1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; water; titanium(IV) oxide at 20℃; for 1h; regioselective reaction; | 98% |
With hydrogenchloride; K9-OThx-9-BBNH) In tetrahydrofuran at 0℃; Product distribution; stereoselectivity, other boranes; | 97.5% |
With Triethoxysilane; cesium fluoride at 25℃; for 0.0166667h; | 95% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
With silica triflate In methanol for 0.333333h; Heating; | 93% |
Borneol, trimethylsilyl ether
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
With silica triflate In methanol for 0.0666667h; Heating; | 90% |
With methanol at 20℃; for 0.916667h; | 89% |
With ammonium chloride In water; acetonitrile at 80℃; for 1.5h; | 83% |
Conditions | Yield |
---|---|
With iron(III) perchlorate for 3h; Ambient temperature; | 85% |
dichloromethane
1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one
A
2-methylenebornane
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
With titanium tetrachloride; magnesium In tetrahydrofuran at 0 - 20℃; for 1h; | A 74% B n/a |
ethanol
toluene-4-sulfonic acid isobornyl ester
sodium ethanolate
dl-camphene
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one
A
d-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
With acetic acid; platinum Hydrogenation; | |
With copper at 120 - 150℃; under 7600 - 69920 Torr; Hydrogenation; |
exo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol formate
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
beim Verseifen; formic acid isobornyl ester; |
Conditions | Yield |
---|---|
at 50℃; |
Conditions | Yield |
---|---|
With hydrogen; nickel | |
With alcoholic alkali | |
With alkali metal | |
With hydrogen; copper | |
With diethyl ether; sodium Zersetzen des Reaktionsprodukts durch Wasser; |
rac O-isoborneol S-methyl carbonodithioate
dl-camphene
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
at 140 - 175℃; |
oxalic acid dibornyl ester
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
oxalic acid di-dl-isobornyl ester; |
4-chloro-2-isopropyl-5-methyl-benzenesulfonic acid bornyl ester
dl-camphene
C
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Beta-pinene
2,3,4-trichlorophenol
A
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
at 145 - 150℃; levorotatory form; |
camphene
phosphoric acid
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
im geschlossenen Gefaess; dl-camphene; |
camphene
o-toluenesulfonic acid
water
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
at 20℃; |
hydrogenchloride
camphene
acetone
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
im geschlossenen Gefaess; dl-camphene; |
camphene
sulfuric acid
acetone
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
im geschlossenen Gefaess; dl-camphene; |
Conditions | Yield |
---|---|
im geschlossenen Gefaess; dl-camphene; |
Pinene
acetic acid
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
folgend Verseifen; dl-α-pinene; |
Pinene
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
dl-α-pinene; |
Pinene
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
dl-α-pinene; |
diethyl ether
(1R,2S,4R)-2-Chloro-1,7,7-trimethyl-bicyclo[2.2.1]heptane
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
bei der Einwirkung auf die Grignard-Verbindung; |
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
ethanol
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
at 180 - 200℃; |
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
ethanol
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
rac-endo-borneol
B
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
at 200 - 220℃; |
(+)-α-pinene
acetic acid
A
terpineol
B
D-limonene
rac-endo-borneol
D
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
at 30℃; anschl. Verseifen; |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one
Conditions | Yield |
---|---|
With acetone; zirconic acid In benzene at 80℃; for 8h; Rate constant; | 100% |
With acetone; zirconic acid In benzene at 80℃; for 8h; | 100% |
