673-31-4

Basic information

• Product Name: Phenprobamate
• Synonyms: Actozin;PHENPROBAMATE;1-Carbamoyloxy-3-phenylpropane;1-Propanol, 3-phenyl-, carbamate;3-phenyl-1-propanocarbamate;3-Phenyl-1-propanol carbamate;3-phenyl-1-propanolcarbamate;3-Phenylpropyl carbamate
• CAS NO: 673-31-4
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• EINECS: 211-606-1
• Product Categories: Anesthetic Agents
• Mol File: 673-31-4.mol

Chemical Properties

• Melting Point: 101-104°
• Boiling Point: 311.75°C (rough estimate)
• Flash Point: 183.1oC
• Appearance: /
• Density: 1.1248 (rough estimate)
• Vapor Pressure: 4.69E-05mmHg at 25°C
• Refractive Index: 1.5710 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.47±0.50(Predicted)
• CAS DataBase Reference: Phenprobamate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenprobamate(673-31-4)
• EPA Substance Registry System: Phenprobamate(673-31-4)

Safety Data

• Hazardous Substances Data: 673-31-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Phenprobamate is used as a muscle relaxant for its ability to relieve muscle spasms and pain. It is particularly effective in treating conditions that involve muscle stiffness and discomfort, such as back pain, muscle strains, and sprains.
Phenprobamate is also used as a sedative due to its mild sedative effects, which can help in calming patients and promoting relaxation.
Additionally, Phenprobamate is used as an anticonvulsant for its ability to prevent and control seizures, making it a valuable asset in the treatment of epilepsy and other seizure disorders.
Used in Narcotic Drug Enhancement:
Phenprobamate is used as an enhancer for narcotic drugs, as it can prolong and enhance their effects. This allows for the use of smaller amounts of alcohol or illicit substances to achieve the desired effect, potentially reducing the risk of overdose and addiction.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Used as a tranquilizer and muscle relaxant. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES and ESTERS

InChI:InChI=1/C10H13NO2/c11-10(12)13-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H2,11,12)

Synthetic route

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

Conditions	Yield
With di-n-butyltin maleate In toluene at 90℃; for 4h;	99%

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

Conditions	Yield
With di-n-butyltin maleate In toluene for 3h; Reflux;	98%

3-Phenyl-1-propanol (122-97-4) + sodium cyanide (143-33-9) → phenprobamate (673-31-4)

Conditions	Yield
With trifluoroacetic acid

C12H12Cl3NO3 → phenprobamate (673-31-4)

Conditions	Yield
With methanol; potassium carbonate In 1,2-dichloro-ethane Inert atmosphere;

3-Phenyl-1-propanol (122-97-4) → phenprobamate (673-31-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 5 h / 0 °C / Inert atmosphere 2: methanol; potassium carbonate / 1,2-dichloro-ethane / Inert atmosphere View Scheme

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

Conditions	Yield
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 View Scheme

3-phenylpropyl [{3,5-bis(trifluoromethyl)benzoyl}oxy]carbamate → phenprobamate (673-31-4)

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate at 25℃; for 12h; Inert atmosphere; Irradiation;	30 %Spectr.

phenprobamate (673-31-4) + pinacol vinylboronate (75927-49-0) → (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene (1000376-26-0)

Conditions	Yield
Stage #1: phenprobamate With (2-methylpropyl)lithium In diethyl ether; hexane; cyclohexane at -78℃; for 5h; Stage #2: pinacol vinylboronate In diethyl ether; hexane; cyclohexane at -78℃; for 1h; Stage #3: With magnesium dibromide etherate In diethyl ether; hexane; cyclohexane at 20℃; for 16h; Reflux; enantioselective reaction;	79%

phenprobamate (673-31-4) + 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane (83947-58-4) → (2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene (1428538-05-9)

Conditions	Yield
Stage #1: phenprobamate With (2-methylpropyl)lithium In diethyl ether; hexane; cyclohexane at -78℃; for 5h; Stage #2: 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78℃; for 1h; Stage #3: With magnesium dibromide etherate In diethyl ether; hexane; cyclohexane at 20℃; for 16h; Reflux; enantioselective reaction;	77%

phenprobamate (673-31-4) → (+/-)-4-phenyl-1,3-oxazinan-2-one

Conditions	Yield
With iodosylbenzene; (±)-trans-N,N′-1,2-cyclohexylenebis(4-nitrobenzylideneamine); tetrakis(acetonitrile)copper(I) hexafluorophosphate In acetonitrile at 45℃; Molecular sieve; Inert atmosphere;	54%

phenprobamate (673-31-4) + 3-trifluoromethylphenyl sulfinic acid sodium salt (118849-61-9) + Glyoxilic acid (298-12-4) → (3-Phenyl-propoxycarbonylamino)-(3-trifluoromethyl-benzenesulfonyl)-acetic acid (41142-04-5)

