (d, 1H), 7.65 (t, 1H), 7.5 (t, 1H), 7.35 (d, 2H), 6.9 (d, 2H), 4.15 (m, 1H), 4.0 (d, 2H), 2.95 (m, 3H), 2.8 (m, 2H), 2.65 (m, 2H), 2.55 (t, 2H), 2.15 (d, 2H), 1.9 (m, 2H), 1.3 (s, 9H); LCMS: 508 [M+H].
29%	With lithium perchlorate; In acetonitrile; at 80℃; for 16h;	E24.1. Synthesis of r-r3-(4-tert-butylphenoxy)-2-hydroxypropyl1spirornaphthori,2-biri,41oxatliiine-2,4'-piperidine1-5,6-dione (Compound 157)To a mixture of spiro[naphtho[l,2-Z)][l,4]oxatliime-2,4'-rhoiperidme]-5,6-dione (0.15 g, 0.5 mmol) in acetonitrile (3.0 mL) was added 2-[(4-tert-burylphenoxy)metliyl]oxirane (0.11 g, 0.55 mmol) followed by lithium perchlorate (0.058 g, 0.55 mmol). The reaction mixture was stirred at 80 0C for 16 hours. The solvent was removed under vacuum. The crude product was purified by flash <n="124"/>column chromatography (SiO2, 100percent EtOAc to 2percent methanol in EtOAc) to give the desired product as a purple solid (0.072 g, 29percent). M.p.=137-1400C; 400 MHz 1HNMR (CDCl3) delta: 8.05 (d, IH), 7.75 (d, IH), 7.65 (t, IH), 7.5 (t, IH), 7.35 (d, 2H), 6.9 (d, 2H), 4.15 (m, IH), 4.0 (d, 2H), 2.95 (m, 3H), 2. (m, 2H), 2.65 (m, 2H), 2.55 (t, 2H), 2.15 (d, 2H), 1.9 (m, 2H), 1.3 (s, 9H); LCMS: 508 [M+H].

Reference： [1]Patent: US2009/105166,2009,A1 .Location in patent: Page/Page column 73
[2]Patent: WO2007/139569,2007,A1 .Location in patent: Page/Page column 122-123

35
ammonium thiocyanate [ No CAS ]
[ 3101-60-8 ]
1-(4-<i>tert</i>-butyl-phenoxy)-3-thiocyanato-propan-2-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 1291 - 1293

36
[ 3101-60-8 ]
(2-Chloro-acetyl)-carbamic acid 1-(4-tert-butyl-phenoxymethyl)-2-(2-nitro-imidazol-1-yl)-ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 591 - 599

37
[ 3101-60-8 ]
(2-Bromo-acetyl)-carbamic acid 1-(4-tert-butyl-phenoxymethyl)-2-(2-nitro-imidazol-1-yl)-ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 591 - 599

38
[ 3101-60-8 ]
[ 60377-43-7 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

39
[ 3101-60-8 ]
[ 56488-59-6 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

40
[ 3101-60-8 ]
[ 60377-92-6 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

41
[ 56490-94-9 ]
[ 3101-60-8 ]
N-[2-Hydroxy-3-(4-t-butylphenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;	EXAMPLE 9: Preparation of N-[2-Hydroxy-3-(4-t-butylphenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride, Compound 6 STR9 Using the method of Example 5, supra, 4-t-butylphenyl glycidyl ether (206 mg, 1 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (269 mg, 1.5 mmol) were used to prepare the free base of the title compound. The hydrochloride was prepared by dilution of the reaction mixture with HCl (3 mmol) and water, which caused the product to precipitate. The mixture was heated to effect solution and allowed to cool slowly to crystallize the product. The crystals were collected by filtration, washed with water/MeOH, and dried under vacuum to give 106 mg of the title compound as a white solid: GC/EI-MS, m/z (rel. int.) 370 (M-15, 0.1), 265 (19), 264 (100), 163 (8), 121 (20), 114 (9), 91 (7), 71 (20), 70 (21), 58 (10), 57 (12).

