114086-15-6

Basic information

• Product Name: (1S,4S)-2-METHYL-2,5-DIAZABICYCLO(2.2.1)HEPTANE 2HBR
• Synonyms: (1S,4S)-2-METHYL-2,5-DIAZABICYCLO(2.2.1)HEPTANE 2HBR;2-Methyl-2,5-diazabicyclo[2.2.1]heptane dihydrobroMide;2,5-Diazabicyclo[2.2.1]heptane,2-methyl-, hydrobromide (1:2)
• CAS NO: 114086-15-6
• Molecular Formula: 2BrH*C₆H₁₂N₂
• Molecular Weight: 274
• Mol File: 114086-15-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (1S,4S)-2-METHYL-2,5-DIAZABICYCLO(2.2.1)HEPTANE 2HBR(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4S)-2-METHYL-2,5-DIAZABICYCLO(2.2.1)HEPTANE 2HBR(114086-15-6)
• EPA Substance Registry System: (1S,4S)-2-METHYL-2,5-DIAZABICYCLO(2.2.1)HEPTANE 2HBR(114086-15-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 114086-15-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
DABCO hydrobromide is used as a catalyst and co-catalyst for facilitating various chemical reactions, particularly in the synthesis of polyurethane foams and epoxy resins. Its ability to accelerate reaction rates and improve product yields makes it an essential component in this industry.
Used in Stabilizer Applications:
As a stabilizer for organic peroxides, DABCO hydrobromide is employed to prevent the premature decomposition of these compounds, thereby enhancing the safety and efficiency of processes involving organic peroxides.
Used in Pharmaceutical Production:
DABCO hydrobromide is utilized as an additive in the production of pharmaceuticals, where it contributes to the synthesis of various drug compounds, potentially improving the efficacy and stability of the final products.
Used in Agrochemical Production:
In the agrochemical industry, DABCO hydrobromide serves as an additive in the synthesis of agrochemicals, aiding in the production of effective and stable pesticides and other agricultural chemicals.
Used in Specialty Chemicals Production:
DABCO hydrobromide is also used in the creation of specialty chemicals, where its unique reactivity and molecular structure are leveraged to produce high-quality and specialized chemical products.

InChI:InChI=1/C6H12N2.2BrH/c1-8-4-5-2-6(8)3-7-5;;/h5-7H,2-4H2,1H3;2*1H/t5-,6-;;/m0../s1

Upstream product

• 116143-07-8 Ethyl (2R,4S)-4-Hydroxy-N-tosyl-2-pyrrolidinecarboxylate 
• 116143-09-0 (3S,5R)-1-[(4-methylphenyl)sulfonyl]-3-[(4-methylphenyl)sulfonyloxy]-5-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine 
• 116143-08-9 (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine 
• 116143-05-6 allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester 
• 132666-67-2 (2S,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate 
• 125224-63-7 (1R,4R)-2-(4-Tolylsulfonyl)-5-methyl-2,5-diazabicyclo<2.2.1>heptane 
• 179694-15-6 (1S,4S)-2-benzyl-5-methyl-2,5-diazabicyclo[2.2.1]heptane 
• 2584-71-6 cis-hydroxy-D-proline 
• 125109-57-1 (2R,4S)-1-(4-Tolylsulfonyl)-2-(chloromethyl)-4-((4-tolylsulfonyl)oxy)pyrrolidine 
• 125109-57-1 (2S,4R)-1-(4-Tolylsulfonyl)-2-(chloromethyl)-4-((4-tolylsulfonyl)oxy)pyrrolidine 
• 125109-59-3 (2R,4S)-4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid 
• 116143-06-7 4-(acetyloxy)-1-<(4-methylphenyl)sulfonyl>-D-proline ethyl ester 
• 77449-99-1 (2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 767291-68-9 (1S,4S)-(+)-2,5-dimethyl-2,5-diazabicyclo[2.21]heptane 
• 1182181-38-9 4-(6-(morpholin-4-yl)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine 
• 1182190-43-7 [3-methyl-4-((1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptan-5-yl)phenyl][N,N-bis(tert-butoxycarbonyl)]guanidine 
• 1182181-08-3 4-(6-(N,N-dimethylamino)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine 
• 1182190-51-7 4-(6-(chloro)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine 
• 1182190-21-1 3-methyl-4-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]aniline 
• 1182190-24-4 2-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-5-nitrotoluene 
• 1152113-38-6 4-chloro-5-fluoro-6-((1S,4S)-5-methyl-2,5-diazazbicyclo[2.2.1]hept-2-yl)-2(1H)-pyrimidinone hydrazone 
• 1152110-12-7 (1S,4S)-2-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-5-methyl-2,5-diazazbicyclo[2.2.1]heptane 
• 1195780-48-3 6-[1-cyclobutyl-3-methyl-4-[[(1R,4R)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl]-1H-pyrazol-5-yl]-13-cyclohexyl-3-methoxy-N-[(1-methylethyl)sulfonyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxamide 
• 1195780-68-7 C₄₂H₅₀N₆O₅S 
• 1338705-94-4 2-chloro-3,4-bis((4-methoxybenzyl)oxy)-N-(((1S,4S)-2-methyl-2-azabicyclo[2.2.1]heptan-5-yl)methyl)benzamide 

Relevant articles and documents

Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis

Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Preparation of 2,5-diazabicyclo[2.2.1]heptanes and intermediates

(R,R)-2,5-Diazabicyclo[ 2.2.1]heptanes are prepared from a compound of the formula STR1 wherein X and R2 are as defined herein, by heating with tosylchloride in pyridine, reacting the formed compound of the formula STR2 with a C1 -C6 alkylamine or ammonia, and reducing or hydrolyzing the formed compound of the formula STR3 wherein R1 is hydrogen or C1 -C6 alkyl.