[ CAS No. 95-12-5 ] {[proInfo.proName]}

Name: 95-12-5|Bicyclo[2.2.1]hept-5-en-2-ylmethanol|98%
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SKU: A130903
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Quality Control of [ 95-12-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 95-12-5 ]

SDS Specification

Alternatived Products of [ 95-12-5 ]

Product Details of [ 95-12-5 ]

CAS No. :	95-12-5	MDL No. :	MFCD00167571
Formula :	C₈H₁₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LUMNWCHHXDUKFI-UHFFFAOYSA-N
M.W :	124.18	Pubchem ID :	78946
Synonyms :

Safety of [ 95-12-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302+H312+H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 95-12-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 95-12-5 ]
Downstream synthetic route of [ 95-12-5 ]

[ 95-12-5 ] Synthesis Path-Upstream 1~16

1
[ 5453-80-5 ]
[ 95-12-5 ]

Reference： [1] European Journal of Organic Chemistry, 2009, # 21, p. 3567 - 3572
[2] Chemistry - A European Journal, 2012, vol. 18, # 50, p. 15935 - 15939
[3] Helvetica Chimica Acta, 2000, vol. 83, # 9, p. 2192 - 2196
[4] Patent: US4328234, 1982, A,
[5] Catalysis Science and Technology, 2017, vol. 7, # 16, p. 3637 - 3646

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Yield	Reaction Conditions	Operation in experiment
74%	at 170 - 180℃; for 9 h; Autoclave	was obtained in a pressure reactor in 9 h at 170–180 °C, pressure of 4–5 at, and the ratio dicyclopentaene : allyl alcohol = 1 : 2.4 [12]. Yield 74 percent, bp 82–83 °(10 mmHg), n_D²⁰ 1.4970, d₄²⁰ 1.027 g/cm³. IR spectrum,ν, cm^–1: 3500 (OH), 2930–2895, 2880–2830 (2),1200–1100 (N). ¹H NMR spectrum, δ, ppm (J, Hz): 0.45 d. d (1H, H^6exo, J = 4.1, 13.4), 1.19 t (1H, H^7anti, J = 7.9), 1.44 t (1H, H^6endo, J = 4.1), 1.68–1.72 m (1H, H^7syn), 2.86 m (1H, H⁵), 3.29 m (1H, H⁴), 3.36–3.46 m(2H, C⁸H₂), 3.46 d. d. d (1H, H¹, J = 4.4, 4.6, 4.8), 3.92br. s (1H, OH), 6.00–6.08 m (2H, H^2,3). ¹³C NMR spectrum, δ_C, ppm: 28.8 (C6), 41.8 (C5), 42.3 (C1), 43.6 (C4), 49.4 (C7), 65.8 (C8), 132.3 (C3), 137.8 (C2).

Reference： [1] Petroleum Chemistry, 2000, vol. 40, # 4, p. 272 - 274
[2] Russian Journal of General Chemistry, 2018, vol. 88, # 10, p. 2204 - 2208[3] Zh. Obshch. Khim., 2018, vol. 88, # 10, p. 1718 - 1722,5
[4] Russian Journal of Organic Chemistry, 2003, vol. 39, # 7, p. 947 - 951
[5] Russian Journal of Applied Chemistry, 2008, vol. 81, # 10, p. 1803 - 1807

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Yield	Reaction Conditions	Operation in experiment
52%	at 210℃; for 1 h; Autoclave	The 397g (3mol) dicyclopentadiene (DCPD) (Company produces Aldric) and 331g (5.7mol) ene propanol (Company produces Aldric) add 2L in the high-pressure reactor, and 2L to the rise of the temperature of the high-pressure reactor 210 °C. The mixture of the 300rpm reaction under stirring 1 hour. When the reaction is complete, cooling reactant and into the distiller. In the 56 °C the use of vacuum pump, in the 1 distillation under reduced pressure of the reactant 2 times, in order to get the product. (Yield: 52percent).

