4-Bromobenzyl chloride supplier

Name
4-Bromobenzyl chloride
EINECS 209-638-6
CAS No. 589-17-3
Article Data37
CAS DataBase
Density 1.541 g/cm³
Solubility insoluble in water
Melting Point 36-40 °C
Formula C₇H₆BrCl
Boiling Point 236 °C at 760 mmHg
Molecular Weight 205.482
Flash Point 111.7 °C
Transport Information UN3261
Appearance light yellow crystal powder to light yellow liqui
Safety 45-36/37/39-25
Risk Codes 36/37-34
Molecular Structure
Hazard Symbols C
Synonyms Toluene,p-bromo-a-chloro- (6CI,7CI,8CI);1-Bromo-4-(chloromethyl)benzene;4-Bromobenzyl chloride;p-Bromo-a-chlorotoluene;p-Bromobenzylchloride;a-Chloro-4-bromotoluene;
PSA 0.00000
LogP 3.18790

Synthetic route

: 873-75-6
4-bromobenzenemethanol

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With oxalyl dichloride In dichloromethane at 20℃; Appel Halogenation; Reflux;	98%
With thionyl chloride In dichloromethane at 0 - 20℃;	95%
With thionyl chloride Inert atmosphere;	95%

: 24856-58-4
1,1-dimethoxy-1-(4-bromophenyl)methane

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With triethylsilane; acetyl chloride; tin(ll) chloride In dichloromethane for 5h; Ambient temperature;	92%

: 589-15-1
1-bromomethyl-4-bromobenzene

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium chloride for 1h; High speed ball milling; Neat (no solvent); neat (no solvent, solid phase);	90%
Multi-step reaction with 2 steps 1: natrium carbonate 2: fuming hydrochloric acid / 150 °C View Scheme

: 106-38-7
para-bromotoluene

A: 586-76-5
4-Bromobenzoic acid

B: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With sodium hypochlorite; bis(2,2'-bipyridine)dichloronickel(II) In acetonitrile for 0.666667h; Ambient temperature; Yields of byproduct given;	A 85% B n/a

: 106-38-7
para-bromotoluene

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With N-chloro-succinimide; tetrachlorosilane In acetonitrile at 60 - 70℃; for 8h;	75%
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;	38%
durch Chlorierung;

: 50-00-0
formaldehyd

: 108-86-1
bromobenzene

A: 578-51-8
2-bromobenzylchloride

B: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With hydrogenchloride; tin(IV) chloride die Trennung der Isomeren erfolgt durch Abkuehlen auf -15grad;

...Expand

: 108-86-1
bromobenzene

: 542-88-1
bis(2-chloromethyl)ether

: 5435-44-9, 22243-66-9
(E)-3-Ureido-but-2-enoic acid ethyl ester

A: 1941-86-2
bis(4-bromophenyl)methane

B: 589-17-3
p-bromobenzyl chloride

...Expand

: 108-86-1
bromobenzene

: 542-88-1
bis(2-chloromethyl)ether

: 589-17-3
p-bromobenzyl chloride

: 108-86-1
bromobenzene

: 542-88-1
bis(2-chloromethyl)ether

A: 1941-86-2
bis(4-bromophenyl)methane

B: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With zinc(II) chloride
With zinc(II) chloride

...Expand

: N,N-bis-(4-bromo-benzyl)-benzamide

A: 100-47-0
benzonitrile

B: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With phosphorus pentachloride folgend Destillieren;

: 100-44-7
benzyl chloride

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
Bromierung;

: 50-00-0
formaldehyd

: 108-86-1
bromobenzene

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
(i) HCl, (heating), (ii) /BRN= 1236661/, ZnCl2, HCl; Multistep reaction;

: 106-38-7
para-bromotoluene

A: 106-43-4
para-chlorotoluene

B: 104-83-6
1-Chloro-4-(chloromethyl)benzene

C: 622-95-7
4-chlorobenzyl bromide

D: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With sodium chlorite; trichloroacetic acid In dichloromethane for 3h; Chlorination; substitution; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 17 % Chromat. D 25 % Chromat.

...Expand

: 106-38-7
para-bromotoluene

A: 106-43-4
para-chlorotoluene

B: 104-83-6
1-Chloro-4-(chloromethyl)benzene

C: 589-15-1
1-bromomethyl-4-bromobenzene

D: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With sodium chlorite; trichloroacetic acid In dichloromethane for 3h; Bromination; chlorination; substitution; Further byproducts given;	A 20 % Chromat. B 18 % Chromat. C 20 % Chromat. D 25 % Chromat.

...Expand

: 7647-01-0
hydrogenchloride

: 50-00-0
formaldehyd

: 108-86-1
bromobenzene

: 7646-78-8
tin(IV) chloride

A: 578-51-8
2-bromobenzylchloride

B: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
Product distribution; folgend Vakuumdestillation;

...Expand

: 106-38-7
para-bromotoluene

: 7782-50-5
chlorine

: 589-17-3
p-bromobenzyl chloride

: 7791-25-5
sulfuryl dichloride

: 106-38-7
para-bromotoluene

: 94-36-0
dibenzoyl peroxide

A: 106-43-4
para-chlorotoluene

B: 104-83-6
1-Chloro-4-(chloromethyl)benzene

C: 589-15-1
1-bromomethyl-4-bromobenzene

D: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
at 110℃;

...Expand

: 10026-13-8, 874483-75-7
phosphorus pentachloride

: N,N-bis-(4-bromo-benzyl)-benzamide

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
folgenden Destillieren im Vakuum;

: 10026-13-8, 874483-75-7
phosphorus pentachloride

: N-(4-bromo-benzyl)-N-(4-iodo-benzyl)-benzamide

A: N-(4-iodobenzyl)benzamide

B: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
at 130℃;

...Expand

: 586-76-5
4-Bromobenzoic acid

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: benzene; pyridine; thionyl chloride View Scheme

: 106-38-7
para-bromotoluene

A: 106-43-4
para-chlorotoluene

B: 67627-98-9
p-bromo-α,α-dichlorotoluene

C: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With tetrachloromethane at 250℃; for 7h; Inert atmosphere; Autoclave;	A 24 %Spectr. B 23 %Spectr. C 27 %Spectr.

...Expand

: 1122-91-4
4-bromo-benzaldehyde

: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 2: thionyl chloride / dichloromethane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: thionyl chloride / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0.17 h / 20 °C / Cooling with ice 2: thionyl chloride; dmap / dichloromethane / 0.17 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 0 - 20 °C / Inert atmosphere 2: thionyl chloride / Reflux View Scheme
Multi-step reaction with 2 steps 1: methanol; sodium tetrahydroborate / 2 h / 0 °C 2: thionyl chloride; 1,2,3-Benzotriazole / dichloromethane / 1.08 h View Scheme

: 873-75-6
4-bromobenzenemethanol

A: 1609172-81-7
C14H12Br2O3S

B: 589-17-3
p-bromobenzyl chloride

Conditions

Conditions	Yield
With pyridine; thionyl chloride In dichloromethane	A 30.1 %Spectr. B 35.6 %Spectr.

: 591-51-5
phenyllithium

: 589-17-3
p-bromobenzyl chloride

: 1667-11-4
biphenyl-4-methylchloride

Conditions

Conditions	Yield
Stage #1: p-bromobenzyl chloride With bis(tri-t-butylphosphine)palladium(0); oxygen In toluene at 20℃; for 0.0166667h; Schlenk technique; Stage #2: phenyllithium In toluene at 0℃; for 0.0833333h; Schlenk technique;	100%

: 589-17-3
p-bromobenzyl chloride

: 108-95-2
phenol

: 20600-22-0
1-bromo-4-(phenoxymethyl)benzene

Conditions

Conditions	Yield
With potassium carbonate In ethanol at 78℃; for 5h;	99%
With methanol; sodium methylate

