941-37-7

Basic information

• Product Name: 1-Bromo-3,5-dimethyladamantane
• Synonyms: 1-Bromo-3,5-dimethyltricyclo[3.3.1.13,7]decane;1-BROMO-3,5-DIMETHYLADAMANTANE;3,5-dimethyl-1-bromo- adamantane;1-Bromo-3,5-Dimethyl;1-BROMO-3,5- DIMETHYL DAMANTANE;1,3-Dimethyl-5-bromoadamantane;tricyclo[3.3.1.1~3,7~]decane, 1-bromo-3,5-dimethyl-;NSC 102293
• CAS NO: 941-37-7
• Molecular Formula: C₁₂H₁₉Br
• Molecular Weight: 243.18
• EINECS: 213-378-9
• Product Categories: Chemical intermediate for Memantine HCl;Adamantane derivatives;Adamantanes;Alkyl;Halogenated Hydrocarbons;Organic Building Blocks;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 941-37-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 201 °C(lit.)
• Flash Point: 228 °F
• Appearance: clear colorless oil
• Density: 1.224 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0385mmHg at 25°C
• Refractive Index: n20/D 1.52(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Dichloromethane (Slightly), Methanol (Slightly)
• BRN: 1927514
• CAS DataBase Reference: 1-Bromo-3,5-dimethyladamantane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-3,5-dimethyladamantane(941-37-7)
• EPA Substance Registry System: 1-Bromo-3,5-dimethyladamantane(941-37-7)

Safety Data

• Hazard Codes: C
• Statements: 34-36
• Safety Statements: 26-27-36/37/39-45
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 941-37-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 941-37-7 differently. You can refer to the following data:
1. 1-Bromo-3,5-dimethyladamantane (cas# 941-37-7) is a compound useful in organic synthesis.
2. 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.

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

Synthetic route

1,3-dimethyladamantane (702-79-4) → 3,5-dimethyl-1-bromoadamantane (941-37-7)

Conditions	Yield
With aluminum (III) chloride; bromine In 1,2-dichloro-ethane at 15℃; Reagent/catalyst; Temperature; Solvent;	92%
With bromine for 12h; Reflux;	91.5%
With iron(III)-acetylacetonate; carbon tetrabromide at 150℃; for 3h; Sealed tube; Inert atmosphere;	85%

1-acetamido-3,5-dimethyladamantane (19982-07-1) → 1,3-dimethyl-5-adamantanol (707-37-9) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + memantine* (19982-08-2) + memantine hydrochloride (41100-52-1)

Conditions	Yield
Stage #1: 1-acetamido-3,5-dimethyladamantane With sodium hydroxide In diethylene glycol at 105 - 170℃; for 10h; Stage #2: With hydrogenchloride In water; toluene at 5 - 15℃; for 2.5h; Product distribution / selectivity;

1,3-dimethyl-5-adamantanol (707-37-9) → 3,5-dimethyl-1-bromoadamantane (941-37-7)

Conditions	Yield
With hydrogen bromide In water for 0.666667h; Inert atmosphere;

1,3-dimethyladamantane (702-79-4) → 1,3-dimethyl-5-adamantanol (707-37-9) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + 2-bromo-3,5-dimethyladamantane

Conditions	Yield
With pyridine; carbon tetrabromide; water; manganese(III) acetylacetonate Catalytic behavior; Concentration; Temperature; Time; Heating;

3,5-dimethyl-1-bromoadamantane (941-37-7) → 1,3-dimethyladamantane (702-79-4)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride at 90℃; for 1h; Solvent; Barton-McCombie Deoxygenation; Inert atmosphere;	100%
With decane; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; tri-n-butyl-tin hydride In toluene at 80℃; for 0.0166667h;	99 % Chromat.
Multi-step reaction with 2 steps 1: 98 percent / aq. HCl / dimethylformamide / 1.5 h 2: H2SO4 (91.5percent) / 72 h / Ambient temperature; var. of conc.of H2SO4, and var. of reaction time View Scheme

acetamide (60-35-5) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → 1-acetamido-3,5-dimethyladamantane (19982-07-1)

