[ CAS No. 934-69-0 ] {[proInfo.proName]}

Name: 934-69-0|4-Methylenecyclohexanecarboxylic acid|95%
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SKU: A511630
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Quality Control of [ 934-69-0 ]

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Product Details of [ 934-69-0 ]

CAS No. :	934-69-0	MDL No. :	MFCD17167321
Formula :	C₈H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DENSHBNKGSMOIU-UHFFFAOYSA-N
M.W :	140.18	Pubchem ID :	14831547
Synonyms :

Safety of [ 934-69-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 934-69-0 ]

* 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 [ 934-69-0 ]
Downstream synthetic route of [ 934-69-0 ]

[ 934-69-0 ] Synthesis Path-Upstream 1~1

1
[ 934-69-0 ]
[ 1004-24-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 404 - 408

[ 934-69-0 ] Synthesis Path-Downstream 1~20

1
[ 934-69-0 ]
[ 1004-24-6 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 404 - 408

2
[ 934-69-0 ]
[ 874-61-3 ]

Yield	Reaction Conditions	Operation in experiment
	(i) O₃, tBuOH, (ii) NaBH₄; Multistep reaction;

Reference： [1]Weinberg,N.L.; Wright,G.F. [Canadian Journal of Chemistry, 1965, vol. 43, p. 24 - 29]

3
C₈H₁₃ClHgO₃ [ No CAS ]
[ 934-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Weinberg,N.L.; Wright,G.F. [Canadian Journal of Chemistry, 1965, vol. 43, p. 24 - 29]

4
[ 934-69-0 ]
4-(4-Chloro-phenyl)-4-dimethylamino-1-(4-methylene-cyclohexylmethyl)-cyclohexanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: LiAlH₄ / tetrahydrofuran / 4 h / Heating 2: pyridine / 18 h 3: NaBr, HMPA / acetone / 6 h / Heating 4: 1.) Mg / 1.) THF, 2.) THF, RT, overnight

Reference： [1]Lednicer; Von Voigtlander; Emmert [Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 404 - 408]

5
[ 934-69-0 ]
[ 76825-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / tetrahydrofuran / 4 h / Heating 2: pyridine / 18 h 3: NaBr, HMPA / acetone / 6 h / Heating

Reference： [1]Lednicer; Von Voigtlander; Emmert [Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 404 - 408]

6
[ 934-69-0 ]
Methanesulfonic acid 4-methylene-cyclohexylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiAlH₄ / tetrahydrofuran / 4 h / Heating 2: pyridine / 18 h

Reference： [1]Lednicer; Von Voigtlander; Emmert [Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 404 - 408]

Yield	Reaction Conditions	Operation in experiment
		...stead of cyclopentane carboxylic acid to yield the appropriate 25-substituted avermectins of formula (I) wherein R is H, R1 is OH, or R and R1 taken together represent a double bond, R3 is H or OH and R4 is 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy: ... cycloheptane carboxylic acid 4,4-difluorocyclohexane carboxylic acid 4-methylenecyclohexane carboxylic acid 3-methylcyclohexane carboxylic acid ...

8
[ 17159-79-4 ]
[ 934-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C 1.2: 0 - 20 °C / Inert atmosphere 2.1: water; sodium hydroxide / methanol / 0.5 h / 50 °C

Reference： [1]Current Patent Assignee: BOHAI WATER INDUSTRY CO., LTD. - EP2738156, 2014, A1

9
[ 145576-28-9 ]
[ 934-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium hydroxide; In methanol; at 50℃; for 0.5h;	Compound 8-2 (16.1g, 0.096mol) and sodium hydroxide (8g, 0.2mol) were dissolved in a mixed solvent of 100mL of methanol and water (volume ratio 1: 1), reacted at 50C for 0.5h, and rotary evaporated to remove methanol. Then added 200mL of water, and adjusted the pH to acidic, extracted with dichloromethane, washed with saturated brine, and then dried over anhydrous sodium sulfate, the desiccant was removed by filtration, the solvent was removed by rotary evaporation, and concentrated to give a white solid.
3.9 g	With water; lithium hydroxide; In tetrahydrofuran; at 20℃; for 12h;	Brief procedure: An aqueous solution of LiOH was added to R-2 in THF at room temperature and resulting mixture stirred at room temperature for 12 h. Work up: The reaction mixture was diluted with pentane. The phases were separated and the aqueous layer was acidified with 4 N HCI at ice bath temperature and extracted with diethyl ether. The combined organic extract was dried and concentrated under reduced pressure to furnish the compound R as a solid. Purification: No purification done. TLC system: 30% Ethyl acetate-petroleum ether, Rf value: 0.3 Nature of the compound: White solid, Yield: 3.9 g
0.042 g	With methanol; sodium hydroxide; In tetrahydrofuran; at 20℃; for 16h;	To a solution of ethyl 4-methylenecyclohexanecarboxylate (0.05 g) in THF (2 mL) and MeOH (0.5 mL) was added 1 N NaOH (1 mL). The resulting solution was stirred at rt for 16 hrs. The reaction mixture was diluted with 1 N HCl and EtOAc. The organic phase was washed with sat. NaCl and dried over anhydrous Na2SO4, filtered and dried to yield Cap N-3 as a yellow oil (0.042 g).1H NMR (400 MHz, CDCl3) delta ppm 4.62-4.73 (2H, m), 2.50 (1H, tt, J=11.01, 3.54 Hz), 2.30-2.41 (2H, m), 1.98-2.14 (4H, m), 1.54-1.69 (2H, m).

0.042 g

With methanol; sodium hydroxide; In tetrahydrofuran; at 20℃; for 16h;

To a solution of ethyl 4-methylenecyclohexanecarboxylate (0.05 g) in THF (2 mL) and MeOH (0.5 mL) was added 1 N NaOH (1 mL). The resulting solution was stirred at rt for 16 hrs. The reaction mixture was diluted with 1 N HC1 and EtOAc. The organic phase was washed with sat. NaC1 and dried over anhydrous Na2504, filtered and dried to yield Cap N-3 as a yellow oil (0.042 g). ?H NMR (400 MHz,CDC13) ppm 4.62 - 4.73 (2 H, m), 2.50 (1 H, tt, J=1 1.01, 3.54 Hz), 2.30 - 2.41 (2 H, m), 1.98-2.14(4 H, m), 1.54- 1.69(2 H, m).

Reference： [1]Patent: EP2738156,2014,A1 .Location in patent: Paragraph 0126-0127
[2]Patent: WO2015/4455,2015,A2 .Location in patent: Page/Page column 27-28
[3]Patent: US2015/23913,2015,A1 .Location in patent: Paragraph 1570-1571
[4]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 538

10
[ 934-69-0 ]
[ 1420294-77-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / dichloromethane / -10 - 20 °C 2: ammonia / 80 °C / Cooling

Reference： [1]Current Patent Assignee: BOHAI WATER INDUSTRY CO., LTD. - EP2738156, 2014, A1

11
[ 934-69-0 ]
[ 1420294-78-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: dicyclohexyl-carbodiimide / dichloromethane / -10 - 20 °C 2: ammonia / 80 °C / Cooling 3: lithium aluminium tetrahydride / tetrahydrofuran / -10 - 20 °C 4: triethylamine / dichloromethane / -10 - 20 °C

Reference： [1]Current Patent Assignee: BOHAI WATER INDUSTRY CO., LTD. - EP2738156, 2014, A1

12
[ 934-69-0 ]
[ 1420294-79-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: dicyclohexyl-carbodiimide / dichloromethane / -10 - 20 °C 2.1: ammonia / 80 °C / Cooling 3.1: lithium aluminium tetrahydride / tetrahydrofuran / -10 - 20 °C 4.1: triethylamine / dichloromethane / -10 - 20 °C 5.1: diethylzinc; trifluoroacetic acid / dichloromethane; hexane / 0.5 h / -40 °C / Inert atmosphere 5.2: -5 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: BOHAI WATER INDUSTRY CO., LTD. - EP2738156, 2014, A1

13
[ 934-69-0 ]
[ 854444-57-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide / dichloromethane / -10 - 20 °C 2: ammonia / 80 °C / Cooling 3: lithium aluminium tetrahydride / tetrahydrofuran / -10 - 20 °C

Reference： [1]Current Patent Assignee: BOHAI WATER INDUSTRY CO., LTD. - EP2738156, 2014, A1

14
[ 6066-82-6 ]
[ 934-69-0 ]
[ 1420294-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide In dichloromethane at -10 - 20℃;	7.2 4-methylenecyclohexanecarboxamide (Compound 8-3) The above obtained white solid and N-hydroxysuccinimide (13.2g, 0.115mol) were dissolved in 200mL of DCM, DCC (23.65g, 0.1 14mol) was added slowly at -10°C. After the addition, the reaction mixture was stirred for 1 hour at room temperature, suction filtered, and rotary evaporated to remove solvents. The resulting residue was dispersed in 200mL of ammonia cooled with an ice-water bath, and then heated to 80°C, maintained at that temperature for 2 hours, and then pressurized to remove most of the ammonia gas, and extracted with ethyl acetate, dried and concentrated, then crystallized from ethyl acrylate/petroleum ether to give Compound 8-3 (9.5g, 71.1% yield).

Reference： [1]Current Patent Assignee: BOHAI WATER INDUSTRY CO., LTD. - EP2738156, 2014, A1 Location in patent: Paragraph 0128

15
(1S,1'S)-1,1'-(4,4'-(biphenyl-4,4'-diyl)bis(1H-imidazole-4,2-diyl))bis(2,2-dimethylpropan-1-amine) tetrahydrochloride [ No CAS ]
[ 934-69-0 ]
[ 76-05-1 ]
C₄₄H₅₆N₆O₂*2C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (1S,1'S)-1,1'-(4,4'-(biphenyl-4,4'-diyl)bis(1H-imidazole-4,2-diyl))bis(2,2-dimethylpropan-1-amine) tetrahydrochloride; 4-methylenecyclohexanecarboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: trifluoroacetic acid In methanol; water	N-118 General procedure: (is, l’s)- 1,1 ‘-(4,4’-([ 1,1 ‘-biphenyl]-4,4’-diyl)bis( 1H-imidazole-4,2- diyl))bis(2,2-dimethylpropan-1-amine), 4 HC1 (50 mg, 0.083 mmol), 2-((tert- butoxycarbonyl)amino)-2-methylpropanoic acid (33.7 mg, 0.166 mmol) and DIEA10 (0.101 mL, 0.58 1 mmol) were combined in DMF (2 mL) and the resulting mixture was stirred for 5 mm, followed by addition of HATU (66.3 mg, 0.174 mmol). The resulting solution was the stirred at rt for 2 h. The yellow solution was then purified by preparatory HPLC (MeOH/H20/TFA) to yield a white solid corresponding to the TFA salt of Example L-3 (40 mg).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/5901, 2015, A1 Location in patent: Page/Page column 202; 238

16
[ 5162-44-7 ]
[ 934-69-0 ]
C₁₃H₂₀O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methylenecyclohexanecarboxylic acid With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 1-bromo-4-butene In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - 20℃; for 2.66667h; Inert atmosphere; Schlenk technique;

Reference： [1]Liu, Wenfei; Xu, Wenhua; Wang, Juanjuan; Lu, Hong; Xu, Peng-Fei; Wei, Hao [Chemistry - A European Journal, 2021, vol. 27, # 28, p. 7651 - 7656]

17
[ 934-69-0 ]
C₁₂H₁₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 2.67 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 2.1: potassium hydroxide / tetrahydrofuran; water; methanol / 4 h / 40 °C / Inert atmosphere; Schlenk technique

Reference： [1]Liu, Wenfei; Xu, Wenhua; Wang, Juanjuan; Lu, Hong; Xu, Peng-Fei; Wei, Hao [Chemistry - A European Journal, 2021, vol. 27, # 28, p. 7651 - 7656]

18
[ 934-69-0 ]
8-methylene-2-((p-tolylthio)methyl)spiro[4.5]decan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 2.67 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 2.1: potassium hydroxide / tetrahydrofuran; water; methanol / 4 h / 40 °C / Inert atmosphere; Schlenk technique 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique 3.2: 2 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 4.1: bis(1,5-cyclooctadiene)nickel⁽⁰⁾; 4-piperidinylpyridine; 1,4-bis(di(thiophen-2-yl)phosphaneyl)butane / tetrahydrofuran; water / 24 h / 120 °C / Inert atmosphere; Glovebox; Schlenk technique; Sealed tube

Reference： [1]Liu, Wenfei; Xu, Wenhua; Wang, Juanjuan; Lu, Hong; Xu, Peng-Fei; Wei, Hao [Chemistry - A European Journal, 2021, vol. 27, # 28, p. 7651 - 7656]

19
[ 934-69-0 ]
S-(p-tolyl) 1-(but-3-en-1-yl)-4-methylenecyclohexane-1-carbothioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 2.67 h / -78 - 20 °C / Inert atmosphere; Schlenk technique 2.1: potassium hydroxide / tetrahydrofuran; water; methanol / 4 h / 40 °C / Inert atmosphere; Schlenk technique 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique 3.2: 2 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Liu, Wenfei; Xu, Wenhua; Wang, Juanjuan; Lu, Hong; Xu, Peng-Fei; Wei, Hao [Chemistry - A European Journal, 2021, vol. 27, # 28, p. 7651 - 7656]

20
[ 934-69-0 ]
C₂₅H₂₁N₅ [ No CAS ]
N-(3-((1-((4-(1H-pyrazol-4-yl)phenyl)amino)isoquinolin-3-yl)amino)phenyl)-4-methylenecyclohexane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.9%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	12 Intermediate 1f (392 mg, 1.0 mmol), compound 12a (140 mg, 1.0 mmol), DIEA (258 mg, 2.0 mmol) were dissolved in N,N-dimethylformamide (50 mL), HATU (570 mg, 1.5mmol), stirred the reaction at room temperature, monitored the reaction by TLC, added water (50mL) to quench the reaction after the reaction, extracted with ethyl acetate (50mL×2), dried the organic layer, concentrated, and separated by column chromatography to obtain an off-white solid (compound 12) 354 mg, the yield is 68.9%

Reference： [1]Current Patent Assignee: BEIJING XINKAIYUAN PHARMACEUTICALS - CN113999206, 2022, B Location in patent: Paragraph 0079-0082

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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
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
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
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. 934-69-0 ] {[proInfo.proName]}

Quality Control of [ 934-69-0 ]

Related Doc. of [ 934-69-0 ]

Product Details of [ 934-69-0 ]

Safety of [ 934-69-0 ]

Application In Synthesis of [ 934-69-0 ]

[ 934-69-0 ] Synthesis Path-Upstream 1~1

[ 934-69-0 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 934-69-0 ]

Alkenes

Aliphatic Cyclic Hydrocarbons

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 934-69-0 ]