Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane at 0 - 20℃; for 1h; | 100% |
With oxalyl dichloride In dichloromethane at 20℃; Appel Halogenation; Reflux; | 98% |
With tetrachloromethane; ring-opening metathesis polymer-supported triphenylphosphine In dichloromethane at 45℃; for 6h; | 89% |
formaldehyd
1,3,5-trimethyl-benzene
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With hydrogenchloride In water at 65 - 75℃; | 90% |
With hydrogenchloride; acetic acid In water at 37℃; for 1.5h; | 68% |
With hydrogenchloride In water at 60 - 70℃; for 7h; | 36% |
2,4,6-trimethylbenzyl alcohol
benzoyl chloride
B
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With 1-methylsulfinyl-2-methoxybenzene In acetonitrile at 20℃; for 14h; Sealed tube; | A n/a B 74% |
chloromethyl isocyanate
1,3,5-trimethyl-benzene
A
2-chloromethyl-1,3,5-trimethylbenzene
B
2-Isocyanatomethyl-1,3,5-trimethyl-benzene
Conditions | Yield |
---|---|
With iron(III) chloride 1.) 40 - 60 deg C, 2.) 100 - 150 deg C, 2 h; | A 15% B 32% |
chloromethyl methyl ether
acetic acid
1,3,5-trimethyl-benzene
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
at 65℃; ohne Katalysator; Geschwindigkeit dieser Reaktion und der analogen Reaktionen mit anderen aromatischen Kohlenwasserstoffen bei 65grad und 100grad; |
chloromethyl methyl ether
acetic acid
1,3,5-trimethyl-benzene
A
2,4-bis(chloromethyl)mesitylene
B
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
at 80℃; |
chloromethyl methyl ether
1,3,5-trimethyl-benzene
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With acetic acid at 65 - 80℃; |
chloromethyl methyl ether
1,3,5-trimethyl-benzene
A
2,4-bis(chloromethyl)mesitylene
B
2-chloromethyl-1,3,5-trimethylbenzene
ethyl chloromethyl ether
1,3,5-trimethyl-benzene
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With carbon disulfide; tin(IV) chloride | |
With tetrachloromethane; tin(IV) chloride at -5℃; | |
With acetic acid |
formaldehyd
1,3,5-trimethyl-benzene
A
2,4-bis(chloromethyl)mesitylene
B
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With hydrogenchloride at 65℃; Einleiten von HCl; |
hydrogenchloride
formaldehyd
1,3,5-trimethyl-benzene
A
2,4-bis(chloromethyl)mesitylene
B
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
at 65℃; Einleiten von HCl; |
hydrogenchloride
2,4,6-trimethylbenzyl acetate
A
methyl-(2,4,6-trimethyl-benzyl)-ether
B
2-chloromethyl-1,3,5-trimethylbenzene
hydrogenchloride
formaldehyd
1,3,5-trimethyl-benzene
A
dimesitylmethane
B
2-chloromethyl-1,3,5-trimethylbenzene
formaldehyd
1,3,5-trimethyl-benzene
A
2,4,6-tris(chloromethyl)-mesitylene
B
2,4-bis(chloromethyl)mesitylene
C
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; Title compound not separated from byproducts.; |
Conditions | Yield |
---|---|
With hydrogenchloride; formaldehyd for 2h; Heating; |
Conditions | Yield |
---|---|
With tetrachlorosilane; NbCl3(N,N′-bis-(2,6-diisopropylphenyl)-1,4-diaza-2,3-dimethyl-1,3-butadiene) In chloroform-d1 at 80℃; for 24h; | 95 %Spectr. |
sodium cyanide
2-chloromethyl-1,3,5-trimethylbenzene
mesitylacetonitrile
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 80℃; for 0.5h; Substitution; | 100% |
Stage #1: sodium cyanide In ethanol; water Heating / reflux; Stage #2: 2-chloromethyl-1,3,5-trimethylbenzene In ethanol; water for 3h; Heating / reflux; | 72% |
In ethanol |
2-chloromethyl-1,3,5-trimethylbenzene
dimethyl amine
2,4,6-trimethyl-<(dimethylamino)methyl>benzene
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 0 - 20℃; for 3.5h; Substitution; | 100% |
In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; | 94% |
In tetrahydrofuran Ambient temperature; | 92% |
2'-O-acetyl-3-O-descladinosyl-3-O-allyl-6-O-methylerythromycin A 9-(E)-O-acetyloxime 11,12-cyclic carbonate
2-chloromethyl-1,3,5-trimethylbenzene
C46H72N2O12
Conditions | Yield |
---|---|
Stage #1: 2'-O-acetyl-3-O-descladinosyl-3-O-allyl-6-O-methylerythromycin A 9-(E)-O-acetyloxime 11,12-cyclic carbonate With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 2-chloromethyl-1,3,5-trimethylbenzene With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
