4-Bromo-N,N-dimethylaniline supplier

Name
4-Bromo-N,N-dimethylaniline
EINECS 209-582-2
CAS No. 586-77-6
Article Data208
CAS DataBase
Density 1.393 g/cm³
Solubility Soluble in methanol. Insoluble in water.
Melting Point 52-54 °C(lit.)
Formula C₈H₁₀BrN
Boiling Point 264 °C at 760 mmHg
Molecular Weight 200.078
Flash Point 104.7 °C
Transport Information
Appearance white to light grey powder
Safety 26-36/37-28-45
Risk Codes 20/21/22-36/38-33
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Aniline,p-bromo-N,N-dimethyl- (6CI,8CI);(4-Bromophenyl)dimethylamine;1-Bromo-4-(dimethylamino)benzene;4-(Dimethylamino)phenyl bromide;
PSA 3.24000
LogP 2.51510

Synthetic route

: 28611-39-4
4-(dimethylamino)benzene-boronic acid

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.166667h;	100%
With 2-bromopentane; sodium hydride In dimethyl sulfoxide at 80℃;
Multi-step reaction with 2 steps 1: toluene / 1 h / 20 °C / Inert atmosphere 2: N-Bromosuccinimide / dichloromethane / 0.17 h / 20 °C View Scheme

: 171364-78-6
(4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 20℃; for 0.166667h;	100%

: 121-69-7
N,N-dimethyl-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With methanol; tetraethylammonium chloride; bromine In dichloromethane at 35℃; other substituted anilines: regioselectivity of bromination;	99%
With methanol; tetraethylammonium chloride; bromine In dichloromethane at 35℃;	99%
With hexabromocyclopenta-1,3-diene; triethylamine In acetonitrile for 24h; Ambient temperature;	99%

: 50-00-0
formaldehyd

: 106-40-1
4-bromo-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With sodium cyanoborohydride; acetic acid at 0 - 65℃; for 3.42h;	99%
With Zr(BH4)2Cl2(dabco)2; zirconium(IV) chloride In methanol; water at 20℃; for 0.1h;	95%
With sodium tetrahydroborate In 2,2,2-trifluoroethanol for 4.3h; Reflux;	94%

: 124-38-9
carbon dioxide

: 6911-87-1
4-bromo-N-methylaniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With phenylsilane; triphenylphosphine In tetrahydrofuran at 120℃; under 3750.38 Torr; for 24h; Autoclave; Green chemistry;	99%
With sodium tetrahydroborate In 1,4-dioxane at 100℃; under 7500.75 Torr; for 24h; Autoclave;	93%
With diphenylsilane; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; chemoselective reaction;	91%

: 67-68-5
dimethyl sulfoxide

: 106-40-1
4-bromo-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With formic acid; triethylamine at 150℃; for 12h; Inert atmosphere; Green chemistry;	97%

: 124-38-9
carbon dioxide

: 106-40-1
4-bromo-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With diphenylsilane; C21H41N3NiP2 In acetonitrile at 120℃; under 2052.14 Torr; for 24h; Autoclave;	87%
With dimanganese decacarbonyl; phenylsilane; C29H33N2P In acetonitrile at 100℃; under 750.075 Torr; for 15h;	79%
With methanesulfonic acid; hydrogen; tris(acetylacetonato)ruthenium(III); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 140℃; for 24h; Autoclave; Inert atmosphere;	89 %Chromat.

: 616-38-6
carbonic acid dimethyl ester

: 106-40-1
4-bromo-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With 0.72 KNaX-BS zeolite at 150℃; for 1h; Reagent/catalyst;	85%

: 616-38-6
carbonic acid dimethyl ester

: 106-40-1
4-bromo-aniline

A: 6911-87-1
4-bromo-N-methylaniline

B: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With 0.94 HY-BS zeolite at 150℃; for 1h;	A 81% B 16%

...Expand

: 67-56-1
methanol

: 106-40-1
4-bromo-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With Cu1-Mo1/TiO2 In neat liquid at 20℃; for 21h; Catalytic behavior; Inert atmosphere; UV-irradiation;	80%
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.5h; chemoselective reaction;	60%
With TiO2 supported nano-Pd(0.3) catalyst In water at 20℃; for 5h; Inert atmosphere; Irradiation; Green chemistry;	8 %Chromat.
With zinc oxide-supported iridium catalyst at 150℃; under 3750.38 Torr; for 8h; Inert atmosphere;	38 %Chromat.

