Conditions | Yield |
---|---|
With chloro-trimethyl-silane; trimethylsilan In acetic acid methyl ester at 0℃; for 4h; | 80% |
3-methylbenzyl Co(III)(dmgH)2py
1-chloromethyl-3-methyl-benzene
Conditions | Yield |
---|---|
With chlorine In chloroform a solution of two equivalents of halogen added dropwise to a solution of organocobaloxime at room temperature under nitrogen in the dark; NMR, UV; | 75% |
With chlorine In acetic acid a solution of two equivalents of halogen added dropwise to a solution of organocobaloxime at room temperature under nitrogen in the dark; NMR, UV; | 75% |
Conditions | Yield |
---|---|
With N-chloro-succinimide In 1,2-dichloro-ethane at 80℃; regiospecific reaction; | 70% |
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; copper(II) acetate monohydrate In dichloromethane at 25℃; for 42h; | 33% |
With N-chloro-succinimide; N-hydroxyphthalimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 80℃; for 16h; Time; Sealed tube; Inert atmosphere; | 26% |
N-chloro-succinimide
m-xylene
A
1-chloromethyl-3-methyl-benzene
B
3-(chloromethyl)benzyl chloride
Conditions | Yield |
---|---|
Irradiation.UV-Licht; |
Conditions | Yield |
---|---|
With hydrogenchloride at 60 - 70℃; |
tetrachloromethane
acetic acid-(2,4,6,N-tetrachloro-anilide)
m-xylene
dibenzoyl peroxide
1-chloromethyl-3-methyl-benzene
Conditions | Yield |
---|---|
With triethylsilane; zinc(II) chloride |
3-methyl-benzylium
1-chloromethyl-3-methyl-benzene
Conditions | Yield |
---|---|
With tertiary butyl chloride In gaseous matrix at 600℃; chloride affinity; |
dichloro-phenyl-methylium
1-chloromethyl-3-methyl-benzene
Conditions | Yield |
---|---|
With tertiary butyl chloride In gaseous matrix at 600℃; chloride affinity; |
3-methylbicyclo<4.1.0>hepta-1,3,5-triene
A
1-chloromethyl-3-methyl-benzene
B
4-Methylbenzyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride In tetrachloromethane for 1h; Yield given. Yields of byproduct given; |
2-methyl-1H-cyclopropabenzene
A
1-chloromethyl-3-methyl-benzene
B
1-chloromethyl-2-methylbenzene
Conditions | Yield |
---|---|
With hydrogenchloride In tetrachloromethane for 1h; Product distribution; Mechanism; reaction regioselectivity; a series of reagents; |
m-xylene
A
1-chloromethyl-3-methyl-benzene
B
3-(chloromethyl)benzyl chloride
C
m-chloromethylbenzylidene chloride
D
α,α-dichloro-m-xylene
E
α,α,α',α'-Tetrachloro-m-xylene
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); chlorine at 70℃; for 1.2h; Product distribution; various educt-reagent ratio, various time; |
<(3-methylphenyl)methyl>trimethylsilane
oxovanadium(V) ethoxydichloride
A
1-chloromethyl-3-methyl-benzene
B
α-ethoxy-m-xylene
Conditions | Yield |
---|---|
In acetonitrile Product distribution; -30 deg C, 2 h; RT, 4 h; |
Conditions | Yield |
---|---|
With perchloric acid; trichloroisocyanuric acid In acetic acid at 35℃; Rate constant; Mechanism; | |
With perchloric acid; trichloroisocyanuric acid In acetic acid at 35℃; |
3-(chloromethyl)benzyl chloride
A
1-chloromethyl-3-methyl-benzene
B
1,2-di-m-tolylethane
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; N,N-dimethyl-formamide Ambient temperature; n-Bu4NBF4, Hg pool cathode, SCE reference electrode; | A 1 % Spectr. B 43 % Spectr. C 12 % Spectr. |
chloromethyl methyl ether
toluene
A
1-chloromethyl-3-methyl-benzene
B
1-chloromethyl-2-methylbenzene
C
4-Methylbenzyl chloride
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 25℃; Rate constant; Mechanism; | A 0.5 % Chromat. B 31 % Chromat. C 69 % Chromat. |
chloromethyl methyl ether
toluene
A
1-chloromethyl-3-methyl-benzene
B
1-chloromethyl-2-methylbenzene
C
4-Methylbenzyl chloride
Conditions | Yield |
---|---|
With aluminium trichloride In nitromethane at 0℃; Product distribution; Mechanism; | A 0.37 % Chromat. B 31 % Chromat. C 68 % Chromat. D n/a |