Reference： [1]Patent: US6022894,2000,A

42
[ 98-54-4 ]
[ 67-68-5 ]
[ 106-89-8 ]
[ 3101-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water; ethyl acetate; mineral oil;	PREPARATIVE EXAMPLE 1 Glycidyl 4-t-butylphenyl ether A suspension was obtained by adding 50 ml of anhydrous dimethyl sulphoxide to 3.23 g (73.3 mmol) of sodium hydride (as a 55percent w/w suspension in mineral oil) which had been washed with dry hexane under a nitrogen atmosphere. 10.0 g (66.6 mmol) of 4-t-butylphenol was added slowly, dropwise, to the suspension, with ice cooling. After the 4-t-butylphenol had been added, the mixture was allowed to return to room temperature and was then stirred for one hour. 15.5 ml (200 mmol) of epichlorhydrin was added to the mixture, which was then stirred at 40°C for one hour. At the end of this time, 300 ml of water was added to the reaction mixture, which was then extracted three times, each time with 100 ml of ethyl acetate. The organic layers were combined, brought to neutrality with dilute aqueous hydrochloric acid, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate and concentrated by evaporation under reduced pressure to afford an oil. The oil was purified by distillation under reduced pressure (140 150/2-2.5 mmHg) to obtain 13.3 g (yield: 96.9percent) of glycidyl 4-t-butylphenyl ether. Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 7.30 (doublet, J=8Hz, 2H), 6.85 (doublet, J=8Hz, 2H), 4.30-4.07 (doublet of doublets, J=3 and 10Hz, 1H), 4.03-3.78 (doublet of doublets, J=5 and 10Hz, 1H), 3.45-3.15 (multiplet, 1H), 2.95-2.60 (multiplet, 2H), 1.35 (singlet, 9H). Following similar procedures to that of Preparative Example 1, but using appropriate starting materials, quantities and conditions, the compounds of Preparative Examples 2 to 7 were prepared.

Reference： [1]Patent: EP583971,1994,A1

43
[ 52829-07-9 ]
[ 3101-60-8 ]
[ 155302-75-3 ]

Yield	Reaction Conditions	Operation in experiment
77.9%		EXAMPLE 34 Di{2,2,6,6-tetramethyl-1-[2-hydroxy-3-(4-t-butylphenoxy)propyl]-4-piperidyl} sebacate (Compound No. 144) Following a procedure similar to that of Example 1, but using 4.8 g (10 mmol) of di(2,2,6,6-tetramethyl-4-piperidyl) sebacate and 12.4 g (60 mmol) of glycidyl 4-t-butylphenyl ether, prepared as described in Preparative Example 1, and purifying the product by silica gel column chromatography (the eluent used was ethyl acetate: hexane in a ratio of 1: 5 by volume), 6.95 g (yield: 77.9percent) of the target compound was obtained as crystals. Melting point: 107 - 108°C Infrared Absorption Spectrum (KBr) numaxcmmin1: 3225, 1732, 1251, 1162

Reference： [1]Patent: EP583971,1994,A1

44
[ 62782-03-0 ]
[ 3101-60-8 ]
[ 155302-72-0 ]

Yield	Reaction Conditions	Operation in experiment
75.2%		EXAMPLE 30 Di{2,2,6,6-tetramethyl-1-[2-hydroxy-3-(4-t-butylphenoxy)propyl]-4-piperidyl} succinate (Compound No. 78) Following a procedure similar to that of Example 1, but using 3.0 g (7.56 mmol) of di(2,2,6,6-tetramethyl-4-piperidyl) succinate and 6.23 g (30.2 mmol) of glycidyl 4-t-butylphenyl ether, prepared as described in Preparative Example 1, and purifying the product by silica gel column chromatography (the eluent used was ethyl acetate: hexane in a ratio of 1: 5 by volume), 4.60 g (yield: 75.2percent) of the target compound was obtained as an amorphous powder. Infrared Absorption Spectrum (KBr) numaxcmmin1: 3446, 1733, 1249, 1182

Reference： [1]Patent: EP583971,1994,A1

45
[ 26275-88-7 ]
[ 3101-60-8 ]
4-benzoyloxy-2,2,6,6-tetramethyl-1-[2-hydroxy-3-(4-t-butylphenoxy)propyl]piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.2%		EXAMPLE 18 4-Benzoyloxy-2,2,6,6-tetramethyl-1-[2-hydroxy-3-(4-t-butylphenoxy)propyl]piperidine (Compound No. 31) Following a procedure similar to that of Example 1, but using 4.0 g (15.3 mmol) of 4-benzoyloxy-2,2,6,6-tetramethylpiperidine and 9.47 g (45.9 mmol) of glycidyl 4-t-butylphenyl ether, prepared as described in Preparative Example 1, and purifying the product by silica gel column chromatography (the eluent used was ethyl acetate: hexane in a ratio of 1: 10 by volume), 5.24 g (yield: 73.2percent) of the target compound was obtained as crystals. Melting point: 111 - 112°C Infrared Absorption Spectrum (KBr) numaxcmmin1: 3300, 1715, 1278, 1114

