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CAS No.: | 6626-15-9 |
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Name: | 4-Bromoresorcinol |
Article Data: | 45 |
Molecular Structure: | |
Formula: | C6H5BrO2 |
Molecular Weight: | 189.008 |
Synonyms: | Resorcinol,4-bromo- (7CI,8CI);1-Bromo-2,4-dihydroxybenzene;2,4-Dihydroxybromobenzene;4-Bromo-1,3-dihydroxybenzene;4-Bromo-3-hydroxyphenol;4-Bromobenzene-1,3-diol;4-Bromoresorcinol;NSC 59699; |
EINECS: | 229-586-8 |
Density: | 1.844 g/cm3 |
Melting Point: | 97-100 °C(lit.) |
Boiling Point: | 302.6 °C at 760 mmHg |
Flash Point: | 136.8 °C |
Solubility: | Slightly soluble in water. |
Appearance: | Pink crystalline powder |
Hazard Symbols: | Xn |
Risk Codes: | 20/21/22-36/37/38 |
Safety: | 26-37/39 |
PSA: | 40.46000 |
LogP: | 1.86030 |
Conditions | Yield |
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With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 2h; Heating; | 100% |
With dihydrogen peroxide; potassium bromide In water; acetonitrile | 96% |
With DMd; sulfuric acid; sodium bromide In acetone at 20℃; for 0.0166667h; | 95% |
Conditions | Yield |
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With isopropyl alcohol; Candida antarctica lipase B; immobilized In di-isopropyl ether at 45℃; for 0.25h; Title compound not separated from byproducts.; | A 91.7% B 8.3% |
3-acetoxy-cyclohex-2-enone
4-Bromoresorcinol
Conditions | Yield |
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Stage #1: 3-acetoxy-cyclohex-2-enone With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: With toluene-p-sulfonyl bromide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #3: With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 22℃; for 0.333333h; Inert atmosphere; regioselective reaction; | 75% |
Conditions | Yield |
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With Diethyl 2-bromomalonate at 100℃; for 48h; Product distribution; Further Variations:; Reagents; | A 67% B 23% |
With potassium peroxomonosulfate; ammonium bromide In water at 20℃; for 0.166667h; regioselective reaction; | A 85 %Chromat. B 14 %Chromat. |
2,4-dibromo-5-hydroxyphenol
4-Bromoresorcinol
Conditions | Yield |
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With hydrogenchloride; sodium hydroxide; sodium sulfite In methanol for 21h; | 62% |
4-Bromoresorcinol
Conditions | Yield |
---|---|
With Candida antarctica lipase B In di-isopropyl ether; isopropyl alcohol at 45℃; for 1h; Enzymatic reaction; regioselective reaction; | 12% |
5-bromo-2-hydroxy-4-methoxybenzoic acid
4-Bromoresorcinol
Conditions | Yield |
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With hydrogen bromide; acetic acid at 100℃; im Rohr; |
Conditions | Yield |
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With sulfuric acid | |
With water |
4-bromo-3-hydroxy-aniline
4-Bromoresorcinol
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite Diazotization.Eintragen in Eiswasser und folgenden Kochen; |
N,N-dichlorourea
sulfuric acid
recorcinol
A
4-Bromoresorcinol
B
2,4,6-tribromoresorcinol
C
2,4-dibromo-5-hydroxyphenol
The IUPAC name of 4-Bromoresorcinol is 4-bromobenzene-1,3-diol. With the CAS registry number 6626-15-9, it is also named as 1,3-benzenediol, 4-bromo-; 1-Bromo-2,4-dihydroxybenzene. The product's categories are benzene series, aromatic phenols, organic building blocks, oxygen compounds and polyols. It is pink crystalline powder.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.99; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.98; (4)ACD/LogD (pH 7.4): 1.92; (5)ACD/BCF (pH 5.5): 18.97; (6)ACD/BCF (pH 7.4): 16.25; (7)ACD/KOC (pH 5.5): 285.85; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.657; (12)Molar Refractivity: 37.7 cm3; (13)Molar Volume: 102.4 cm3; (14)Polarizability: 14.94×10-24 cm3; (15)Surface Tension: 62.2 dyne/cm; (16)Enthalpy of Vaporization: 56.46 kJ/mol; (17)Vapour Pressure: 0.000545 mmHg at 25°C; (18)Tautomer Count: 9; (19)Exact Mass: 187.947292; (20)MonoIsotopic Mass: 187.947292; (21)Topological Polar Surface Area: 40.5; (22)Heavy Atom Count: 9.
Preparation of 4-Bromoresorcinol: It can be obtained by benzene-1,3-diol with NaBr, DMD and aq. H2SO4 in the solvent acetone at 20 °C. The reaction time is 1 min. The yield is 95%.
Uses of 4-Bromoresorcinol: It is commonly used as an organic reagent and pharmaceutical intermediate. For example: It reacts with toluene-4-sulfonyl chloride to get 2,4-bis(tosyloxy)bromobenzene. This reaction needs reagent K2CO3 and solvent acetone by heating. The reaction time is 1 hours. The yield is 89%.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. And it is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES: Brc1ccc(O)cc1O;
2. InChI: InChI=1/C6H5BrO2/c7-5-2-1-4(8)3-6(5)9/h1-3,8-9H.