[ CAS No. 14510-36-2 ] {[proInfo.proName]}

Name: 14510-36-2|3-Acetoxy-2-phenylpropanoic acid|97%
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3d Animation Molecule Structure of 14510-36-2

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Quality Control of [ 14510-36-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 14510-36-2 ]

SDS Specification

Alternatived Products of [ 14510-36-2 ]

Product Details of [ 14510-36-2 ]

CAS No. :	14510-36-2	MDL No. :	MFCD09750984
Formula :	C₁₁H₁₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OXGQBORIYFGJPM-UHFFFAOYSA-N
M.W :	208.21	Pubchem ID :	10921700
Synonyms :

Calculated chemistry of [ 14510-36-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.27
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.69
TPSA :	63.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.66
Log Po/w (XLOGP3) :	1.34
Log Po/w (WLOGP) :	1.42
Log Po/w (MLOGP) :	1.57
Log Po/w (SILICOS-IT) :	1.54
Consensus Log Po/w :	1.51

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.94
Solubility :	2.38 mg/ml ; 0.0115 mol/l
Class :	Very soluble
Log S (Ali) :	-2.28
Solubility :	1.1 mg/ml ; 0.00528 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.31
Solubility :	1.03 mg/ml ; 0.00493 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Safety of [ 14510-36-2 ]

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

Application In Synthesis of [ 14510-36-2 ]

* 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.

Downstream synthetic route of [ 14510-36-2 ]

[ 14510-36-2 ] Synthesis Path-Downstream 1~13

1
[ 529-64-6 ]
[ 108-24-7 ]
[ 37504-67-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1901,vol. <2> 64,p. 281
Justus Liebigs Annalen der Chemie,1898,vol. 303,p. 157
[2]Chemische Berichte,1968,vol. 101,p. 2413 - 2418

2
[ 529-64-6 ]
[ 75-36-5 ]
[ 37504-67-9 ]

Yield	Reaction Conditions	Operation in experiment
		In a 250 mL three-necked flask, add 14.5 g (0.087 mol) of Tropinic acid (Compound 4), 60 mL of toluene, heat to 50 C, add 0.2 g (0.002 mol) of triethylamine, drop Add 13.7g (0.14mol) of acetyl chloride, react at 50 C for 3 hours, dropwise add 14.8g (0.124mol) of dichlorosulfoxide, continue the reaction for 5 hours, concentrate in vacuo to a small volume, add 60mL of toluene, and cool to room temperature; A 500mL three-necked flask was charged with 20.7g (0.087mol) of N-ethylpyridylamine trifluoroacetate (Compound 2), 8.8g (0.087mol) of triethylamine, 80mL of toluene, cooled to 0 C, and acetyl was added dropwise. The solution of tropine acid was reacted at 0-10 C overnight, and washed with 60 mL of saturated saline five times. The organic phase was added with 10.2 g (0.14 mol) of 31% hydrochloric acid and heated to 90 C. The reaction was allowed to proceed overnight, and the organic phase was separated. Aqueous ammonia, dilute hydrochloric acid, saturated brine, washed with purified water, the organic phase was concentrated in vacuo at 50 C, the concentrated solution was recrystallized with ethyl acetate / n-heptane, the filter cake was washed with n-heptane, and dried under vacuum to obtain 21.7 g of tropinamide , Purity 99.5%, yield 87.5%.
	With triethylamine; In toluene; at 50℃; for 3h;	Preparation of Tropicamide (Compound 7): Add 20.4g (0.123mol) to a 250mL three-necked bottleTropic acid (Compound 4), 50mL toluene, heated to 50 , added 0.3g (0.003mol) triethylamine, added dropwise 19.0g (0.24mol) acetyl chloride, reacted at 50 for 3 hours, added dropwise 20.5g (0.17 mol) Dichlorosulfoxide, continue the reaction for 5 hours, concentrate in vacuo to a small volume, add 50 mL of toluene, and cool to room temperature; add 18.2 g (0.134 mol) of pure N-ethylpyridine to another 500 mL three-necked bottle ( Compound 1), 13.7g (0.136mol) of triethylamine, 100mL of toluene, cooled to 0 C, add a solution of acetotropic acid dropwise, react overnight at 0-10 C, add 80mL of saturated brine and wash five times, the organic phase is added 27g (0.23mol) 31% hydrochloric acid, heated to 90 C, reacted overnight, liquid separation, the organic phase was washed with ammonia, dilute hydrochloric acid, saturated brine, purified water, the organic phase was concentrated in vacuo at 50 C, the concentrated solution was with ethyl acetate / N-heptane recrystallized, the filter cake was washed with n-heptane, and dried in vacuum to obtain 26.5 g of tropinamide with a purity of 98.8% and a yield of 75.9%.