Reference： [1]Patent: EP583971,1994,A1

46
[ 24886-40-6 ]
[ 3101-60-8 ]
[ 155302-74-2 ]

Yield	Reaction Conditions	Operation in experiment
62.6%		EXAMPLE 32 Di{2,2,6,6-tetramethyl-1-[2-hydroxy-3-(4-t-butylphenoxy)propyl]-4-piperidyl} adipate (Compound No. 90) Following a procedure similar to that of Example 1, but using 3.0 g (7.07 mmol) of di(2,2,6,6-tetramethyl-4-piperidyl) adipate and 5.84 g (28.3 mmol) of glycidyl 4-t-butylphenyl ether, prepared as described in Preparative Example 1, and purifying the product by silica gel column chromatography (the eluent used was ethyl acetate: hexane in a ratio of 1: 10 by volume), 3.70 g (yield: 62.6percent) of the target compound was obtained as an amorphous powder. Infrared Absorption Spectrum (KBr) numaxcmmin1: 3450, 1732, 1248, 1181

Reference： [1]Patent: EP583971,1994,A1

47
[ 3101-60-8 ]
[ 227940-72-9 ]
tert-Butyl 7-[3-(4-tert-butylphenoxy)-2-hydroxypropyl]-3,7-diazabicyclo-[3.3.1nonane-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	In water; isopropyl alcohol;	(b) tert-Butyl 7-[3-(4-tert-butylphenoxy)-2-hydroxypropyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate A mixture of tert-butyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (2.2 g; 9.70 mmol; see Example F above) and <strong>[3101-60-8]4-tert-butyl-1-(2-oxiranylmethoxy)benzene</strong> (2.0 g; 9.70 mmol; from step (a) above) in 2-propanol (10 mL) and water (1 mL) was stirred at 60° C. for 18 h. The reaction mixture was concentrated to give an oil which was dissolved in hexanes and allowed to stand until solids formed. The solids were collected and dried to give the desired product (0.28 g; 7percent) as a white solid. mp 75-77° C.; 1H NMR (CDCl3): delta 1.32 (s, 9H), 1.47 (s, 9H), 1.62-1.78 (m, 2H), 1.79-1.96 (m, 2H), 2.13-2.38 (m, 2H), 2.42-2.57 (m, 2H), 2.87-3.25 (m, 4H), 3.82-4.30 (m, 5H), 6.86 (d, 2H), 7.31 (d, 2H); 13C NMR (CDCl3): delta 28.9, 29.1, 29.4, 29.7, 31.3, 31.7, 32.1, 34.3, 47.9, 48.1, 48.9, 49.6, 57.4, 58.1, 60.6, 61.9, 62.5, 65.5, 65.9, 70.7, 77.4, 79.7, 114.3, 126.4, 143.6, 155.8, 156.2, 156.8; CI-MS (M+1)+433 (m/z).

Reference： [1]Patent: US6291475,2001,B1

48
[ 3101-60-8 ]
6-tert-butylchroman-3-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 16838 - 16839

49
[ 4248-19-5 ]
[ 3101-60-8 ]
[ 250778-94-0 ]
[ 1173884-51-9 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 2863 - 2871
[2]Journal of Organic Chemistry,2013,vol. 78,p. 9076 - 9084

50
[ 621-84-1 ]
[ 3101-60-8 ]
[ 250778-94-0 ]
[ 1173884-62-2 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 2863 - 2871
[2]Journal of Organic Chemistry,2013,vol. 78,p. 9076 - 9084

51
[ 51-79-6 ]
[ 3101-60-8 ]
[ 250778-94-0 ]
[ 1173884-61-1 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 2863 - 2871
[2]Journal of Organic Chemistry,2013,vol. 78,p. 9076 - 9084

52
[ 124-38-9 ]
[ 3101-60-8 ]
[ 57230-66-7 ]

