1,2-Bis(chloromethyl)benzene supplier

Name
1,2-Bis(chloromethyl)benzene
EINECS 210-291-8
CAS No. 612-12-4
Article Data23
CAS DataBase
Density 1.208 g/cm³
Solubility hydrolysis with water
Melting Point 51-55 °C(lit.)
Formula C₈H₈Cl₂
Boiling Point 239.5 °C at 760 mmHg
Molecular Weight 175.058
Flash Point 114.1 °C
Transport Information UN 3261 8/PG 2
Appearance white to light yellow crystal powder
Safety 26-27-28-36/37/39-45-24/25-61-29-28A
Risk Codes 34-36/37-36/37/38-50/53-26-22-36
Molecular Structure
Hazard Symbols C, Xi
Synonyms o-Xylene, a,a'-dichloro- (7CI,8CI);NSC 71934;o-Bis(chloromethyl)benzene;o-Xylene-a,a'-dichloride;o-Xylylene dichloride;a,a'-Dichloro-o-xylene;
PSA 0.00000
LogP 3.16420

Synthetic route

: 612-14-6
phthalyl alcohol

A: 496-14-0
1,3-dihydroisobenzofuran

B: 612-12-4
o-Xylylene dichloride

C: 142066-41-9
2-(chloromethyl)-phenyl methanol

Conditions

Conditions	Yield
With hydrogenchloride In water at 70℃; for 1h;	A n/a B n/a C 91%

...Expand

: 98-07-7
Benzotrichlorid

: 612-14-6
phthalyl alcohol

A: 98-87-3
benzylidene dichloride

B: 612-12-4
o-Xylylene dichloride

Conditions

Conditions	Yield
With TOP; phenylsilane In neat (no solvent) at 100℃; for 24h; Appel Halogenation; Inert atmosphere;	A n/a B 65%

...Expand

: 95-47-6
o-xylene

A: 612-12-4
o-Xylylene dichloride

B: 30293-58-4
α,α,α'-trichloro-o-xylene

C: 60973-59-3
α,α-dichloro-o-xylene

D: 552-45-4
1-chloromethyl-2-methylbenzene

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); chlorine at 90℃; for 4h;	A 50.5% B n/a C n/a D n/a

...Expand

: 128-09-6
N-chloro-succinimide

: 95-47-6
o-xylene

: 612-12-4
o-Xylylene dichloride

Conditions

Conditions	Yield
Irradiation.UV-Licht;

: 128-09-6
N-chloro-succinimide

: 95-47-6
o-xylene

A: 612-12-4
o-Xylylene dichloride

B: 552-45-4
1-chloromethyl-2-methylbenzene

Conditions

Conditions	Yield
UV-Licht.Irradiation;

...Expand

: 95-47-6
o-xylene

: 612-12-4
o-Xylylene dichloride

Conditions

Conditions	Yield
With phosphorus pentachloride at 190℃;
durch Chlorierung im Sonnenlicht;
With chlorine Irradiation;

: 131-11-3
phthalic acid dimethyl ester

: 612-12-4
o-Xylylene dichloride

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether Erhitzen des Reaktionsgemisches mit konz. wss. Salzsaeure;

: 861338-62-7
bis-(2-ethoxymethyl-benzyl)-amine

A: 612-12-4
o-Xylylene dichloride

B: 38379-25-8
o-chloromethylbenzylamine

Conditions

Conditions	Yield
With hydrogenchloride; ethanol

: 50-00-0
formaldehyd

: 100-44-7
benzyl chloride

A: 612-12-4
o-Xylylene dichloride

B: 623-25-6
p-Xylylene dichloride

Conditions

Conditions	Yield
With zinc(II) chloride at 80℃; Einleiten von HCl;
With aluminium trichloride; 1,2-dichloro-ethane; zinc(II) chloride at 50℃; Einleiten von HCl;

...Expand

: 612-14-6
phthalyl alcohol

: 612-12-4
o-Xylylene dichloride

Conditions

Conditions	Yield
With hydrogenchloride
With acetyl chloride; zinc(II) chloride
With tetrachloromethane; triphenylphosphine

: 50-00-0
formaldehyd

: 108-88-3
toluene

A: 612-12-4
o-Xylylene dichloride

B: 623-25-6
p-Xylylene dichloride

Conditions

Conditions	Yield
With hydrogenchloride at 80 - 90℃; Leiten von Chlor in das Reaktionsgemisch bei 125-135grad;
With hydrogenchloride at 80 - 90℃; Behandlung des Reaktionsgemisches mit Chlor bei 125-135grad;

...Expand

: 95-47-6
o-xylene

A: 612-12-4
o-Xylylene dichloride

B: 30293-58-4
α,α,α'-trichloro-o-xylene

C: 552-45-4
1-chloromethyl-2-methylbenzene

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); benzyl(trimethyl)ammonium tetrachloroiodate In tetrachloromethane for 6h; Heating;	A 49 % Spectr. B 12 % Spectr. C 30 % Spectr.

