Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; carbon tetrabromide at 120℃; for 2h; Sealed tube; Inert atmosphere; | 99% |
With hydrogen bromide at 130℃; for 2h; | 90% |
With boron tribromide for 0.5h; | 86% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; carbon tetrabromide Reagent/catalyst; Sealed tube; Inert atmosphere; | A 99% B 23% |
With bromine; iron at 0 - 50℃; for 3h; | A n/a B 93% |
With iodine(I) bromide In tetrachloromethane for 3h; Heating; | A 75 % Chromat. B 25 % Chromat. |
With iodine(I) bromide In tetrachloromethane for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With oxygen; 1,2-dibromomethane for 10h; Reflux; | 99% |
With iron(III)-acetylacetonate; carbon tetrabromide at 120℃; for 2h; Sealed tube; Inert atmosphere; | 99% |
With dibromo sulfoxide In toluene for 22h; | 96% |
Conditions | Yield |
---|---|
With bromine; Nitrogen dioxide In trifluoroacetic acid at 20℃; for 0.5h; | 98% |
With water; bromine for 0.166667h; | 93% |
With bromine at 85 - 110℃; Temperature; | 93% |
1-Adamantanecarbonyl chloride
A
1-Adamantyl bromide
B
2-<(trichloromethyl)thio>pyridine
Conditions | Yield |
---|---|
With Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt; dmap at 105℃; for 0.5h; | A 98% B n/a |
1-Adamantyl bromide
Conditions | Yield |
---|---|
With bromine In tetrachloromethane at 20℃; for 12h; | 97% |
1-(Dibromoamino)adamantane
1-Adamantyl bromide
Conditions | Yield |
---|---|
In acetone at 250 - 260℃; | 94% |
In acetone at 250 - 260℃; also at 250 deg C, 6 Torr, without solvent; | 94% |
Conditions | Yield |
---|---|
With hydrogen bromide at 105℃; for 0.5h; | 92% |
With boron tribromide In hexane at 0℃; for 0.0833333h; | 90% |
4-(1-adamantyl)benzene-1,3-diol
A
1-Adamantyl bromide
B
2,4,6-tribromoresorcinol
C
2,6-Dibromo-4-(1-adamantyl)resorcinol
Conditions | Yield |
---|---|
With bromine In methanol; acetic acid for 1h; Ambient temperature; | A n/a B n/a C 91.5% |
Bromotrichloromethane
adamantane
acetonitrile
A
1-Adamantyl bromide
B
chloroform
C
N-(1-adamantyl)acetamide
Conditions | Yield |
---|---|
With water; molybdenum hexacarbonyl at 140℃; for 2h; | A n/a B n/a C 90% |
Conditions | Yield |
---|---|
With Ag(Phen)2OTf; dibromoisocyanuric acid In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 89% |
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; caesium carbonate; Diethyl 2-bromomalonate In ethyl acetate at 20℃; for 4h; Solvent; Inert atmosphere; Irradiation; | 70% |
With Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt; dmap 2.) reflux; Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: (COBr)2 2: Fe / 1 h / Ambient temperature View Scheme |
1-nitroxyadamantane
1-Adamantyl bromide
Conditions | Yield |
---|---|
With sulfuric acid; potassium bromide for 1h; | 89% |
adamantane
acetonitrile
A
1-Adamantyl bromide
B
Bromoform
C
1-adamantanecarbonitrile
Conditions | Yield |
---|---|
With carbon tetrabromide; molybdenum hexacarbonyl at 140 - 160℃; for 6h; Reactivity; Mechanism; Reagent/catalyst; | A 15% B n/a C 85% |
adamantane
benzoyl chloride
A
1-Adamantyl bromide
B
2-adamantyl bromide
C
benzaldehyde
Conditions | Yield |