2-chloromethyl-1,3,5-trimethylbenzene
(2S,3S)-1,4-bis(allyloxy)-2,3-dihydroxybutane
(2S,3S)-2,3-bis(2,4,6-trimethyl-phenylmethoxy)-1,4-bis(allyloxy)butane
Conditions | Yield |
---|---|
Stage #1: (2S,3S)-1,4-bis(allyloxy)-2,3-dihydroxybutane With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-chloromethyl-1,3,5-trimethylbenzene In N,N-dimethyl-formamide at 50℃; for 7h; | 99% |
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 60℃; | 99% |
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
In tetrahydrofuran addn. of 111 μmol of the benzylchloride to a soln. of 111 μmol of the bis(imido) compound in 7 ml THF at -40°C and evaporation;; extraction with pentane, filtration and concentration; coupling product present as an impurity; detn. by (1)H-NMR- and (13)C-NMR spectroscopy;; | 99% |
Conditions | Yield |
---|---|
With triethylamine for 1h; Heating; Inert atmosphere; Ionic liquid; | 99% |
sodium cyanide
2-chloromethyl-1,3,5-trimethylbenzene
mesitylacetonitrile
Conditions | Yield |
---|---|
With trimethyldodecylammonium chloride In toluene at 68 - 72℃; for 6h; Reagent/catalyst; Temperature; | 98.8% |
Conditions | Yield |
---|---|
With iron(III) sulfate; water In toluene at 110℃; for 0.7h; Ionic liquid; | 98% |
With potassium carbonate; acetone | |
Multi-step reaction with 2 steps 1: silver acetate; glacial acetic acid 2: aqueous KOH View Scheme |
1,4-dichloro-5-hydroxy-9,10-anthracenedione
2-chloromethyl-1,3,5-trimethylbenzene
1,4-dichloro-5-<(2,4,6-trimethylphenyl)methoxy>-9,10-anthracenedione
Conditions | Yield |
---|---|
With caesium carbonate | 98% |
With caesium carbonate In N,N-dimethyl-formamide; acetone for 23h; Heating; | 78% |
With caesium carbonate In N,N-dimethyl-formamide; acetone |
2-chloromethyl-1,3,5-trimethylbenzene
triphenylphosphine
Triphenyl<(2,4,6-trimethylphenyl)methyl>phosphoniumchlorid
Conditions | Yield |
---|---|
In benzene for 120h; Ambient temperature; | 98% |
In toluene for 12h; Heating; | 95% |
In benzene at 70℃; for 48h; | 80% |
2-chloromethyl-1,3,5-trimethylbenzene
Re{NC6H3(CH(CH3)2)2}3(CH2C6H2(CH3)3)
Conditions | Yield |
---|---|
In tetrahydrofuran addn. of 0.06 mmol of the benzyl compound (in 2 ml THF) to a soln. of 0.06 mmol of the tris(imido) compound in 8 ml THF and evaporation after 20 minutes;; extraction with pentane and cooling to -40°C; small amounts of the dibenzyl coupling product; detn. by (1)H-NMR- and (13)C-NMR spectroscopy;; | 98% |
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
In tetrahydrofuran addn. of 116 μmol of 2,4,6-trimethylbenzylchloride to a soln. of 116 μmol of the Na(THF)2 salt in 10 ml THF at -40°C and evaporation;; extraction with pentane, filtration, evaporation, solvation in pentane and concentration; contamination with the dibenzyl coupling product; detn. by (1)H-NMR- and (13)C-NMR spectroscopy;; | 98% |
Conditions | Yield |
---|---|
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h; | 98% |
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation; | 91% |
With sodium nitrate; acetic acid In water for 8h; Reflux; | 83% |
With potassium hydroxide; cetyltrimethylammonim bromide; potassium nitrate In water for 7.5h; pH=10 - 11; Reflux; | 82% |
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h; | 81% |
(S)-4-benzyl-1-(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazole
2-chloromethyl-1,3,5-trimethylbenzene
(S)-4-benzyl-1-(2,6-diisopropylphenyl)-3-(2,4,6-trimethylbenzyl)-4,5-dihydro-1H-imidazol-3-ium chloride
Conditions | Yield |
---|---|
In toluene at 100℃; for 1h; | 98% |
In acetonitrile at 110℃; for 5h; | 85% |
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
With Ni(1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene)(PPh3)Br2; magnesium In tetrahydrofuran at 0 - 60℃; for 24.5h; Glovebox; Inert atmosphere; Schlenk technique; | 98% |
Dichloromethyl methyl ether
2-chloromethyl-1,3,5-trimethylbenzene
