1585-16-6

Basic information

• Product Name: alpha-2-Chloroisodurene
• Synonyms: 4,6-trimethylbenzyl chloride;Mesitylmethyl chloride;1-(Chloromethyl)-2,4,6-trimethylbenzene;2-(Chloromethyl)mesitylene;alpha-2-Chloroisodurene,98%;2,4,6-Trimethylbenzyl chloride;2,4,6-Trimethyl henzyl chloride;2-(Chloromethyl)-1,3,5-trimethylbenzene, alpha-2-Chloroisodurene
• CAS NO: 1585-16-6
• Molecular Formula: C₁₀H₁₃Cl
• Molecular Weight: 168.67
• EINECS: 216-440-3
• Product Categories: Aromatics;Miscellaneous;Aromatics Compounds
• Mol File: 1585-16-6.mol
• Article Data: 20

Chemical Properties

• Melting Point: 87-89 °C(lit.)
• Boiling Point: 140 °C15 mm Hg(lit.)
• Flash Point: 223 °F
• Appearance: White/Fused Solid, Crystals, and/or Chunks
• Density: 1.0131 (estimate)
• Vapor Pressure: 0.047mmHg at 25°C
• Refractive Index: 1.5162 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Stability: Air Sensitive, Moisture Sensitive
• BRN: 386678
• CAS DataBase Reference: alpha-2-Chloroisodurene(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-2-Chloroisodurene(1585-16-6)
• EPA Substance Registry System: alpha-2-Chloroisodurene(1585-16-6)

Safety Data

• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 26-27-28-36/37/39-45-23
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: DP1402000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1585-16-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

2,4,6-Trimethylbenzyl Chloride (cas# 1585-16-6) is a compound useful in organic synthesis.

General Description

α2-Chloroisodurene undergoes coupling reaction with methylmagnesium iodide to yield 1,2-dimesitylethane.

InChI:InChI=1/C10H13Cl/c1-7-4-8(2)10(6-11)9(3)5-7/h4-5H,6H2,1-3H3

Synthetic route

2,4,6-trimethylbenzyl alcohol (4170-90-5) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

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 (50-00-0) + 1,3,5-trimethyl-benzene (108-67-8) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

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 (4170-90-5) + benzoyl chloride (98-88-4) → (2,4,6-trimethylphenyl)methyl benzoate + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
With 1-methylsulfinyl-2-methoxybenzene In acetonitrile at 20℃; for 14h; Sealed tube;	A n/a B 74%

chloromethyl isocyanate (7093-91-6) + 1,3,5-trimethyl-benzene (108-67-8) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) + 2-Isocyanatomethyl-1,3,5-trimethyl-benzene (92277-70-8)

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 (107-30-2) + acetic acid (64-19-7) + 1,3,5-trimethyl-benzene (108-67-8) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
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) + acetic acid (64-19-7) + 1,3,5-trimethyl-benzene (108-67-8) → 2,4-bis(chloromethyl)mesitylene (1585-17-7) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
at 80℃;

chloromethyl methyl ether (107-30-2) + 1,3,5-trimethyl-benzene (108-67-8) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
With acetic acid at 65 - 80℃;

chloromethyl methyl ether (107-30-2) + 1,3,5-trimethyl-benzene (108-67-8) → 2,4-bis(chloromethyl)mesitylene (1585-17-7) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

ethyl chloromethyl ether (3188-13-4) + 1,3,5-trimethyl-benzene (108-67-8) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
With carbon disulfide; tin(IV) chloride
With tetrachloromethane; tin(IV) chloride at -5℃;
With acetic acid

formaldehyd (50-00-0) + 1,3,5-trimethyl-benzene (108-67-8) → 2,4-bis(chloromethyl)mesitylene (1585-17-7) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
With hydrogenchloride at 65℃; Einleiten von HCl;

hydrogenchloride (7647-01-0) + formaldehyd (50-00-0) + 1,3,5-trimethyl-benzene (108-67-8) → 2,4-bis(chloromethyl)mesitylene (1585-17-7) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
at 65℃; Einleiten von HCl;

hydrogenchloride (7647-01-0) + 2,4,6-trimethylbenzyl acetate (63548-92-5) → methyl-(2,4,6-trimethyl-benzyl)-ether (5336-55-0) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

hydrogenchloride (7647-01-0) + formaldehyd (50-00-0) + 1,3,5-trimethyl-benzene (108-67-8) → dimesitylmethane (733-07-3) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) + 1,3-dichloromethyl-2,4,6-trimethyl-benzene

formaldehyd (50-00-0) + 1,3,5-trimethyl-benzene (108-67-8) → 2,4,6-tris(chloromethyl)-mesitylene (3849-01-2) + 2,4-bis(chloromethyl)mesitylene (1585-17-7) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
With hydrogenchloride for 2h; Heating; Title compound not separated from byproducts.;

