1,3-Dimethyladamantane Chemical Properties

Melting point:

-30 °C

Boiling point:

201.5 °C

Density 

0.886 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.478(lit.)

Flash point:

127 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

clear liquid

Specific Gravity

0.886

color 

Colorless to Almost colorless

Stability:

Stable. Incompatible with strong oxidizing agents. Flammable.

InChI

InChI=1S/C12H20/c1-11-4-9-3-10(5-11)7-12(2,6-9)8-11/h9-10H,3-8H2,1-2H3

InChIKey

CWNOIUTVJRWADX-UHFFFAOYSA-N

SMILES

C12(C)CC3CC(CC(C)(C3)C1)C2

CAS DataBase Reference

702-79-4(CAS DataBase Reference)

NIST Chemistry Reference

Adamantane, 1,3-dimethyl-(702-79-4)

Safety Information

Hazard Codes 

F

Risk Statements 

10

Safety Statements 

16-60

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29021990

MSDS

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1,3-Dimethyladamantane Usage And Synthesis

Chemical Properties

clear colourless liquid

Uses

1,3-Dimethyladamantane is a dimethylated adamantane derivative. Memantine impurity A. Memantine Related Compound A (1,3-Dimethyladamantane).

Application

1,3-Dimethyladamantane was used in the synthesis of 1,3-dibromo-5,7-dimethyladamantane.

Definition

ChEBI: 1,3-dimethyladamantane is a polycyclic alkane and a member of adamantanes. It derives from a hydride of an adamantane.

General Description

1,3-Dimethyladamantane undergoes C-H insertion reaction with phenylchlorocarbene. It reacts with with molecular oxygen in the presence of N-hydroxyphthalimide combined with cobalt salts to yield 3,5-dimethyladamantan-1-ol and 5,7-dimethyladamantane-1,3-diol.

Synthesis

GENERAL METHODS: A thiocarbonate solution was prepared by dissolving 5 g (107 mg, 0.200 mmol) of 1-bromo-3,5-dimethyladamantane in CPME (0.5 mL). Subsequently, a solution of n-Bu3SnH (75.7 mg, 0.260 mmol) and AIBN (6.6 mg, 0.040 mmol) in CPME (1.5 mL) was slowly added dropwise by syringe pump to the above thiocarbonate solution, and the reaction lasted for 30 min at 90 °C. After completion of the reaction, the mixture was continued to be stirred at the same temperature for 30 min, followed by concentration. The residue was purified by 10% w/w K2CO3-silica gel fast column chromatography using gradient elution (hexane → hexane/EtOAc = 100/1 → 50/1 → 20/1) to afford 6 g of cis-consistently cyclized product (53.6 mg, 0.140 mmol, 70% yield) and a mixture of cis- and trans-consistently diastereoisomers (22.0 mg. 0.0572 mmol, 29% yield, cis-trans ratio of 2.8:1). For spectral analysis, these isomers were separated by repeated column chromatography.

References

[1] Tetrahedron, 2013, vol. 69, # 10, p. 2251 - 2259
[2] Organic Letters, 2008, vol. 10, # 4, p. 533 - 536
[3] Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2762 - 2765

1,3-Dimethyladamantane(702-79-4)Related Product Information

• Altrenogest
• Decane
• Amantadine
• Adamantane
• Dimethyl 1,3-adamantanedicarboxylate
• 1,3-Adamantanediacetic acid
• 1,3-adamantanedimethanol
• 4,4'-(1,3-ADAMANTANEDIYL)DIPHENOL
• 1,3-Adamantanedicarboxylic acid
• 1-Acetamido-3,5-dimethyladamantane
• 1-Hydroxy-3,5-dimethyladamantane
• 1-Amino-3,5-dimethyladamantane
• Memantine HCl
• 1-BROMO-3,5-DIMETHYLADAMANTANE
• 3,5-DIMETHYLADAMANTANE-1-CARBOXYLIC ACID
• 5-chloro-1,3-dimethyladamantane,1-CHLORO-3,5-DIMETHYLADAMANTANE
• 1,3-BIS(4-METHYLPHENYL)ADAMANTANE
• 3-(1,1,2,3,3,3-HEXAFLUOROPROPYL)ADAMANTANE-1-CARBOXYLIC ACID