Phenprobamate

Base Information

• Chemical Name: Phenprobamate
• CAS No.: 673-31-4
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2924299090
• European Community (EC) Number: 211-606-1
• NSC Number: 64270,50538,44682
• UNII: UJZ473TPS0
• DSSTox Substance ID: DTXSID2046464
• Nikkaji Number: J3.316B
• Wikipedia: Phenprobamate
• Wikidata: Q7181402
• NCI Thesaurus Code: C98239
• Metabolomics Workbench ID: 121617
• ChEMBL ID: CHEMBL1079576
• Mol file: 673-31-4.mol

Synonyms:3-phenylpropylcarbamate;Gamaquil;phenprobamate

Chemical Property of Phenprobamate

Chemical Property:

• Vapor Pressure: 4.69E-05mmHg at 25°C
• Melting Point: 101-104°
• Refractive Index: 1.5710 (estimate)
• Boiling Point: 349.5oC at 760 mmHg
• PKA: 13.47±0.50(Predicted)
• Flash Point: 183.1oC
• PSA: 52.32000
• Density: 1.103g/cm3
• LogP: 2.41480
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

Phenprobamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCCOC(=O)N
• Uses: Phenprobamate (3-phenylpropylcarbamate) is a centrally acting muscle relaxant with mild sedative and anticonvulsant effects. Muscle relaxants can enhance and prolong the effect of narcotic drugs and enable to obtain same effect with a smaller amount of alcohol or illicit substance.

Technology Process of Phenprobamate

There total 8 articles about Phenprobamate 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: 99.0%

3-Phenyl-1-propanol (122-97-4) + carbamic acid phenyl ester (622-46-8) → phenprobamate (673-31-4)

Guidance literature:

With di-n-butyltin maleate; In toluene; at 90 ℃; for 4h;

DOI:10.1055/s-0030-1258102

Reference yield: 98.0%

3-Phenyl-1-propanol (122-97-4) + methyl carbamate (598-55-0) → phenprobamate (673-31-4)

Guidance literature:

With di-n-butyltin maleate; In toluene; for 3h; Reflux;

DOI:10.1055/s-0040-1708020

Reference yield:

3-phenylpropyl hydroxycarbamate → phenprobamate (673-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / diethyl ether / 12 h / 0 - 20 °C

2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate / 12 h / 25 °C / Inert atmosphere; Irradiation

With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate; In diethyl ether;

DOI:10.1021/jacs.0c00868

upstream raw materials:

3-Phenyl-1-propanol

sodium cyanide

carbamic acid phenyl ester

methyl carbamate

Downstream raw materials:

(1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol

(1R,2R,3Z)-2-methyl-1,6-diphenylhex-3-en-1-ol

(1R,3Z)-1,6-diphenylhex-3-en-1-ol

(1S,3E)-1,6-diphenylhex-3-en-1-ol

Refernces

• 1、 Hasegawa, Tomoyuki,Ichikawa, Yoshiyasu,Masuda, Toshiya,Minami, Takahiro,Morishita, Yukinori,Ochi, Rika,Sato, Hiroshi. "Further development of the tin-catalyzed transcarbamoylation reaction". supporting information. p. 2373 - 2378. Retrieved 2020/08/19.
• 2、 Ichikawa, Yoshiyasu,Morishita, Yukinori,Kusaba, Shuhei,Sakiyama, Naoto,Matsuda, Yasunori,Nakano, Keiji,Kotsuki, Hiyoshizo. "An efficient synthesis of carbamates by tin-catalyzed transcarbamoylation reactions of primary and secondary alcohols". experimental part. p. 1815 - 1818. Retrieved 2010/10/05.