Yield	Reaction Conditions	Operation in experiment
	With water; cetyltrimethylammonim bromide; at 120℃; under 33753.4 Torr; for 7h;Autoclave;	General procedure: The general process of CO2-PO coupling reaction was given as following: a 100 ml autoclave equipped with a mechanical stirrer was pre-dried under vacuum at 80 °C for 2 h. Zn?CoIII DMCC (10 mg) and appropriate amounts of quaternary ammonium salts were transferred into the autoclave, which was then dried for another 2 h. After the autoclave was cooled down to 25 °C, PO (30 ml) was injected into the autoclave using a syringe under negative pressure. The reactor was then heated and pressured to the desired temperature and CO2 pressure under vigorous stirring (500 rpm). After the reaction, the autoclave was cooled with ice-water bath and the pressure was vented. A small amount of sample was removed for 1H NMR measurement. The crude products were then transferred to a round-bottomed flask and dried under reduced pressure. Pure propylene carbonate (PC, 4-methyl-1, 3-dioxolan-2-one) was obtained4-((4-tert-butylphenoxy)methyl)-1, 3-dioxolan-2-one: 1H NMR (CDCl3, TMS, 400 MHz): delta (ppm) = 1.30(s, 9H), 4.14(m, 1H), 4.24(m, 1H), 4.53(m, 1H), 4.60(m, 1H), 5.01(m, 1H), 6.86 (d, 2H), 7.34 (t, 2H).
	With C132H136Al2N4O5P4(4+)*4Cl(1-); tetrabutylammomium bromide; at 100℃; under 760.051 Torr;	General procedure: The coupling reactions were carried out in 5 mL reaction vial equipped with a magnetic bar on an automated stirrer with heating mantle. The clean reaction vial was dried at 100 0C for1 h in an oven before use. The reaction vial was charged with appropriate amount of immobilized catalyst 1-Mont and co-catalyst and closed with septa. Next epoxide 2a-2i (10 mmol) was subjected to this vial using a hypodermic syringe followed by evacuation. Afterwards CO2 was introduced to thereaction vial at 1 atm pressure and the resulting suspension was allowed to stir at specified temperature for an appropriate time. The conversion and selectivity of the product was determined by 1H NMR of an aliquot taken from the reaction mass at a regular interval with respect to an internal standard.
90%Spectr.	With Al(3+)C15H15NO2(2-)Cl(1-); tetrabutylammomium bromide; In neat (no solvent); at 90℃; under 760.051 Torr; for 12h;	General procedure: The cycloaddition reactions were carried out in a dry 5 mL reac-tion vial equipped with a magnetic bar on an automated stirrerwith heating mantle. The reaction vial was charged with appro-priate amount of homogeneous catalyst 1?6 (1.0 molpercent) and TBAB(1.0 molpercent) as co-catalyst and closed with a septum. An appropriateepoxide 7a?n (10 mmol) was introduced to this vial with the helpof a syringe. The vial was purged with nitrogen followed by CO2and the reaction mixture was allowed to stir at a specified temper-ature for a specified time at around atmosphere pressure of CO2.The conversion and selectivity of the product was determined by1H NMR by taking an aliquot from the reaction mass at a regularinterval [19].

Reference： [1]ChemSusChem,2012,vol. 5,p. 2032 - 2038
[2]Journal of Molecular Catalysis A: Chemical,2013,vol. 379,p. 38 - 45
[3]Catalysis Communications,2015,vol. 61,p. 78 - 82
[4]Journal of Molecular Catalysis A: Chemical,2016,vol. 417,p. 135 - 144

53
[ 79-41-4 ]
[ 3101-60-8 ]
3-(4-tert-butylphenoxy)-2-hydroxypropyl methacrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 2,6-di-tert-butyl-4-methyl-phenol; triethylamine; at 60℃; for 24h;Inert atmosphere;	9. Synthesis of 4-tert-butylphenoxy-2-hydroxypropyl methacrylate In a two neck flask equipped with a condenser under nitrogen atmosphere were placed 13.80 g (0.0668 mol) of 4-tert-butylphenylglycidyl ether, 6.05 g (0.070 mol) of methacrylic acid, 0.90 g (0.009 mol) of triethylamine and 30 mg of BHT. The reaction mixture was stirred at 60° C. 1H NMR showed reaction completion at 24 hours. Reaction mixtures was dissolved in methylene chloride and extracted with saturated solution of sodium hydroxide (NaOH) 325 ml, diluted solution of acid chloride (HCl) 225 ml, 225 ml of saturated solution of sodium bicarbonate (NaHCO3) and finally with brine 125 ml. Organic layer was dried over sodium sulfate (Na2SO4), filtered and vacuum dried, 14.24 grams (yield: 98percent) of low viscosity (eta=0.4894 Pa*s) colorless material were obtained.

