Product Name

  • Name

    Phenprobamate

  • EINECS 211-606-1
  • CAS No. 673-31-4
  • Article Data9
  • CAS DataBase
  • Density 1.103g/cm3
  • Solubility
  • Melting Point 101-104°
  • Formula C10H13 N O2
  • Boiling Point 349.5oC at 760 mmHg
  • Molecular Weight 179.219
  • Flash Point 183.1oC
  • Transport Information
  • Appearance
  • Safety 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.
  • Risk Codes
  • Molecular Structure Molecular Structure of 673-31-4 (Phenprobamate)
  • Hazard Symbols
  • Synonyms 1-Propanol,3-phenyl-, carbamate (8CI); Benzenepropanol, carbamate (9CI); Carbamic acid,3-phenylpropyl ester (6CI,7CI); 3-Phenyl-1-propanol carbamate; 3-Phenylpropylcarbamate; Ansepron; Eirenal; Extacol; Gamaquil; MH 532; NSC 44682; NSC 50538;NSC 64270; Palmita; Phenprobamate; Proformiphen; Quamaquil; Spantol; Tranquil; g-Phenylpropyl carbamate
  • PSA 52.32000
  • LogP 2.41480

Synthetic route

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

carbamic acid phenyl ester
622-46-8

carbamic acid phenyl ester

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
With di-n-butyltin maleate In toluene at 90℃; for 4h;99%
3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

methyl carbamate
598-55-0

methyl carbamate

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
With di-n-butyltin maleate In toluene for 3h; Reflux;98%
3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

sodium cyanide
143-33-9

sodium cyanide

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
With trifluoroacetic acid
C12H12Cl3NO3

C12H12Cl3NO3

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
With methanol; potassium carbonate In 1,2-dichloro-ethane Inert atmosphere;
3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
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

3-phenylpropyl hydroxycarbamate

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
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

3-phenylpropyl [{3,5-bis(trifluoromethyl)benzoyl}oxy]carbamate

phenprobamate
673-31-4

phenprobamate

Conditions
ConditionsYield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate at 25℃; for 12h; Inert atmosphere; Irradiation;30 %Spectr.
phenprobamate
673-31-4

phenprobamate

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

(3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene
1000376-26-0

(3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene

Conditions
ConditionsYield
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

phenprobamate

4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane
83947-58-4

4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane

(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene
1428538-05-9

(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

Conditions
ConditionsYield
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

phenprobamate

(+/-)-4-phenyl-1,3-oxazinan-2-one

(+/-)-4-phenyl-1,3-oxazinan-2-one

Conditions
ConditionsYield
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

phenprobamate

3-trifluoromethylphenyl sulfinic acid sodium salt
118849-61-9

3-trifluoromethylphenyl sulfinic acid sodium salt

Glyoxilic acid
298-12-4

Glyoxilic acid

(3-Phenyl-propoxycarbonylamino)-(3-trifluoromethyl-benzenesulfonyl)-acetic acid
41142-04-5

(3-Phenyl-propoxycarbonylamino)-(3-trifluoromethyl-benzenesulfonyl)-acetic acid

Conditions
ConditionsYield
(i) aq. HCO2H, (ii) /BRN= 1959273/; Multistep reaction;
...Expand
phenprobamate
673-31-4

phenprobamate

Sodium; 2-chloro-5-trifluoromethyl-benzenesulfinate

Sodium; 2-chloro-5-trifluoromethyl-benzenesulfinate

Glyoxilic acid
298-12-4

Glyoxilic acid

(2-Chloro-5-trifluoromethyl-benzenesulfonyl)-(3-phenyl-propoxycarbonylamino)-acetic acid
41142-18-1

(2-Chloro-5-trifluoromethyl-benzenesulfonyl)-(3-phenyl-propoxycarbonylamino)-acetic acid

Conditions
ConditionsYield
(i) H2O, (ii) /BRN= 6307616/, HCO2H; Multistep reaction;
...Expand
(E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester

(E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester

phenprobamate
673-31-4

phenprobamate

C17H25BO2

C17H25BO2

Conditions
ConditionsYield
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

(E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester

phenprobamate
673-31-4

phenprobamate

C17H25BO2

C17H25BO2

Conditions
ConditionsYield
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

phenprobamate

9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane

9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane

C20H29B

C20H29B

Conditions
ConditionsYield
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

phenprobamate

9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane

9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane

C20H29B

C20H29B

Conditions
ConditionsYield
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

phenprobamate

9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane

9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane

C23H35B

C23H35B

Conditions
ConditionsYield
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

phenprobamate

9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane

9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane

C23H35B

C23H35B

Conditions
ConditionsYield
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

phenprobamate

((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane

((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane

C23H37BOSi

C23H37BOSi

Conditions
ConditionsYield
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

phenprobamate

((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane

((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane

C23H37BOSi

C23H37BOSi

Conditions
ConditionsYield
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

phenprobamate

B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane
1218988-11-4

B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane

C20H31BO2

C20H31BO2

Conditions
ConditionsYield
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

phenprobamate

B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane
1218988-11-4

B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane

C20H31BO2

C20H31BO2

Conditions
ConditionsYield
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

phenprobamate

(Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane
83947-59-5

(Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane

C18H27BO2

C18H27BO2

Conditions
ConditionsYield
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

phenprobamate

(Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane
83947-59-5

(Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane

C18H27BO2

C18H27BO2

Conditions
ConditionsYield
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

phenprobamate

(Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
91083-23-7

(Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C21H33BO2

C21H33BO2

Conditions
ConditionsYield
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

phenprobamate

(Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
91083-23-7

(Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C21H33BO2

C21H33BO2

Conditions
ConditionsYield
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

phenprobamate

(1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol
1218988-28-3

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

Conditions
ConditionsYield
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

phenprobamate

A

(1R,2R,3Z)-2-methyl-1,6-diphenylhex-3-en-1-ol
1218988-13-6

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

B

(1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol
1218988-28-3

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

Conditions
ConditionsYield
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

phenprobamate

((3R)-5-phenylpent-1-en-3-yl)trifluoroborate

((3R)-5-phenylpent-1-en-3-yl)trifluoroborate

Conditions
ConditionsYield
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

phenprobamate

A

(1R,3Z)-1,6-diphenylhex-3-en-1-ol
1428537-74-9

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

B

(1S,3E)-1,6-diphenylhex-3-en-1-ol
1428537-73-8

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

Conditions
ConditionsYield
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

phenprobamate

(1S,3E)-1,6-diphenylhex-3-en-1-ol
1428537-73-8

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

Conditions
ConditionsYield
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

Phenprobamate Chemical Properties

IUPAC Name: Phenprobamate
The MF of Phenprobamate (673-31-4) is C10H13NO2.

                 
The MW of Phenprobamate (673-31-4) is 179.22.
Synonyms of Phenprobamate (673-31-4): Quamaquil ; 1-Carbamoyloxy-3-phenylpropane ; 1-Propanol, 3-phenyl-, carbamate ; 3-Phenyl-1-propanol carbamate
Index of Refraction: 1.532
EINECS: 211-606-1
Density: 1.103 g/ml 
Flash Point: 183.1 °C
Boiling Point: 349.5 °C

Phenprobamate Uses

   Phenprobamate (673-31-4) is the axial skeletal muscle relaxant used for the shoulders, stiff neck, lower back pain, limb pain, muscle pain after exercise, twisting contusion, rheumatoid arthritis, neuralgia, and other muscle cramps, often accompanied by tension in the disease.

Phenprobamate Toxicity Data With Reference

1.    

orl-rat LD50:1110 mg/kg

     ARZNAD    Arzneimittel-Forschung. Drug Research. 13 (1963),856.
2.    

ipr-rat LD50:275 mg/kg

     AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 123 (1959),140.
3.    

orl-mus LD50:840 mg/kg

     ARZNAD    Arzneimittel-Forschung. Drug Research. 12 (1962),340.
4.    

ipr-mus LD50:150 mg/kg

     NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .
5.    

ivn-mus LD50:320 mg/kg

     MEIEDD    Merck Index. 10 (1983),1047.
6.    

orl-rbt LD50:1125 mg/kg

     27ZQAG    Psychotropic Drugs and Related Compounds E. Usdin andD.H. Efron,2nd ed.,Washington, DC.: 1972,402.
7.    

ipr-rbt LD50:285 mg/kg

     27ZQAG    Psychotropic Drugs and Related Compounds E. Usdin andD.H. Efron,2nd ed.,Washington, DC.: 1972,402.

Phenprobamate 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.

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