1-Bromo-3,5-dimethyladamantane Chemical Properties

Boiling point:

201 °C (lit.)

Density 

1.224 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.52(lit.)

Flash point:

228 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Dichloromethane (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless to Pale Yellow

Specific Gravity

1.224

BRN 

1927514

InChI

InChI=1S/C12H19Br/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8H2,1-2H3

InChIKey

QUCXLVDIVQWYJR-UHFFFAOYSA-N

SMILES

C12(Br)CC3(C)CC(CC(C)(C3)C1)C2

CAS DataBase Reference

941-37-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36

Safety Statements 

26-27-36/37/39-45

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2903890002

MSDS

• Language:English Provider:SigmaAldrich

1-Bromo-3,5-dimethyladamantane Usage And Synthesis

Uses

1-Bromo-3,5-dimethyladamantane (cas# 941-37-7) is a compound useful in organic synthesis.

Description

1-Bromo-3,5-dimethyladamantane is a precursor substance of memantine and memantine hydrochloride (MH), which can be synthesised by direct amination with thiourea. MH is an FDA-approved first-line treatment for moderate to severe Alzheimer's disease.

Chemical Properties

Clear Colorless Oil

Uses

1-Bromo-3,5-dimethyladamantane was used in the one pot synthesis of 1,3-dicarbonyl adamantanes. It was also used in the synthesis of 3,5-dimethyladamantan-1-ol.

Synthesis

A) Add 59.9 g (0.345 mol) of bromine, 10 g (0.075 mol) of anhydrous aluminum trichloride, and 37.8 g of 1,2-dichloroethane to the reactor with thorough stirring; B) Heat the reaction mixture A to 15°C; C) Add 50 g (0.3 mol) of 1,3-dimethyladamantane to the mixture obtained in step B, and absorb the resulting gas using a 5% sodium hydroxide solution; D) Add 400 g of saturated sodium bisulfite solution to reaction mixture B until the red color of the reaction solution completely disappears, and separate the organic phase C and the aqueous phase D; and D) Add 400 g of saturated sodium bisulfite solution to the reaction mixture B until the red color of the reaction solution completely disappears, and separate the organic phase C and the aqueous phase D; E) Wash the organic phase C with 400 g of water, and then dry it with 20 g of anhydrous sodium sulfate; F) Perform distillation on the organic phase C obtained in step E to obtain the crude product E; G) Perform decompression distillation on the crude product E to obtain the 1-(3-methyladamantyl)-1,3-dimethyladamantane. G) the crude product E was distilled under reduced pressure to obtain 1-bromo-3,5-dimethyladamantane in 92% yield and ≥99% purity by gas chromatography.

References

[1] Patent: CN104592034, 2016, B. Location in patent: Paragraph 0092-0099
[2] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5107 - 5110
[3] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187
[4] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[5] Patent: US5061703, 1991, A

1-Bromo-3,5-dimethyladamantane(941-37-7)Related Product Information

• Amantadine
• Adamantane
• Decane
• 3-Bromoanisole
• 1-Adamantanecarboxylic acid
• N-(3,5-DiMethyladaMantan-1-yl)forMaMide
• Memantine-Galactose Adduct 1
• Memantine-glucose Adduct 1
• 1-BROMO-3-METHYLCYCLOHEXANE
• 1-BROMO-5-METHYLHEXANE
• 3-BROMOOCTANE
• CYCLOOCTYL BROMIDE
• 2-CYCLOHEXYLETHYL BROMIDE
• 1-BROMO-3,3-DIMETHYLBUTANE
• 2-Bromoheptane
• Bromocyclohexane
• 2-BROMO-6-METHYLHEPTANE
• Bromine