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| CAS No.: | 586-77-6 |
|---|---|
| Name: | 4-Bromo-N,N-dimethylaniline |
| Article Data: | 208 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H10BrN |
| Molecular Weight: | 200.078 |
| Synonyms: | Aniline,p-bromo-N,N-dimethyl- (6CI,8CI);(4-Bromophenyl)dimethylamine;1-Bromo-4-(dimethylamino)benzene;4-(Dimethylamino)phenyl bromide; |
| EINECS: | 209-582-2 |
| Density: | 1.393 g/cm3 |
| Melting Point: | 52-54 °C(lit.) |
| Boiling Point: | 264 °C at 760 mmHg |
| Flash Point: | 104.7 °C |
| Solubility: | Soluble in methanol. Insoluble in water. |
| Appearance: | white to light grey powder |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 20/21/22-36/38-33 |
| Safety: | 26-36/37-28-45 |
| PSA: | 3.24000 |
| LogP: | 2.51510 |
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4-(dimethylamino)benzene-boronic acid
- 586-77-6
4-bromo-N,N-dimethylaniline
| 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 | Yield |
|---|---|
| With N-Bromosuccinimide In dichloromethane at 20℃; for 0.166667h; | 100% |
| 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% |
| 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% |
| 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% |
| Conditions | Yield |
|---|---|
| With formic acid; triethylamine at 150℃; for 12h; Inert atmosphere; Green chemistry; | 97% |
| 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. |
| Conditions | Yield |
|---|---|
| With 0.72 KNaX-BS zeolite at 150℃; for 1h; Reagent/catalyst; | 85% |
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- 106-40-1
4-bromo-aniline
A
- 6911-87-1
4-bromo-N-methylaniline
B
- 586-77-6
4-bromo-N,N-dimethylaniline
| Conditions | Yield |
|---|---|
| With 0.94 HY-BS zeolite at 150℃; for 1h; | A 81% B 16% |
| 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. |
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Chemistry
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
Uses
4-Bromo-N,N-dimethylaniline (CAS NO.586-77-6) is used in organic synthesis, pharmaceuticals, etc.
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. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Safety Information about 4-Bromo-N,N-dimethylaniline (CAS NO.586-77-6):
Hazard Codes: 
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 NOx.
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.