Conditions	Yield
With dimanganese decacarbonyl at 120 - 130℃; Inert atmosphere; Autoclave;	99%
at 125℃; Temperature;	94%
at 70 - 160℃; for 6h; Temperature; Inert atmosphere;	92.4%

3,5-dimethyl-1-bromoadamantane (941-37-7) → 1,3-dimethyl-5-adamantanol (707-37-9)

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide for 1.5h;	98%
With sodium hydroxide In ethanol at 70℃; Temperature;	85%
With potassium carbonate at 150℃; for 6h;
With sodium hydroxide In water for 4h; Reflux;

3,5-dimethyl-1-bromoadamantane (941-37-7) + methylmagnesium bromide (75-16-1) → 1,3-dimethyladamantane (702-79-4) + 1,3,5-trimethyladamantane (707-35-7)

Conditions	Yield
In dibutyl ether at 95℃;	A 2% B 98%

3,5-dimethyl-1-bromoadamantane (941-37-7) + Propionamid (79-05-0) → N-(3,5-dimethyladamant-1-yl)propanamide

Conditions	Yield
With dimanganese decacarbonyl at 120 - 130℃; Inert atmosphere; Autoclave;	98%

3,5-dimethyl-1-bromoadamantane (941-37-7) + benzamide (55-21-0) → N-(3,5-dimethyladamant-1-yl)benzamide

Conditions	Yield
With dimanganese decacarbonyl at 120 - 130℃; Inert atmosphere; Autoclave;	97%

3,5-dimethyl-1-bromoadamantane (941-37-7) + urea (57-13-6) → memantine hydrochloride (41100-52-1)

Conditions	Yield
Stage #1: 3,5-dimethyl-1-bromoadamantane; urea In 1-methyl-pyrrolidin-2-one at 120℃; for 4h; Stage #2: With sodium hydroxide In 1-methyl-pyrrolidin-2-one at 120℃; for 6h; Stage #3: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; water at 25℃; for 16h; Solvent; Temperature;	97%

3,5-dimethyl-1-bromoadamantane (941-37-7) + acetonitrile (75-05-8) → 1-acetamido-3,5-dimethyladamantane (19982-07-1)

Conditions	Yield
With sulfuric acid for 12h;	96%
Stage #1: 3,5-dimethyl-1-bromoadamantane; acetonitrile With phosphoric acid at 20 - 87℃; for 3.75 - 4.33h; Stage #2: With sodium hydroxide; water; butan-1-ol at 35 - 45℃; pH=5.5 - 7;	95.5%
With sulfuric acid at 20℃;	80%

3,5-dimethyl-1-bromoadamantane (941-37-7) + methylmagnesium bromide (75-16-1) → 1,3,5-trimethyladamantane (707-35-7)

Conditions	Yield
In dibutyl ether at 116℃;	95%

Isopropenyl acetate (108-22-5) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → 1-(3,5-dimethyladamantan-1-yl)propan-2-one

Conditions	Yield
Stage #1: 3,5-dimethyl-1-bromoadamantane With aluminum tri-bromide In dichloromethane at -10℃; for 0.5h; Stage #2: Isopropenyl acetate In dichloromethane at -10℃; for 0.5h;	91%

3,5-dimethyl-1-bromoadamantane (941-37-7) → memantine* (19982-08-2)

Conditions	Yield
Stage #1: 3,5-dimethyl-1-bromoadamantane With ammonium acetate In N,N-dimethyl-formamide at 150℃; for 5.5h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 5℃; for 0.5h;	90%
Stage #1: 3,5-dimethyl-1-bromoadamantane With acetamide at 130℃; for 5h; Stage #2: With sodium hydroxide In ethylene glycol at 200℃; for 7h;	75%
Multi-step reaction with 2 steps 1: H2SO4 2: KOH View Scheme

2-phenyl-1,2,3,4-tetrahydroisoquinoline (3340-78-1) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → 1-(3,5-dimethyladamantan-1-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline

Conditions	Yield
With 2,4,6-trimethyl-pyridine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; Schlenk technique; Irradiation;	90%

3,5-dimethyl-1-bromoadamantane (941-37-7) → memantine hydrochloride (41100-52-1)