Reference： [1]Patent: US8513326,2013,B2 .Location in patent: Page/Page column 31

54
[ 3101-60-8 ]
C₄₂H₆₀N₂O₁₀ [ No CAS ]

Reference： [1]Patent: US8513326,2013,B2

55
[ 3101-60-8 ]
C₄₉H₇₀N₂O₁₀ [ No CAS ]

Reference： [1]Patent: US8513326,2013,B2

56
[ 3101-60-8 ]
C₃₈H₅₂N₂O₁₀ [ No CAS ]

Reference： [1]Patent: US8513326,2013,B2

57
[ 3101-60-8 ]
C₄₅H₆₂N₂O₁₀ [ No CAS ]

Reference： [1]Patent: US8513326,2013,B2

58
[ 3101-60-8 ]
[ 75-05-8 ]
[ 1612190-31-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With boron trifluoride diethyl etherate; at 20 - 80℃; for 2h;	General procedure: To a stirred solution of the corresponding epoxide 1 or oxiranes 4?7 (0.2mmol) in the corresponding nitrile (1ml) was added BF3*OEt2 (0.025ml, 0.2mmol) at room temperature. After that the mixture was stirred at 80°C for 12h. An aqueous saturated solution of sodium bicarbonate (5ml) was added and the mixture was stirred at room temperature for 5min. Then, the aqueous phase was extracted with ethyl acetate (3×5ml), and the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. Column chromatography on silica gel (60?120mesh) using chloroform/methanol (10:1) as eluent provided the desired compounds 2?3 and 8?21.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 135 - 144

59
[ 107-13-1 ]
[ 3101-60-8 ]
[ 1612190-32-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With boron trifluoride diethyl etherate; at 20 - 80℃; for 2h;	General procedure: To a stirred solution of the corresponding epoxide 1 or oxiranes 4?7 (0.2mmol) in the corresponding nitrile (1ml) was added BF3*OEt2 (0.025ml, 0.2mmol) at room temperature. After that the mixture was stirred at 80°C for 12h. An aqueous saturated solution of sodium bicarbonate (5ml) was added and the mixture was stirred at room temperature for 5min. Then, the aqueous phase was extracted with ethyl acetate (3×5ml), and the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. Column chromatography on silica gel (60?120mesh) using chloroform/methanol (10:1) as eluent provided the desired compounds 2?3 and 8?21.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 135 - 144

60
[ 100-47-0 ]
[ 3101-60-8 ]
[ 1612190-33-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With boron trifluoride diethyl etherate; at 20 - 80℃; for 2h;	General procedure: To a stirred solution of the corresponding epoxide 1 or oxiranes 4?7 (0.2mmol) in the corresponding nitrile (1ml) was added BF3*OEt2 (0.025ml, 0.2mmol) at room temperature. After that the mixture was stirred at 80°C for 12h. An aqueous saturated solution of sodium bicarbonate (5ml) was added and the mixture was stirred at room temperature for 5min. Then, the aqueous phase was extracted with ethyl acetate (3×5ml), and the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. Column chromatography on silica gel (60?120mesh) using chloroform/methanol (10:1) as eluent provided the desired compounds 2?3 and 8?21.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 135 - 144

61
[ 874-90-8 ]
[ 3101-60-8 ]
[ 692275-65-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With boron trifluoride diethyl etherate; at 20 - 80℃; for 2h;	General procedure: To a stirred solution of the corresponding epoxide 1 or oxiranes 4?7 (0.2mmol) in the corresponding nitrile (1ml) was added BF3*OEt2 (0.025ml, 0.2mmol) at room temperature. After that the mixture was stirred at 80°C for 12h. An aqueous saturated solution of sodium bicarbonate (5ml) was added and the mixture was stirred at room temperature for 5min. Then, the aqueous phase was extracted with ethyl acetate (3×5ml), and the combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. Column chromatography on silica gel (60?120mesh) using chloroform/methanol (10:1) as eluent provided the desired compounds 2?3 and 8?21.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 135 - 144

62
[ 3101-60-8 ]
[ 1620289-12-4 ]

Reference： [1]Chemistry of Natural Compounds,2014,vol. 50,p. 511 - 514
Khim. Prir. Soedin.,2014,p. 442 - 444,3