Conditions	Yield
(i) aq. HCO2H, (ii) /BRN= 1959273/; Multistep reaction;

phenprobamate (673-31-4) + Sodium; 2-chloro-5-trifluoromethyl-benzenesulfinate + Glyoxilic acid (298-12-4) → (2-Chloro-5-trifluoromethyl-benzenesulfonyl)-(3-phenyl-propoxycarbonylamino)-acetic acid (41142-18-1)

Conditions	Yield
(i) H2O, (ii) /BRN= 6307616/, HCO2H; Multistep reaction;

(E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester + phenprobamate (673-31-4) → C17H25BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester In diethyl ether; hexane; cyclohexane at -78 - 20℃;

(E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester + phenprobamate (673-31-4) → C17H25BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane → C20H29B

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane → C20H29B

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane → C23H35B

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane → C23H35B

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane → C23H37BOSi

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane → C23H37BOSi

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane (1218988-11-4) → C20H31BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane (1218988-11-4) → C20H31BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane (83947-59-5) → C18H27BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane (83947-59-5) → C18H27BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (91083-23-7) → C21H33BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (91083-23-7) → C21H33BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) → (1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol (1218988-28-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 °C 2.3: 16 h / -78 - 20 °C View Scheme

phenprobamate (673-31-4) → (1R,2R,3Z)-2-methyl-1,6-diphenylhex-3-en-1-ol (1218988-13-6) + (1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol (1218988-28-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: tetrahydrofuran / 96 h / 20 °C View Scheme

phenprobamate (673-31-4) → ((3R)-5-phenylpent-1-en-3-yl)trifluoroborate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: L-Tartaric acid / acetonitrile; water; tetrahydrofuran; methanol / 20 °C View Scheme

phenprobamate (673-31-4) → (1R,3Z)-1,6-diphenylhex-3-en-1-ol (1428537-74-9) + (1S,3E)-1,6-diphenylhex-3-en-1-ol (1428537-73-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: tetrahydrofuran / 96 h / 20 °C View Scheme

phenprobamate (673-31-4) → (1S,3E)-1,6-diphenylhex-3-en-1-ol (1428537-73-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 °C 2.3: -78 - 20 °C View Scheme

Upstream product

• 122-97-4 3-Phenyl-1-propanol 
• 143-33-9 sodium cyanide 
• 622-46-8 carbamic acid phenyl ester 
• 598-55-0 methyl carbamate 

Downstream Products

• 41142-04-5 (3-Phenyl-propoxycarbonylamino)-(3-trifluoromethyl-benzenesulfonyl)-acetic acid 
• 41142-18-1 (2-Chloro-5-trifluoromethyl-benzenesulfonyl)-(3-phenyl-propoxycarbonylamino)-acetic acid 
• 1428538-05-9 (2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene 
• 1000376-26-0 (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene 
• 1428537-73-8 (1S,3E)-1,6-diphenylhex-3-en-1-ol 
• 1428537-74-9 (1R,3Z)-1,6-diphenylhex-3-en-1-ol 
• 1218988-13-6 (1R,2R,3Z)-2-methyl-1,6-diphenylhex-3-en-1-ol 
• 1218988-28-3 (1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol 

Relevant articles and documents

Further development of the tin-catalyzed transcarbamoylation reaction

Studies carried out to further develop tin-catalyzed trans-carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate was found to be an economical carabamoyl donor in tin-catalyzed transcarbamoylation, which showed broad functional group tolerance and allowed a streamlined workup procedure. Finally, a unique synthetic method was developed for the preparation of carbamate-tethered terpene glycoconjugates.

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

Copper-catalyzed intramolecular C-H amination

The amino-functionalization of tertiary, secondary and benzylic C-H bonds of tethered carbamates and sulfamates by iodosobenzene is catalyzed by Cu I-diimine complexes in moderate to good yield. Employing homochiral imine-Cucatalysts affords oxazolidinones and oxathiazinanes with modest enantioselectivity.

An efficient synthesis of carbamates by tin-catalyzed transcarbamoylation reactions of primary and secondary alcohols

A new approach to the synthesis of carbamates based on a tin-catalyzed transcarbamoylation process has been developed. Reactions of primary and secondary alcohols with phenyl carbamate in toluene at 90 ° C proceed smoothly in the presence of tin-catalyst to generate the corresponding carbamates in good yields. This mild method exhibits a broad functional-group tolerance. Georg Thieme Verlag Stuttgart.