[ CAS No. 104-54-1 ] {[proInfo.proName]}

Name: 104-54-1|3-Phenylprop-2-en-1-ol|95%
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SKU: A210953
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3d Animation Molecule Structure of 104-54-1

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Quality Control of [ 104-54-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 104-54-1 ]

SDS Specification

Alternatived Products of [ 104-54-1 ]

Product Details of [ 104-54-1 ]

CAS No. :	104-54-1	MDL No. :	MFCD00002921
Formula :	C₉H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OOCCDEMITAIZTP-QPJJXVBHSA-N
M.W :	134.18	Pubchem ID :	5315892
Synonyms :		Chemical Name :	3-Phenylprop-2-en-1-ol

Calculated chemistry of [ 104-54-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.11
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.5
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.98
Log Po/w (XLOGP3) :	1.95
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	2.1
Log Po/w (SILICOS-IT) :	2.17
Consensus Log Po/w :	1.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.21
Solubility :	0.823 mg/ml ; 0.00613 mol/l
Class :	Soluble
Log S (Ali) :	-2.0
Solubility :	1.34 mg/ml ; 0.01 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.28
Solubility :	0.699 mg/ml ; 0.00521 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Safety of [ 104-54-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 104-54-1 ]

* 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 [ 104-54-1 ]
Downstream synthetic route of [ 104-54-1 ]

[ 104-54-1 ] Synthesis Path-Upstream 1~14

1
[ 107-31-3 ]
[ 104-54-1 ]
[ 104-65-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium hexamethylsilazane; 1,3-bis(mesityl)imidazolium chloride In toluene at 45℃; for 16 h; Inert atmosphere; Molecular sieve; Sealed tube	General procedure: To a flame-dried flask containing a stirrer bar and activated 5 Å molecular sieves was added IMes·HCl (A1·HCl, 6.8 mg, 0.02 mmol) and toluene (2 mL) under an inert atmosphere. To this stirred suspension 0.5 M KHMDS in toluene (0.04 mL) was added and the mixture stirred for 15 min. An appropriate alcohol (1 mmol) and methyl formate (600mg, 10 mmol) were then added as a solution in toluene (2 mL) and the flask sealed and heated to 45 °C for 16 h. The crude mixture was loaded directly on to a chromatography column (silica gel) to give the formates.

Reference： [1] Synthesis (Germany), 2017, vol. 49, # 15, p. 3505 - 3510

2
[ 104-54-1 ]
[ 109-94-4 ]
[ 104-65-4 ]

Reference： [1] Tetrahedron, 2001, vol. 57, # 39, p. 8333 - 8337
[2] New Journal of Chemistry, 2017, vol. 41, # 12, p. 5075 - 5081
[3] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 4, p. 1399 - 1402
[4] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 3, p. 455 - 458

3
[ 124-38-9 ]
[ 104-54-1 ]
[ 104-65-4 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 14, p. 1739 - 1743

4
[ 104-55-2 ]
[ 104-53-0 ]
[ 122-97-4 ]
[ 104-65-4 ]
[ 104-54-1 ]
[ 33795-14-1 ]
[ 103-41-3 ]
[ 621-82-9 ]
[ 54518-01-3 ]

Reference： [1] Journal of Chemistry, 2018, vol. 2018,

5
[ 104-54-1 ]
[ 75-87-6 ]
[ 104-65-4 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 15, p. 2997 - 3001

6
[ 64-18-6 ]
[ 104-54-1 ]
[ 104-65-4 ]

Reference： [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2003, vol. 178, # 7, p. 1617 - 1621
[2] Chinese Journal of Catalysis, 2011, vol. 32, # 1, p. 60 - 64

7
[ 104-54-1 ]
[ 2258-42-6 ]
[ 104-65-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 18, p. 5139 - 5142[2] Angew. Chem., 2018, vol. 130, # 18, p. 5233 - 5236,4

8
[ 104-55-2 ]
[ 67-63-0 ]
[ 104-53-0 ]
[ 104-65-4 ]
[ 104-54-1 ]
[ 33795-14-1 ]
[ 103-41-3 ]
[ 621-82-9 ]
[ 54518-01-3 ]

Reference： [1] ChemCatChem, 2014, vol. 6, # 11, p. 3246 - 3253

9
[ 104-55-2 ]
[ 67-63-0 ]
[ 104-53-0 ]
[ 122-97-4 ]
[ 104-65-4 ]
[ 104-54-1 ]
[ 33795-14-1 ]
[ 103-41-3 ]
[ 621-82-9 ]
[ 54518-01-3 ]

Reference： [1] ChemCatChem, 2014, vol. 6, # 11, p. 3246 - 3253

10
[ 104-54-1 ]
[ 219500-45-5 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 38, p. 13562 - 13569

11
[ 75-11-6 ]
[ 104-54-1 ]
[ 61826-40-2 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 20, p. 4944 - 4947
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 23, p. 6780 - 6783[3] Angew. Chem., 2016, vol. 128, # 23, p. 6892 - 6895,4
[4] Advanced Synthesis and Catalysis, 2017, vol. 359, # 7, p. 1170 - 1176

12
[ 104-54-1 ]
[ 61826-40-2 ]
[ 104-55-2 ]

Reference： [1] Applied Catalysis A: General, 2011, vol. 394, # 1-2, p. 79 - 85

13
[ 104-54-1 ]
[ 14399-53-2 ]
[ 61826-40-2 ]