---|---|
With aluminum tri-bromide In various solvent(s) at 20℃; for 2h; | A 70% B 3% C 82% |
With aluminum tri-bromide In various solvent(s) at 20℃; for 2h; | A 70% B 3% C 82% |
1-(1-adamantyl)-3,4-dimethylbenzene
A
1-Adamantyl bromide
B
1,3-dibromoadamantane
C
1,2,3,4-tetrabromo-5,6-dimethylbenzene
Conditions | Yield |
---|---|
With bromine; iron for 3.5h; Product distribution; Ambient temperature; | A n/a B n/a C 82% |
1-chloroadamantane
A
1-Adamantyl bromide
B
2-adamantyl bromide
C
adamantane
D
1,3-dibromoadamantane
Conditions | Yield |
---|---|
With hydrogen bromide; ferric(III) bromide In dichloromethane at 25℃; for 0.3h; | A 78% B 3% C 9% D 9 % Chromat. |
With hydrogen bromide; ferric(III) bromide In dichloromethane at 25℃; for 0.3h; | A 78% B 3% C 9% D 3 % Chromat. |
adamantane
A
1-Adamantyl bromide
B
2-Adamantanone
C
1-chloroadamantane
D
2-adamantyl bromide
E
1-adamanthanol
F
1-adamantanol
Conditions | Yield |
---|---|
With Bromotrichloromethane; 3,3-dimethyldioxirane In acetone at 20℃; Product distribution; Mechanism; | A 12.2% B 1.8% C 0.7% D 2.3% E 77.2% F 1.1% |
With Bromotrichloromethane; 3,3-dimethyldioxirane In acetone for 1h; Mechanism; Product distribution; Ambient temperature; concentration depending investigated; |
adamantane
A
1-Adamantyl bromide
B
1-chloroadamantane
C
2-adamantyl bromide
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; Bromotrichloromethane; iron(III) chloride In pyridine; acetic acid at 60℃; for 18h; | A 69.2% B 4.1% C 26.7% |
With tert.-butylhydroperoxide; Bromotrichloromethane; iron(III) chloride In pyridine; acetic acid at 60℃; for 18h; Product distribution; Mechanism; various conditions; | A 69.2% B 4.1% C 26.7% |
(1s,3s)-adamantan-1-yl(phenyl)sulfide
1-Adamantyl bromide
Conditions | Yield |
---|---|
With bromine In dichloromethane at 20℃; for 1h; | 68% |
1-(Dibromoamino)adamantane
A
1-Adamantyl bromide
B
1,3-dibromoadamantane
Conditions | Yield |
---|---|
at 95 - 250℃; under 6 Torr; for 1h; | A 65% B n/a |
Conditions | Yield |
---|---|
Stage #1: adamantane With [2,2]bipyridinyl; N-Bromosuccinimide; manganese(II) acetate for 0.0833333h; Inert atmosphere; Stage #2: With trimethylsilylazide at 60℃; for 0.5h; Inert atmosphere; Sealed tube; regioselective reaction; | A 62% B 15% |
Stage #1: adamantane With [2,2]bipyridinyl; N-Bromosuccinimide; manganese(II) acetate for 0.0833333h; Inert atmosphere; Stage #2: With trimethylsilylazide at 60℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction; | A 16% B 62% |
C10H15Ge(CH3)3
A
1-Adamantyl bromide
B
1-adamantyldimethylbromogermane
Conditions | Yield |
---|---|
With bromine In tetrachloromethane soln. of Br2 added to soln. of 1-AdGeMe3; boiled (18 h, 78°C); solvent removed; recrystd. (hexane); elem.anal.; | A 54.7% B 28.7% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; bromine In water; 1,2-dichloro-ethane for 4h; | A 48.7% B 51.3% |
With Li2MnO3; bromine; oxygen at 100℃; under 760.051 Torr; for 24h; Photolysis; | A 42% B 5% |
With hydrogenchloride; oxygen; potassium bromide; sodium nitrite In chloroform; water at 20 - 30℃; under 760.051 Torr; for 24h; Sealed tube; Irradiation; | A 20% B 17% |