Conditions	Yield
Stage #1: 3,5-dimethyl-1-bromoadamantane With sulfuric acid; toluene-4-sulfonic acid; acetonitrile at 30 - 50℃; for 2h; Stage #2: With hydrogenchloride In water; ethyl acetate for 2h; Reagent/catalyst;	88.44%
Stage #1: 3,5-dimethyl-1-bromoadamantane With formic acid; urethane at 20 - 90℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20 - 110℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere;	85%
Multi-step reaction with 3 steps 1: sulfuric acid / 12 h 2: sodium hydroxide / water; ethylene glycol / 12 h / 150 °C 3: hydrogenchloride / pH 6 / Gas phase View Scheme

carbon monoxide (201230-82-2) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + aniline (62-53-3) → 1,3-Me2-5,7-Ad(CONHC6H5)2 (1344030-14-3)

Conditions	Yield
Stage #1: carbon monoxide; 3,5-dimethyl-1-bromoadamantane With aluminum tri-bromide; carbon tetrabromide In methylene dibromide at 0 - 20℃; under 760.051 Torr; for 3h; Stage #2: aniline In methylene dibromide at 0℃;	88%

1,1'-azobis (cyclohexanecarbonitrile) (2094-98-6) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + tri-n-butyl-tin hydride (688-73-3) + acrylonitrile (107-13-1) → 3-(3, 5-Dimethyl-1-adamantyl)propionitrile (227323-46-8)

Conditions	Yield
In toluene	86%

carbon dioxide (124-38-9) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + N-benzyl-2-phenyl-1-prop-2-enamine (123974-18-5) → 3-benzyl-5-((3,5-dimethyladamantan-1-yl)methyl)-5-phenyloxazolidin-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In dimethyl sulfoxide under 760.051 Torr; for 24h; Schlenk technique; Irradiation; Sealed tube;	86%

3,5-dimethyl-1-bromoadamantane (941-37-7) → 1-azido-3,5-dimethyladamantane (63534-29-2)

Conditions	Yield
With trimethylsilylazide; tin(IV) chloride In dichloromethane at 50℃; for 10h; Inert atmosphere;	85%
With trimethylsilylazide; tin(IV) chloride In dichloromethane for 12h; Ambient temperature;	71%

morpholine (110-91-8) + carbon monoxide (201230-82-2) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → C22H34N2O4 (1344030-15-4)

Conditions	Yield
Stage #1: carbon monoxide; 3,5-dimethyl-1-bromoadamantane With aluminum tri-bromide; carbon tetrabromide In methylene dibromide at 0 - 20℃; under 760.051 Torr; for 3h; Stage #2: morpholine In methylene dibromide at 0℃;	85%

3,5-dimethyl-1-bromoadamantane (941-37-7) → (3,5-dimethyladamantyl)phosphonic acid dichloride (125282-04-4)

Conditions	Yield
With sulfuric acid; phosphorus trichloride at 20 - 50℃; for 2h;	82%

carbon monoxide (201230-82-2) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → (3,5-dimethyl-adamantan-1-yl)-methanol (26919-42-6)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); α,α,α-trifluorotoluene; (C6F13CH2CH2)3SnH; sodium cyanoborohydride In tert-butyl alcohol at 90℃; under 60800 Torr; for 3h;	79%

carbon monoxide (201230-82-2) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + isopropyl alcohol (67-63-0) → 1.3-Me2-5,7-Ad(COOiPr)2 (1344030-12-1)

Conditions	Yield
Stage #1: carbon monoxide; 3,5-dimethyl-1-bromoadamantane With aluminum tri-bromide; carbon tetrabromide In methylene dibromide at 0 - 20℃; under 760.051 Torr; for 3h; Stage #2: isopropyl alcohol In methylene dibromide at 0℃;	79%

3,5-dimethyl-1-bromoadamantane (941-37-7) + potassium phtalimide (1074-82-4) → 2-(3,5-dimethyladamantan-1-yl)isoindoline-1,3-dione (1204184-74-6)

Conditions	Yield
In N,N-dimethyl-formamide at 25 - 130℃;	78.64%

3,5-dimethyl-1-bromoadamantane (941-37-7) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 1-formamido-3,5-dimethyltricyclo[3.3.1.13,7]decane (351329-88-9)

