10293-06-8

Basic information

• Product Name: (1R-endo)-3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• Synonyms: D-(+)-3-BROMOCAMPHOR;ENDO-3-BROMO-D-CAMPHOR;ENDO-(1R)-3-BROMO-1,7,7-TRIMETHYLBICYCLO[2.2.1]HEPTAN-2-ONE;(+)-CAMPHOR BROMIDE;3-BROMO-D-CAMPHOR;(+)-3-BROMOCAMPHOR;(1r-endo)-3-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one;(1R)-ENDO-(+)-3-BROMOCAMPHOR
• CAS NO: 10293-06-8
• Molecular Formula: C₁₀H₁₅BrO
• Molecular Weight: 231.13
• EINECS: 233-652-1
• Product Categories: Miscellaneous Biochemicals;Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 10293-06-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 75-78 °C(lit.)
• Boiling Point: 274 °C
• Flash Point: 35.8 °C
• Appearance: White/Crystalline
• Density: 1.2896 (rough estimate)
• Vapor Pressure: 0.028mmHg at 25°C
• Refractive Index: 137.5 ° (C=2, EtOH)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• Sensitive: Light Sensitive
• Merck: 14,1414
• BRN: 3197237
• CAS DataBase Reference: (1R-endo)-3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R-endo)-3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one(10293-06-8)
• EPA Substance Registry System: (1R-endo)-3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one(10293-06-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: ED6750000
• F: 8-10
• Hazardous Substances Data: 10293-06-8(Hazardous Substances Data)

Usage

Chemical Properties

White needles or crystalline powder

Uses

Medicine, manufacture of camphor derivatives.

InChI:InChI=1/C10H15BrO/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6-7H,4-5H2,1-3H3/t6-,7+,10+/m0/s1

Upstream product

• 464-48-2 (1S)-camphor 
• 4695-62-9 fenchone 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 76-22-2 Camphor 
• 56613-17-3 1,7,7-trimethyl-2-trimethylsilyloxy<2.2.1>bicyclohept-2-ene 

Downstream Products

• 10293-10-4 3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one 
• 131357-90-9 (1R)-endo-(+)-3-methyldiphenylphosphinocamphor iodide 
• 2767-84-2 (1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione 
• 508-32-7 tricyclene 
• 5794-04-7 camphene 
• 759457-76-6 N-isobornylaniline 
• 75946-22-4 N-bornylaniline 
• 464-48-2 (1S)-camphor 
• 13675-77-9 camphor anil 
• 51297-38-2 (rac)-3exo-(2-phenylhydrazino)-campher phenylhydrazone 
• 51297-38-2 (1R)-3exo-(2-phenylhydrazino)-campher phenylhydrazone 
• 131339-30-5 (1R)-endo-(+)-3-diphenylphosphinocamphor 
• 10293-10-4 rac-3,9-dibromocamphor 
• 76-29-9 3-exo-Bromocamphor 

Relevant articles and documents

New chiral cyclopalladated complexes based on the pinane and bornane imines

2α-Hydroxypinan-3-one imino derivatives react with lithium tetrachloropalladate to form palladacycles, while similar bornane derivative undergo cyclopalladation only when treated with palladium acetate.

REACTIVITY OF 3-BROMOCAMPHOR AND 3-BROMOISOCAMPHANONE UNDER THE CONDITIONS OF THE RITTER REACTION

The bromination of camphor and isocamphanone yield, respectively, 3-endo- and 3-exo-bromo ketones.Under the conditions of the Ritter reaction 3-bromocamphor does not react with nitriles, while 3-isocamphanone is selectively converted into the corresponding N,N'-diacyl-3-bromo-2,2-gem-diamino-5,5,6-trimethylbicycloheptanes.

ENANTIOSPECIFIC SYNTHESIS OF ESTRONE

Efiicient cleavage of the C(1)-C(2) bond in 9,10-dibromocamphor (3) provides a chiral intermediate (5) that can be used in a new enantiospecific synthesis of estrone.