Product Name

  • Name

    alpha-2-Chloroisodurene

  • EINECS 216-440-3
  • CAS No. 1585-16-6
  • Article Data34
  • CAS DataBase
  • Density 1.016 g/cm3
  • Solubility
  • Melting Point 87-89 °C(lit.)
  • Formula C10H13Cl
  • Boiling Point 244.6 °C at 760 mmHg
  • Molecular Weight 168.666
  • Flash Point 106.1 °C
  • Transport Information UN 3261 8/PG 2
  • Appearance white to light yellow crystal powder
  • Safety 26-27-28-36/37/39-45-23
  • Risk Codes 34-20/21/22
  • Molecular Structure Molecular Structure of 1585-16-6 (alpha-2-Chloroisodurene)
  • Hazard Symbols CorrosiveC
  • Synonyms (Chloromethyl)mesitylene;1,3,5-Trimethyl-2-(chloromethyl)benzene;1-Chloromethyl-2,4,6-trimethylbenzene;2,4,6-Trimethylbenzyl chloride;Mesitylmethyl chloride;NSC 405484;o,o,p-Trimethylbenzyl chloride;a-Chloroisodurene;
  • PSA 0.00000
  • LogP 3.35060

Synthetic route

2,4,6-trimethylbenzyl alcohol
4170-90-5

2,4,6-trimethylbenzyl alcohol

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
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
50-00-0

formaldehyd

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
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
4170-90-5

2,4,6-trimethylbenzyl alcohol

benzoyl chloride
98-88-4

benzoyl chloride

A

(2,4,6-trimethylphenyl)methyl benzoate

(2,4,6-trimethylphenyl)methyl benzoate

B

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
With 1-methylsulfinyl-2-methoxybenzene In acetonitrile at 20℃; for 14h; Sealed tube;A n/a
B 74%
chloromethyl isocyanate
7093-91-6

chloromethyl isocyanate

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

A

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

B

2-Isocyanatomethyl-1,3,5-trimethyl-benzene
92277-70-8

2-Isocyanatomethyl-1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With iron(III) chloride 1.) 40 - 60 deg C, 2.) 100 - 150 deg C, 2 h;A 15%
B 32%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

acetic acid
64-19-7

acetic acid

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
at 65℃; ohne Katalysator; Geschwindigkeit dieser Reaktion und der analogen Reaktionen mit anderen aromatischen Kohlenwasserstoffen bei 65grad und 100grad;
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

acetic acid
64-19-7

acetic acid

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

A

2,4-bis(chloromethyl)mesitylene
1585-17-7

2,4-bis(chloromethyl)mesitylene

B

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
at 80℃;
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
With acetic acid at 65 - 80℃;
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

A

2,4-bis(chloromethyl)mesitylene
1585-17-7

2,4-bis(chloromethyl)mesitylene

B

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
With carbon disulfide; tin(IV) chloride
With tetrachloromethane; tin(IV) chloride at -5℃;
With acetic acid
formaldehyd
50-00-0

formaldehyd

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

A

2,4-bis(chloromethyl)mesitylene
1585-17-7

2,4-bis(chloromethyl)mesitylene

B

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
With hydrogenchloride at 65℃; Einleiten von HCl;
hydrogenchloride
7647-01-0

hydrogenchloride

formaldehyd
50-00-0

formaldehyd

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

A

2,4-bis(chloromethyl)mesitylene
1585-17-7

2,4-bis(chloromethyl)mesitylene

B

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
at 65℃; Einleiten von HCl;
hydrogenchloride
7647-01-0

