1-Chloro-3,5-dimethyladamantane

Base Information

• Chemical Name: 1-Chloro-3,5-dimethyladamantane
• CAS No.: 707-36-8
• Molecular Formula: C12H19 Cl
• Molecular Weight: 198.736
• Hs Code.: 2903890090
• European Community (EC) Number: 615-149-2
• UNII: Q8E5DB8WPY
• DSSTox Substance ID: DTXSID70390748
• Mol file: 707-36-8.mol

Synonyms:1-Chloro-3,5-dimethyladamantane;707-36-8;5-Chloro-1,3-dimethyladamantane;1,3-Dimethyl-5-chloroadamantane;1-chloro-3,5-dimethyl-adamantane;Q8E5DB8WPY;MFCD00074841;EC 615-149-2;C12H19Cl;Chlorodimethyladamantane;UNII-Q8E5DB8WPY;SCHEMBL810646;1-Chloro-3,5-dimethyltricyclo[3.3.1.13,7]decane;Tricyclo[3.3.1.13,7]decane, 1-chloro-3,5-dimethyl-;3,5-dimethyl-1-chloroadamantane;DTXSID70390748;PXDRFQZLDWZHPX-UHFFFAOYSA-N;5-chloro-1,3-dimethyl adamantane;1-chloranyl-3,5-dimethyl-adamantane;STL452977;AKOS015850596;CS-W010523;AS-60554;SY053163;ADAMANTANE, 1-CHLORO-3,5-DIMETHYL-;C1981;FT-0620206;D78261;A836976;1-chloro-3,5-dimethyltricyclo[3.3.1.1~3,7~]decane;TRICYCLO(3.3.1.1(SUP 3,7))DECANE, 1-CHLORO-3,5-DIMETHYL-

Chemical Property of 1-Chloro-3,5-dimethyladamantane

Chemical Property:

• Vapor Pressure: 0.0583mmHg at 25°C
• Refractive Index: n/D1.4962
• Boiling Point: 87 °C / 4mmHg
• Flash Point: 93 °C
• PSA: 0.00000
• Density: 1.02
• LogP: 3.97420
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 198.1175283
• Heavy Atom Count: 13
• Complexity: 240

Purity/Quality:

99% ^*data from raw suppliers

1-Chloro-3,5-dimethyladamantane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC3CC(C1)(CC(C3)(C2)Cl)C
• Uses: 1-Chloro-3,5-dimethyladamantane is an adamantane derivative used in the preparation of organosilicon compounds with antiviral activity. Memantine impurity C. Building block has been shown to be used as a key intermediate in the synthesis of memantine hydrochloride, which was reported to be a FDA approved drug for Alzheimer′s treatment.

Technology Process of 1-Chloro-3,5-dimethyladamantane

There total 6 articles about 1-Chloro-3,5-dimethyladamantane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1,3-dimethyl-5-adamantanol (707-37-9) → 1-chloro-3,5-dimethyl-adamantane (707-36-8)

Guidance literature:

With thionyl chloride; In 1,2-dichloro-ethane; at 50 ℃; for 2h;

Reference yield:

1,3-dimethyladamantane (702-79-4) → 1-chloro-3,5-dimethyl-adamantane (707-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine; water / 25 °C / Reflux

2: hydrogenchloride / water / 15 h / 25 - 30 °C

With hydrogenchloride; water; bromine; In water;

DOI:10.1021/op060246+

Reference yield:

3,5-dimethyl-1-bromoadamantane (941-37-7) → 1-chloro-3,5-dimethyl-adamantane (707-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 14 h / 157 °C

1.2: 5 - 25 °C

2.1: hydrogenchloride / water / 21 h / 28 °C

With hydrogenchloride; In water;

upstream raw materials:

1,3-dimethyladamantane

1-acetamido-3,5-dimethyladamantane

1,3-dimethyl-5-adamantanol

3,5-dimethyl-1-bromoadamantane

Downstream raw materials:

1,3-dimethyladamantane

1-formamido-3,5-dimethyltricyclo[3.3.1.1^3,7]decane

1-acetamido-3,5-dimethyladamantane

memantine hydrochloride

Refernces

• 1、 Reddy, Jambula Mukunda,Prasad, Ganji,Raju, Veeramalla,Ravikumar, Mylavarapu,Himabindu, Vurumidi,Reddy, Ghanta Mahesh. "An improved synthesis of memantine hydrochloride: Anti-Alzhelmer's drug". . p. 268 - 269. Retrieved 2012/12/26.
• 2、 Fedotov, N. S.,Grishina, E. V.,Sheludyakov, V. D.,Bernadskii, A. A.,Bochkarev, V. N.. "REACTION OF CHLOROMETHYLSILANES WITH ADAMANTANE AND 1,3-DIMETHYLADAMANTANE IN THE PRESENCE OF tert-BUTYL PEROXIDE". . p. 2258 - 2261. Retrieved 2007/10/02.