Reference： [1] Patent: CN102731303, 2016, B, . Location in patent: Paragraph 0093; 0094

4
[ 6203-08-3 ]
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Reference： [1] Journal of Organic Chemistry, 1992, vol. 57, # 4, p. 1061 - 1063
[2] Organic letters, 2002, vol. 4, # 11, p. 1847 - 1849

5
[ 10471-24-6 ]
[ 95-12-5 ]

Yield	Reaction Conditions	Operation in experiment
83 %Chromat.	at 45℃; for 2 h; Autoclave; Inert atmosphere; Large scale	Into a suitably sized and jacketed reactor were placed a mixture of exo-/endo- norbornene methylacetate (>99.6percent purity, 4.8 kg) and methanol (11.2 kg). The reactor was equipped with an agitator, overhead condenser, overhead condensate receiver tank, and feed tank with metering pump. The temperature of the reactor was controlled by a dedicated oil circulation unit; reactor pressure was manually controlled, with nitrogen addition to increase pressure and vent takeoff to decrease pressure.The reactor was purged with nitrogen using three pressure/vacuum swings to remove any oxygen in the reactor headspace. After this nitrogen purge process, the reactor was left in a fully vented mode through the overhead condenser and receiver system, and then heated to the initial reaction temperature (45°C). A catalyst solution consisting of sodium methoxide in methanol (25wtpercent, 0.125 kg) was added to the glass feed tank and then metered into the reactor over a 15 minute period (addition rate 8.33 g min), while maintaining reactor temperature (45°C). After completion of the catalyst metered addition, the reactor was maintained at temperature (45°C) for an additional 1.75 hours. After completion of the reaction process, the reactor was heated to solvent stripping temperature (60-68°C) in vented mode, and a mixture of methanol/methylacetate (4 kg) was flashed overhead and collected in the overhead receiver tank. Additional methanol (4 kg) was transferred to the reactor, and a second solvent stripping operation was conducted to remove a mixture of methanol/methylacetate (4 kg). Finally, a third solvent stripping operation was conducted to remove a mixture of methanol/methylacetate (6 kg). After completion of this solvent stripping process, acetic acid (0.04 kg) was added to the reaction concentrate, which was then transferred out of the reactor and analyzed via GC to confirm that the trans-esterification reaction was complete. Composition of the reaction concentrate was as follows: norbornene methanol 83percent, norbornene methyl acetate trace amounts, methanol 17percent and MeOAc trace amounts.The norbornene methanol reaction concentrate (6 kg) was then charged to a suitably equipped vacuum distillation system consisting of a still pot with electric heating mantle, distillation column with stainless steel structured packing (4 theoretical plates), reflux splitter, water cooled condenser, overhead condensate receiver, and vacuum pump. Still pot temperature was controlled by adjusting the heat input on the heating mantle, and system vacuum was controlled by adjusting vacuum pressure at the overhead receiver. The still pot was initially heated in fully vented mode until reflux conditions were established in the distillation column. The reflux splitter was then started at the desired reflux ratio and fractional distillation proceeded by periodically removing liquid fractions from the overhead receiver. GC analysis was used to determine composition of the overhead fractions. Still pot temperature, overhead receiver vacuum, and reflux ratio were adjusted as needed to affect composition of the overhead stream. Initial overheadfractions contained primarily methanol with trace amounts of methylacetate. After removal of these solvents, high purity norbornene methanol was then distilled overhead under the following conditions: overhead temperature (70-75 °C), vacuum (4-5 mm Hg), and reflux ratio (2:1). The distillation process was terminated once the majority of the product had been removed from the still pot. Approximately 90percent of the contained norbornene methanol in the starting mixture was recovered as high-purity (>99.8percent assay) product, with trace amount of norbornene methyl acetate ( The GC analysis was performed on an Ultra 1 (crosslinked methyl siloxane) column, 25 m, 0.2 mm ID, 0.33 μπι film. Initial Conditions: 70°C, hold 1.0 min.; Gradient Conditions: 70°C to 240°C 10°C /min.; Final Conditions: 240°C, hold 10.0 min. Injector: 200°C. Detector: 250°C (FID). GC retention times: NBMeOH 7.1-7.3 min., NBAMeOH 7.5-7.6 min., and NBMeOAc 8.8-8.9 min.

