Catecholborane
1,3,2-benzodioxaborole
CAS: 274-07-7
Molecular Formula: C6H5BO2
Catecholborane - Names and Identifiers
| Name | 1,3,2-benzodioxaborole |
| Synonyms | Ctecholborane Catecholborane CATECHOLBORANE Benzcatechinborane RARECHEM AK VD 0002 1,3,2-BENZODIOXABOROLE 1,3,2-benzodioxaborole Benzo[d][1,3,2]dioxaborole(1.0M) Catecholborane, 1.0 M solution in THF Catecholborane, Benzo[d][1,3,2]dioxaborole |
| CAS | 274-07-7 |
| EINECS | 205-991-5 |
| InChI | InChI=1/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H |
| InChIKey | CENMEJUYOOMFFZ-UHFFFAOYSA-N |
Catecholborane - Physico-chemical Properties
| Molecular Formula | C6H5BO2 |
| Molar Mass | 119.91 |
| Density | 1.125g/mLat 25°C(lit.) |
| Melting Point | 12°C(lit.) |
| Boling Point | 50°C50mm Hg(lit.) |
| Flash Point | 36°F |
| Water Solubility | Reacts with water. |
| Solubility | Miscible with diethyl ether, tetrahydrofuran, dichloromethane, chloroform, carbon tetrachloride, toluene, and benzene. |
| Vapor Presure | 17.554mmHg at 25°C |
| Appearance | liquid |
| Color | Hazy Colourless |
| BRN | 972072 |
| Storage Condition | 2-8°C |
| Sensitive | Moisture Sensitive |
| Refractive Index | n20/D 1.507(lit.) |
Catecholborane - Risk and Safety
| Risk Codes | R11 - Highly Flammable R19 - May form explosive peroxides R34 - Causes burns R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R63 - Possible risk of harm to the unborn child R48/20 - R14 - Reacts violently with water R40 - Limited evidence of a carcinogenic effect R37 - Irritating to the respiratory system |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S16 - Keep away from sources of ignition. S43 - In case of fire use ... (there follows the type of fire-fighting equipment to be used.) |
| UN IDs | UN 2924 3/PG 2 |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 1-10 |
| TSCA | Yes |
| HS Code | 29209090 |
| Hazard Class | 3 |
| Packing Group | II |
Catecholborane - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Uses | Catechol borane has the characteristics of simple preparation method, stable properties, easy storage, fast reaction rate with alkenes and alkynes under mild conditions, high regioselectivity and stereoselectivity, easy functionalization and free radical, etc. Therefore, it has been widely used in borohydride reaction and reduction reaction. Compared with borane, borane derivatives have lower activity in organic reactions, but they have unique advantages in the regioselectivity and stereoselectivity of the reaction. Therefore, the synthesis of borane derivatives and their application in organic reactions have been concerned by relevant researchers. Monofunctional borohydride reagent can reduce β-hydroxy ketone to 1, 3-diol. Can affect the conjugated reduction reaction of α,β-enone. |
| Preparation | Diborate compounds were subjected to high-pressure hydrogen cracking reaction of B- B bonds under the action of heterogeneous metal catalysts, and three types of monohydroboranes including catechol borane were synthesized. Among them, palladium catalysts have the most ideal catalytic effect. Such catalysts can efficiently catalyze the breaking of B- B bonds in diborates at room temperature, and then react with hydrogen to produce catechol borane. |
| Production method | 1. Coupling 4-bromobutene-1 and catecholborane provides bromobutylboron and α-pinanediol production 2 .. This is regioselectively chlorination to displaced chlorine atoms and lithium hexamethyldisilazide 3. Secondly, acid treatment provides intermediate. 4. In a 500-liter dry flask communicating with a mercury-sealed bubbling device (the tail pipe is introduced into the fume hood), 100 ml of 2 mol/l borane (200 mmol) tetrahydrofuran solution is placed in the presence of nitrogen "dead. Under full stirring at 0 ℃, 22g (200 mol) of 50 ml of tetrahydroenan solution of catechol (catechol) was added dropwise within 30 minutes. After stirring at 25 ℃ for 30 minutes, 19.2 grams (80%) of product |
Last Update：2024-04-09 15:16:44
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View History
Catecholborane
trisodium [5-acetamido-4-hydroxy-3-[[2-hydroxy-5-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonato(5-)]cuprate(3-)
Chloromethyl methyl ethe
2-甲基-3-氨基-5-硝基吡啶
2-氨基-3-硝基-5-甲基吡啶
(4S)-6,7-DIFLUOROCHROMANE-4-YLAMINE
异硫氰酸异丁酯
4-甲氧基-3-甲基苯酚
苯并[D]噻唑-2-甲酸乙酯
ACID BLUE 41
trisodium [5-acetamido-4-hydroxy-3-[[2-hydroxy-5-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonato(5-)]cuprate(3-)
Chloromethyl methyl ethe
2-甲基-3-氨基-5-硝基吡啶
2-氨基-3-硝基-5-甲基吡啶
(4S)-6,7-DIFLUOROCHROMANE-4-YLAMINE
异硫氰酸异丁酯
4-甲氧基-3-甲基苯酚
苯并[D]噻唑-2-甲酸乙酯
ACID BLUE 41