7-Bromo-1-heptanol Chemical Properties

Boiling point:

111-112 °C/4 mmHg (lit.)

Density 

1.269 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.482(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Oil

pka

15.18±0.10(Predicted)

color 

Pale Yellow to Light Brown

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C7H15BrO/c8-6-4-2-1-3-5-7-9/h9H,1-7H2

InChIKey

MMXRRNUXCHUHOE-UHFFFAOYSA-N

SMILES

C(O)CCCCCCBr

CAS DataBase Reference

10160-24-4(CAS DataBase Reference)

NIST Chemistry Reference

1-Heptanol, 7-bromo-(10160-24-4)

EPA Substance Registry System

1-Heptanol, 7-bromo- (10160-24-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

29055900

MSDS

• Language:English Provider:SigmaAldrich

7-Bromo-1-heptanol Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

7-Bromo-1-heptanol was used in the synthesis of (9Z,12E)-[1-13C]-octadeca-9,12-dienoic acid and(9Z,12Z,15E)-[1-13C]-octadeca-9,12,15-trienoic acid. It can be used to prepare N-substituted [(carboxymethyl)phenoxy]ethyl benzoxazinones as PPARγ agonists and antidiabetic (type 2) agents. It can also be used to prepare thiochroman and chroman derivatives as pure antiestrogens.

Synthesis

The general procedure for the synthesis of 7-bromo-1-heptanol from 1,7-heptanediol was as follows: 4860 g of 40% hydrobromic acid, 2110 g of concentrated sulfuric acid, and 25,000 mL of toluene were added sequentially to a 50-liter glass reactor equipped with a stirrer and thermometer. Subsequently, 2710 g of 1,7-heptanediol was added, stirring was initiated, and the reaction mixture was heated to reflux and maintained for 26 hours. After confirming complete consumption of the feedstock by sampling, the reaction was stopped. The reaction mixture was left to stratify and the aqueous layer was extracted once with 5000 mL of toluene. The organic layer was combined and washed once with 5000 ml of saturated sodium chloride solution and then with saturated sodium bicarbonate solution until neutral. After separation of the aqueous layer, the solvent was evaporated from the organic layer under reduced pressure to give 3780 g of crude 7-bromo-1-heptanol. The crude product was further purified by high-vacuum distillation, setting the oil bath temperature at 110 °C and the system vacuum at 42 Pa. The fraction at 74 °C was collected to obtain 3520 g of 7-bromo-1-heptanol with 99.4% purity and 88% yield.

References

[1] Angewandte Chemie - International Edition, 2012, vol. 51, # 32, p. 8110 - 8113
[2] Patent: CN107417496, 2017, A. Location in patent: Paragraph 0012; 0013; 0014
[3] Polish Journal of Chemistry, 2004, vol. 78, # 7, p. 937 - 942
[4] Journal of Natural Products, 2016, vol. 79, # 1, p. 244 - 247
[5] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1233 - 1239

7-Bromo-1-heptanol(10160-24-4)Related Product Information

• Ambroxol
• 1-Heptanol
• 7-Bromo-1-heptene
• 7-Bromoheptanoic acid
• 7-Ethyl tryptophol
• 6-Bromo-1-hexanol
• Bronopol
• Bromine
• Ethyl 7-bromoheptanoate
• 3-Bromo-1-adamantaneacetic acid
• (5-BROMOPENTYL)MALONIC ACID DIETHYL ESTER
• 7-Bromo-1-heptanol
• bromo-Dragonfly
• 6-(BROMOMETHYL)BICYCLO[2.2.1]HEPT-2-YL 4-METHYLBENZENE-1-SULFONATE
• CHOLESTAN-5-ALPHA-BROMO-6,19-EPOXY-3-BETA-OL ACETATE
• 7-PHENOXYHEPTYL BROMIDE
• 5-BETA-CHOLANIC ACID-12-ALPHA-BROMO-3,11-DIONE METHYL ESTER
• 5-BETA-PREGNAN-12-ALPHA-BROMO-3-ALPHA, 21-DIOL-11,20-DIONE 21-ACETATE