: 589-17-3
p-bromobenzyl chloride

: 2050-16-0
4,4'-dihydroxyazobenzene

: bis-[4-(4-bromo-benzyloxy)-phenyl]-diazene

Conditions

Conditions	Yield
With potassium hydroxide; Aliquat 336 for 3h; Heating;	99%

: 75852-28-7
2-biphenyl-3yl-acetic acid methyl ester

: 589-17-3
p-bromobenzyl chloride

: 501031-51-2
2-biphenyl-3-yl-3-(4-bromo-phenyl)-propionic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2-biphenyl-3yl-acetic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78 - -40℃; for 1.25h; Stage #2: p-bromobenzyl chloride In tetrahydrofuran at -40 - 20℃; Further stages.;	99%

: 536-74-3
phenylacetylene

: 589-17-3
p-bromobenzyl chloride

: 126800-09-7
1-(4-bromobenzyl)-4-phenyl-1H-1,2,3-triazole

Conditions

Conditions	Yield
With sodium azide; sodium L-ascorbate In water at 50℃; for 3h; Huisgen Cycloaddition; Green chemistry;	99%
With sodium azide In water at 20℃; for 5h; Green chemistry;	97%
With sodium azide In ethanol; water at 20℃; for 0.133333h; Sonication;	90%
With copper(l) iodide; sodium azide; eosin Y disodium salt In ethanol; water at 20℃; for 2h; Irradiation; Green chemistry; regioselective reaction;	86%
With sodium azide In water at 30℃; for 24h; regioselective reaction;	83%

: 589-17-3
p-bromobenzyl chloride

: 127-06-0
acetone oxime

: O-(p-bromobenzyl)acetoxime

Conditions

Conditions	Yield
Stage #1: acetone oxime With potassium hydroxide; lithium hydroxide In N,N-dimethyl acetamide; water at 50℃; Stage #2: p-bromobenzyl chloride In N,N-dimethyl acetamide; water at 65℃; for 2.25h;	98.28%

: 589-17-3
p-bromobenzyl chloride

: potassium 4-(chloromethyl)phenyltrifluoroborate

Conditions

Conditions	Yield
Stage #1: p-bromobenzyl chloride With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With potassium hydrogen difluoride In tetrahydrofuran; hexane; water at -78 - 20℃;	98%
Stage #1: p-bromobenzyl chloride With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: With potassium hydrogen bifluoride In tetrahydrofuran; hexane; water at -78 - 20℃;	98%

: 589-17-3
p-bromobenzyl chloride

: 107047-10-9
p-bromobenzylazide

Conditions

Conditions	Yield
With sodium azide; potassium iodide In water; acetone at 20℃; for 60h; Inert atmosphere;	98%
With sodium azide In acetonitrile at 80℃; for 20h;	85%
With sodium azide; triethylamine In water; tert-butyl alcohol at 20℃; for 0.5h;

: 589-17-3
p-bromobenzyl chloride

: 105-53-3
diethyl malonate

: diethyl 2,2-bis-(4-bromobenzyl)malonate

Conditions

Conditions	Yield
Stage #1: diethyl malonate With sodium ethanolate In ethanol at 20℃; for 0.5h; Stage #2: p-bromobenzyl chloride In ethanol at 0 - 20℃; for 1h;	98%

: 17933-03-8
m-tolylboronic acid

: 589-17-3
p-bromobenzyl chloride

: 4′-(chloromethyl)-3-methyl-1,1′-biphenyl

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine tetrafluoroborate In water; toluene at 80℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	98%

: 39093-93-1
thiomorpholine 1,1-dioxide

: 589-17-3
p-bromobenzyl chloride

: 4-[(4-bromophenyl)methyl]-1,4-thiazinane 1,1-dioxide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 48h;	97%

