3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
Conditions | Yield |
---|---|
With hydrogen; 0.5% Pd/Al2O3 In 4-methyl-2-pentanone at 98℃; under 3750.38 Torr; for 1h; Conversion of starting material; | 85% |
With sodium sulfite In water; 4-methyl-2-pentanone Heating / reflux; |
Conditions | Yield |
---|---|
With sodium hydroxide; oxygen |
1,3-diisopropylbenzene
A
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
B
3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene
C
3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene
D
1,3-di(2-hydroperoxy-2-propyl)benzene
E
2-(3-isopropyl-phenyl)-propan-2-ol
Conditions | Yield |
---|---|
With oxygen; 1,10-Phenanthroline; magnesium naphthenate at 80 - 120℃; Rate constant; Kinetics; Thermodynamic data; E(act.) for various reaction products formation, other catalyst; |
1,3-diisopropylbenzene
oxygen
B
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
C
3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene
D
1,3-di(2-hydroperoxy-2-propyl)benzene
E
acetylisopropylbenzene monocarbinol
F
2-(3-isopropyl-phenyl)-propan-2-ol
G
1-[3-(propan-2-yl)phenyl]ethan-1-one
Conditions | Yield |
---|---|
With sodium hydroxide; 3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene In water at 90℃; |
3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene
B
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
C
3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene
D
1,3-di(2-hydroperoxy-2-propyl)benzene
E
acetylisopropylbenzene monocarbinol
F
2-(3-isopropyl-phenyl)-propan-2-ol
G
1-[3-(propan-2-yl)phenyl]ethan-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In water; 4-methyl-2-pentanone at 90℃; Heating / reflux; |
3-(2-hydroxy-2-propyl)-1-(2-hydroperoxy-2-propyl)benzene
B
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
C
3-isopropyl-1-(2-hydroperoxy-2-propyl)benzene
D
1,3-di(2-hydroperoxy-2-propyl)benzene
E
acetylisopropylbenzene monocarbinol
F
2-(3-isopropyl-phenyl)-propan-2-ol
Conditions | Yield |
---|---|
With sodium sulfite In water; 4-methyl-2-pentanone Heating / reflux; |
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
Methyl thioglycolate
dimethyl [1,3-phenylenebis(1-methylethylidenethio)]diacetate
Conditions | Yield |
---|---|
With zinc(II) iodide In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; toluene-4-sulfonic acid at 100℃; under 15001.5 Torr; for 20h; Autoclave; Inert atmosphere; | 96% |
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
Conditions | Yield |
---|---|
With hydrogenchloride; calcium chloride In dichloromethane at 0℃; for 2h; | 93% |
With hydrogenchloride; calcium chloride In dichloromethane at 0℃; |
tert.-butylhydroperoxide
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
1-(1-methyl-1-hydroxyethyl)-3-(1-methyl-1-tert-butylperoxyethyl)benzene
Conditions | Yield |
---|---|
With perchloric acid In acetic acid at 20℃; for 5h; | 76% |
Cumene hydroperoxide
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
1-(1-methyl-1-hydroxyethyl)-3-<1-methyl-1-(1-methyl-1-phenylethylperoxy)ethyl>benzene
Conditions | Yield |
---|---|
With perchloric acid In acetic acid | 74% |
Conditions | Yield |
---|---|
With sodium carbonate; chloro(1,5-cyclooctadiene)iridium(I) dimer In toluene at 100℃; for 6h; | A 8% B 70% |
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
1,3-bis-[1'-(pyrrol-2-yl)-1',1'-(dimethyl)methyl]benzene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetonitrile at 20℃; for 0.333333h; | 68% |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
50% |
Conditions | Yield |
---|---|
32% |
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 27℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 27℃; for 2h; Further stages.; | 27% |
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; benzaldehyde With boron trifluoride diethyl etherate In dichloromethane Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane |
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 27℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 27℃; for 2h; | A 27% B 0.8% C 4% |
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 4-nitrobenzaldehdye With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane | 27% |
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene With boron trifluoride diethyl etherate In acetonitrile at 20℃; for 0.0833333h; Stage #2: acetone In acetonitrile at 20℃; for 0.916667h; Further stages.; | 18% |
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
4-chlorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 4-chlorobenzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 17% |
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 4-chlorobenzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