63
[ 3101-60-8 ]
[ 1620289-13-5 ]

Reference： [1]Chemistry of Natural Compounds,2014,vol. 50,p. 511 - 514
Khim. Prir. Soedin.,2014,p. 442 - 444,3

64
[ 3101-60-8 ]
[ 1620289-14-6 ]

Reference： [1]Chemistry of Natural Compounds,2014,vol. 50,p. 511 - 514
Khim. Prir. Soedin.,2014,p. 442 - 444,3

65
[ 3101-60-8 ]
[ 1620289-15-7 ]

Reference： [1]Chemistry of Natural Compounds,2014,vol. 50,p. 511 - 514
Khim. Prir. Soedin.,2014,p. 442 - 444,3

66
[ 3101-60-8 ]
[ 1620289-16-8 ]

Reference： [1]Chemistry of Natural Compounds,2014,vol. 50,p. 511 - 514
Khim. Prir. Soedin.,2014,p. 442 - 444,3

67
[ 3101-60-8 ]
[ 1620289-17-9 ]

Reference： [1]Chemistry of Natural Compounds,2014,vol. 50,p. 511 - 514
Khim. Prir. Soedin.,2014,p. 442 - 444,3

68
[ 93703-24-3 ]
[ 3101-60-8 ]
[ 1620289-11-3 ]

Reference： [1]Chemistry of Natural Compounds,2014,vol. 50,p. 511 - 514
Khim. Prir. Soedin.,2014,p. 442 - 444,3

69
[ 62-53-3 ]
[ 3101-60-8 ]
[ 42313-66-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sulfated zirconia; In neat (no solvent); at 20℃; for 0.5h;	General procedure: A solid SZ catalyst (20 mg), an epoxide (1 mmol) and an amine(1 mmol) were taken in a 5 mL screw capped vial and stirred mag-netically for a given time period (monitored by GC or TLC) undersolvent free condition at RT. On completion of the reaction, vis-cous liquid or solid product obtained was treated with methanol(2 × 3 mL) and centrifuged for the complete removal of organiccompounds from the solid catalyst. The evaporation of solvent fromthe combined organic layers furnished the crude product. A smallfraction of the crude product was directly injected to HPLC to findout the regioselectivity. The remaining portion of the crude mix-ture was purified by flash column chromatography (hexane/ethylacetate, 80:20) to get the major regioisomer in pure form. The puri-fied product was characterized by1H and13C NMR analysis. Theresidue thus obtained from centrifugation was dried in air (2 h) andthen at 200C for 3 h to get back the active catalyst (>97percent recovery)for the next catalytic run.
88%	With iron(III) hydroxide; In neat (no solvent); at 20℃; for 0.25h;Sealed tube;	General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97percentrecovery) for further use.

Reference： [1]Applied Catalysis A: General,2014,vol. 486,p. 105 - 114
[2]Applied Catalysis A: General,2014,vol. 469,p. 442 - 450

70
[ 3101-60-8 ]
[ 100-46-9 ]
C₂₀H₂₇NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With silica gel; at 20℃;	General procedure: A solution of an appropriate epoxide (2 mmol) and benzyl amine(2 mmol) were taken in a 5 mL reaction vial to which silica gel(20 mg) was added and the reaction mixture was stirred with thehelp of magnetic bar at room temperature for 4?6 h. The resultingmass was diluted with 20percent of ethyl acetate in hexane, filtered andcooled to ?25C. A white solid precipitated out was filtered andthe solid thus obtained was dried under vacuum and used as suchwithout further purification.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2016,vol. 417,p. 135 - 144

71
[ 56621-48-8 ]
[ 3101-60-8 ]
4-(4-(3-(4-(tert-butyl)phenoxy)-2-hydroxypropyl)piperazin-1-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.06%	In ethanol;Reflux;	General procedure: Analogues 9a-m,were synthesized by stirring 1eq of the appropriate intermediate compound (3a-m) with 4-(piperazin-1-yl)phenol(1.1eq) in ethanol (10 ml) at reflux for 5 to 8h. After concentration under reducedpressure of reaction mixture, the crude compounds were purified by columnchromatography or recrystallization in EtOAc or EtOH.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2423 - 2432