...Expand

: 7647-01-0
hydrogenchloride

: 50-00-0
formaldehyd

: 100-44-7
benzyl chloride

ZnCl2: ZnCl2

A: 612-12-4
o-Xylylene dichloride

B: 623-25-6
p-Xylylene dichloride

Conditions

Conditions	Yield
at 80℃;

...Expand

: 7647-01-0
hydrogenchloride

: 50-00-0
formaldehyd

: 7446-70-0
aluminium trichloride

: 100-44-7
benzyl chloride

ZnCl2: ZnCl2

A: 14568-83-3
4,4'-bis(chloromethyl)diphenylmethane

B: 612-12-4
o-Xylylene dichloride

C: 626-16-4
3-(chloromethyl)benzyl chloride

D: 623-25-6
p-Xylylene dichloride

Conditions

Conditions	Yield
at 50℃; Verb. 5: 1.2-Dichlor-aethan;

...Expand

: 95-47-6
o-xylene

A: 612-12-4
o-Xylylene dichloride

B: 552-45-4
1-chloromethyl-2-methylbenzene

Conditions

Conditions	Yield
With chlorine In tetrachloromethane for 0.0833333h; Photolysis;
With 2,2'-azobis(isobutyronitrile); 1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril In tetrachloromethane at 81℃; for 2h; Temperature; Time; Inert atmosphere;	A 26 %Chromat. B 41 %Chromat.

: 88-95-9
Phthaloyl dichloride

: 612-12-4
o-Xylylene dichloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; sodium amalgam 2: concentrated hydrochloric acid View Scheme

: 288-32-4
1H-imidazole

: 612-12-4
o-Xylylene dichloride

: C14H16N4

Conditions

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: o-Xylylene dichloride In N,N-dimethyl-formamide at 20℃; for 4h;	100%

: bis{1,2-bis(methylphosphino)ethane}palladium(II) dichloride

: 612-12-4
o-Xylylene dichloride

: Pd(C6H4(CH2P(CH3)CH2CH2P(CH3)CH2)2C6H4)(2+)*2Cl(1-)=(Pd(C6H4(CH2P(CH3)CH2CH2P(CH3)CH2)2C6H4))Cl2

Conditions

Conditions	Yield
With potassium carbonate In ethanol (under Ar); addn. of K2CO3 and the dihalogenide to a soln. of the Pd complex in EtOH, stirring at room temp. for 2 h; filtn., washing the ppt. with EtOH, evapn. of the solvent under vac. at 40°C, recrystn. from EtOH at -20°C;	99%

: 612-12-4
o-Xylylene dichloride

: 62-53-3
aniline

: 19375-67-8
2-phenylisoindoline

Conditions

Conditions	Yield
With potassium carbonate In water at 105℃; for 0.333333h; Concentration; Microwave irradiation; Green chemistry;	99%

: 612-12-4
o-Xylylene dichloride

: 5,6-dibromo-4,7-dibutylbenzo[1,2,3]triselenole

: 1,2-(o-xylylenediseleno)-3,6-dibutyl-4,5-dibromobenzene

Conditions

Conditions	Yield
Stage #1: 5,6-dibromo-4,7-dibutylbenzo[1,2,3]triselenole With sodium tetrahydroborate In tetrahydrofuran; methanol for 0.0833333h; Stage #2: o-Xylylene dichloride With potassium carbonate In tetrahydrofuran; methanol at 20℃;	99%

: 612-12-4
o-Xylylene dichloride

: 106-40-1
4-bromo-aniline

: 2-(4-bromophenyl)isoindoline

Conditions

Conditions	Yield
With potassium carbonate In water at 105℃; for 0.333333h; Concentration; Microwave irradiation; Green chemistry;	98%

