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| | 1,2-Bis(bromomethyl)benzene Basic information |
| | 1,2-Bis(bromomethyl)benzene Chemical Properties |
| Melting point | 91-94 °C(lit.) | | Boiling point | 140 °C / 20mmHg | | density | 1.96 g/mL at 25 °C(lit.) | | refractive index | 1.6113 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | sol ethanol, ether, chloroform; slightly sol petroleum ether. | | form | Crystals or Crystalline Powder | | color | White to light cream | | Water Solubility | soluble, hydrolyses | | BRN | 637159 | | InChI | InChI=1S/C8H8Br2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5-6H2 | | InChIKey | KGKAYWMGPDWLQZ-UHFFFAOYSA-N | | SMILES | C1(CBr)=CC=CC=C1CBr | | CAS DataBase Reference | 91-13-4(CAS DataBase Reference) | | NIST Chemistry Reference | Benzene, 1,2-bis(bromomethyl)-(91-13-4) | | EPA Substance Registry System | Benzene, 1,2-bis(bromomethyl)- (91-13-4) |
| Hazard Codes | C | | Risk Statements | 22-34 | | Safety Statements | 26-36/37/39-45 | | RIDADR | UN 3448 6.1/PG 2 | | WGK Germany | 2 | | F | 8-19-21 | | TSCA | TSCA listed | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29036990 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| | 1,2-Bis(bromomethyl)benzene Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powde | | Uses | 1,2-Bis(bromomethyl)benzene is used in the synthesis of isothioureas involved in the inhibition of human nitric oxide synthases. Also used in the synthesis of tridentate carbene ligands. | | Application | 1,2-Bis(bromomethyl)benzene (α,α′-Dibromo-o-xylene) is a source of o-quinodimethane, a highly reactive diene useful in Diels-Alder reactions; an electrophile for
the synthesis of carbo- and heterocyclic compounds including macrocycles (cyclophanes, crown ethers,
hemispherands, spherands), cryptands, hemicarcerands, vaulted cappedophanes, bicyclic compounds,
spirocyclic compounds; a protective group reagent for diols. | | Synthesis | General procedure for the synthesis of 2-methylbenzyl bromide and 1,2-bis(bromomethyl)benzene from o-xylene: To a mixture of N-bromosuccinimide (NXS) and substrate (o-xylene or its derivatives) in acetonitrile (CH3CN) at room temperature, silicon tetrachloride (SiCl4) was slowly added, and the reaction mixture was stirred continuously until thin layer chromatography (TLC) monitoring showed that the feedstock completely disappeared. Upon completion of the reaction, the reaction mixture was poured into water (H2O) and extracted with dichloromethane (CH2Cl2). All organic phase extracts were combined and dried with anhydrous magnesium sulfate (MgSO4) followed by evaporation under reduced pressure to remove the solvent. The resulting residue can be purified by recrystallization (using a solvent mixture of petroleum ether-ether (3:1)) to give pure 2-methylbenzyl bromide or 1,2-bis(bromomethyl)benzene or by silica gel column chromatography (using hexane-ethyl acetate (10:1 or 30:1) as eluent) to give the target product. | | storage | 1,2-Bis(bromomethyl)benzene should be avoided moisture; corrosive (forms HBr on hydrolysis); lachrymator;
not mutagenic in Ames test; decontaminate by soaking apparatus, etc. in alcoholic alkali for 24 h or longer. | | Purification Methods | Crystallise it from CHCl3 or pet ether, and/or distil it under vacuum. [Wenner Org Chem 17 527 1952, Beilstein 5 H 366, 5 I 180, 5 II 285, 5 III 819, 5 IV 929.] | | References | [1] Tetrahedron Letters, 2006, vol. 47, # 40, p. 7245 - 7247
[2] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[3] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[4] Chemistry Letters, 2004, vol. 33, # 7, p. 916 - 917 |
| | 1,2-Bis(bromomethyl)benzene Preparation Products And Raw materials |
| Raw materials | o-Xylene-->1,2-Benzenedimethanol-->N-Bromosuccinimide-->Tetrachlorosilane-->Acetonitrile | | Preparation Products | 2H-Isoindole-->3',4'-dihydro-6-methylenespiro(2,4-cyclohexadiene-1,2'(1'H)-naphthalene)-->1,2-Bis(diphenylphosphinomethyl)benzene-->2-Benzyl-2,3-dihydro-1H-isoindole-->1,2-Bis(cyanomethyl)benzene-->1,2-Benzenedimethanol-->1,2-Phenylenediacetic acid-->P,P'-[(1,2-Phenylene)bis(Methylene)]bisphosphonic Acid P,P,P',P'-tetraethyl ester-->Carbamic acid, N-(1,3-dihydro-2H-isoindol-2-yl)-N-methyl-, 1,1-dimethylethyl ester |
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