hydrogenchloride

2,4,6-trimethylbenzyl acetate
63548-92-5

2,4,6-trimethylbenzyl acetate

A

methyl-(2,4,6-trimethyl-benzyl)-ether
5336-55-0

methyl-(2,4,6-trimethyl-benzyl)-ether

B

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

hydrogenchloride
7647-01-0

hydrogenchloride

formaldehyd
50-00-0

formaldehyd

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

A

dimesitylmethane
733-07-3

dimesitylmethane

B

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

C

1,3-dichloromethyl-2,4,6-trimethyl-benzene

1,3-dichloromethyl-2,4,6-trimethyl-benzene

formaldehyd
50-00-0

formaldehyd

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

A

2,4,6-tris(chloromethyl)-mesitylene
3849-01-2

2,4,6-tris(chloromethyl)-mesitylene

B

2,4-bis(chloromethyl)mesitylene
1585-17-7

2,4-bis(chloromethyl)mesitylene

C

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating; Title compound not separated from byproducts.;
1,2,3,5-Tetramethylbenzene
527-53-7

1,2,3,5-Tetramethylbenzene

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
With hydrogenchloride; formaldehyd for 2h; Heating;
bis-(2,4,6-trimethyl-benzyl)-ether
4709-84-6

bis-(2,4,6-trimethyl-benzyl)-ether

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Conditions
ConditionsYield
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
143-33-9

sodium cyanide

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

mesitylacetonitrile
34688-71-6

mesitylacetonitrile

Conditions
ConditionsYield
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
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

dimethyl amine
124-40-3

dimethyl amine

2,4,6-trimethyl-<(dimethylamino)methyl>benzene
34274-10-7

2,4,6-trimethyl-<(dimethylamino)methyl>benzene

Conditions
ConditionsYield
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
1360059-83-1

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
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

C46H72N2O12
1360059-88-6

C46H72N2O12

Conditions
ConditionsYield
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
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

(2S,3S)-1,4-bis(allyloxy)-2,3-dihydroxybutane
713132-48-0

(2S,3S)-1,4-bis(allyloxy)-2,3-dihydroxybutane

(2S,3S)-2,3-bis(2,4,6-trimethyl-phenylmethoxy)-1,4-bis(allyloxy)butane
713132-54-8

(2S,3S)-2,3-bis(2,4,6-trimethyl-phenylmethoxy)-1,4-bis(allyloxy)butane

Conditions
ConditionsYield
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
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

9b-(3-butyl-phenyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-5,9b-dihydro-1H-2a,5-diaza-benzo[a]cyclobuta[c]cycloheptene-2,4-dione

9b-(3-butyl-phenyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-5,9b-dihydro-1H-2a,5-diaza-benzo[a]cyclobuta[c]cycloheptene-2,4-dione

9b-(3-butyl-phenyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(2,4,6-trimethyl-benzyl)-5,9b-dihydro-1H-2a,5-diaza-benzo[a]cyclobuta[c]cycloheptene-2,4-dione

9b-(3-butyl-phenyl)-1-(4,6-dimethyl-pyrimidin-2-yloxy)-5-(2,4,6-trimethyl-benzyl)-5,9b-dihydro-1H-2a,5-diaza-benzo[a]cyclobuta[c]cycloheptene-2,4-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 60℃;99%
{Re(NC6H3(CH(CH3)2)2)2(C2(CH2C(CH3)3)2)}(1-)*{Na(C4H8O)2}(1+)={Re(NC6H3(CH(CH3)2)2)2(C2(CH2C(CH3)3)2)}{Na(C4H8O)2}

{Re(NC6H3(CH(CH3)2)2)2(C2(CH2C(CH3)3)2)}(1-)*{Na(C4H8O)2}(1+)={Re(NC6H3(CH(CH3)2)2)2(C2(CH2C(CH3)3)2)}{Na(C4H8O)2}

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

{Re(NC6H3(CH(CH3)2)2)2(C2(CH2C(CH3)3)2)CH2C6H2(CH3)3}

{Re(NC6H3(CH(CH3)2)2)2(C2(CH2C(CH3)3)2)CH2C6H2(CH3)3}

Conditions
ConditionsYield
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%
2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

benzoic acid
65-85-0

benzoic acid

(2,4,6-trimethylphenyl)methyl benzoate

(2,4,6-trimethylphenyl)methyl benzoate

Conditions
ConditionsYield
With triethylamine for 1h; Heating; Inert atmosphere; Ionic liquid;99%
sodium cyanide
773837-37-9

sodium cyanide

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

mesitylacetonitrile
34688-71-6

mesitylacetonitrile

Conditions
ConditionsYield
With trimethyldodecylammonium chloride In toluene at 68 - 72℃; for 6h; Reagent/catalyst; Temperature;98.8%
2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

2,4,6-trimethylbenzyl alcohol
4170-90-5

2,4,6-trimethylbenzyl alcohol

Conditions
ConditionsYield
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
6770-15-6

1,4-dichloro-5-hydroxy-9,10-anthracenedione

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

1,4-dichloro-5-<(2,4,6-trimethylphenyl)methoxy>-9,10-anthracenedione
123839-74-7

1,4-dichloro-5-<(2,4,6-trimethylphenyl)methoxy>-9,10-anthracenedione

Conditions
ConditionsYield
With caesium carbonate98%
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
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

triphenylphosphine
603-35-0

triphenylphosphine

Triphenyl<(2,4,6-trimethylphenyl)methyl>phosphoniumchlorid
54757-04-9

Triphenyl<(2,4,6-trimethylphenyl)methyl>phosphoniumchlorid

Conditions
ConditionsYield
In benzene for 120h; Ambient temperature;98%
In toluene for 12h; Heating;95%
In benzene at 70℃; for 48h;80%
C36H51N3Re(1-)

C36H51N3Re(1-)

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

Re{NC6H3(CH(CH3)2)2}3(CH2C6H2(CH3)3)
135228-48-7

Re{NC6H3(CH(CH3)2)2}3(CH2C6H2(CH3)3)

Conditions
ConditionsYield
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%
{Re(NC6H3(CH(CH3)2)2)(C2(CH2C(CH3)3)2)2}{Na(C4H8O)2}

{Re(NC6H3(CH(CH3)2)2)(C2(CH2C(CH3)3)2)2}{Na(C4H8O)2}

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

{Re(NC6H3(CH(CH3)2)2)(C2(CH2C(CH3)3)2)2CH2C6H2(CH3)3}

{Re(NC6H3(CH(CH3)2)2)(C2(CH2C(CH3)3)2)2CH2C6H2(CH3)3}

Conditions
ConditionsYield
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%
2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

mesytaldehyde
487-68-3

mesytaldehyde

Conditions
ConditionsYield
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
1353761-69-9

(S)-4-benzyl-1-(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazole

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

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
1450713-42-4

(S)-4-benzyl-1-(2,6-diisopropylphenyl)-3-(2,4,6-trimethylbenzyl)-4,5-dihydro-1H-imidazol-3-ium chloride

Conditions
ConditionsYield
In toluene at 100℃; for 1h;98%
In acetonitrile at 110℃; for 5h;85%
(1R,5S)-1,8,8-trimethyl-4-(o-tolyl)-2,4-diazabicyclo[3.2.1]oct-2-ene

(1R,5S)-1,8,8-trimethyl-4-(o-tolyl)-2,4-diazabicyclo[3.2.1]oct-2-ene

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

(1R,5S)-1,8,8-trimethyl-4-(o-tolyl)-2-(2,4,6-trimethylbenzyl)-2,4-diazabicyclo[3.2.1]oct-2-en-2-ium chloride

(1R,5S)-1,8,8-trimethyl-4-(o-tolyl)-2-(2,4,6-trimethylbenzyl)-2,4-diazabicyclo[3.2.1]oct-2-en-2-ium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique;98%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

(4-methoxyphenyl)-(2,4,6-trimethylphenyl)methane

(4-methoxyphenyl)-(2,4,6-trimethylphenyl)methane

Conditions
ConditionsYield
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
4885-02-3