1,2,3,5-Tetramethylbenzene (527-53-7) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

Conditions	Yield
With hydrogenchloride; formaldehyd for 2h; Heating;

bis-(2,4,6-trimethyl-benzyl)-ether (4709-84-6) → 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6)

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 (143-33-9) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → mesitylacetonitrile (34688-71-6)

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 (1585-16-6) + dimethyl amine (124-40-3) → 2,4,6-trimethyl-<(dimethylamino)methyl>benzene (34274-10-7)

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 (1360059-83-1) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → C46H72N2O12 (1360059-88-6)

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 (1585-16-6) + (2S,3S)-1,4-bis(allyloxy)-2,3-dihydroxybutane (713132-48-0) → (2S,3S)-2,3-bis(2,4,6-trimethyl-phenylmethoxy)-1,4-bis(allyloxy)butane (713132-54-8)

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 (1585-16-6) + 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

Conditions	Yield
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} + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → {Re(NC6H3(CH(CH3)2)2)2(C2(CH2C(CH3)3)2)CH2C6H2(CH3)3}

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%

2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) + benzoic acid (65-85-0) → (2,4,6-trimethylphenyl)methyl benzoate

Conditions	Yield
With triethylamine for 1h; Heating; Inert atmosphere; Ionic liquid;	99%

sodium cyanide (773837-37-9) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → mesitylacetonitrile (34688-71-6)

Conditions	Yield
With trimethyldodecylammonium chloride In toluene at 68 - 72℃; for 6h; Reagent/catalyst; Temperature;	98.8%

2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 2,4,6-trimethylbenzyl alcohol (4170-90-5)

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 (6770-15-6) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 1,4-dichloro-5-<(2,4,6-trimethylphenyl)methoxy>-9,10-anthracenedione (123839-74-7)

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 (1585-16-6) + triphenylphosphine (603-35-0) → Triphenyl<(2,4,6-trimethylphenyl)methyl>phosphoniumchlorid (54757-04-9)

Conditions	Yield
In benzene for 120h; Ambient temperature;	98%
In toluene for 12h; Heating;	95%
In benzene at 70℃; for 48h;	80%

C36H51N3Re(1-) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → Re{NC6H3(CH(CH3)2)2}3(CH2C6H2(CH3)3) (135228-48-7)

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%

{Re(NC6H3(CH(CH3)2)2)(C2(CH2C(CH3)3)2)2}{Na(C4H8O)2} + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → {Re(NC6H3(CH(CH3)2)2)(C2(CH2C(CH3)3)2)2CH2C6H2(CH3)3}

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%

2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → mesytaldehyde (487-68-3)

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 (1353761-69-9) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → (S)-4-benzyl-1-(2,6-diisopropylphenyl)-3-(2,4,6-trimethylbenzyl)-4,5-dihydro-1H-imidazol-3-ium chloride (1450713-42-4)

Conditions	Yield
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 + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → (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	Yield
In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique;	98%

4-chloromethoxybenzene (623-12-1) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → (4-methoxyphenyl)-(2,4,6-trimethylphenyl)methane

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 (4885-02-3) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 2,4,6-trimethyl-3-(chloromethyl)benzaldehyde (105041-52-9)

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 (1585-16-6) + thiophenol (108-98-5) → 2,4,6-trimethylbenzyl phenyl sulfide (65597-70-8)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In chloroform; water for 16h; Ambient temperature;	97%

1-Methylbenzimidazole (1632-83-3) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 1-methyl-3-(2,4,6-trimethylbenzyl)benzimidazolium chloride (1258272-04-6)

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 (1585-16-6) + 1-(2,4,6-trimethylbenzyl)-4,5-dihydroimidazole (587887-00-1) → 1,3-bis(2,4,6-trimethylbenzyl)-4,5-dihydroimidazolium chloride

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 6h;	96%

1-(3,5-dimethylbenzyl)-5,6-dimethyl-1H-benzo[d]imidazole + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 5,6-dimethyl-1,3-bis(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole-3-ium chloride

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; Schlenk technique;	96%

2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 2-(fluoromethyl)-1,3,5-trimethylbenzene (75142-57-3)

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 (103-16-2) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 1-benzyloxy-4-(2,4,6-trimethylbenzyloxy)benzene (187328-97-8)

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 (290313-19-8) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 4-cyclohexyl-6-oxo-2-(2,4,6-trimethyl-benzylsulfanyl)-1,6-dihydro-pyrimidine-5-carbonitrile (1383539-70-5)

Conditions	Yield
With potassium carbonate In acetone at 0 - 20℃; for 36h;	95%

piperazine (110-85-0) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 1-(2,4,6-trimethylbenzyl)-piperazine (41717-26-4)