Methoxyacetyl chloride
toluene
A
carbon monoxide
B
1-chloromethyl-3-methyl-benzene
C
1-chloromethyl-2-methylbenzene
D
4-Methylbenzyl chloride
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 25℃; Rate constant; |
Methoxyacetyl chloride
toluene
A
carbon monoxide
B
1-chloromethyl-3-methyl-benzene
C
1-chloromethyl-2-methylbenzene
D
4-Methylbenzyl chloride
Conditions | Yield |
---|---|
With aluminium trichloride In nitromethane at 0℃; for 0.555h; Product distribution; Rate constant; Mechanism; effects of various periods of time (up to 1072.5 min) and conc. of AlCl3; | A n/a B 0.52 % Chromat. C 26.54 % Chromat. D 73.22 % Chromat. E n/a |
4-(1-Chloro-2,2,2-trifluoro-ethyl)-1,2-dimethyl-benzene
3-methyl-benzylium
A
1-chloromethyl-3-methyl-benzene
B
C10H10F3(1+)
Conditions | Yield |
---|---|
at 69.85℃; Thermodynamic data; chloride-transfer; |
Conditions | Yield |
---|---|
Dampfphase.Irradiation; | |
Irradiation; |
tetrachloromethane
sulfuryl dichloride
m-xylene
dibenzoyl peroxide
1-chloromethyl-3-methyl-benzene
hydrogenchloride
formaldehyd
water
toluene
A
1-chloromethyl-3-methyl-benzene
B
1-chloromethyl-2-methylbenzene
C
4-Methylbenzyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous-alcoholic sulfuric acid / bei der elektrolytischen Reduktion 2: hydrogen chloride / 60 - 70 °C View Scheme |
m-xylene
A
1-chloromethyl-3-methyl-benzene
B
3-(chloromethyl)benzyl chloride
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); 1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril In tetrachloromethane at 81℃; for 2h; Inert atmosphere; | A 52 %Chromat. B 16 %Chromat. |
1-chloromethyl-3-methyl-benzene
triphenylphosphine
(3-methylbenzyl)triphenylphosphonium chloride
Conditions | Yield |
---|---|
In acetonitrile for 4.5h; Reflux; | 100% |
In benzene | |
Yield given; | |
In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; Reflux; | 28 g |
In toluene at 20℃; Reflux; |
1-chloromethyl-3-methyl-benzene
(Z)-6-methoxy-2-(pyridin-4-ylmethylene)benzofuran-3(2H)-one
(Z)-1-(3-methylbenzyl)-4-((6-methoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)pyridinium chloride
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 100% |
1-chloromethyl-3-methyl-benzene
(Z)-6-ethoxy-2-(pyridin-4-ylmethylene)benzofuran-3(2H)-one
(Z)-1-(3-methylbenzyl)-4-((6-ethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)pyridinium chloride
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 100% |
1-chloromethyl-3-methyl-benzene
(Z)-6-propoxy-2-(pyridin-4-ylmethylene)benzofuran-3(2H)-one
(Z)-1-(3-methylbenzyl)-4-((6-propoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)pyridinium chloride
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 100% |
Conditions | Yield |
---|---|
With palladium dichloride In methanol at 40℃; for 1h; Green chemistry; chemoselective reaction; | 99% |
With Perbenzoic acid; tri-n-butyl-tin hydride In benzene at 90℃; for 12h; Mechanism; in the presence of α-chlorotoluene (competitor), relative reactivity; |
1-chloromethyl-3-methyl-benzene
phenylboronic acid
1-methyl-3-(phenylmethyl)-benzene
Conditions | Yield |
---|---|
With C58H82Cl4N6Pd2; potassium tert-butylate In water; isopropyl alcohol at 80℃; for 4h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 99% |
With potassium phosphate; triphenylphosphine; palladium diacetate In toluene for 19h; Suzuki cross-coupling reaction; | 96% |
With potassium phosphate; C114H132Cl6N10Pd3 In water; isopropyl alcohol at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 96% |
With potassium carbonate; N,N-dimethyl-formamide; palladium dichloride In water at 90℃; for 1h; Suzuki Coupling; | 90% |
With potassium carbonate; sodium chloride; palladium dichloride; cucurbituril In ethanol; water at 90℃; for 1h; Suzuki Coupling; Inert atmosphere; | 76% |
1-chloromethyl-3-methyl-benzene
tributyl(p-tolyl)stannane
1-methyl-3-(4-methylbenzyl)benzene
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium fluoride; palladium diacetate In 1,4-dioxane at 80℃; for 3h; Stille cross-coupling; | 99% |
4-morpholinecarboxaldehyde
1-chloromethyl-3-methyl-benzene
4-(3-methylbenzyl)morpholine
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique; | 99% |
With potassium hydroxide In water at 50℃; for 3h; Green chemistry; | 80% |
1-chloromethyl-3-methyl-benzene
para-thiocresol
1-methyl-3-((p-tolylsulfinyl)methyl)benzene
Conditions | Yield |
---|---|
With iodine pentoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 6h; | 99% |
With iodine pentoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 100℃; for 6h; | 98% |
Conditions | Yield |
---|---|
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation; | 98% |
With 4-methylmorpholine N-oxide; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; potassium iodide at 100℃; for 0.0333333h; Microwave irradiation; Ionic liquid; | 90% |
With 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃; for 12h; Reflux; | 80% |
1-chloromethyl-3-methyl-benzene
2-iodophenylamine
2-(m-tolyl)benzo[d]thiazole
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate; sodium carbonate; sulfur In dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; | 98% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 95℃; for 4h; Inert atmosphere; Schlenk technique; | 97% |
1-methyl-1H-imidazole
1-chloromethyl-3-methyl-benzene
1-methyl-3-(3’-methylbenzyl)imidazolium chloride
Conditions | Yield |
---|---|
In acetonitrile for 48h; Inert atmosphere; Reflux; | 96% |
In tetrahydrofuran at 69.84℃; for 48h; | 94% |
In acetonitrile at 59.84℃; Kinetics; Mechanism; Solvent; Menshutkin reaction; | |
In toluene at 45 - 105℃; for 24.5h; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; | 96% |
1-chloromethyl-3-methyl-benzene
2-Chloronitrobenzene
2-(m-tolyl)benzo[d]thiazole
Conditions | Yield |
---|---|
With N-methylcyclohexylamine; sulfur at 110℃; for 24h; Sealed tube; Inert atmosphere; | 96% |
1-chloromethyl-3-methyl-benzene
potassium thioacyanate
3-methylbenzyl thiocyanate
Conditions | Yield |
---|---|
With silica gel at 30℃; for 48h; | 95% |
With Fe3O4*SiO2/DABCO In water at 90℃; for 1.5h; | 85% |
1-chloromethyl-3-methyl-benzene
2-chloroindole-3-carboxaldehyde
2-Chloro-1-(3-methyl-benzyl)-1H-indole-3-carbaldehyde
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 6h; | 95% |
With potassium carbonate In acetone at 20℃; for 2h; |
1-chloromethyl-3-methyl-benzene
phenyltriisopropoxytitanium(IV)
1-methyl-3-(phenylmethyl)-benzene
Conditions | Yield |
---|---|
With palladium diacetate; Tri(p-tolyl)phosphine In toluene at 25℃; for 2h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: 4-Methylbenzyl bromide With thiourea In methanol Inert atmosphere; Reflux; Stage #2: With sodium hydroxide In methanol Inert atmosphere; Reflux; Stage #3: 1-chloromethyl-3-methyl-benzene In methanol at 20℃; Inert atmosphere; Reflux; | 95% |
1-chloromethyl-3-methyl-benzene
1-(azidomethyl)-3-methylbenzene
Conditions | Yield |
---|---|
With sodium azide; potassium iodide In water; acetone at 20℃; for 60h; Inert atmosphere; | 95% |
With sodium azide In water at 90℃; for 0.25h; | 88% |
With sodium azide In water at 80℃; for 0.333333h; Green chemistry; | 82% |
1-chloromethyl-3-methyl-benzene
potassium 2-cyano-2-methyl-propanoate
2,2-dimethyl-3-(m-tolyl)propanenitrile
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)) In toluene at 110℃; for 12h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; lithium tert-butoxide In toluene at 130℃; for 3h; Inert atmosphere; Sealed tube; | 95% |
Conditions | Yield |
---|---|