Dichloromethyl methyl ether

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

2,4,6-trimethyl-3-(chloromethyl)benzaldehyde
105041-52-9

2,4,6-trimethyl-3-(chloromethyl)benzaldehyde

Conditions
ConditionsYield
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
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

thiophenol
108-98-5

thiophenol

2,4,6-trimethylbenzyl phenyl sulfide
65597-70-8

2,4,6-trimethylbenzyl phenyl sulfide

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In chloroform; water for 16h; Ambient temperature;97%
1-Methylbenzimidazole
1632-83-3

1-Methylbenzimidazole

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

1-methyl-3-(2,4,6-trimethylbenzyl)benzimidazolium chloride
1258272-04-6

1-methyl-3-(2,4,6-trimethylbenzyl)benzimidazolium chloride

Conditions
ConditionsYield
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
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

1-(2,4,6-trimethylbenzyl)-4,5-dihydroimidazole
587887-00-1

1-(2,4,6-trimethylbenzyl)-4,5-dihydroimidazole

1,3-bis(2,4,6-trimethylbenzyl)-4,5-dihydroimidazolium chloride

1,3-bis(2,4,6-trimethylbenzyl)-4,5-dihydroimidazolium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; for 6h;96%
1-(3,5-dimethylbenzyl)-5,6-dimethyl-1H-benzo[d]imidazole

1-(3,5-dimethylbenzyl)-5,6-dimethyl-1H-benzo[d]imidazole

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

5,6-dimethyl-1,3-bis(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole-3-ium chloride

5,6-dimethyl-1,3-bis(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole-3-ium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70℃; Schlenk technique;96%
2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

2-(fluoromethyl)-1,3,5-trimethylbenzene
75142-57-3

2-(fluoromethyl)-1,3,5-trimethylbenzene

Conditions
ConditionsYield
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
103-16-2

4-Benzyloxyphenol

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

1-benzyloxy-4-(2,4,6-trimethylbenzyloxy)benzene
187328-97-8

1-benzyloxy-4-(2,4,6-trimethylbenzyloxy)benzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃;95%
4-cyclohexyl-2-mercapto-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile
290313-19-8

4-cyclohexyl-2-mercapto-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

4-cyclohexyl-6-oxo-2-(2,4,6-trimethyl-benzylsulfanyl)-1,6-dihydro-pyrimidine-5-carbonitrile
1383539-70-5

4-cyclohexyl-6-oxo-2-(2,4,6-trimethyl-benzylsulfanyl)-1,6-dihydro-pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone at 0 - 20℃; for 36h;95%
piperazine
110-85-0

piperazine

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

1-(2,4,6-trimethylbenzyl)-piperazine
41717-26-4

1-(2,4,6-trimethylbenzyl)-piperazine

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Reflux;94.3%
In tetrahydrofuran for 4h; Reflux; Inert atmosphere;49%
2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

benzonitrile
100-47-0

benzonitrile

N-(2,4,6-trimethylbenzyl)benzamide
20781-30-0

N-(2,4,6-trimethylbenzyl)benzamide

Conditions
ConditionsYield
With iron(III) chloride for 8h; Ritter reaction; Heating;94%
2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

N-(isobutyl)benzimidazole
305346-88-7

N-(isobutyl)benzimidazole

1-(isobutyl)-3-(2,4,6-trimethylbenzyl)benzimidazolium chloride

1-(isobutyl)-3-(2,4,6-trimethylbenzyl)benzimidazolium chloride

Conditions
ConditionsYield
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%
5,6-dimethyl-1H-benzo[d]imida-zole
582-60-5

5,6-dimethyl-1H-benzo[d]imida-zole

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

5,6-dimethyl-1-(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole

5,6-dimethyl-1-(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
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%

alpha-2-Chloroisodurene Chemical Properties

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

alpha-2-Chloroisodurene Safety Profile

Hazard Codes of Benzene,2-(chloromethyl)-1,3,5-trimethyl- (CAS NO.1585-16-6): CorrosiveC
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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