Reference： [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 34, p. 5588 - 5591

14
[ 64-17-5 ]
[ 104-55-2 ]
[ 104-53-0 ]
[ 122-97-4 ]
[ 104-54-1 ]
[ 7148-78-9 ]

Reference： [1] Dalton Transactions, 2008, # 19, p. 2542 - 2548

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Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride In acetone at 20℃; for 0.25h;
100%	With ethanol; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 45℃; for 1h;

Yield	Reaction Conditions	Operation in experiment
94%	With K5<CoW12O40> for 0.5h; Heating;
90%	With sulfonic acid supported on polydopamine (PDA)-encapsulated Fe₃O₄ nanoparticles In neat (no solvent) at 40℃; for 2h; Green chemistry;
69%	With poly(4-vinylpyridinium tribromide) at 20℃; for 1.5h; neat (no solvent);

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid; silica gel In hexane for 0.666667h; Heating;
76%	With Iron(III) nitrate nonahydrate; sodium iodide at 20℃; for 1.5h; neat (no solvent);

Yield	Reaction Conditions	Operation in experiment
69%		Example 2 (i?)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid, (III) Procedure AQuinine (28.7g, 88 mmol) was suspended in toluene (380 mL). Cinnamyl alcohol (15.5 g, 115 mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (15.0 g, 88 mmol) in toluene (10 mL) was added during 15 min and the reaction mixture was stirred at -35 C for 24 hours. Toluene solution was washed with 5% HCl (250 mL) and evaporated. Oily residue was dissolved in 2-PrOH (300 mL), warmed to 45 0C, and the solution of 1-adamantylamine (12.0 g, 79 mmol) in MTBE (100 mL) was added. The mixture was stirred at 25 0C for 6 hours, filtered, washed with 2-PrOH (100 mL) and dried under reduced pressure to yield 28.1 g of 1-adamantylamine salt of (/?)-3-(2-(cinnamyloxy)-2-oxoethyl)-5- methylhexanoic acid. The salt was suspended in toluene (15OmL) and stirred with 3% HCl (100 mL) until a clear solution was obtained. Aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (3OmL). Evaporation of toluene afforded 18.1 g (69%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 91.2 % ee. 1H NMR (CDCl3), delta/ppm: 0.87 (d, 6H, J=6.5 Hz), 1.21-1.27 (m, 2H), 1.56-1.70 (m, IH), 2.38-2.48 (m, 5H), 4.73 (dd, 2H, J/=6.5 Hz, J2=1.2 Hz), 6.27 (dt, IH J/=15.8 Hz, J2=6.5 Hz), 6.65 (d, IH, J=I 5.8 HZ), 7.22-7.40 (m, 2H).13C NMR (CDCl3), delta/ppm: 22.34, 25.07, 29.64, 38.30, 38.48, 43.26, 64.92, 122.95, 126.50, 127.96, 128.49, 134.18, 136.07, 172.26, 178.64.
66%		Example 3(i?)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid, (III) Procedure BQuinine (28.7g, 88mmol) was suspended in toluene (38OmL). Cinnamyl alcohol (15.5 g, 115mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (15.0 g, 88 mmol) in toluene (1OmL) was added during 15 min and the reaction mixture was stirred at -35 0C for 24 hours. Toluene solution was washed with 5% HCl (250 + 5OmL), and than extracted with 2% K2CO3 solution (1000 + 25OmL). Aqueous extracts were washed with EtOAc (3x10OmL), acidified to pH 1 with cone. HCl and extracted with diisopropylether (150 + 5OmL). Combined extracts were warmed to 35 0C and (S)-alpha- phenylethylamine (9.7 g, 80 mmol) was added, followed by seed crystals (10 mg). Mixture was stirred for 4 hours at 25 C and filtered to obtain 24.8 g of (5)-alpha-phenylethylamine salt of (/?)-3-(2- (cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid. The salt was suspended in toluene (15OmL) and stirred with 3% HCl (10OmL) until clear solution was obtained. The aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (30 mL). Evaporation of toluene afforded 17.3 g (66%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 90.7 % ee.

[ CAS No. 104-54-1 ] {[proInfo.proName]}

Quality Control of [ 104-54-1 ]

Related Doc. of [ 104-54-1 ]

Product Details of [ 104-54-1 ]

Calculated chemistry of [ 104-54-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 104-54-1 ]

Application In Synthesis of [ 104-54-1 ]

[ 104-54-1 ] Synthesis Path-Upstream 1~14

[ 104-54-1 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

60%	With cerium(IV) trifluoromethanesulfonate at 20℃; for 4h;
	With recombinant acyltransferase from Mycobacterium smegmatis In aq. phosphate buffer at 25℃; for 0.5h; Green chemistry; Enzymatic reaction;

Yield	Reaction Conditions	Operation in experiment
86%	With hydroxylamine hydrochloride; NAD; alcohol dehydrogenase HeADH-II from Halomonas elongata; NADH-oxidase from Lactobacillu spentosus; flavin-adenin dinucleotide, disodium salt In dimethyl sulfoxide at 30℃; for 3h; Enzymatic reaction;
30%	With hydroxylamine hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 100℃; for 10h; Neat (no solvent); chemoselective reaction;

Precautionary Statements-General
Code	Phrase
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P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
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
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling