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Cas Database

Name	Phenprobamate	EINECS	211-606-1
CAS No.	673-31-4	Density	1.103g/cm3
PSA	52.32000	LogP	2.41480
Solubility	N/A	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	N/A	Appearance	N/A
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 NO_x. See also CARBAMATES and ESTERS.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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	Article Data	9

Phenprobamate Synthetic route

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

: 622-46-8
carbamic acid phenyl ester

: 673-31-4
phenprobamate

Conditions

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

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

: 598-55-0
methyl carbamate

: 673-31-4
phenprobamate

Conditions

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

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

: 143-33-9
sodium cyanide

: 673-31-4
phenprobamate

Conditions

Conditions	Yield
With trifluoroacetic acid

: C12H12Cl3NO3

: 673-31-4
phenprobamate

Conditions

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

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

: 673-31-4
phenprobamate

Conditions

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

: 673-31-4
phenprobamate

Conditions

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

: 673-31-4
phenprobamate

Conditions

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

: 673-31-4
phenprobamate

: 75927-49-0
pinacol vinylboronate

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

Conditions

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%

: 673-31-4
phenprobamate

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

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

Conditions

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%

: 673-31-4
phenprobamate

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

Conditions

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 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 NO_x. See also CARBAMATES and ESTERS.

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