3-Phenyl-1-propanol

Base Information

• Chemical Name: 3-Phenyl-1-propanol
• CAS No.: 122-97-4
• Molecular Formula: C9H12O
• Molecular Weight: 136.194
• Hs Code.: 29062900
• European Community (EC) Number: 204-587-6
• NSC Number: 16942
• UNII: U04IC2765C
• DSSTox Substance ID: DTXSID6041638
• Nikkaji Number: J44.158I
• Wikidata: Q27160792
• Metabolomics Workbench ID: 46311
• ChEMBL ID: CHEMBL1606391
• Mol file: 122-97-4.mol

Synonyms:3-phenyl-1-propanol;3-phenylpropanol-1

Chemical Property of 3-Phenyl-1-propanol

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Vapor Pressure: 1.13-25Pa at 20-25℃
• Melting Point: -18 °C
• Refractive Index: n20/D 1.526(lit.)
• Boiling Point: 235.753 °C at 760 mmHg
• PKA: 15.04±0.10(Predicted)
• Flash Point: 106.163 °C
• PSA: 20.23000
• Density: 0.999 g/cm³
• LogP: 1.61150
• Storage Temp.: Store below +30°C.
• Solubility.: 0.1g/l insoluble
• Water Solubility.: 10.3 g/L (20 ºC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 136.088815002
• Heavy Atom Count: 10
• Complexity: 74.8

Purity/Quality:

99% ^*data from raw suppliers

3-Phenyl-1-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38-R36/38
• Safety Statements: 26-37/39-S37/39-S26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C1=CC=C(C=C1)CCCO
• Uses: (1) Temporarily allowed as food flavouring agent in GB 2760-1996. Mainly used in the preparation of essence of peach, apricot, plum, watermelon, strawberry and nuts like walnut and hazel. (2) Mainly used in the preparation of essence and medicine. An intermediate of proformiphen (a central skeletal muscle relaxant) Temporarily allowed as food flavouring agent in GB 2760-1996. It has a sweet scent of flowers and sweetmeat and a pleasant flavor of fresh fruit after dilution Natural 3-Phenyl-1-propanol can be found in strawberries, Styrax cream, benzoin cream, tea, Peru Balsam, Cassia leaf oil, cinnamon oil and so on. (3) As a medicine, it can be applied to Cholecystitis, cholangitis, cholelithiasis, biliary postoperative syndrome, hypercholesterolemia, etc. (4) Mainly used in the preparation of essence and medicine. An intermediate of proformiphen, a central skeletal muscle relaxant. As an antiputrefactiva in cosmetic in combination with piperonal or pepper, 3-Phenyl-1-propanol has a mold resistance on germ and mycete, along with a natural fragrance. 3-Phenyl-1-propanol or its ester derivatives can be used as flavor constituents of flowers such as lilac, hyacinth and keiskei for its aromatic vinegar. 3-Phenyl-1-propanol is used as a reagent in the synthesis of Dihydrocinnamyl Cilnidipine (D448605) and is a potent aroma biotransformation product. Preservative in cosmetics - This alcohol a natural fragrance with antimicrobial properties against bacteria and molds. It is used in combination with Heliotropin or Piperonal as a preservative for cosmetic products.
• Production Method: (1) the catalytic hydrogenation of ethyl cinnamate. The hydrogenation reaction is conducted in autoclave with chromium-copper-barium catalyst at 200℃ and 20MPa for 5-9h. The filtrate obtained after cooling and filtration is extracted by diethyl ether.? After the recycling of diethyl ether, reduced pressure distillation of the extracting solution is conducted to collect the fraction of 110-112℃（1.06kPa）, which is the finished product. The yield is about 85%. Grignard reaction of benzyl chloride and oxirane, followed by the hydrolysis with sulfuric acid to obtain 3-Phenyl-1-propanol. The yield is about 65-70%。 (2) The hydrogenation of peruvin or cinnamaldehyde.