Conditions	Yield
In tetrahydrofuran for 4h; Reflux;	94.3%
In tetrahydrofuran for 4h; Reflux; Inert atmosphere;	49%

2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) + benzonitrile (100-47-0) → N-(2,4,6-trimethylbenzyl)benzamide (20781-30-0)

Conditions	Yield
With iron(III) chloride for 8h; Ritter reaction; Heating;	94%

2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) + N-(isobutyl)benzimidazole (305346-88-7) → 1-(isobutyl)-3-(2,4,6-trimethylbenzyl)benzimidazolium chloride

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%

5,6-dimethyl-1H-benzo[d]imida-zole (582-60-5) + 2-chloromethyl-1,3,5-trimethylbenzene (1585-16-6) → 5,6-dimethyl-1-(2,4,6-trimethylbenzyl)-1H-benzo[d]imidazole

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%

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 64-19-7 acetic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 3188-13-4 ethyl chloromethyl ether 
• 50-00-0 formaldehyd 
• 7093-91-6 chloromethyl isocyanate 
• 7647-01-0 hydrogenchloride 
• 63548-92-5 2,4,6-trimethylbenzyl acetate 
• 4709-84-6 bis-(2,4,6-trimethyl-benzyl)-ether 
• 4170-90-5 2,4,6-trimethylbenzyl alcohol 
• 98-88-4 benzoyl chloride 
• 527-53-7 1,2,3,5-Tetramethylbenzene 

Downstream Products

• 3982-67-0 ethylmesitylene 
• 4674-23-1 1,2-dimesitylethane 
• 36211-32-2 dodecyl-dimethyl-(2,4,6-trimethyl-benzyl)-ammonium; chloride 
• 132707-72-3 (2,4,6-trimethyl-benzylsulfanyl)-acetic acid 
• 60282-84-0 2-(2,4,6-Trimethylbenzyl)-2-thiopseudoharnstoff-hydrochlorid 
• 97268-36-5 diethyl 2,4,6-trimethylbenzylacetamidomalonate 
• 109444-41-9 trimethyl-(2,4,6-trimethyl-benzyl)-ammonium; chloride 
• 4170-90-5 2,4,6-trimethylbenzyl alcohol 
• 527-53-7 1,2,3,5-Tetramethylbenzene 
• 6319-71-7 2,4,6-Trimethylbenzylethylether 
• 63548-92-5 2,4,6-trimethylbenzyl acetate 
• 90794-13-1 1,2,3,5-tetrakis-chloromethyl-benzene 
• 5336-55-0 methyl-(2,4,6-trimethyl-benzyl)-ether 
• 40393-99-5 (2,4,6-trimethylbenzyl)amine 

Relevant articles and documents

Mechanism of solvolysis of substituted benzyl chlorides in aqueous ethanol

The mechanism of solvolyses of activated ortho-, meta- and para-substituted benzyl chlorides in aqueous ethanol has been studied by using the Hammett-Brown and Yukawa-Tsuno treatments as well as by correlating logarithms of solvolysis rate constants with relative stabilities of corresponding benzyl carbocations in water calculated at the IEFPCM-M06–2X/6-311+G(3df,3pd) level of theory. Benzyl chlorides containing strong conjugative electron-donors in the para-position solvolyze by the SN1 mechanism, whereas other activated benzyl chlorides solvolyze by the SN2 mechanism via loose transition states.

Selective Pd-catalyzed monoarylation of small primary alkyl amines through backbone-modification in ylide-functionalized phosphines (YPhos)

Ylide-substituted phosphines have been shown to be excellent ligands for C-N coupling reactions under mild reaction conditions. Here we report studies on the impact of the steric demand of the substituent in the ylide-backbone on the catalytic activity. Two new YPhos ligands with bulky ortho-tolyl (pinkYPhos) and mesityl (mesYPhos) substituents were synthesized, which are slightly more sterically demanding than their phenyl analogue but considerably less flexible. This change in the ligand design leads to higher selectivities and yields in the arylation of small primary amines compared to previously reported YPhos ligands. Even MeNH2 and EtNH2 could be coupled at room temperature with a series of aryl chlorides in high yields.

α-Diimine-Niobium Complex-Catalyzed Deoxychlorination of Benzyl Ethers with Silicon Tetrachloride

α-Diimine niobium complexes serve as catalysts for deoxygenation of benzyl ethers by silicon tetrachloride (SiCl4) to cleanly give two equivalents of the corresponding benzyl chlorides, where SiCl4 has the dual function of oxygen scavenger and chloride source with the formation of a silyl ether or silica as the only byproduct. The reaction mechanism has two successive trans-etherification steps that are mediated by the niobium catalyst, first forming one equivalent of benzyl chloride along with the corresponding silyl ether intermediate that undergoes the same reaction pathway to give the second equivalent of benzyl chloride and silyl ether.