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 3334 - 3340
[2]Chemische Berichte,1908,vol. 41,p. 731
[3]European Journal of Medicinal Chemistry,1997,vol. 32,p. 595 - 605
[4]Organic Letters,2018,vol. 20,p. 1175 - 1178
[5]Patent: CN110872251,2020,A .Location in patent: Paragraph 0052-0057
[6]Patent: CN110950795,2020,A .Location in patent: Paragraph 0024; 0025

3
[ 14510-36-2 ]
[ 6509-95-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With tert-butylhypochlorite; silver triflate-bis(1,10-phenanthroline) complex In acetonitrile at 20℃; for 5h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Wang, Zhentao; Zhu, Lin; Yin, Feng; Su, Zhongquan; Li, Zhaodong; Li, Chaozhong [Journal of the American Chemical Society, 2012, vol. 134, # 9, p. 4258 - 4263]

4
[ 37504-67-9 ]
[ 529-64-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 747 - 752

5
[ 37504-67-9 ]
[ 14510-37-3 ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1156 - 1164
[2]Organic Letters,2018,vol. 20,p. 1175 - 1178

6
[ 103-82-2 ]
[ 590-97-6 ]
[ 37504-67-9 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 15807 - 15811
Angew. Chem.,2016,vol. 128,p. 16039 - 16043,5

7
[ 14510-36-2 ]
[ 87767-94-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With silver triflate-bis(1,10-phenanthroline) complex; dibromoisocyanuric acid In 1,2-dichloro-ethane at 20℃; for 2h; Inert atmosphere; Schlenk technique;

Reference： [1]Tan, Xinqiang; Song, Tao; Wang, Zhentao; Chen, He; Cui, Lei; Li, Chaozhong [Organic Letters, 2017, vol. 19, # 7, p. 1634 - 1637]

8
[ 37504-67-9 ]
[ 33403-97-3 ]
[ 1508-75-4 ]

Yield	Reaction Conditions	Operation in experiment
26.5 g	With triethylamine; In toluene; at 0 - 10℃;	Add 20.4g (0.123mol) of Tropinac (Compound 4), 50mL of toluene to a 250mL three-necked flask, heat to 50 C, add 0.3g (0.003mol) of triethylamine, drop Add 19.0g (0.24mol) of acetyl chloride, and react at 50 C for 3 hours, add 20.5g (0.17mol) of dichlorosulfoxide dropwise, continue the reaction for 5 hours, concentrate in vacuo to a small volume, add 50mL of toluene, and cool to room temperature; A 500mL three-necked flask was charged with 18.2g (0.134mol) of pure N-ethylpyridylamine (Compound 1), 13.7g (0.136mol) of triethylamine, 100mL of toluene, cooled to 0 C, and acetyltropine acid was added dropwise. The solution was reacted overnight at 0-10 C. 80 mL of saturated saline was added and washed five times. The organic phase was added with 27 g (0.23 mol) of 31% hydrochloric acid and heated to 90 C. The reaction was allowed to proceed overnight. The organic phase was separated with ammonia and dilute hydrochloric acid. , Saturated brine, washed with purified water, the organic phase was concentrated in vacuo at 50 C, the concentrated solution was recrystallized with ethyl acetate / n-heptane, the filter cake was washed with n-heptane, and dried in vacuo to obtain 26.5 g of tropinamide, with a purity of 98.8% The yield is 75.9%.
26.5 g		Preparation of Tropicamide (Compound 7): Add 20.4g (0.123mol) to a 250mL three-necked bottleTropic acid (Compound 4), 50mL toluene, heated to 50 , added 0.3g (0.003mol) triethylamine, added dropwise 19.0g (0.24mol) acetyl chloride, reacted at 50 for 3 hours, added dropwise 20.5g (0.17 mol) Dichlorosulfoxide, continue the reaction for 5 hours, concentrate in vacuo to a small volume, add 50 mL of toluene, and cool to room temperature; add 18.2 g (0.134 mol) of pure N-ethylpyridine to another 500 mL three-necked bottle ( Compound 1), 13.7g (0.136mol) of triethylamine, 100mL of toluene, cooled to 0 C, add a solution of acetotropic acid dropwise, react overnight at 0-10 C, add 80mL of saturated brine and wash five times, the organic phase is added 27g (0.23mol) 31% hydrochloric acid, heated to 90 C, reacted overnight, liquid separation, the organic phase was washed with ammonia, dilute hydrochloric acid, saturated brine, purified water, the organic phase was concentrated in vacuo at 50 C, the concentrated solution was with ethyl acetate / N-heptane recrystallized, the filter cake was washed with n-heptane, and dried in vacuum to obtain 26.5 g of tropinamide with a purity of 98.8% and a yield of 75.9%.

