| Identification | More | [Name]
16-Bromohexadecanoic acid | [CAS]
2536-35-8 | [Synonyms]
16-BROMO-HEXADECANECARBOXYLIC ACID
16-BROMOHEXADECANOIC ACID
16-BROMOHEXADECANOIC ACID, TECHNICAL GRADE, 85%
16-BROMOHEXADECANOIC ACID, 99+%
16-Brom-hexadecaneSre
16-Brom-hexadecanoicacid
16-Bromohexadecanoic acid (work in progress) | [Molecular Formula]
C16H31BrO2 | [MDL Number]
MFCD00040779 | [Molecular Weight]
335.32 | [MOL File]
2536-35-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
68-71 °C (lit.)
70-73 °C (lit.) | [Boiling point ]
214-217 °C/1 mmHg (lit.) | [density ]
1.116±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
solid | [pka]
4.78±0.10(Predicted) | [color ]
White | [InChI]
InChI=1S/C16H31BrO2/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h1-15H2,(H,18,19) | [InChIKey]
PFNCOYVEMJYEED-UHFFFAOYSA-N | [SMILES]
C(O)(=O)CCCCCCCCCCCCCCCBr | [CAS DataBase Reference]
2536-35-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R38:Irritating to the skin. | [Safety Statements ]
S37:Wear suitable gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
2915907098 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Uses]
16-Bromohexadecanoic acid can be used:
- As a starting material in the synthesis of ceramides with ultralong chains.
- In the synthesis of 6-(nitrooxy)hexadecanoic acid intermediate, which on reacting with (L)-carnitine ethyl ester iodide gave carnitine nitro-derivatives.
| [Synthesis]
Synthesis of 16-bromohexadecanoic acid 2: To a 2 L three-necked round-bottomed flask equipped with a mechanical stirrer, a reflux condenser tube, and a nitrogen introduction tube was added 177 g (0.63 mol) of 16-hydroxyhexadecanoic acid 1. Subsequently, 1000 mL (5 mol) of 30% hydrogen bromide in acetic acid solution and 310 mL of concentrated sulfuric acid were added. The system was connected to sequential trapping devices, sequentially a sodium hydroxide particle trap, a 25% aqueous sodium hydroxide solution trap and a saturated sodium carbonate solution trap. The reaction mixture was stirred overnight at room temperature and subsequently heated to reflux for 6 hours. Upon completion of the reaction, the mixture was cooled and poured into ice water and the precipitated solid was vacuum filtered. After high vacuum drying, 196 g of 16-bromohexadecanoic acid 2 was obtained Yield: 88%; Purity: >95%; Melting point: 67-69 °C; DSC: 69.0 °C (sharp); IR (paraffin paste): 1700 cm?1 (strong), 650 cm?1 (strong); 1H NMR (200 MHz, CD2Cl2): δ 3.4 (t, J = 8 Hz, 2H), 2.3 (t, J = 8 Hz, 2H), 1.8 (m, 2H), 1.6 (m, 2H), 1.2 (br.s, 22H). | [References]
[1] Tetrahedron Letters, 1999, vol. 40, # 10, p. 2011 - 2014
[2] Tetrahedron, 2000, vol. 56, # 51, p. 9975 - 9984
[3] Patent: US5502226, 1996, A
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 10, p. 1183 - 1190
[5] Helvetica Chimica Acta, 1929, vol. 12, p. 478 |
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