72
[ 57244-61-8 ]
[ 3101-60-8 ]
C₂₁H₂₉O₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; at 160℃; for 2h;Inert atmosphere;	Example 2 (0037) The phosphorus-containing compound [I-1] weighing 17.0 mg (0.25 mmol) and 20.6 mg (0.25 mmol) of Adeka Glycirol ED-509S were allowed to react with each other in the presence of 0.9 mg (7.5 mol percent) of DMAP as a catalyst in a nitrogen stream at 160° C. for 2 hours. P2 shown in [Chem. 13] described below was obtained with high selectivity according to the reaction mechanism shown in [Chem. 13] described below. The 1H-NMR, 31P-NMR, and GC-MS spectra of the resulting P2 are shown in FIGS. 4 to 6, respectively.
	With dmap; at 160℃; for 2h;Inert atmosphere;	In DMAP0.9mg (7.5mol percent) in the presence of catalyst, the phosphorus-containing compound (I-1) 17.0 mg (0.25mmol) and AdekaGlycirolED-509S20.6 mg (0.25mmol) in the nitrogen flow, 160 °C reaction under 2 hours. By the following [chemical formula 13] is shown in the reaction mechanism, to obtain a high selectivity [chemical formula 13] the shown in P2.

Reference： [1]Patent: US2016/152643,2016,A1 .Location in patent: Paragraph 0037
[2]Patent: CN105452263,2016,A .Location in patent: Paragraph 0070; 0071; 0072; 0073

73
[ 7450-70-6 ]
[ 3101-60-8 ]
C₂₃H₃₅N₂O₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; at 140℃; for 2h;Inert atmosphere;	The phosphorus-containing compound [1-2] obtained in Example 2 and weighing 57.1 mg (0.25 mmol) and 51.6 mg (0.25 mmol) of Adeka Glycirol ED-509S were allowed to react with each other in the presence of 2.3mg (7.5 mol percent) of DMAP as a catalyst in a nitrogen stream at 140°C. for 2 hours in accordance with the following reaction scheme. The results of ?H-NMR and 31P-NMR analyses shown in FIGS. 12 and 13, respectively, revealed that S4 (see below) was obtained as a main product.

Reference： [1]Patent: US2016/200747,2016,A1 .Location in patent: Paragraph 0061

74
[ 3101-60-8 ]
[ 1754-58-1 ]
C₂₁H₃₁N₂O₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; at 130℃; for 2h;Inert atmosphere;	The phosphorus-containing compound [1-3] prepared in Example 3 and weighing 50.0 mg (0.25 mmol) and 51.6 mg (0.25 mmol) of Adeka Glycirol ED-5095 were allowed to react with each other in the presence of 2.3mg (7.5 mol percent) of DMAP as a catalyst in a nitrogen stream at 130° C. for 2 hours in accordance with the following reaction scheme. The results of ?H-NMR and 31P-NMR analyses shown in FIGS. 15 and 16, respectively, revealed that S5 (see below) was obtained as a main product.

Reference： [1]Patent: US2016/200747,2016,A1 .Location in patent: Paragraph 0062

75
[ 106-49-0 ]
[ 3101-60-8 ]
C₂₀H₂₇NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With iron(III) hydroxide; In neat (no solvent); at 20℃; for 0.25h;Sealed tube;	General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97percentrecovery) for further use.

Reference： [1]Applied Catalysis A: General,2014,vol. 469,p. 442 - 450

76
[ 104-94-9 ]
[ 3101-60-8 ]
S⁽⁰²⁰⁾J₀₀₁₁₆₆-1 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With iron(III) hydroxide; In neat (no solvent); at 20℃; for 0.25h;Sealed tube;	General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97percentrecovery) for further use.

Reference： [1]Applied Catalysis A: General,2014,vol. 469,p. 442 - 450

77
[ 106-47-8 ]
[ 3101-60-8 ]
C₁₉H₂₄ClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With iron(III) hydroxide; In neat (no solvent); at 20℃; for 0.333333h;Sealed tube;	General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97percentrecovery) for further use.

Reference： [1]Applied Catalysis A: General,2014,vol. 469,p. 442 - 450

78
[ 90-04-0 ]
[ 3101-60-8 ]
C₂₀H₂₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron(III) hydroxide; In neat (no solvent); at 20℃; for 0.333333h;Sealed tube;	General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97percentrecovery) for further use.