: 22841-91-4
8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-thione

: 589-17-3
p-bromobenzyl chloride

: 3-((4-bromobenzyl)thio)-8-chloro-[1,2,4]triazolo[4,3-a]pyridine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 90℃; for 0.25h; Microwave irradiation;	96%
With sodium hydroxide In N,N-dimethyl-formamide at 90℃; for 0.25h; Microwave irradiation;	89%

: 18197-26-7
sodium diformamide

: 589-17-3
p-bromobenzyl chloride

: 128038-37-9
C9H8BrNO2

Conditions

Conditions	Yield
In acetonitrile for 2h; Heating;	95%

: 15852-34-3
2,5-dihydroxycyclohepta-2,4,6-trien-1-one

: 589-17-3
p-bromobenzyl chloride

: 106257-50-5
2,5-bis(4-bromobenzyloxy)tropone

Conditions

Conditions	Yield
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 13h;	95%

: 51009-66-6
5-(4-methylbenzylidene)-2-thioxoimidazolidin-4-one

: 589-17-3
p-bromobenzyl chloride

: 3-(4-Bromo-benzyl)-2-thioxo-5-[1-p-tolyl-meth-(Z)-ylidene]-imidazolidin-4-one

Conditions

Conditions	Yield
With caesium carbonate In ethanol at 20℃; for 25h;	95%

: 589-17-3
p-bromobenzyl chloride

: 37428-88-9
5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one

: 3-(4-Bromo-benzyl)-5-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-imidazolidin-4-one

Conditions

Conditions	Yield
With caesium carbonate In ethanol at 20℃; for 25h;	95%

: C16H24O3

: 589-17-3
p-bromobenzyl chloride

: C23H29BrO3

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 2h;	95%

: 5142-75-6
tri(p-tolyl)bismuth

: 589-17-3
p-bromobenzyl chloride

: 17100-53-7
1-(4-methylbenzyl)-4-bromobenzene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 90℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;	95%

: C28H43N3O7

: 589-17-3
p-bromobenzyl chloride

: C35H46BrN3O8

Conditions

Conditions	Yield
With triethylamine; trifluoroacetic acid In dichloromethane at 20℃; for 9h; Inert atmosphere;	95%

: 471-53-4
enoxolone

: 589-17-3
p-bromobenzyl chloride

: 3-(4-bromo-benzyloxy)-11-oxoolean-12-ene-29-oic acid

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere;	95%

: 589-17-3
p-bromobenzyl chloride

: 766-97-2
4-n-methylphenylacetylene

: 1352060-37-7
1-(4-bromobenzyl)-4-(4-methylphenyl)-1H-1,2,3-triazole

Conditions

Conditions	Yield
With sodium azide In ethanol; water at 20℃; for 0.166667h; Sonication;	95%
With copper(l) iodide; sodium azide; eosin Y disodium salt In ethanol; water at 20℃; for 2h; Irradiation; Green chemistry; regioselective reaction;	85%

: 6165-69-1
Thien-3-ylboronic acid

: 589-17-3
p-bromobenzyl chloride

: 118150-28-0
3-(4-bromobenzyl)thiophene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Large scale reaction;	94%

: 589-17-3
p-bromobenzyl chloride

: 1122-91-4
4-bromo-benzaldehyde

Conditions

Conditions	Yield
With water; sodium hydroxide at 20℃; for 0.0666667h; Microwave irradiation;	93%
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;	87%
With dihydrogen peroxide; vanadia; Aliquat 336 In water for 15h; Heating;	85%

: 121219-12-3
(4-pentylphenyl)boronic acid

: 589-17-3
p-bromobenzyl chloride

: 4-(chloromethyl)-4′-pentyl-1,1′-biphenyl

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine tetrafluoroborate In water; toluene at 80℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	93%