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane | 100% |
Conditions | Yield |
---|---|
molybdophosphoric acid; silica gel In chloroform for 0.5h; Heating; | 99% |
With bis(2,2,2-trifluoroethoxy)triphenylphosphorane | 61% |
With sulfuric acid; water dl-camphene; |
Conditions | Yield |
---|---|
With lithium perchlorate at 25℃; for 6h; | 98% |
samarium(III) trifluoromethanesulfonate at 20℃; for 0.25h; | 96% |
With iron(III) p-toluenesulfonate hexahydrate In acetonitrile at 50℃; for 30h; | 92% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
1,7,7-trimethyltricyclo[2.2.1.02,6]heptane
Conditions | Yield |
---|---|
molybdophosphoric acid; silica gel In chloroform for 2h; Heating; | 98% |
Conditions | Yield |
---|---|
With P(MeNCH2CH2)3N In tetrahydrofuran at 50℃; for 16h; | 96% |
trimethylsilylazide
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Borneol, trimethylsilyl ether
Conditions | Yield |
---|---|
tetrabutylammomium bromide at 30℃; for 0.166667h; | 96% |
Conditions | Yield |
---|---|
With silica triflate In hexane at 20℃; for 0.316667h; | 95% |
With iodine In tetrahydrofuran for 0.1h; microwave irradiation; | 78% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
In octane heated for 40 h; cooled, washed (water), residue filtered, precipiated from acetone withwater; elem. anal.; | 95% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
allyl-trimethyl-silane
A
propene
B
Borneol, trimethylsilyl ether
Conditions | Yield |
---|---|
iodine In chloroform at 60℃; for 1h; | A n/a B 94% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
In octane boiled for 4 h; cooled, washed (water), evapd., precipitated from CHCl3 with hexane; elem. anal.; | 94% |
8-Phenyl-tetrahydro-8λ5-[1,3,2]oxazaphospholo[2,3-b][1,3,2]oxazaphosphole
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
{Rh(CO)Cl(P(OC6(CH3)C(CH3)2H8)(OC2H4)2NH)}
Conditions | Yield |
---|---|
In dichloromethane (under Ar) bornil in CH2Cl2 is added dropwise with stirring to a soln. of BAP in CH2Cl2, the soln. is stirred for 1 h and then is added (Rh(CO)2Cl)2 in CH2Cl2; ppt. is separated, washed with ether and pentane and dried in air in vac. (1mm Hg), elem. anal.; | 93% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
In octane boiled for 4 h; cooled, washed (water), evapd., precipitated from CHCl3 with hexane; elem. anal.; | 93% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
In octane heated for 40 h; cooled, washed (water), residue filtered, precipiated from acetone withwater; elem. anal.; | 93% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
1,1,1,3,3,3-hexamethyl-disilazane
Borneol, trimethylsilyl ether
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane at 20℃; for 9h; | 92% |
With 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Neat (no solvent); | 90% |
In acetonitrile at 20℃; for 0.916667h; | 90% |
With copper(II) nitrate trihydrate at 20℃; for 5h; Neat (no solvent); | 50% |
Conditions | Yield |
---|---|
In hexane byproducts: CH4; (Ar), heated under reflux for 48 h; solvent removed in vac., recrystd., chromy.( Al2O3, hexane- ether 5:1 ); NMR; | 92% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
In octane boiled for 4 h; cooled, washed (water), evapd., precipitated from CHCl3 with hexane; elem. anal.; | 92% |
Conditions | Yield |
---|---|
With benzyltriphenylphosphonium tribromide In chloroform for 0.916667h; Reflux; | 92% |
With melamine-N2,N4,N6-trisulfonic acid In chloroform for 1h; Reflux; | 80% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 8h; Inert atmosphere; | 91% |
malonic acid
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Malonic acid bis-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl) ester
Conditions | Yield |
---|---|
With diphenylammonium trifluoromethanesulfonate In toluene at 80℃; for 22h; | 90.8% |
Conditions | Yield |
---|---|
Stage #1: bromobenzene; 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol With hydrogenchloride for 0.333333h; Stage #2: With sulfuric acid at 125℃; for 6h; | 90% |