: bis{1,2-bis(methylphosphino)ethane}palladium(II) dichloride

: 612-12-4
o-Xylylene dichloride

: 102258-62-8
chloro(5,6,7,8,9,10,15,16,17,18,19,20-dodecahydro-6,9,16,19-tetramethyldibenzo{f,n}-{1,4,9,12}-tetraphosphacyclohexadecine-P,P',P'',P''')palladium(II)-hydrogencarbonate

Conditions

Conditions	Yield
With K2CO3 In ethanol (N2); added K2CO3 and 1,2-bis(chloromethyl)benzene to soln. of Pd-compound; filtered after 1 h; washed with ethanol; elem. anal.;	97%

: 107-31-3
Methyl formate

: 612-12-4
o-Xylylene dichloride

: 1933-00-2
o-xylyleneglycolbisformate

Conditions

Conditions	Yield
With sodium chloride; sodium formate; triethylamine	96.5%

: 612-12-4
o-Xylylene dichloride

: 78499-87-3
bis(chloromagnesiummethyl)benzol

Conditions

Conditions	Yield
With magnesium; ethylene dibromide In tetrahydrofuran	96%
With magnesium; iodine In tetrahydrofuran	91%
With polymer supported 'magnesium(anthracene)'	90%
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 20.25h;

: 612-12-4
o-Xylylene dichloride

: 496-14-0
1,3-dihydroisobenzofuran

Conditions

Conditions	Yield
With sodium hydroxide In water at 100℃; for 4h; pH=12;	96%
With aluminum oxide for 0.166667h; microwave irradiation;	69%

: 612-12-4
o-Xylylene dichloride

: 536-74-3
phenylacetylene

: 137959-33-2
1,1'-(o-phenylenedimethylene)bis<4-phenyl-1H-1,2,3-triazole>

Conditions

Conditions	Yield
With copper(l) iodide; sodium azide In water at 100℃; for 10h;	96%
With sodium azide In water at 60℃; for 4h; Huisgen Cycloaddition;	85%

: 14044-65-6
borane-THF

: 612-12-4
o-Xylylene dichloride

: 6372-48-1
methylphenylphosphine

: 882176-74-1, 882176-75-2
1,2-bis((methylphenylphosphino-borane)methyl)benzene

Conditions

Conditions	Yield
With NaOCH(CH3)2CH2CH2; [RuH(1,2-bis(dimethylphosphino)ethane)((R)-MeO-BiPHEP)][tetraphenylborate] In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at room temp. for 30 min; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 75:25 hexanes/ethyl acetate);	96%
With NaOCH(CH3)2CH2CH2; [RuH((R)-iPr-PHOX)2][tetraphenylborate] In tetrahydrofuran treatment of phosphine deriv. with benzyl chloride deriv. and sodium alcoholate deriv. in THF in presence of ruthenium compd. at -30°C for 60 h, treatment with borane deriv.; chiral HPLC;	87%

Yield

With NaOCH(CH3)2CH2CH2; [RuH(1,2-bis(dimethylphosphino)ethane)((R)-MeO-BiPHEP)][tetraphenylborate] In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at room temp. for 30 min; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 75:25 hexanes/ethyl acetate);

96%

With NaOCH(CH3)2CH2CH2; [RuH((R)-iPr-PHOX)2][tetraphenylborate] In tetrahydrofuran treatment of phosphine deriv. with benzyl chloride deriv. and sodium alcoholate deriv. in THF in presence of ruthenium compd. at -30°C for 60 h, treatment with borane deriv.; chiral HPLC;

87%

...Expand

: 612-12-4
o-Xylylene dichloride

: 102437-79-6
1,2-bis(azidomethyl)benzene

Conditions

Conditions	Yield
With sodium azide In water at 120℃; for 0.5h; microwave irradiation;	95%
With sodium azide In methanol; water at 100℃; for 48h;	88%
With sodium azide In N,N-dimethyl-formamide Ambient temperature;
With sodium azide; N-benzyl-N,N,N-triethylammonium chloride In water at 95℃; for 12h;

: 616-47-7
1-methyl-1H-imidazole

: 612-12-4
o-Xylylene dichloride

: 3,3’-[1,2-phenylenebis(methylene)]bis(1-methyl-1H-imidazol-3-ium) chloride

Conditions

Conditions	Yield
at 150℃; for 12h;	95%
In toluene for 16h; Reflux;	80%

: 612-12-4
o-Xylylene dichloride

: C12H22OSi

: 2-cyclopropyl-3-(tert-butyldimethylsiloxymethyl)-1,4-dihydronaphthalene

Conditions

Conditions	Yield
With manganese; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; cobalt(II) bromide In acetonitrile at 50℃; for 20h; Inert atmosphere; Schlenk technique;	95%