Conditions | Yield |
---|---|
With [(hydrotris(3,5-diphenyl-pyrazol-1-yl)borate)FeII(benzilate)]; tetrabutylammomium bromide; oxygen; pyridinium perchlorate In acetonitrile at 20℃; | A 7% B 48% |
With ruthenium hydroxide trichloride; carbon tetrabromide; water at 160℃; for 9h; Inert atmosphere; regioselective reaction; | A 30% B 30% |
adamantane
A
1-Adamantyl bromide
B
1-chloroadamantane
C
2-adamantyl bromide
D
1-adamanthanol
E
1-adamantanol
F
2-chloroadamantane
Conditions | Yield |
---|---|
With Bromotrichloromethane; 3,3-dimethyldioxirane In acetone at 20℃; for 3.5h; Rate constant; Product distribution; Kinetics; | A 42.3% B 9.2% C 10.5% D 33% E 2% F 2.5% |
Conditions | Yield |
---|---|
In dichloromethane at 250 - 260℃; 15-30percent SE-30 on Chromosorb W; | A 30% B n/a |
tetrabutylammomium bromide
3-chloro-benzenecarboperoxoic acid
A
1-Adamantyl bromide
B
2-adamantyl bromide
C
n-butyl 3-chlorobenzoate
Conditions | Yield |
---|---|
With adamantane In acetonitrile at 20℃; for 1h; Yields of byproduct given; | A n/a B n/a C 24% |
tetramethylammonium bromide
3-chloro-benzenecarboperoxoic acid
A
1-Adamantyl bromide
B
2-adamantyl bromide
C
methyl 3-chlorobenzoate
Conditions | Yield |
---|---|
With adamantane In acetonitrile at 20℃; for 1h; Yields of byproduct given; | A n/a B n/a C 19% |
Acetyl bromide
1-chloroadamantane
A
1-Adamantyl bromide
B
acetyl chloride
Conditions | Yield |
---|---|
With iron(III) chloride at 25℃; for 168h; Equilibrium constant; Thermodynamic data; ΔG; | |
With iron(III) chloride In chloroform at 25℃; for 168h; Equilibrium constant; Thermodynamic data; ΔG; |
Conditions | Yield |
---|---|
With molybdenum hexacarbonyl Sealed tube; regioselective reaction; | 100% |
With potassium carbonate; palladium on activated charcoal at 120℃; for 12h; | 91% |
With palladium 10% on activated carbon; potassium carbonate for 20h; Heating; | 82.65% |
Conditions | Yield |
---|---|
With triethylsilane; dilauryl peroxide; 1-dodecylthiol at 70℃; for 1h; | 100% |
With triethylsilane; dilauryl peroxide; 1-dodecylthiol In cyclohexane at 80℃; for 1h; | 100% |
With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); cPS-SnBu2Cl In 1,2-dimethoxyethane at 80℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate Heating; | 100% |
With bromine for 0.05h; | 90% |
1-Adamantyl bromide
(2S,4R)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid
1-adamantyl (2S,4R)-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
With silver(l) oxide In diethyl ether at 20℃; for 30h; | 100% |
Conditions | Yield |
---|---|
With triethylamine | 100% |
1-Adamantyl bromide
Conditions | Yield |
---|---|
In acetic acid Heating; | 100% |
Conditions | Yield |
---|---|
With molybdenum hexacarbonyl at 100℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Sealed tube; regioselective reaction; | 99% |
With potassium carbonate; palladium on activated charcoal at 120℃; for 12h; | 97% |
With iron pentacarbonyl; Bromotrichloromethane at 80℃; for 5h; Friedel-Crafts Alkylation; | 95% |
Conditions | Yield |
---|---|
In dibutyl ether at 85℃; for 1h; | 99% |
