Bicyclo[2.2.1]heptan-2-ol

Base Information

• Chemical Name: Bicyclo[2.2.1]heptan-2-ol
• CAS No.: 1632-68-4
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.172
• Hs Code.: 2906199090
• European Community (EC) Number: 216-637-4,207-844-0,207-845-6
• NSC Number: 167460,149927,22454
• DSSTox Substance ID: DTXSID001030874
• Nikkaji Number: J13.036B
• Wikipedia: Endo-Norborneol,Exo-Norborneol
• Wikidata: Q5420475
• ChEMBL ID: CHEMBL1907997
• Mol file: 1632-68-4.mol

Synonyms:Bicyclo[2.2.1]heptan-2-ol;1632-68-4;Norborneol;exo-Norborneol;2-Norbornanol;Norbornyl alcohol;exo-Norbornyl alcohol;exo-2-Norborneol;endo-Norbornanol;endo-2-Norborneol;.alpha.-Norborneol;2-endo-Norbornanol;endo-2-Norbornanol;exo-Norbornanol;Bicyclo(2.2.1)heptan-2-ol;2-Norbornanol, endo-;exo-2-Norbornanol;EINECS 216-637-4;NSC 22454;497-37-0;endo-Norborneol;exo-2-Norbornyl alcohol;Bicyclo[2.2.1]heptan-2-ol, endo-;2-Norbornanol, exo-;exo-Bicyclo[2.2.1]heptan-2-ol;endo-Bicyclo[2.2.1]heptan-2-ol;Bicyclo[2.2.1]heptan-2-ol, exo-;2-exo-Norbornanol;exo-Bicyclo(2.2.1)heptan-2-ol;EINECS 207-845-6;NSC 167460;AI3-51349;(+/-)-Exo-Norborneol;OC1CC2CCC1C2;Bicyclo(2.2.1)heptan-2-ol, (1R,2R,4S)-rel-;endo-Bicyclo(2.2.1)heptan-2-ol;NSC-167460;Bicyclo[2.2.1]heptan-2-ol, (1R,2R,4S)-rel-;SCHEMBL232962;CHEMBL1907997;2-hydroxybicyclo[2.2.1]heptane;DTXSID001030874;NSC22454;MFCD00167747;NSC-22454;NSC149927;NSC167460;AKOS000120212;AKOS016843444;AT23095;NSC 149927;NSC-149927;SB45601;SB46406;SB84273;SDCCGMLS-0066190.P001;BS-42136;LS-97126;LS-184880;CS-0214941;FT-0604544;FT-0604558;FT-0612299;N0775;EN300-20650;rac-(1R,2R,4S)-bicyclo[2.2.1]heptan-2-ol;J-010027;Q5420475;Z104479470

Chemical Property of Bicyclo[2.2.1]heptan-2-ol

Chemical Property:

• Vapor Pressure: 0.332mmHg at 25°C
• Melting Point: 149 °C
• Boiling Point: 176.5°Cat760mmHg
• PKA: 15.31±0.20(Predicted)
• Flash Point: 74.4°C
• PSA: 20.23000
• Density: 1.097g/cm³
• LogP: 1.16730
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 112.088815002
• Heavy Atom Count: 8
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Bicyclo[2.2.1]heptan-2-ol 95% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2CC1CC2O

Technology Process of Bicyclo[2.2.1]heptan-2-ol

There total 49 articles about Bicyclo[2.2.1]heptan-2-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(1S,4R)-bicyclo[2.2.1]heptan-2-one (497-38-1,2630-41-3) → (1S,2S,4R)-2-norbornanol (497-36-9,497-37-0,1632-68-4,24325-44-8,29583-34-4,36779-79-0,60133-16-6,61277-90-5,61277-93-8)

Guidance literature:

With [RuCl₂(triphenylphosphine)₂(1,2-diaminoethane)]; potassium tert-butylate; hydrogen; In isopropyl alcohol; tert-butyl alcohol; at 20 ℃; under 7240.26 Torr; Reagent/catalyst; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/op060063n

Reference yield: 93.0%

2-((1S,2S,4R)-Bicyclo[2.2.1]hept-2-yloxy)-tetrahydro-pyran → (1S,2S,4R)-2-norbornanol (497-36-9,497-37-0,1632-68-4,24325-44-8,29583-34-4,36779-79-0,60133-16-6,61277-90-5,61277-93-8)

Guidance literature:

With trichloroisocyanuric acid; In methanol; at 20 ℃; for 4h;

DOI:10.1081/SCC-200031053

Reference yield: 92.0%

exo-2,3-epoxynorbornane (278-74-0) → (1S,2S,4R)-2-norbornanol (497-36-9,497-37-0,1632-68-4,24325-44-8,29583-34-4,36779-79-0,60133-16-6,61277-90-5,61277-93-8)

Guidance literature:

With N,N'-Dimethylurea; tris(pyrrolidino)phosphine oxide; lithium bromide; In tetrahydrofuran; at 20 ℃; Electrochemical reaction;

DOI:10.1126/science.aav5606

upstream raw materials:

norborn-2-ene

exo-2-norbornanol

norbornene

exo-2-trichlorosilylnorbornane

Downstream raw materials:

1,3-diphenylpropane-2-(bicyclo[2.2.1]heptan-2-yl)-1,3-dione

(2S)-exo-norbornyl (R)-α-methoxy-α-trifluoromethylphenylacetate

2-cyclopentylacetaldehyde

(1S,4R)-bicyclo[2.2.1]heptan-2-one

Refernces

• 1、 Brown et al.. "-". . p. 2209,2212, 2216. Retrieved 1973.
• 2、 Cha, Jin Soon,Kwon, Oh Oun,Kim, Jong Mi,Cho, Sung Dong. "Reexamination of diisobutylaluminum hydride as a stereoselective reducing agent for reduction of cyclic ketones to thermodynamically more stable alcohols". . p. 1465 - 1466. Retrieved 1997.
• 3、 Watanabe et al.. "". . p. 3934,3937. Retrieved 1962.
• 4、 Brown,Murray. "". . p. 631. Retrieved 1961.
• 5、 De Koning, Pieter D.,Jackson, Mark,Lennon, Ian C.. "Use of achiral (diphosphine)RuCl2(diamine) precatalysts as a practical alternative to sodium borohydride for ketone reduction". . p. 1054 - 1058. Retrieved 2006.
• 6、 Huang, Buwen,Elleraas, Jeff,Ewanicki, Jason,Sutton, Scott C.. "A short asymmetric synthesis of methyl 2-((1S,3R)-3-((tert-butyldiphenylsilyl)oxy)cyclopentyl)acetate from norbornene". . . Retrieved 2020.
• 7、 Matsuoka, Keitaro,Komami, Narumi,Kojima, Masahiro,Mita, Tsuyoshi,Suzuki, Kimichi,Maeda, Satoshi,Yoshino, Tatsuhiko,Matsunaga, Shigeki. "Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)". supporting information. p. 103 - 108. Retrieved 2021/01/13.
• 8、 Liu, Xin,Longwitz, Lars,Spiegelberg, Brian,T?njes, Jan,Beweries, Torsten,Werner, Thomas. "Erbium-Catalyzed Regioselective Isomerization-Cobalt-Catalyzed Transfer Hydrogenation Sequence for the Synthesis of Anti-Markovnikov Alcohols from Epoxides under Mild Conditions". . p. 13659 - 13667. Retrieved 2020/11/30.