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CAS No.: | 108-36-1 |
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Name: | 1,3-Dibromobenzene |
Article Data: | 68 |
Molecular Structure: | |
Formula: | C6H4Br2 |
Molecular Weight: | 235.906 |
Synonyms: | Benzene,m-dibromo- (8CI);m-Dibromobenzene;Benzene, 1,3-dibromo-; |
EINECS: | 203-574-2 |
Density: | 1.937 g/cm3 |
Melting Point: | -7 °C |
Boiling Point: | 217.537 °C at 760 mmHg |
Flash Point: | 93.889 °C |
Solubility: | insoluble in water |
Appearance: | clear colourless to light yellow liquid |
Hazard Symbols: | Xi,C |
Risk Codes: | 36/37/38 |
Safety: | 26-36-24/25 |
Transport Information: | UN 2711 |
PSA: | 0.00000 |
LogP: | 3.21160 |
1,3-dibromobenzene
Conditions | Yield |
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With dihydrogen peroxide In tetrahydrofuran for 0.333333h; Heating; | 92% |
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 11 percent / aq. HI; HBF4 / acetonitrile / 24 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 12 percent / aq. HCl; Cu / acetonitrile / 0.25 h / 20 - 25 °C View Scheme |
Conditions | Yield |
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With bromine; dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; UV-irradiation; | 92% |
n-butyllithium
(3,5-dibromophenyl)trimethyltin
B
1,3-dibromobenzene
C
n-butyltrimethyltin
D
(3-bromophenyl)trimethylstannane
Conditions | Yield |
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In diethyl ether; hexane byproducts: C4H9Br; n-BuLi in hexane adding to an ether soln. of the stannane at -78°C, stirring for 30 min, hydrolyzing with 2 N HCl, org. layer sepg., drying over MgSO4; identified by gas chromy. and chromato-mass spectrometry; | A 1% B 82% C n/a D 13% |
Conditions | Yield |
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Stage #1: 2,6-dibromoaniline With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 3h; Stage #2: With hypophosphorous acid In water at 70 - 80℃; for 3h; Reagent/catalyst; Temperature; | 81% |
Diazotization.Behandlung der Diazoniumsalz-Loesungen mit H3PO2 bei 5grad; | |
With tetrahydrofuran; n-Amyl nitrite |
1,3-dibromobenzene
Conditions | Yield |
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With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution; | 80% |
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution; | 78% |
Conditions | Yield |
---|---|
With tetrafluoroboric acid; hydrogen iodide In acetonitrile at 60℃; for 24h; | A 11% B 79% |
Conditions | Yield |
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With hydrogenchloride; copper In acetonitrile at 20 - 25℃; for 0.25h; | A 12% B 79% |
3-bromophenyl trifluoromethanesulfonate
1,3-dibromobenzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triisobutylaluminum; butanone; potassium bromide In toluene at 100℃; for 24h; Inert atmosphere; | 78% |
(3-bromophenyl)boronic acid
1,3-dibromobenzene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 81℃; for 8h; | 65% |
Conditions | Yield |
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at 450℃; under 0.0001 Torr; for 4h; Title compound not separated from byproducts; | A n/a B 60% C n/a |
1,3-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 108-36-1, it is also named as m-Dibromobenzene. It belongs to the product categories of Benzene derivates; Bromine Compounds; Aryl; C6; Halogenated Hydrocarbons. Its EINECS number is 203-574-2. In addition, the molecular weight is 235.90. This chemical should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. It is used as solvent and organic synthesis intermediate.
Physical properties of 1,3-Dibromobenzene are: (1)ACD/LogP: 3.715; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.72; (4)ACD/LogD (pH 7.4): 3.72; (5)ACD/BCF (pH 5.5): 392.16; (6)ACD/BCF (pH 7.4): 392.16; (7)ACD/KOC (pH 5.5): 2500.35; (8)ACD/KOC (pH 7.4): 2500.35; (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: 41.03 dyne/cm; (17)Density: 1.937 g/cm3; (18)Flash Point: 93.889 °C; (19)Enthalpy of Vaporization: 43.542 kJ/mol; (20)Boiling Point: 217.537 °C at 760 mmHg; (21)Vapour Pressure: 0.19 mmHg at 25°C.
Preparation: this chemical can be prepared by (3-bromo-phenyl)-dihydroxy-borane at the temperature of 81 °C. This reaction will need reagent NBS and solvent acetonitrile with the reaction time of 8 hours. The yield is about 65%.
Uses of 1,3-Dibromobenzene: it can be used to produce 5-(3-bromo-phenyl)-2,4-di-tert-butoxy-pyrimidine by heating. It will need reagents 1M aq. NaHCO3, Pd(0)(PPh3)4 and solvent 1,2-dimethoxy-ethane with the reaction time of 1 hour. The yield is about 89%.
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 must avoid contact with skin and eyes and you need to wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1cccc(Br)c1
(2)Std. InChI: InChI=1S/C6H4Br2/c7-5-2-1-3-6(8)4-5/h1-4H
(3)Std. InChIKey: JSRLURSZEMLAFO-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 900mg/kg (900mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979. | |
mouse | LD50 | oral | 2250mg/kg (2250mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979. |