2,6-dichlorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 2,6-dichlorobenzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 17% |
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 2,6-dichlorobenzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
pyrrole
2,6-difluorobenzaldehyde
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
Conditions | Yield |
---|---|
Stage #1: pyrrole; 2,6-difluorobenzaldehyde; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 17% |
Stage #1: pyrrole; 2,6-difluorobenzaldehyde; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
4-Trifluoromethylbenzaldehyde
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 4-Trifluoromethylbenzaldehyde; pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 17% |
Stage #1: 4-Trifluoromethylbenzaldehyde; pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
3,4,5-trimethoxy-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 3,4,5-trimethoxy-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 17% |
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 3,4,5-trimethoxy-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetonitrile at 20℃; for 1h; | 16% |
pyrrole
perfluorobenzaldehyde
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
Conditions | Yield |
---|---|
Stage #1: pyrrole; perfluorobenzaldehyde; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 16% |
Stage #1: pyrrole; perfluorobenzaldehyde; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
4-methoxy-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 4-methoxy-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 16% |
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 4-methoxy-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
4-bromo-benzaldehyde
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 4-bromo-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 2h; | 14% |
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; 4-bromo-benzaldehyde With boron trifluoride diethyl etherate In dichloromethane at 20℃; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; |
pyrrole
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
Stage #1: pyrrole; 1,3-bis(1',1'-dimethylhydroxymethyl)benzene; methyl 4-formylbenzoate With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.5h; | A 11% B 1.25% C 2.9% |
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
1-(1-methyl-1-tert-butylperoxyethyl)-3-isopropenylbenzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / 0.1 N perchloric acid / acetic acid / 5 h / 20 °C 2: 75 percent / iodine / acetic acid / 3 h / 80 °C View Scheme |
1,3-bis(1',1'-dimethylhydroxymethyl)benzene
1-<1-methyl-1-(1-methyl-1-phenylethylperoxy)ethyl>-3-isopropenylbenzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 74 percent / 0.1 N perchloric acid / acetic acid 2: 72 percent / iodine / acetic acid View Scheme |
The 1,3-Benzenedimethanol, α1,α1,α3,α3-tetramethyl-, with the CAS registry number 1999-85-5, is also known as α,α'-Dihydroxy-1,3-diisopropylbenzene. Its EINECS number is 217-886-1. It belongs to the product categories of Organic Building Blocks; Oxygen Compounds; Polyols. This chemical's molecular formula is C12H18O2 and molecular weight is 194.27. What's more, its systematic name is 2,2'-Benzene-1,3-diyldipropan-2-ol. Its classification code is TSCA Flag P. The product should be sealed and stored in containers which are placed in cool, ventilated and dry places and protected from oxidizers. What's more, it should be ensured that the workshop is well ventilated or equipped with exhaust device.
Physical properties of 1,3-Benzenedimethanol, α1,α1,α3,α3-tetramethyl- are: (1)ACD/LogP: 1.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.24; (4)ACD/LogD (pH 7.4): 1.24; (5)ACD/BCF (pH 5.5): 5.2; (6)ACD/BCF (pH 7.4): 5.2; (7)ACD/KOC (pH 5.5): 113.27; (8)ACD/KOC (pH 7.4): 113.27; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.527; (14)Molar Refractivity: 56.83 cm3; (15)Molar Volume: 184.8 cm3; (16)Polarizability: 22.52×10-24 cm3; (17)Surface Tension: 37.4 dyne/cm; (18)Density: 1.051 g/cm3; (19)Flash Point: 134.6 °C; (20)Enthalpy of Vaporization: 56.54 kJ/mol; (21)Boiling Point: 295.6 °C at 760 mmHg; (22)Vapour Pressure: 0.000681 mmHg at 25°C.
Uses of 1,3-Benzenedimethanol, α1,α1,α3,α3-tetramethyl-: it can be used to produce 1,3-bis-[1'-(pyrrol-2-yl)-1',1'-(dimethyl)methyl]benzene at the temperature of 20 °C. It will need reagent BF3•Et2O and solvent acetonitrile with the reaction time of 20 min. The yield is about 68%.
When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(C)(C1=CC(=CC=C1)C(C)(C)O)O
(2)InChI: InChI=1S/C12H18O2/c1-11(2,13)9-6-5-7-10(8-9)12(3,4)14/h5-8,13-14H,1-4H3
(3)InChIKey: UGPWRRVOLLMHSC-UHFFFAOYSA-N
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