In dibutyl ether at 105℃; for 4.5h; | 80% |
In dibutyl ether at 70 - 90℃; Rate constant; Thermodynamic data; ΔE; |
1-Adamantyl bromide
ortho-cresol
4-((3r,5r,7r)-adamantan-1-yl)-2-methylphenol
Conditions | Yield |
---|---|
With molybdenum hexacarbonyl at 120℃; for 0.5h; Sealed tube; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In acetic anhydride; acetic acid; N,N-dimethyl-formamide at 0 - 10℃; for 4h; Substitution; Electrochemical reaction; | 98% |
With water; bromine for 1h; | 95.5% |
With hydrogenchloride In N,N-dimethyl-formamide at 105℃; for 0.5h; | 95% |
1-Adamantyl bromide
4-methylquinoline trifluoroacetate
4-methyl-2-(tricyclo[3.3.1.13,7]dec-1-yl)quinolone
Conditions | Yield |
---|---|
With {Au(dppm)}2Cl2 In methanol Inert atmosphere; UV-irradiation; | 98% |
With 2,2'-azobis(isobutyronitrile); 1,1,2,2-tetraphenyldisilane In ethanol for 24h; Product distribution; Heating; other reagents; | 93% |
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In benzene for 14h; Heating; | 90% |
With tetrakis(trimethylsilyl)silane In dichloromethane at 30℃; for 14h; Irradiation; | 83% |
Conditions | Yield |
---|---|
With hydrogen iodide; cetyltributylphosphonium bromide at 105℃; for 1.75h; | 98% |
With hydrogen iodide at 105℃; for 0.5h; | 90% |
Stage #1: 1-Adamantyl bromide With zinc In tetrahydrofuran for 2h; Reflux; Stage #2: With iodine In tetrahydrofuran at 20℃; | 79% |
With potassium iodide at 19.9℃; under 45003600 Torr; under shear deformation (360 deg); | 19% |
1-Adamantyl bromide
4,4'-bipyridine
1-Adamantan-1-yl-[4,4']bipyridinyl-1-ium; bromide
Conditions | Yield |
---|---|
With water at 180℃; for 4h; | 98% |
styrene
1-Adamantyl bromide
1-[(1E)-2-phenylethenyl]-tricyclo[3.3.1.13,7]decane
Conditions | Yield |
---|---|
Stage #1: 1-Adamantyl bromide With palladium diacetate; heptakis(6-amino-6-deoxy)-β-cyclodextrin In water; N,N-dimethyl-formamide for 0.5h; Stage #2: styrene With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 8h; | 98% |
With (trimethylsilyl)methylmagnesium chloride; Co(1,3-bis(diphenylphosphino)hexane)Cl2 In diethyl ether at 20℃; for 8h; Heck reaction; | 87% |
With Co(1,3-bis(diphenylphosphino)hexane)Cl2; (trimethylsilyl)methylmagnesium chloride In diethyl ether at 20℃; for 8h; Heck reaction; | 87% |
With potassium carbonate; palladium on activated charcoal In N,N-dimethyl-formamide at 100 - 120℃; | 41% |
Conditions | Yield |
---|---|
With potassium carbonate; palladium on activated charcoal at 120℃; for 12h; | 98% |
With zinc(II) chloride Substitution; Heating; | 92% |
With zinc(II) chloride for 10h; Heating; | 90% |
With molybdenum hexacarbonyl at 120℃; for 2h; Sealed tube; regioselective reaction; | 72% |
Conditions | Yield |
---|---|
With triethylamine at 180℃; for 23h; | 98% |
With triethylamine | 93% |
With triethylamine In dichloromethane at 180℃; | 91% |
1-Adamantyl bromide
pentafluorophenyl potassium carboxylate
1-(perfluorophenyl)adamantane
Conditions | Yield |
---|---|
With copper(l) iodide In diethylene glycol dimethyl ether at 130℃; for 24h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With water at 180℃; for 6h; | 97% |