: 121-69-7
N,N-dimethyl-aniline

A: 586-77-6
4-bromo-N,N-dimethylaniline

B: 64230-27-9
2,4-dibromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With dihydrogen peroxide; vanadia; potassium bromide In chloroform; water at 24.84℃; under 760.051 Torr;	A 75% B 12%
With [bis(acetoxy)iodo]benzene; lithium bromide In tetrahydrofuran at 20℃; for 0.5h;	A 73% B 18%
With bromine; acetic acid In tetrachloromethane for 0.0833333h; Ambient temperature; other reagents: bromine, bromodimethylsulfonium bromide, bromodimethylsulfonium bromide/acetic acid;	A 68% B 29%

: 29972-74-5
(4-dimethylamino-phenyl)-phosphonous acid dichloride

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With pyridine; bromine In dichloromethane at 20℃; for 12h;	67%

: 874-52-2
N,N-dimethylaniline N-oxide

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
Stage #1: N,N-dimethylaniline N-oxide With dibromo sulfoxide In tetrahydrofuran at -78℃; for 4h; Inert atmosphere; Stage #2: With triethylamine In tetrahydrofuran at -78 - 23℃; for 0.75h; Solvent; Temperature; Inert atmosphere; regioselective reaction;	55%

: 67-56-1
methanol

: 6911-87-1
4-bromo-N-methylaniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With rhodium(III) chloride hydrate; potassium tert-butylate at 130℃; for 24h; Sealed tube; High pressure;	44%

: 106-40-1
4-bromo-aniline

: 74-88-4
methyl iodide

A: 6911-87-1
4-bromo-N-methylaniline

B: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃;	A 26% B 20%
With potassium carbonate In tetrahydrofuran at 20℃;	A 26% B 20%
With potassium carbonate In tetrahydrofuran	A 26% B 20%

...Expand

: 50-00-0
formaldehyd

: 147-82-0
2,4,6-tribromoaniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With hydrogenchloride; amalgamated zinc; acetic acid

: 511-67-1
5,5-dibromobarbituric acid

: 64-17-5
ethanol

: 121-69-7
N,N-dimethyl-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

...Expand

: 511-67-1
5,5-dibromobarbituric acid

: 121-69-7
N,N-dimethyl-aniline

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With ethanol

: 7494-77-1
4-(dimethylamino)phenyl(phenyl)methanol

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With chloroform; bromine
With diethyl ether; bromine

: 157671-45-9
2-[(4-bromophenyl)(methyl)amino]acetonitrile

: 586-77-6
4-bromo-N,N-dimethylaniline

Conditions

Conditions	Yield
With sulfuric acid

: 586-77-6
4-bromo-N,N-dimethylaniline

: 121-69-7
N,N-dimethyl-aniline

Conditions

Conditions	Yield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h;	100%
With lithium aluminium tetrahydride; di-tert-butyl peroxide In tetrahydrofuran for 3h; Irradiation;	93%
With isopropyl alcohol at 20℃; for 24h; UV-irradiation; chemoselective reaction;	82%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 98-80-6
phenylboronic acid

: 1137-79-7
N,N-dimethyl-4-biphenylamine

Conditions

Conditions	Yield
With potassium phosphate; naphthidine di(radical cation)s-stabilized Pd nanoparticles In 1,4-dioxane at 80℃; for 8h; Suzuki-Miyaura cross-coupling reaction;	100%
With tetrabutylammomium bromide; potassium carbonate; cyclopalladated N-dodecylferrocenylimine In methanol; water at 20℃; for 18h; Suzuki-Miyaura cross-coupling reaction;	99%
With potassium carbonate In ethanol; water at 50℃; for 4h; Suzuki-Miyaura Coupling;	99%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 80-62-6
methacrylic acid methyl ester