2,4,6-trimethyl-3-(chloromethyl)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: Dichloromethyl methyl ether; 2-chloromethyl-1,3,5-trimethylbenzene With titanium tetrachloride In dichloromethane at 17 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: With water In dichloromethane for 0.25h; Inert atmosphere; | 97% |
With titanium tetrachloride In dichloromethane at 20℃; for 0.5h; | 84% |
With titanium tetrachloride In dichloromethane at 20℃; for 0.25h; | 64% |
2-chloromethyl-1,3,5-trimethylbenzene
thiophenol
2,4,6-trimethylbenzyl phenyl sulfide
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In chloroform; water for 16h; Ambient temperature; | 97% |
1-Methylbenzimidazole
2-chloromethyl-1,3,5-trimethylbenzene
1-methyl-3-(2,4,6-trimethylbenzyl)benzimidazolium chloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 95℃; for 4h; Inert atmosphere; Schlenk technique; | 97% |
In N,N-dimethyl-formamide at 80℃; Inert atmosphere; Schlenk technique; |
2-chloromethyl-1,3,5-trimethylbenzene
1-(2,4,6-trimethylbenzyl)-4,5-dihydroimidazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 25℃; for 6h; | 96% |
2-chloromethyl-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 70℃; Schlenk technique; | 96% |
2-chloromethyl-1,3,5-trimethylbenzene
2-(fluoromethyl)-1,3,5-trimethylbenzene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In acetonitrile for 2h; Reflux; | 95% |
With potassium fluoride; 18-crown-6 ether In acetonitrile at 80℃; for 90h; |
4-Benzyloxyphenol
2-chloromethyl-1,3,5-trimethylbenzene
1-benzyloxy-4-(2,4,6-trimethylbenzyloxy)benzene
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; | 95% |
4-cyclohexyl-2-mercapto-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile
2-chloromethyl-1,3,5-trimethylbenzene
4-cyclohexyl-6-oxo-2-(2,4,6-trimethyl-benzylsulfanyl)-1,6-dihydro-pyrimidine-5-carbonitrile
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 0 - 20℃; for 36h; | 95% |
piperazine
2-chloromethyl-1,3,5-trimethylbenzene
1-(2,4,6-trimethylbenzyl)-piperazine
Conditions | Yield |
---|---|
In tetrahydrofuran for 4h; Reflux; | 94.3% |
In tetrahydrofuran for 4h; Reflux; Inert atmosphere; | 49% |
2-chloromethyl-1,3,5-trimethylbenzene
benzonitrile
N-(2,4,6-trimethylbenzyl)benzamide
Conditions | Yield |
---|---|
With iron(III) chloride for 8h; Ritter reaction; Heating; | 94% |
2-chloromethyl-1,3,5-trimethylbenzene
N-(isobutyl)benzimidazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; Schlenk technique; | 94% |
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; Schlenk technique; | 94% |
In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere; Schlenk technique; | 94% |
In N,N-dimethyl-formamide at 80℃; for 24h; | 94% |
Conditions | Yield |
---|---|
Stage #1: 5,6-dimethyl-1H-benzo[d]imida-zole With potassium hydroxide In ethanol at 20℃; for 0.25h; Stage #2: 2-chloromethyl-1,3,5-trimethylbenzene In ethanol at 20℃; for 17h; Reflux; | 94% |
IUPAC Name: 2-(Chloromethyl)-1,3,5-trimethylbenzene
Synonyms of Benzene,2-(chloromethyl)-1,3,5-trimethyl- (CAS NO.1585-16-6): AI3-15521 ; EINECS 216-440-3 ; 2,4,6-Trimethylbenzyl chloride
CAS NO: 1585-16-6
Molecular Formula: C10H13Cl
Molecular Weight: 168.6632
Molecular Structure:
Melting Point: 87-89 °C
Product Categories: Miscellaneous ; Aromatics Compounds ; Aromatics
Freely Rotating Bonds: 1
Index of Refraction: 1.52
Molar Refractivity: 50.49 cm3
Molar Volume: 165.9 cm3
Surface Tension: 32.2 dyne/cm
Density of Benzene,2-(chloromethyl)-1,3,5-trimethyl- (CAS NO.1585-16-6): 1.016 g/cm3
Flash Point: 106.1 °C
Enthalpy of Vaporization: 46.22 kJ/mol
Boiling Point: 244.6 °C at 760 mmHg
Vapour Pressure: 0.047 mmHg at 25°C
Hazard Codes of Benzene,2-(chloromethyl)-1,3,5-trimethyl- (CAS NO.1585-16-6): C
Risk Statements: 34-20/21/22
R34: Causes burns.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-27-28-36/37/39-45-23
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27: Take off immediately all contaminated clothing.
S28: After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S23: Do not breathe vapour.
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
RTECS: DP1402000
HazardClass: 8
PackingGroup: II
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