Reference： [1]Patent: CN110872251,2020,A .Location in patent: Paragraph 0052-0054
[2]Patent: CN110950795,2020,A .Location in patent: Paragraph 0024

9
[ 37504-67-9 ]
C₈H₁₂N₂*C₂HF₃O₂ [ No CAS ]
[ 1508-75-4 ]

Yield	Reaction Conditions	Operation in experiment
21.7 g	With triethylamine; In toluene; at 0 - 10℃;	In a 250 mL three-necked flask, add 14.5 g (0.087 mol) of Tropinic acid (Compound 4), 60 mL of toluene, heat to 50 C, add 0.2 g (0.002 mol) of triethylamine, drop Add 13.7g (0.14mol) of acetyl chloride, react at 50 C for 3 hours, dropwise add 14.8g (0.124mol) of dichlorosulfoxide, continue the reaction for 5 hours, concentrate in vacuo to a small volume, add 60mL of toluene, and cool to room temperature; A 500mL three-necked flask was charged with 20.7g (0.087mol) of N-ethylpyridylamine trifluoroacetate (Compound 2), 8.8g (0.087mol) of triethylamine, 80mL of toluene, cooled to 0 C, and acetyl was added dropwise. The solution of tropine acid was reacted at 0-10 C overnight, and washed with 60 mL of saturated saline five times. The organic phase was added with 10.2 g (0.14 mol) of 31% hydrochloric acid and heated to 90 C. The reaction was allowed to proceed overnight, and the organic phase was separated. Aqueous ammonia, dilute hydrochloric acid, saturated brine, washed with purified water, the organic phase was concentrated in vacuo at 50 C, the concentrated solution was recrystallized with ethyl acetate / n-heptane, the filter cake was washed with n-heptane, and dried under vacuum to obtain 21.7 g of tropinamide , Purity 99.5%, yield 87.5%.

Reference： [1]Patent: CN110872251,2020,A .Location in patent: Paragraph 0055-0057

10
[ 37504-67-9 ]
C₈H₁₂N₂*CH₄O₃S [ No CAS ]
[ 1508-75-4 ]

Yield	Reaction Conditions	Operation in experiment
17.5 g		Preparation of tropine amide (Compound 7): In a 250 mL three-necked flask, add 11.6 g (0.07 mol) of tropine acid (Compound 4), 50 mL of toluene, heat to 50 C, add 0.2 g (0.002 mol) of triethylamine Add 11.0g (0.14mol) of acetyl chloride, react at 50 for 3 hours, dropwise add 11.5g (0.10mol) of dichlorosulfoxide, continue the reaction for 5 hours, concentrate in vacuo to a small volume, add toluene 50mL, and cool to room temperature; Add 16.24g (0.07mol) to a 500mL three-necked bottleN-ethylpyridine methylamine methanesulfonate (Compound 2), 7.05g (0.07mol) triethylamine,60mL toluene, cooled to 0 , add acetotropic acid dropwiseThe solution,The reaction was carried out at 0-10 C overnight, and 50 mL of saturated saline was added to wash five times. The organic phase was added with 16.5 g (0.14 mol) of 31% hydrochloric acid, heated to 90 C, and reacted overnight. The liquid was separated, and the organic phase was separated with ammonia, dilute hydrochloric acid, and saturated Brine, washed with purified water, the organic phase was concentrated in vacuo at 50 C, the concentrated solution was recrystallized with ethyl acetate / n-heptane, the filter cake was washed with n-heptane, and dried in vacuo to obtain 17.5 g of tropinamide, with a purity of 99.4%. The rate is 88.2%.

Reference： [1]Patent: CN110950795,2020,A .Location in patent: Paragraph 0025

11
[ CAS Unavailable ]
[ 14510-36-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium-t-butoxide / dimethyl sulfoxide / 0.5 h / 20 °C / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere 2.1: tetrabutylammonium bromide / N,N-dimethyl-formamide / 3 h / 0 °C / 760.05 Torr / Schlenk technique; Electrochemical reaction 3.1: pyridine / dichloromethane / 2 h / Schlenk technique; Inert atmosphere

Reference： [1]Zhang, Ke; Ren, Bai-Hao; Liu, Xiao-Fei; Wang, Lin-Lin; Zhang, Min; Ren, Wei-Min; Lu, Xiao-Bing; Zhang, Wen-Zhen [Angewandte Chemie - International Edition, 2022, vol. 61, # 38][Angew. Chem., 2022, vol. 134, # 38]

12
[ 14510-36-2 ]
[ 120-29-6 ]
[ 51-55-8 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: acetyltropic acid With oxalyl dichloride In dichloromethane at 0 - 20℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: 3-tropanol With methanesulfonic acid In dichloromethane at 45℃; for 18h; Schlenk technique; Inert atmosphere;

13
[ 96-09-3 ]
[ 14510-36-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammonium bromide / N,N-dimethyl-formamide / 3 h / 0 °C / 760.05 Torr / Schlenk technique; Electrochemical reaction 2: pyridine / dichloromethane / 2 h / Schlenk technique; Inert atmosphere

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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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. 14510-36-2 ] {[proInfo.proName]}

Quality Control of [ 14510-36-2 ]

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[ 14510-36-2 ] Synthesis Path-Downstream 1~13

Related Functional Groups of [ 14510-36-2 ]

Aryls

Esters

Carboxylic Acids

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[ 14510-36-2 ]