: 50704-04-6
(E)-3-(4-dimethylaminophenyl)-2-methyl acrylic acid methyl ester

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; Cy2NMe2 In 1,4-dioxane at 20℃; for 24h; Heck coupling;	100%
With [(C6H5)PdBr2]2[HPtBu3]2 In 1,4-dioxane at 20℃; for 18h; Heck reaction; Inert atmosphere;	97%
With N-Methyldicyclohexylamine; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butylphosphonium tetraphenylborate In tetrahydrofuran at 30℃; for 25h; Product distribution / selectivity;	87%

: 773837-37-9
sodium cyanide

: 586-77-6
4-bromo-N,N-dimethylaniline

: 157671-45-9
2-[(4-bromophenyl)(methyl)amino]acetonitrile

Conditions

Conditions	Yield
With C47H45Cl2N5Ru2(2+)*2F6P(1-); dihydrogen peroxide; acetic acid In methanol at 60℃; for 10h; Inert atmosphere;	100%
With dihydrogen peroxide; acetic acid In water at 20℃; for 0.583333h;	95%
With oxygen; vanadia; acetic acid In methanol at 60℃; for 2h;	92%

: 1719-57-9
Chloro(chloromethyl)dimethylsilane

: 586-77-6
4-bromo-N,N-dimethylaniline

: 60457-97-8
(chloromethyl)[4-(dimethylamino)phenyl]dimethylsilane

Conditions

Conditions	Yield
Stage #1: 4-bromo-N,N-dimethylaniline With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: Chloro(chloromethyl)dimethylsilane	99%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 134-85-0
4-chlorobenzophenone

: 94869-73-5
(4'-(dimethylamino)-[1,1'-biphenyl]-4-yl)(phenyl)methanone

Conditions

Conditions	Yield
Stage #1: 4-bromo-N,N-dimethylaniline With lithium Stage #2: With zinc(II) chloride Stage #3: 4-chlorobenzophenone; nickel phosphine amido pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 8h; Negishi cross-coupling; Further stages.;	99%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 108-90-7
chlorobenzene

: 1137-79-7
N,N-dimethyl-4-biphenylamine

Conditions

Conditions	Yield
Stage #1: 4-bromo-N,N-dimethylaniline With lithium Stage #2: With zinc(II) chloride Stage #3: chlorobenzene; nickel phosphine amido pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Negishi cross-coupling; Further stages.;	99%

: 354-38-1
2,2,2-trifluoroacetamide

: 586-77-6
4-bromo-N,N-dimethylaniline

: 41116-22-7
2,2,2-trifluoro-(4-N,N-dimethyphenyl)acetamide

Conditions

Conditions	Yield
With potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide In 1,4-dioxane at 75℃;	99%

: 773837-37-9
sodium cyanide

: 586-77-6
4-bromo-N,N-dimethylaniline

: 1197-19-9
4-cyano-N,N-dimethylaniline

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;	99%

: 101-81-5
Diphenylmethane

: 586-77-6
4-bromo-N,N-dimethylaniline

: 13865-57-1
4-benzhydryl-N,N-dimethylaniline

Conditions

Conditions	Yield
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	99%
With 15-crown-5; NiXantphos; palladium diacetate; sodium hexamethyldisilazane at 23℃; for 12h; Catalytic behavior; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;	99%

: 587-79-1
4-fluorodiphenylmethane

: 586-77-6
4-bromo-N,N-dimethylaniline

: 39768-73-5
{4-[(4-Fluoro-phenyl)-phenyl-methyl]-phenyl}-dimethyl-amine

Conditions

Conditions	Yield
With 15-crown-5; NiXantphos; palladium diacetate; sodium hexamethyldisilazane at 23℃; for 12h; Catalytic behavior; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;	99%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 331627-96-4
N-(quinolin-8-yl)-3-(trifluoromethyl)benzamide

: 1436849-50-1
C25H20F3N3O

Conditions

Conditions	Yield
With Ru(OAc)2(p-cymene); sodium carbonate; triphenylphosphine In toluene at 130℃; for 15h;	99%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 195062-57-8
p-tolylboronic pinacol ester

: 141082-00-0
4-dimethylamino-4'-methylbiphenyl

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium hydroxide In neat (no solvent) at 110℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	99%

