| Identification | More | [Name]
1,10-Dibromodecane | [CAS]
4101-68-2 | [Synonyms]
1,10-DECAMETHYLENE BROMIDE
1,10-DECAMETHYLENE DIBROMIDE
1,10-DECANE DIBROMIDE
1,10-DIBROMODECANE
DECAMETHYLENE BROMIDE
DECAMETHYLENE DIBROMIDE
TIMTEC-BB SBB008900
,w-Dibromodecane
1,10-dibromo-decan
Decene, 1,10-dibromo
Dibromodecane,95%
Decane, 1,10-dibromo- | [EINECS(EC#)]
223-871-0 | [Molecular Formula]
C10H20Br2 | [MDL Number]
MFCD00000222 | [Molecular Weight]
300.07 | [MOL File]
4101-68-2.mol |
| Chemical Properties | Back Directory | [Appearance]
beige to brown crystalline low melting mass | [Melting point ]
25-27 °C (lit.) | [Boiling point ]
160 °C/15 mmHg (lit.) | [density ]
1.335 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4912(lit.)
| [Fp ]
26°C | [storage temp. ]
2-8°C
| [form ]
Crystalline Low Melting Solid | [color ]
Beige to brown | [Specific Gravity]
1.335 | [Water Solubility ]
insoluble | [BRN ]
506156 | [Dielectric constant]
6.5599999999999996 | [InChI]
1S/C10H20Br2/c11-9-7-5-3-1-2-4-6-8-10-12/h1-10H2 | [InChIKey]
GTQHJCOHNAFHRE-UHFFFAOYSA-N | [SMILES]
BrCCCCCCCCCCBr | [CAS DataBase Reference]
4101-68-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Decane, 1,10-dibromo-(4101-68-2) | [EPA Substance Registry System]
4101-68-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29049090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
beige to brown crystalline low melting mass | [Uses]
1,10-Dibromodecane is used as an alkylating agent and as synthetic organic intermediate. | [Synthesis]
The general procedure for the synthesis of 1,10-dibromodecane from 1,10-decanediol is as follows: 1,10-decanediol (1 eq.), 48% aqueous hydrobromic acid (ca. 3 eq./hydroxyl), and octane (ca. 7:1 volume-to-weight ratio to the diol) were added to a single-necked, round-bottomed flask and assembled with a fractionating column/Dean-Stark trap. The reaction mixture was placed in a heated oil bath (145-150°C) with rapid magnetic stirring. The aqueous (lower) layer at the initial boiling point (89-92°C) was condensed and gently separated, and subsequently collected at about half the theoretical volume of water; at this point the temperature of the azeotrope (still at head temperature) began to rise. The condenser was set to full reflux for a few hours, then turned back on and the aqueous-phase material continued to be collected for 1 hour (top temperature 96-100°C). The final volume of the aqueous phase distillate reaches 90-100% of the theoretical value (up to 24% hydrobromic acid in the high boiling distillate). When the octane phase (which is light tan in color) contains dibromides and brominated streptanols (e.g., 6 band 6c), it is washed with cold 85% v/v sulfuric acid (10 mL first, then 5 mL) to remove all color and brominated streptanols. For all three dibromides (3b, 4b, 6b), the neutralized octane solution was passed through a Vigreux column under reduced pressure to remove the solvent, and the residue (which was confirmed to be essentially pure by 1H NMR) was purified by Kugelrohr distillation. Trace amounts of 4-methyltetrahydropyran were detected prior to distillation of 4b. | [References]
[1] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
[2] Green Chemistry, 2014, vol. 16, # 2, p. 836 - 843
[3] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5386 - 5394
[4] Journal of the American Chemical Society, 1936, vol. 58, p. 488
[5] Journal of the Chemical Society, 1958, p. 2068 |
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