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl; 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol With hydrogenchloride for 0.333333h; Stage #2: With sulfuric acid at 120℃; for 4h; Temperature; | 90% |
2-bromo-3,4,4-trichloro-3-butenoyl chloride
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
Conditions | Yield |
---|---|
With pyridine In benzene at 20 - 23℃; | 89% |
With pyridine In benzene at 20 - 23℃; | 87% |
Conditions | Yield |
---|---|
With sodium hydride | 88% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
3,3,4,4,4-pentachlorobutanoic acid chloride
Conditions | Yield |
---|---|
With pyridine In diethyl ether at 20 - 23℃; | 88% |
With pyridine In diethyl ether at 20 - 23℃; | 86% |
Conditions | Yield |
---|---|
With 2,2'-(phenylimino)bis[ethanol]; diethylzinc In hexane; toluene at 20℃; for 24h; | 86% |
1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol
(1R,3S)-2,2-dimethyl-3-(1,3-dithian-2-yl)cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; | 85% |
Molecular Formula: C10H18O
Molar mass: 154.25 g/mol
EINECS: 207-353-1
Density: 0.992 g/cm3
Flash Point: 65.6 °C
Index of Refraction: 1.502
Boiling Point: 212 °C at 760 mmHg
Vapour Pressure: 0.0398 mmHg at 25°C
Melting point: 206-209 °C
Water solubility: Insoluble
Appearance: A white colored lump-solid
Product categories: Bicyclic Monoterpenes ; Alcohols ; Oxygen Compounds ; Terpenes ; Biochemistry
Structure of Borneol (CAS NO.507-70-0) :
XLogP3-AA: 2.7
H-Bond Donor: 1
H-Bond Acceptor: 1
IUPAC Name: (1R,4R,6R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-6-ol
Canonical SMILES: CC1(C2CCC1(C(C2)O)C)C
Isomeric SMILES: C[C@@]12CC[C@@H](C1(C)C)C[C@H]2O
InChI: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,
8-,10+/m1/s1
InChIKey: DTGKSKDOIYIVQL-MRTMQBJTSA-N
Borneol (CAS NO.507-70-0) is used in traditional Chinese medicine as moxa. An early description can be found in the Bencao Gangmu.Isoborneol is its exo isomer.Derivatives of isoborneol are used as chiral ligands in asymmetric synthesis.
Borneol (CAS NO.507-70-0) is easily oxidized to the ketone yielding camphor. Borneol can be synthesized by reduction of camphor by the Meerwein-Ponndorf-Verley Reduction. The same reduction but then fast and irreversible with Sodium borohydride gives isoborneol as the kinetically controlled reaction product.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 1059mg/kg (1059mg/kg) | Shika Gakuho. Journal of Dentistry. Vol. 75, Pg. 934, 1975. | |
rabbit | LDLo | oral | 2gm/kg (2000mg/kg) | Reviews of Environmental Contamination and Toxicology. Vol. 113, Pg. 47, 1990. | |
rat | LD50 | oral | 500mg/kg (500mg/kg) | French Demande Patent Document. Vol. #2448856, |
Hazard Codes: F; Xi,Xn
Risk Statements: 11-43-22
R11:Highly flammable.
R43:May cause sensitization by skin contact.
R22:Harmful if swallowed.
Safety Statements: 16-36/37
S16:Keep away from sources of ignition.
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 1312 4.1/PG 3
WGK Germany: 2
RTECS: DT5095000
HazardClass: 4.1
PackingGroup: III
Borneol (CAS NO.507-70-0) also can be called for Baros camphor ; 2-Borneol ; Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, (1R,2S,4R)-rel- ; 1R-endo)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol .It is a bicyclic organic compound and a terpene. The hydroxyl group in this compound is placed in an endo position.Borneol exists as two enantiomers, found in several species of Artemisia and Dipterocarpaceae, which have two different CAS numbers.And it is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen.And as soon as to get medical aid.Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically. In addition, Borneol (CAS NO.507-70-0) can be stable under normal temperature and pressure conditions.It is not compatible with strong oxidizing agents, ignition sources, and you must not take it with incompatible materials.And also prevent it to broken down into hazardous decomposition products: carbon dioxide,carbon monoxide.
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