: 361544-93-6
1-lithio-2-tert-butyldimethylsilyl-1,2-dicarba-closo-dodecaborane(12)

: 612-12-4
o-Xylylene dichloride

: 419562-77-9
1-(α-C,α'-chloro-o-xylyl)-2-(tert-butyldimethylsilyl)-1,2-dicarba-closo-dodecaborane

Conditions

Conditions	Yield
In diethyl ether; benzene to soln. Li(tBuMe2Si-1,2-C2B10H10) in benzene-Et2O (2:1) at 0°C was added dropwise soln. α,α'-dichloro-o-xylene in benzene-Et2O (2:1), allowed to warm to room temp. and refluxed for 12 h; soln. was evapd. to dryness in vacuo, residue was triturated with EtOH, cooled to -10°C overnight, ppt. was filtered, washed with chilledMeOh and dried in vacuo; elem. anal.;	94%

: 1202027-87-9
N-(2,3,4,5,6-pentamethylbenzyl)imidazoline

: 612-12-4
o-Xylylene dichloride

: C38H52N4(2+)*2Cl(1-)

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25 - 50℃; Inert atmosphere;	94%

: 612-12-4
o-Xylylene dichloride

: 556-90-1
pseudothiohydantoin

: 20932-68-7
5,10-dihydrobenzo[e]thiazolo[3,2-a][1,3]diazepin-3(2H)-one

Conditions

Conditions	Yield
at 290℃; for 1.5h;	94%

: 612-12-4
o-Xylylene dichloride

: C8H10O5P2

Conditions

Conditions	Yield
Stage #1: o-Xylylene dichloride With tri-n-butyl phosphite at 160℃; under 7.50075 Torr; for 11h; Stage #2: With water; hydrogen bromide at 100℃; for 12h;	94%

: 612-12-4
o-Xylylene dichloride

: 100-83-4
meta-hydroxybenzaldehyde

: 95912-31-5
3,3′-[benzene-1,2-diylbis(methanediyloxy)]dibenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Ambient temperature;	93%

: 106-42-3
para-xylene

: 612-12-4
o-Xylylene dichloride

: 32094-53-4
1,2-bis(2,5-dimethylbenzyl)benzene

Conditions

Conditions	Yield
With silica gel; zinc(II) chloride at 30℃; for 0.5h;	93%

: 4184-79-6
5,6-dimethylbenzotriazole

: 612-12-4
o-Xylylene dichloride

: 1-(2-((5,6-dimethyl-1H-benzo[d][1,2,3]triazol-1-yl)-methyl)benzyl)-5,6-dimethyl-1H-benzo[d][1,2,3]triazole

Conditions

Conditions	Yield
Stage #1: 5,6-dimethylbenzotriazole With potassium carbonate; potassium iodide In acetone for 0.5h; Stage #2: o-Xylylene dichloride In acetone for 5h; Reflux;	93%

: 621-59-0
isovanillin

: 612-12-4
o-Xylylene dichloride

: 95912-30-4
C24H22O6

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Ambient temperature;	92%

: 612-12-4
o-Xylylene dichloride

A: 496-14-0
1,3-dihydroisobenzofuran

B: 612-14-6
phthalyl alcohol

C: 142066-41-9
2-(chloromethyl)-phenyl methanol

Conditions

Conditions	Yield
With sodium hydroxide In water at 100℃; for 4h; pH=7;	A n/a B 92% C n/a
In water; dimethyl sulfoxide at 100℃; for 4h;	A n/a B 92% C n/a
In water at 100℃; for 4h;	A n/a B 90% C n/a

...Expand

: 612-12-4
o-Xylylene dichloride

: 64-04-0
phenethylamine

: 6,13‑diphenethyl‑5,6,7,12,13,14‑hexahydrodibenzo[c,h][1,6]diazecine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Solvent;	92%

: 612-12-4
o-Xylylene dichloride

: 17154-34-6
(trimethylsilyl)diphenylphosphine

: 2,2-diphenyl-1,2-dihydro-2λ5-phosphonia-inden-chlorid

Conditions

Conditions	Yield
In toluene for 13h;	91%

: 243-28-7
2,3-benzocarbazole

: 612-12-4
o-Xylylene dichloride

: 1,2-bis[(2,3-benzocarbazol-9-yl)methyl]benzene

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; potassium hydroxide at 80℃; for 10h;	91%