Reference： [1] Patent: WO2014/99546, 2014, A1, . Location in patent: Page/Page column 16; 17

6
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Reference： [1] Journal of the American Chemical Society, 2018, vol. 140, # 25, p. 7961 - 7969

7
[ 77-73-6 ]
[ 107-18-6 ]
[ 95-12-5 ]

Reference： [1] Patent: WO2014/99546, 2014, A1, . Location in patent: Page/Page column 19; 20

8
[ 591-87-7 ]
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[ 10471-24-6 ]
[ 95-12-5 ]

Yield	Reaction Conditions	Operation in experiment
80 %Chromat.	at 220℃; for 4 h; Autoclave; High pressure	Into a suitable high pressure tube reactor were placed allyl acetate and dicyclopentadiene (DCPD) at 4:1 molar ratio based on cyclopentadiene monomer, and heated in a hot oil bath maintained at 220°C, and maintained at that temperature for four hours. At the end of the reaction, the high pressure tube was removed from the bath and quenched in a wet ice bath. The tube was washed then with methanol and dichloromethane and weighed to verify that no leakage had occurred. The resultant crude monomer sample was analyzed by GC-MS, which showed about 7.5percent unreacted allyl acetate, 10percent exo-/endo-norbornene methanol, 82percent exo-/endo-norbornene methyl acetate and 0.6percent (l,2,3,4,4a,5,8,8a-octahydro-l,4:5,8-dimethanonaphthalen-2-yl)methanol. Fractional distillation of the crude mixture resulted in the isolation of norbomene methyl acetate of greater than > 99.6percent purity. The GC-MS analysis was performed on an Altech EC-5 column, 30 m, 0.25 mm ID, 0.25 μηι film; Inlet-F: 250, MS source: 230°C, electron ionization. The GC conditions used are as follows: Gradient: 45°C to 120°C at 10°C/min, then heat at 40°C/min to 300°C, hold 2 min at 300°C.

Reference： [1] Patent: WO2014/99546, 2014, A1, . Location in patent: Page/Page column 16

9
[ 77-73-6 ]
[ 107-18-6 ]
[ 7329-04-6 ]
[ 7158-25-0 ]
[ 23197-86-6 ]
[ 95-12-5 ]

Reference： [1] Patent: EP1757580, 2007, A1, . Location in patent: Page/Page column 10-11

10
[ 5453-80-5 ]
[ 1218-65-1 ]
[ 95-12-5 ]

Reference： [1] Journal of Organic Chemistry, 1989, vol. 54, # 8, p. 2003 - 2006

11
[ 542-92-7 ]
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Reference： [1] European Journal of Organic Chemistry, 2006, # 5, p. 1166 - 1176

12
[ 46169-02-2 ]
[ 95-12-5 ]

Reference： [1] Russian Journal of Applied Chemistry, 2006, vol. 79, # 10, p. 1621 - 1625

13
[ 106988-45-8 ]
[ 95-12-5 ]

Reference： [1] Angewandte Chemie, 1987, vol. 99, # 3, p. 269 - 271

14
[ 497-35-8 ]
[ 498-66-8 ]
[ 822-96-8 ]
[ 110-83-8 ]
[ 95-12-5 ]

Reference： [1] Russian Journal of Organic Chemistry, 2003, vol. 39, # 7, p. 947 - 951

15
[ 822-96-8 ]
[ 498-66-8 ]
[ 693-89-0 ]
[ 110-83-8 ]
[ 95-12-5 ]

Reference： [1] Russian Journal of Organic Chemistry, 2003, vol. 39, # 7, p. 947 - 951

16
[ 5240-72-2 ]
[ 497-35-8 ]
[ 693-89-0 ]
[ 822-96-8 ]
[ 95-12-5 ]

Reference： [1] Russian Journal of Organic Chemistry, 2003, vol. 39, # 7, p. 947 - 951

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Code	Phrase
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P222	Do not allow contact with air.
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P230	Keep wetted
P231	Handle under inert gas.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P270	Do not eat, drink or smoke when using this product.
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Code	Phrase
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P321
P322
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
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P411 + P235	Keep cool.
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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 95-12-5 ] {[proInfo.proName]}

Quality Control of [ 95-12-5 ]

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Product Details of [ 95-12-5 ]

Safety of [ 95-12-5 ]

Application In Synthesis of [ 95-12-5 ]

[ 95-12-5 ] Synthesis Path-Upstream 1~16

[ 95-12-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 95-12-5 ]

Alkenes

Aliphatic Cyclic Hydrocarbons

Alcohols

Precautionary Statements-General

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Health hazards

Environmental hazards

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Related Functional Groups of
[ 95-12-5 ]