Technology Process of 3-Phenyl-1-propanol

There total 679 articles about 3-Phenyl-1-propanol 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: 98.0%

(C5(CH3)5)Fe(CO)2(CH2CH2(C6H5)) + trimethylstannane (1631-73-8) → (C5(CH3)5)Fe(H)(CO)(Sn(CH3)3)2 + 3-Phenyl-1-propanol (122-97-4) + ethylbenzene (100-41-4,27536-89-6)

Guidance literature:

In benzene-d6; under Ar; 90°C, 6 h;

Reference yield: 91.0%

(η5-C5H5)Fe(CO)(PPh3)(C(O)CH2CH2Ph) + trimethylstannane (1631-73-8) → 3-phenyl-propionaldehyde (104-53-0) + (C5H5)Fe(H)(CO)(Sn(CH3)3)2 + (C5H5)Fe(CO)(P(C6H5)3)Sn(CH3)3 + 3-Phenyl-1-propanol (122-97-4) + ethylbenzene (100-41-4,27536-89-6)

Guidance literature:

In benzene-d6; under Ar; 120°C, 6 h;

Reference yield: 89.0%

(η5-C5H5)Fe(CO)2CH2CH2C6H5 + trimethylstannane (1631-73-8) → (C5H5)Fe(H)(CO)(Sn(CH3)3)2 + 3-Phenyl-1-propanol (122-97-4) + ethylbenzene (100-41-4,27536-89-6)

Guidance literature:

In benzene-d6; under Ar; 90°C, 3 h; not isolated; NMR;

upstream raw materials:

oxirane

benzylmagnesium chloride

trimethylene oxide

phenyllithium

Downstream raw materials:

β-(phenylmethyl)benzenepentanol

1-phenylpropene

(3-nitro-phenyl)-carbamic acid-(3-phenyl-propyl ester)

3-phenyl-propionaldehyde

Refernces

• 1、 Parlett, Christopher M.A.,Durndell, Lee J.,Machado, Andreia,Cibin, Giannantonio,Bruce, Duncan W.,Hondow, Nicole S.,Wilson, Karen,Lee, Adam F.. "Alumina-grafted SBA-15 as a high performance support for Pd-catalysed cinnamyl alcohol selective oxidation". . p. 46 - 55. Retrieved 2014.
• 2、 Musolino, Maria Grazia,Busacca, Concetta,Mauriello, Francesco,Pietropaolo, Rosario. "Aliphatic carbonyl reduction promoted by palladium catalysts under mild conditions". . p. 77 - 86. Retrieved 2010.
• 3、 Datta, Arunabha,Khwaja, Hanif I.,Kelkar, Ravindra Y.,Saple, Ashok R.,Datta, Monika. "Characterization and catalytic activity of palladium dispersed on Kratschmer-Huffman (K-H) soot". . p. 851 - 852. Retrieved 1996.
• 4、 Kaya, U?ur,Tran, Uyen P.N.,Enders, Dieter,Ho, Junming,Nguyen, Thanh V.. "N-Heterocyclic Olefin Catalyzed Silylation and Hydrosilylation Reactions of Hydroxyl and Carbonyl Compounds". . p. 1398 - 1401. Retrieved 2017.
• 5、 Lee, Seung Hwan,Nam, Mi Hye,Cho, Min Young,Yoo, Byung Woo,Rhee, Hak June,Yoon, Cheol Min. "Chemoselective reduction of aldehydes using decaborane in aqueous solution". . p. 2469 - 2474. Retrieved 2006.
• 6、 Sanzone, Jillian R.,Hu, Chunhua T.,Woerpel. "Uncatalyzed Carboboration of Seven-Membered-Ring trans-Alkenes: Formation of Air-Stable Trialkylboranes". . p. 8404 - 8407. Retrieved 2017.
• 7、 Karimi, Babak,Ebrahimian, G. Reza,Seradj, Hassan. "Efficient and chemoselective conversion of carbonyl compounds to 1,3-dioxanes catalyzed with N-bromosuccinimide under almost neutral reaction conditions". . p. 1737 - 1739. Retrieved 1999.
• 8、 Jang, Youngjin,Kim, Seyoung,Jun, Samuel Woojoo,Kim, Byung Hyo,Hwang, Sunhwan,Song, In Kyu,Kim, B. Moon,Hyeon, Taeghwan. "Simple one-pot synthesis of Rh-Fe3O4 heterodimer nanocrystals and their applications to a magnetically recyclable catalyst for efficient and selective reduction of nitroarenes and alkenes". . p. 3601 - 3603. Retrieved 2011.
• 9、 Klumbys, Evaldas,Zebec, Ziga,Weise, Nicholas J.,Turner, Nicholas J.,Scrutton, Nigel S.. "Bio-derived production of cinnamyl alcohol: Via a three step biocatalytic cascade and metabolic engineering". . p. 658 - 663. Retrieved 2018.
• 10、 v. Miller. "". . p. 189,190, 202. Retrieved 1877.