: 612-12-4
o-Xylylene dichloride

: 17356-08-0
thiourea

: 1,2-phenylenebis(methylene)dicarbamimidothioate dihydrochloride

Conditions

Conditions	Yield
In ethanol for 0.5h; Heating;	91%
In ethanol for 7h; Reflux;	85%

: 612-12-4
o-Xylylene dichloride

: 108-91-8
cyclohexylamine

: 117135-94-1
2-cyclohexyl-isoindoline

Conditions

Conditions	Yield
With potassium carbonate In water at 120℃; for 0.333333h; microwave irradiation;	91%
With potassium carbonate In water at 105℃; for 0.333333h; Concentration; Microwave irradiation; Green chemistry;	68%

: 612-12-4
o-Xylylene dichloride

: 333-20-0
potassium thioacyanate

: 62855-78-1
1,2-bis(thiocyanatomethyl)benzene

Conditions

Conditions	Yield
In water at 110℃; for 0.333333h; microwave irradiation;	91%

1,2-Bis(chloromethyl)benzene Chemical Properties

The molecular structure of α,α'-Dichloro-o-xylene (612-12-4) as follow:
EINECS: 210-291-8
Molecular formula: C₈H₈Cl₂
Formula weight: 175.06
Synonyms: 1,2-Bis(chloromethyl)benzene ; o-Xylylene dichloride ; o-Bis(chloromethyl)benzene ; Benzene,1,2-bis(chloromethyl)-
Density: 1.208 g/cm³
Melting point: 51-55 ℃(lit.)
Boiling point: 239-241 ℃(lit.)
Flash point: 107 ℃
Index of refraction: 1.544
Vapour pressure: 0.0618 mmHg at 25 ℃
Appearance: white to light yellow crystal powder
α,α'-Dichloro-o-xylene (612-12-4) can hydrolysis in water. The product categories about it belong to pharmaceutical intermediates.

1,2-Bis(chloromethyl)benzene Uses

α,α'-Dichloro-o-xylene(612-12-4) is used as pharmaceutical, chemical and pesticide intermediates.

1,2-Bis(chloromethyl)benzene Toxicity Data With Reference

mouse	LD₅₀	intravenous	320mg/kg (320mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03225,
mouse	LD₅₀	oral	1131mg/kg (1131mg/kg)	BEHAVIORAL:SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION	National Technical Information Service. Vol. OTS0555290,
rat	LD₅₀	oral	2263mg/kg (2263mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION	National Technical Information Service. Vol. OTS0555290,

1,2-Bis(chloromethyl)benzene Consensus Reports

Reported in EPA TSCA Inventory.

1,2-Bis(chloromethyl)benzene Safety Profile

Poison by intravenous route. Mutation data reported. See also CHLORINATED HYDROCARBONS, AROMATIC. When heated to decomposition it emits toxic Cl⁻.

Hazard codes: C Corrosive Xi Irriitant
Risk statements: 22 Harmful if swallowed.
                       26 Very toxic by inhalation.
                       34 Causes burns.
                       36 Irritating to the eyes.
                       36/37 Irritating to eyes and respiratory system.
                       36/37/38 Irritating to eyes, respiratory system and skin.
                       50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety statements: 24/25 Avoid contact with skin and eyes.
                           26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
                           27 Take off immediately all contaminated clothing.
                           28A After contact with skin, wash immediately with plenty of water.
                           29 Do not empty into drains.
                           36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
                           45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
                           61 Avoid release to the environment. Refer to special instructions/safety data sheets.

1,2-Bis(chloromethyl)benzene Specification

α,α'-Dichloro-o-xylene (612-12-4) is stable at room temperature in closed containers under normal storage and handling conditions. It must be away from incompatible substances such as strong oxidizing agents, bases, alcohols, aluminum and amines. Its hazardous decomposition products are hydrogen chloride, phosgene, carbon monoxide and carbon dioxide. The hazardous polymerization of α,α'-Dichloro-o-xylene (612-12-4) has not been reported.

Product Name

1,2-Bis(chloromethyl)benzene

Synthetic route

1,2-Bis(chloromethyl)benzene Chemical Properties

1,2-Bis(chloromethyl)benzene Uses

1,2-Bis(chloromethyl)benzene Toxicity Data With Reference

1,2-Bis(chloromethyl)benzene Consensus Reports

1,2-Bis(chloromethyl)benzene Safety Profile

1,2-Bis(chloromethyl)benzene Specification

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