Stage #1: 1-H-perimidine With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 1-chloromethyl-3-methyl-benzene In dimethyl sulfoxide at 110℃; for 0.5h; Microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 6h; Reflux; Inert atmosphere; | 95% |
1-chloromethyl-3-methyl-benzene
5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-thiol
5,7-dimethyl-2-(3-methyl-benzylsulfanyl)-[1,2,4]triazolo[1,5-a]pyrimidine
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 25℃; | 94% |
1-chloromethyl-3-methyl-benzene
phenylacetylene
1‐(3‐methylbenzyl)‐4‐phenyl‐1H‐1,2,3‐triazole
Conditions | Yield |
---|---|
With sodium azide; sodium L-ascorbate In water; tert-butyl alcohol at 70℃; for 0.75h; Huisgen Cycloaddition; Green chemistry; regioselective reaction; | 94% |
With sodium azide In water at 70℃; for 7h; Huisgen Cycloaddition; Green chemistry; regioselective reaction; | 91% |
With sodium azide; sodium L-ascorbate In water at 70℃; for 3h; | 90% |
1-chloromethyl-3-methyl-benzene
(E)-3,3'-dimethylstilbene
Conditions | Yield |
---|---|
With Benzyl phenyl selenoxide; potassium hexamethylsilazane In toluene at 25℃; for 4h; Inert atmosphere; | 94% |
With potassium phenyl selenide In 1,2-dimethoxyethane for 5h; Inert atmosphere; Sealed tube; | 84% |
With sodium 4-methylbenzenesulfinate; potassium hydroxide In dimethyl sulfoxide at 100℃; for 16h; | 66% |
Conditions | Yield |
---|---|
Stage #1: 1-chloromethyl-3-methyl-benzene With thiourea In methanol Inert atmosphere; Reflux; Stage #2: With sodium hydroxide In methanol Inert atmosphere; Reflux; Stage #3: 1-chloromethyl-2-methylbenzene In methanol at 20℃; Inert atmosphere; Reflux; | 94% |
Diisopropylsilyl dichloride
1-chloromethyl-3-methyl-benzene
diisopropyl(3-methylbenzyl)silanol
Conditions | Yield |
---|---|
Stage #1: Diisopropylsilyl dichloride; 1-chloromethyl-3-methyl-benzene With iodine; magnesium In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; | 94% |
Stage #1: 1-chloromethyl-3-methyl-benzene With magnesium In diethyl ether at 0℃; Reflux; Stage #2: Diisopropylsilyl dichloride In tetrahydrofuran; diethyl ether at 0℃; for 12h; Reflux; Stage #3: With triethylamine; sodium chloride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; | 76% |
IUPAC Name: 1-(Chloromethyl)-3-methylbenzene
Canonical SMILES: CC1=CC(=CC=C1)CCl
InChI: InChI=1S/C8H9Cl/c1-7-3-2-4-8(5-7)6-9/h2-5H,6H2,1H3
InChIKey: LZBOHNCMCCSTJX-UHFFFAOYSA-N
Molecular Weight: 140.61006 [g/mol]
Molecular Formula: C8H9Cl
XLogP3: 2.9
EINECS: 210-628-9
Index of Refraction: 1.524
Molar Refractivity: 40.84 cm3
Molar Volume: 133.4 cm3
Surface Tension: 33.1 dyne/cm
Density: 1.054 g/cm3
Flash Point: 75.6 °C
Enthalpy of Vaporization: 41.63 kJ/mol
Boiling Point: 197.9 °C at 760 mmHg
Vapour Pressure: 0.521 mmHg at 25 °C
storage temp.: Refrigerator (+4 °C)
Water Solubility: Insoluble
Appearance of m-Xylyl chloride (CAS NO.620-19-9): clear colorless to slightly yellow liquid
Hazard Codes: C,Xi
Risk Statements: 34-36/37-36/37/38
R34:Causes burns.
R36/37:Irritating to eyes and respiratory system.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-26-27-36/37/39-45-37/39
S23:Do not breathe vapour.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27:Take off immediately all contaminated clothing.
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.)
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 3265 8/PG 2
WGK Germany: 2
Hazard Note: Irritant/Corrosive
HazardClass: 8
PackingGroup of m-Xylyl chloride (CAS NO.620-19-9): III
m-Xylyl chloride (CAS NO.620-19-9), its Synonyms are 3-(Chloromethyl)toluene ; 3-Methylbenzyl chloride ; alpha-Chloro-m-xylene ; m-(Chloromethyl)toluene ; m-Methylbenzyl chloride ; m-Xylyl-alpha-chloride ; Benzene, 1-(chloromethyl)-3-methyl- (9CI) ; m-Xylene, alpha-chloro- (8CI) .
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