at 180℃; for 6h; | 97% |
at 180℃; for 24h; | 12% |
Conditions | Yield |
---|---|
With sodium nitrate; (HF)x*C5H5N In dichloromethane for 5h; Ambient temperature; | 97% |
With nitronium tetrafluoborate; pyridine polyhydrogen fluoride In dichloromethane for 3h; Ambient temperature; | 96% |
With n-Bu4PF at 150℃; for 5h; | 91% |
1-Adamantyl bromide
2-[(1-benzyloxycarbonylamino-ethyl)-hydroxy-phosphinoylmethyl]-4-phenyl-butyric acid ethyl ester
2-[(adamantan-1-yloxy)-(1-benzyloxycarbonylamino-ethyl)-phosphinoylmethyl]-4-phenyl-butyric acid ethyl ester
Conditions | Yield |
---|---|
With silver(l) oxide In chloroform for 0.5h; Heating; | 97% |
1-Adamantyl bromide
2-[(1-benzyloxycarbonylamino-ethyl)-hydroxy-phosphinoylmethyl]-5-phenyl-pentanoic acid ethyl ester
2-[(adamantan-1-yloxy)-(1-benzyloxycarbonylamino-ethyl)-phosphinoylmethyl]-5-phenyl-pentanoic acid ethyl ester
Conditions | Yield |
---|---|
With silver(l) oxide In chloroform for 0.5h; Heating; | 97% |
1-Adamantyl bromide
silver(I)-di(4-methylbenzolsulfonyl)amide
Conditions | Yield |
---|---|
In benzene at 20℃; for 96h; Substitution; | 97% |
1-Adamantyl bromide
trimethyleneglycol
3-(adamantane-1-yloxy)propan-1-ol
Conditions | Yield |
---|---|
With triethylamine Heating; | 97% |
1-Adamantyl bromide
(R,S)-2-isopropyl-3-((1-(N-(9-fluorenylmethoxycarbonyl)amino)methyl)phosphinic acid) propanoic acid allyl ester
Conditions | Yield |
---|---|
With silver(l) oxide In chloroform for 2h; Heating; | 97% |
With silver(l) oxide In chloroform for 2.83333h; Heating / reflux; | 97% |
1-Adamantyl bromide
trimethylstannane
A
adamantane
B
n-butyltrimethyltin
Conditions | Yield |
---|---|
With n-butyllithium In hexane 1-bromoadamantane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC; | A 97% B 95% |
IUPAC Name: 1-Bromoadamantane
Canonical SMILES: C1C2CC3CC1CC(C2)(C3)Br
InChI: InChI=1S/C10H15Br/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
InChIKey: VQHPRVYDKRESCL-UHFFFAOYSA-N
Molecular Weight: 215.1301 [g/mol]
Molecular Formula: C10H15Br
XLogP3: 3.6
H-Bond Donor: 0
H-Bond Acceptor: 0
EINECS: 212-200-7
Melting Point: 116-118 °C(lit.)
Index of Refraction: 1.586
Molar Refractivity: 49.9 cm3
Molar Volume: 148.5 cm3
Surface Tension: 45.1 dyne/cm
Density: 1.448 g/cm3
Flash Point: 96.4 °C
Enthalpy of Vaporization: 45.8 kJ/mol
Boiling Point: 240.5 °C at 760 mmHg
Vapour Pressure: 0.0587 mmHg at 25 °C
Product Categories: Adamantanes
Sensitive: Moisture Sensitive
Appearance of 1-Bromoadamantane (CAS NO.768-90-1): white to almost white crystals or cryst. powder
Hazard Codes : Xn
Risk Statements :
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements :
S22: Do not breathe dust
S24/25: Avoid contact with skin and eyes
S36: Wear suitable protective clothing
S26: In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice
WGK Germany of 1-Bromoadamantane (CAS NO.768-90-1): 3
1-Bromoadamantane (CAS NO.768-90-1), its Synonyms are 1-Bromotricyclo(3.3.1.13,7)decane ; 3-Amino-1-adamantanol ; Tricyclo[3.3.1.13, 7]decane, 1-bromo- ; 1-Adamantyl bromide ; Adamantane, 1-bromo- ; Adamantyl bromide .
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