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Cas Database |
| Name |
1,2-Dibromobenzene |
EINECS | 209-507-3 |
| CAS No. | 583-53-9 | Density | 1.936 g/cm3 |
| PSA | 0.00000 | LogP | 3.21160 |
| Solubility | Insoluble in water, but soluble in ethanol, ethyl ether, acetone, acetic acid, benzene, petroleum ether, tetrachloromethane | Melting Point |
4-6 °C(lit.) |
| Formula | C6H4Br2 | Boiling Point | 225.421 °C at 760 mmHg |
| Molecular Weight | 235.906 | Flash Point | 95.5 °C |
| Transport Information | UN 2711 | Appearance | Clear colourless to light yellow liquid |
| Safety | 26-36-37/39 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi
|
| Synonyms |
Benzene,o-dibromo- (8CI);Benzene,1,2-dibromo-;NSC 60643;o-Dibromobenzene; |
Article Data | 61 |
1,2-Dibromobenzene Synthetic route
| Conditions | Yield |
|---|---|
| With dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Solvent; Temperature; UV-irradiation; | 100% |
| Conditions | Yield |
|---|---|
| Stage #1: 3,4-dibromoaniline With hydrogenchloride In diethyl ether; water for 0.0833333h; Stage #2: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #3: With hypophosphorous acid In water at 4 - 25℃; for 72h; | 81% |
| Conditions | Yield |
|---|---|
| With PyHBrCl2; iron(III) chloride In dichloromethane at 20℃; for 2h; | A 19% B 72% |
| With lead(IV) acetate; trifluoroacetic acid; potassium bromide at 25℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
| With bromine; ZnBr2 on silica (100 Angstroem) In hexane at 25℃; for 0.116667h; Yields of byproduct given; |
- 583-53-9
1,2-dibromobenzene
| Conditions | Yield |
|---|---|
| With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution; | 53% |
| With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution; | 51% |
- 107573-20-6
1,2-dibromobenzene-4-sulfonic acid
- 583-53-9
1,2-dibromobenzene
| Conditions | Yield |
|---|---|
| With hydrogen bromide at 250℃; |
| Conditions | Yield |
|---|---|
| With hydrogen bromide at 250 - 260℃; |
| Conditions | Yield |
|---|---|
| With bromine; Nitrogen dioxide In water; trifluoroacetic acid at 20℃; for 0.16h; Product distribution; | |
| With bromine | |
| With ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; bromine; zinc(II) oxide In dichloromethane for 3h; Heating; | |
| Multi-step reaction with 2 steps 1: bromine / 1.5 h / 40 °C / Darkness; Inert atmosphere; Green chemistry 2: bromine / dichloromethane / 2 h / 40 °C / Darkness; Inert atmosphere; Green chemistry View Scheme |
- 108-86-1
bromobenzene
A
- 106-39-8
bromochlorobenzene
B
- 106-46-7
para-dichlorobenzene
C
- 694-80-4
2-bromo-1-chlorobenzene
D
- 106-37-6
1.4-dibromobenzene
E
- 108-90-7
chlorobenzene
F
- 583-53-9
1,2-dibromobenzene
| Conditions | Yield |
|---|---|
| With potassium chloride; cobalt(III) acetate; trifluoroacetic acid at 20℃; for 15h; Product distribution; Mn(CH3COO)3, 600 - 216 h, various conc. of aq. CF3COOH; |
- 108-86-1
bromobenzene
A
- 108-36-1
1,3-dibromobenzene
B
- 106-37-6
1.4-dibromobenzene
C
- 583-53-9
1,2-dibromobenzene
| Conditions | Yield |
|---|---|
| With hypobromous acid In 1,4-dioxane; water at 25℃; Rate constant; | A 1 % Chromat. B 64.3 % Chromat. C 35.7 % Chromat. |
1,2-Dibromobenzene Specification
1,2-Dibromobenzene is an organic compound with the formula C6H4Br2, and its systematic name is the same with the product name. With the CAS registry number 583-53-9, it is also named as o-Dibromobenzene. It belongs to the product categories of Aromatic Hydrocarbons (substituted) & Derivatives; Organics; Benzene derivates; Miscellaneous; Bromine Compounds; Aryl; C6; Halogenated Hydrocarbons. Its EINECS number is 209-507-3. In addition, the molecular weight is 235.90. This chemical is used in organic synthesis.
Physical properties of 1,2-Dibromobenzene are: (1)ACD/LogP: 3.628; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.63; (4)ACD/LogD (pH 7.4): 3.63; (5)ACD/BCF (pH 5.5): 336.99; (6)ACD/BCF (pH 7.4): 336.99; (7)ACD/KOC (pH 5.5): 2243.20; (8)ACD/KOC (pH 7.4): 2243.20; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.599; (13)Molar Refractivity: 41.633 cm3; (14)Molar Volume: 121.803 cm3; (15)Polarizability: 16.505×10-24cm3; (16)Surface Tension: 41.02 dyne/cm; (17)Density: 1.937 g/cm3; (18)Flash Point: 95.5 °C; (19)Enthalpy of Vaporization: 44.316 kJ/mol; (20)Boiling Point: 225.421 °C at 760 mmHg; (21)Vapour Pressure: 0.13 mmHg at 25°C.
Preparation : this chemical can be prepared by bromobenzene at the temperature of 20 °C. This reaction will need reagents PyHBrCl2, FeCl3 and solvent CH2Cl2 with the reaction time of 2 hours. The yield is about 72%.
Uses of 1,2-Dibromobenzene: it can be used to produce 3-(2-Bromophenylthio)-4H-[1]benzopyran-4-on by heating. It will need reagent Cu with the reaction time of 30 min. The yield is about 54%.
![1,2-Dibromobenzene can be used to produce 3-(2-Bromophenylthio)-4H-[1]benzopyran-4-on by heating](/UserFilesUpload/Uses of 1,2-Dibromobenzene.jpeg)
When you are using this chemical, please be cautious about it as the following:
This chemcial is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ccccc1Br
(2)Std. InChI: InChI=1S/C6H4Br2/c7-5-3-1-2-4-6(5)8/h1-4H
(3)Std. InChIKey: WQONPSCCEXUXTQ-UHFFFAOYSA-N
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