: 586-77-6
4-bromo-N,N-dimethylaniline

: 696-61-7
4-tolylmagnesium chloride

: 141082-00-0
4-dimethylamino-4'-methylbiphenyl

Conditions

Conditions	Yield
With C36H52Br2N4NiSi In tetrahydrofuran at 70℃; for 24h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;	99%

: 54512-79-7
benzo[c]-[1,2,5]thiadiazole-5,6-dicarbonitrile

: 586-77-6
4-bromo-N,N-dimethylaniline

: 4,7-bis(4-(dimethylamino)phenyl)benzo[c][1,2,5]thiadiazole-5,6-dicarbonitrile

Conditions

Conditions	Yield
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate; Trimethylacetic acid In toluene at 120℃; Inert atmosphere; Sealed tube;	99%
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate; Trimethylacetic acid In toluene at 120℃; Inert atmosphere; Sealed tube;

4-Bromo-N,N-dimethylaniline Chemical Properties

IUPAC Name: 4-bromo-N,N-dimethylaniline
Synonyms of 4-Bromo-N,N-dimethylaniline (CAS NO.586-77-6): 1-Bromo-4-(dimethylamino)benzene ; 4-(Dimethylamino)phenyl bromide ; 4-Bromo-N,N-dimethylaniline ; Aniline, 4-bromo-N,N-dimethyl- ; p-(Dimethylamino)phenyl bromide ; p-Bromo(dimethylamino)benzene ; p-N,N-Dimethylaminobromobenzene
CAS NO: 586-77-6
The Molecular formula: C₈H₁₀BrN
The Molecular Weight: 200.08
The Molecular Structure :
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: Å²
EINECS: 209-582-2
Melting point: 52-54 °C(lit.)
Boiling Point: 264 °C at 760 mmHg
Flash Point: 104.7 °C
Index of Refraction: 1.586
Molar Refractivity: 48.25 cm³
Molar Volume: 143.6 cm³
Surface Tension: 39.3 dyne/cm
Density: 1.393 g/cm ³
Enthalpy of Vaporization: 50.19 kJ/mol
Vapour Pressure: 0.00996 mmHg at 25°C
Storage temp: 2-8°C
Appearance: white to light grey powder
Stability: Stable. Incompatible with oxidizing agents, acids, metals.
Product Categories of 4-Bromo-N,N-dimethylaniline (CAS NO.586-77-6): Anilines, Aromatic Amines and Nitro Compounds;Aniline;Miscellaneous;Amines;C8;Nitrogen Compounds

4-Bromo-N,N-dimethylaniline Uses

4-Bromo-N,N-dimethylaniline (CAS NO.586-77-6) is used in organic synthesis, pharmaceuticals, etc.

4-Bromo-N,N-dimethylaniline Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LDLo	oral	500mg/kg (500mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947.

4-Bromo-N,N-dimethylaniline Consensus Reports

Reported in EPA TSCA Inventory.

4-Bromo-N,N-dimethylaniline Safety Profile

Safety Information about 4-Bromo-N,N-dimethylaniline (CAS NO.586-77-6):
Hazard Codes: Harmful Xn,Xi
Risk Statements: 20/21/22-36/38-33
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/38: Irritating to eyes and skin.
R33: Danger of cumulative effects.
Safety Statements: 26-36/37-28-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28: After contact with skin, wash immediately with plenty of soap-suds.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37: Wear suitable protective clothing and gloves.
RIDADR: 2811
WGK Germany: 3
RTECS: BW9300000
F: 8
Hazard Note: Irritant
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29214290
Moderately toxic by ingestion. May explode if heated. When heated to decomposition it emits toxic fumes of Br- and NO_x.

4-Bromo-N,N-dimethylaniline Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.

Product Name

4-Bromo-N,N-dimethylaniline

Synthetic route

4-Bromo-N,N-dimethylaniline Chemical Properties

4-Bromo-N,N-dimethylaniline Uses

4-Bromo-N,N-dimethylaniline Toxicity Data With Reference

4-Bromo-N,N-dimethylaniline Consensus Reports

4-Bromo-N,N-dimethylaniline Safety Profile

4-Bromo-N,N-dimethylaniline Specification

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