: 3179-31-5
3-mercapto-1,2,4-triazole

: 589-17-3
p-bromobenzyl chloride

: 3-(4-bromo-benzylsulfanyl)-4H-[1,2,4]triazole

Conditions

Conditions	Yield
Stage #1: 3-mercapto-1,2,4-triazole With sodium In methanol; 1,2-dimethoxyethane at 20℃; for 0.166667h; Stage #2: p-bromobenzyl chloride In methanol; 1,2-dimethoxyethane at 20℃; for 1h;	92%

: 589-17-3
p-bromobenzyl chloride

: 479486-96-9
N,N-dimethyl (trimethylsilyl)methanamide

: 19715-80-1
2-(4-bromophenyl)-N,N-dimethyl acetamide

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In toluene at 65℃; for 20h;	92%

: 20277-69-4
sodium methansulfinate

: 589-17-3
p-bromobenzyl chloride

: 1-(4-bromobenzyl)-2-methyldisulfide

Conditions

Conditions	Yield
Stage #1: p-bromobenzyl chloride With Sodium thiosulfate pentahydrate In ethanol; water at 100℃; for 2h; Inert atmosphere; Stage #2: sodium methansulfinate In 1,4-dioxane at 110℃; for 11h; Inert atmosphere;	92%

: 585-71-7, 38661-81-3
(1-bromoethyl)benzne

: 57-13-6
urea

: 589-17-3
p-bromobenzyl chloride

: 114857-84-0
6-(4-bromophenyl)-4-phenyl-1H-pyrimidin-2-one

Conditions

Conditions	Yield
With pyridine N-oxide In neat (no solvent) at 90℃; for 0.666667h;	92%

...Expand

4-Bromobenzyl chloride Specification

The Benzene,1-bromo-4-(chloromethyl)-, with CAS registry number 589-17-3, has the systematic name of 1-bromo-4-(chloromethyl)benzene. This chemical is a kind of light yellow crystal powder to light yellow liquid. And it should be stored in cool, dry place in tightly closed containers. What's more, its EINECS is 209-638-6.

Physical properties of Benzene,1-bromo-4-(chloromethyl)-: (1)ACD/LogP: 3.26; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.26; (4)ACD/LogD (pH 7.4): 3.26; (5)ACD/BCF (pH 5.5): 176.42; (6)ACD/BCF (pH 7.4): 176.42; (7)ACD/KOC (pH 5.5): 1411.51; (8)ACD/KOC (pH 7.4): 1411.51; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 0 Å²; (13)Index of Refraction: 1.569; (14)Molar Refractivity: 43.7 cm³; (15)Molar Volume: 133.3 cm³; (16)Polarizability: 17.32×10^-24cm³; (17)Surface Tension: 38.9 dyne/cm; (18)Enthalpy of Vaporization: 45.36 kJ/mol; (19)Vapour Pressure: 0.0744 mmHg at 25°C.

Preparation: this chemical can be prepared by p-bromobenzaldehyde dimethyl acetal. This reaction will need reagents triethylsilane, AcCl and solvent CH₂Cl₂. The reaction time is 5 hour(s). The yield is about 92%.

Uses of Benzene,1-bromo-4-(chloromethyl)-: it can be used to produce (4-bromo-benzyl)-phenyl ether. This reaction will need reagents sodium, methylate, methanol.

When you are using this chemical, please be cautious about it as the following:
The Benzene,1-bromo-4-(chloromethyl)- irritates to eyes, respiratory system and skin. And this chemical may cause burns. When use it, avoid contact with eyes and wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
(1)SMILES: ClCc1ccc(Br)cc1
(2)InChI: InChI=1/C7H6BrCl/c8-7-3-1-6(5-9)2-4-7/h1-4H,5H2
(3)InChIKey: BSIIGUGKOPPTPZ-UHFFFAOYAH
(4)Std. InChI: InChI=1S/C7H6BrCl/c8-7-3-1-6(5-9)2-4-7/h1-4H,5H2
(5)Std. InChIKey: BSIIGUGKOPPTPZ-UHFFFAOYSA-N

Product Name

4-Bromobenzyl chloride

Synthetic route

4-Bromobenzyl chloride Specification

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