Reference： [1]Applied Catalysis A: General,2014,vol. 469,p. 442 - 450

79
[ 78-90-0 ]
[ 3101-60-8 ]
1-((2-aminopropyl)amino)-3-(4-tert-butylphenoxy)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 70 - 80℃; for 2h;Inert atmosphere;	77.4 g (1.04 mol) of 1,2-propylenediamine were introduced under a nitrogen atmosphere and heated to 70° C., and slowly 67.5 g (0.3 mol) of Araldite® DY-P were added, accompanied by thorough stirring. The reaction mixture was left at 80° C. for 2 hours. The volatile constituents were then removed on a rotary evaporator at 65° C. and 1 mbar over 3 hours. This gave a clear, slightly yellowish liquid having a viscosity of 105 Pa·s, an amine number of 374.9 mg KOH/g, and a theoretical AHEW of about 99.7 g/eq.

Reference： [1]Patent: US2017/29364,2017,A1 .Location in patent: Paragraph 0166

80
[ 3101-60-8 ]
[ 250778-94-0 ]
(R)-3-(4-(tert-butyl)phenoxy)propane-1,2-diol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3990 - 4001
[2]Catalysis science and technology,2014,vol. 4,p. 3899 - 3908

81
[ 62-53-3 ]
[ 3101-60-8 ]
[ 250778-94-0 ]
(R)-1-(4-(tert-butyl)phenoxy)-3-(phenylamino)propan-2-ol [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3990 - 4001

82
[ 19438-10-9 ]
[ 3101-60-8 ]
[ 60377-54-0 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

83
[ 3943-97-3 ]
[ 3101-60-8 ]
[ 60377-55-1 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

84
[ 3943-95-1 ]
[ 3101-60-8 ]
[ 60377-57-3 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

85
[ 3101-60-8 ]
[ 619-45-4 ]
[ 60377-64-2 ]

Reference： [1]Patent: DE2460689,1976,
Chem.Abstr.,1979,vol. 90

86
[ 3101-60-8 ]
1-(tert-butyl)-4-(2,3-dibromopropoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetra-(n-butyl)ammonium iodide; ethylene dibromide; triphenylphosphine; at 40℃; for 2h;Sealed tube; Inert atmosphere;	General procedure: Epoxide 1a (1.0 equiv, 0.5 mmol, 60.1 mg), Ph3P (1.2 equiv, 0.6 mmol, 157.4 mg), nBu4NI (1.4 equiv, 0.7 mmol, 258.6 mg) and BrCH2CH2Br (5.0 mL) were added into a10 mL sealed tube under a N2 atmosphere. The resulting mixture was stirred at 40 °Cfor 2 h. After the reaction solvent was removed by concentration under vacuum, the residue was subjected to flash column chromatography with hexane/ethyl acetate (100:1-4:1) as the eluent to afford the product 3a.

Reference： [1]Synlett,2019,vol. 30,p. 181 - 184

87
[ 3101-60-8 ]
1-(tert-butyl)-4-(2,3-dichloropropoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetra-(n-butyl)ammonium iodide; 1,2-dichloro-ethane; triphenylphosphine; at 80℃; for 4h;Sealed tube; Inert atmosphere;	General procedure: Epoxide 1a (1.0 equiv, 0.5 mmol, 60.1 mg), Ph3P (1.2 equiv, 0.6 mmol, 157.4mg), nBu4NI (1.4 equiv, 0.7 mmol, 258.6 mg) and ClCH2CH2Cl (5.0 mL) were added into a 10 mL sealed tube under a N2 atmosphere. The resulting mixture was stirred at 80 °C for 4 h. After the reaction solvent was removed by concentration under vacuum, the residue was subjected to flash column chromatography with hexane/ethyl acetate (100:1-4:1) as the eluent to afford the product 2a.

Reference： [1]Synlett,2019,vol. 30,p. 181 - 184

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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.
P202	Do not handle until all safety precautions have been read and understood.
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.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
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
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 3101-60-8 ] {[proInfo.proName]}

Quality Control of [ 3101-60-8 ]

Related Doc. of [ 3101-60-8 ]

Product Details of [ 3101-60-8 ]

Calculated chemistry of [ 3101-60-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3101-60-8 ]

Application In Synthesis of [ 3101-60-8 ]

[ 3101-60-8 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 3101-60-8 ]

Aryls

Ethers

Related Parent Nucleus of [ 3101-60-8 ]

Epoxides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3101-60-8 ]

Related Parent Nucleus of
[ 3101-60-8 ]