Conditions	Yield
With dimanganese decacarbonyl at 120 - 130℃; Inert atmosphere; Autoclave;	78%
at 22 - 75℃; Product distribution / selectivity; Inert atmosphere;
Stage #1: 3,5-dimethyl-1-bromoadamantane; formamide at 120℃; Stage #2: With sodium hydroxide In dichloromethane
at 150℃; for 8h;
at 140℃; for 12h; Temperature;

carbon monoxide (201230-82-2) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + diethylamine (109-89-7) → 1,3-Me2-5,7-Ad(CONEt2)2 (1344030-13-2)

Conditions	Yield
Stage #1: carbon monoxide; 3,5-dimethyl-1-bromoadamantane With aluminum tri-bromide; carbon tetrabromide In methylene dibromide at 0 - 20℃; under 760.051 Torr; for 3h; Stage #2: diethylamine In methylene dibromide at 0℃;	75%

carbon monoxide (201230-82-2) + 3,5-dimethyl-1-bromoadamantane (941-37-7) + methoxybenzene (100-66-3) → 1,3-Me2-5,7-Ad(COC6H4OMe)2

Conditions	Yield
Stage #1: carbon monoxide; 3,5-dimethyl-1-bromoadamantane With aluminum tri-bromide; carbon tetrabromide In methylene dibromide at 0 - 20℃; under 760.051 Torr; for 3h; Stage #2: methoxybenzene In methylene dibromide at 0℃;	73%

N,N'-Dimethylurea (96-31-1) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → 1-N-methylamino-3,5-dimethyl-adamantane hydrochloride

Conditions	Yield
In water	72%

1,1-Dichloroethylene (75-35-4) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → 2-(3,5-dimethyladamantan-1-yl)acetic acid (14202-14-3)

Conditions	Yield
With boron trifluoride diethyl etherate In sulfuric acid at 15℃;	70%
With sulfuric acid; boron trifluoride
Stage #1: 1,1-Dichloroethylene; 3,5-dimethyl-1-bromoadamantane With sulfuric acid In water at 10℃; for 1h; Stage #2: With boron trifluoride diethyl etherate In 1,1-dichloroethane; water at 10 - 15℃; for 2.5h;

2-Adamantanone (700-58-3) + 3,5-dimethyl-1-bromoadamantane (941-37-7) → 3,5-Dimethyl-[1,2']bi[tricyclo[decyl]-2'-ol

Conditions	Yield
With lithium sodium In diethyl ether at -25℃;	70%

3,5-dimethyl-1-bromoadamantane (941-37-7) + 3-hydroxy-trans-cinnamic acid (14755-02-3) → 3-((E)-2-((1s,3R,5S,7r)-3,5-dimethyladamantan-1-yl)vinyl)phenol

Conditions	Yield
With palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine In dimethyl sulfoxide at 28℃; for 24h; Inert atmosphere; Irradiation; Sealed tube; stereoselective reaction;	70%

Upstream product

• 702-79-4 1,3-dimethyladamantane 
• 707-37-9 3,5-dimethyladamantane-1-ol 
• 876-53-9 1,3-dibromoadamantane 
• 707-37-9 1,3-dimethyl-5-adamantanol 
• 19982-07-1 1-acetamido-3,5-dimethyladamantane 
• 702-79-4 1,3-dimethyladamantane 

Downstream Products

• 14202-14-3 acide dimethyl-3,5 adamantylacetique 
• 702-79-4 1,3-dimethyladamantane 
• 707-35-7 1,3,5-trimethyladamantane 
• 19982-07-1 1-acetamido-3,5-dimethyladamantane 
• 63263-14-9 3,3'-dibromo-5,5',7,7'-tetramethyl-1,1'-biadamantane 
• 26919-42-6 (3,5-dimethyl-adamantan-1-yl)-methanol 
• 14670-94-1 3,5-dimethyl-1-adamantanecarboxylic acid 
• 63971-25-5 3-amino-5,7-dimethyladamantan-1-ol 
• 707-36-8 1-chloro-3,5-dimethyl-adamantane 
• 351329-88-9 1-formamido-3,5-dimethyltricyclo[3.3.1.1^3,7]decane 
• 41100-52-1 memantine hydrochloride 

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