| Identification | More | [Name]
4-Bromo-1,2-benzenediamine | [CAS]
1575-37-7 | [Synonyms]
2-AMINO-4-BROMOPHENYLAMINE
4-BROMO-1,2-BENZENEDIAMINE
4-BROMO-1,2-DIAMINOBENZENE
4-BROMO-2-AMINOANILINE
4-BROMO-BENZENE-1,2-DIAMINE
4-BROMO-O-PHENYLENEDIAMINE
BUTTPARK 95\04-56
3-BROMO-1,2-DIAMINOBENZENE
1,2-Benzenediamine, 4-bromo-
1-BROMO-3,4-DIAMINOBENZENE
4-Bromo-1,2-phenylenediamine
1,2-Diamino-4-bromobenzene
4-Bromo-o-phenyle
4-Bromo-2-aminoaniline, 4-Bromo-o-phenylenediamine | [Molecular Formula]
C6H7BrN2 | [MDL Number]
MFCD02660622 | [Molecular Weight]
187.04 | [MOL File]
1575-37-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
65-69 °C (dec.)(lit.)
| [Boiling point ]
289.3±20.0 °C(Predicted) | [density ]
1.697±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Soluble in chloroform. | [form ]
powder to crystal | [pka]
3.46±0.10(Predicted) | [color ]
White to Brown | [InChI]
InChI=1S/C6H7BrN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2 | [InChIKey]
WIHHVKUARKTSBU-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C(Br)C=C1N | [CAS DataBase Reference]
1575-37-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301-H315-H317-H319 | [Precautionary statements ]
P280-P301+P310+P330-P302+P352-P305+P351+P338 | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36/38:Irritating to eyes and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [Hazard Note ]
Toxic | [REACH Registrations]
Active | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29215110 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
4-Bromo-o-phenylenediamine, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. | [General Description]
4-Bromo-1,2-diaminobenzene can be obtained from 1,2-diaminobenzene via acetylation followed by bromination and alkaline hydrolysis. | [Synthesis]
1. 4-Bromo-2-nitroaniline (600 mg, 2.76 mmol) was dissolved in 25 mL of anhydrous ethanol.
2. Stannous chloride (SnCl2, 2.72 g, 14 mmol) was added to the solution.
3. The reaction mixture was heated to reflux overnight. 4.
4. After completion of the reaction, the ethanol was removed by rotary evaporator under reduced pressure.
5. The residue was alkalized to pH 11 with 2 N sodium hydroxide solution.
6. The organic layer was collected by extraction with ether.
7. The organic layer was dried with anhydrous sodium sulfate.
8. After filtration, the organic layer was concentrated by rotary evaporator under reduced pressure to give the crude product 4-bromophthalimide (486 mg, 2.6 mmol, 94% yield).
9. The crude product was used directly in the next reaction without further purification. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 5, p. 827 - 832
[2] Australian Journal of Chemistry, 1983, vol. 36, # 11, p. 2317 - 2325
[3] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 11, p. 2591 - 2600
[4] Patent: US6063801, 2000, A
[5] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3186 - 3193 |
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