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496-67-3

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496-67-3 Usage

Chemical Properties

White Solid

Originator

Bromisovalum,Linhai Duqiao Fine Chemical Factory

Uses

2-Bromo-3-methylbutyrylurea is a hypnotic and sedative drug marketed over the counter in Asian under various brand names.

Definition

ChEBI: An N-acylurea that is urea in which one of the hydrogens is replaced by a 2-bromo-3-methybutanoyl group.

Manufacturing Process

A mixture of 2 kg 2-bromoisovalerylbromide and 1 kg dry urea is heated at 70°C. Then to the reaction mixture is added sodium hydrogen carbonate. 2- Bromo-3-methylbutyrylurea is recrystallized from toluene or water, melting point 149°C.

Brand name

Bromural (Knoll).

Therapeutic Function

Sedative, Hypnotic

World Health Organization (WHO)

Bromisoval is a monureide sedative of long standing. It remains available in several countries. However, it releases the bromide ion and prolonged usage can result in chronic bromide accumulation and intoxication.

Safety Profile

Moderately toxic by ingestion. Human systemic effects by ingestion: nausea or vomiting, and coma. A sedative and hypnotic agent. When heated to decomposition it emits very toxic fumes of Brand NOx

Purification Methods

Crystallise it from aqueous EtOH or toluene, and dry it in air. [Beilstein 3 H 63, 3 I 29, 3 II 51, 3 III 123, 3 IV 117.]

Check Digit Verification of cas no

The CAS Registry Mumber 496-67-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 6 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 496-67:
(5*4)+(4*9)+(3*6)+(2*6)+(1*7)=93
93 % 10 = 3
So 496-67-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11)/t4-/m0/s1

496-67-3 Well-known Company Product Price

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  • TCI America

  • (B2842)  1-(2-Bromoisovaleryl)urea  >98.0%(T)

  • 496-67-3

  • 25g

  • 290.00CNY

  • Detail

496-67-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-bromo-N-carbamoyl-3-methylbutanamide

1.2 Other means of identification

Product number -
Other names Alural

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:496-67-3 SDS

496-67-3Synthetic route

urea
57-13-6

urea

bromisoval
496-67-3

bromisoval

Conditions
ConditionsYield
at 35 - 40℃; for 6h; Time;86%
N-(α-bromo-isovaleryl)-O-methyl-isourea
860762-74-9

N-(α-bromo-isovaleryl)-O-methyl-isourea

bromisoval
496-67-3

bromisoval

Conditions
ConditionsYield
With hydrogenchloride
O-ethyl-N-(α-bromo-isovaleryl)-isourea

O-ethyl-N-(α-bromo-isovaleryl)-isourea

bromisoval
496-67-3

bromisoval

Conditions
ConditionsYield
With hydrogenchloride
N,N'-bis-(α-bromo-isovaleryl)-urea

N,N'-bis-(α-bromo-isovaleryl)-urea

bromisoval
496-67-3

bromisoval

Conditions
ConditionsYield
With sodium hydroxide
2-bromo-3-methyl-butyryl bromide
26464-05-1

2-bromo-3-methyl-butyryl bromide

urea
57-13-6

urea

bromisoval
496-67-3

bromisoval

N,N'-bis-(α-bromo-isovaleryl)-urea

N,N'-bis-(α-bromo-isovaleryl)-urea

diluted NaOH-solution

diluted NaOH-solution

bromisoval
496-67-3

bromisoval

2-bromo-3-methyl-butyryl bromide
26464-05-1

2-bromo-3-methyl-butyryl bromide

mercurocyanate

mercurocyanate

bromisoval
496-67-3

bromisoval

Conditions
ConditionsYield
With Petroleum ether und Behandeln des entstandenen <α-Brom-isovaleryl>-isocyanats mit Ammoniak;
hydrogenchloride
7647-01-0

hydrogenchloride

N-(α-bromo-isovaleryl)-O-methyl-isourea
860762-74-9

N-(α-bromo-isovaleryl)-O-methyl-isourea

A

methylene chloride
74-87-3

methylene chloride

B

bromisoval
496-67-3

bromisoval

hydrogenchloride
7647-01-0

hydrogenchloride

O-ethyl-N-(α-bromo-isovaleryl)-isourea

O-ethyl-N-(α-bromo-isovaleryl)-isourea

A

bromisoval
496-67-3

bromisoval

B

chloroethane
75-00-3

chloroethane

2-bromo-3-methyl-butyryl bromide
26464-05-1

2-bromo-3-methyl-butyryl bromide

bromisoval
496-67-3

bromisoval

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; benzene; NaOH-solution
2: hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: diethyl ether
2: hydrochloric acid
View Scheme
bromisoval
496-67-3

bromisoval

N-carbamoyl-3-methylbutanamide
2274-08-0

N-carbamoyl-3-methylbutanamide

Conditions
ConditionsYield
With water; zinc In acetonitrile at 80℃; for 7h; Sealed tube; Inert atmosphere;94%
With water; zinc In acetonitrile at 80℃; for 9h; Inert atmosphere; Sealed tube;94%
With sodium hydroxide; potassium dihydrogenphosphate; rat liver microsomes; NADPH In water at 37℃; Product distribution; other reagents;
bromisoval
496-67-3

bromisoval

N-carbamoyl-3-methylbutanamide-2-d

N-carbamoyl-3-methylbutanamide-2-d

Conditions
ConditionsYield
With water-d2; zinc In acetonitrile at 80℃; for 18h; Time; Inert atmosphere; Sealed tube;91%
With water-d2; zinc In acetonitrile at 80℃; for 18h; Inert atmosphere; Sealed tube;84%
bromisoval
496-67-3

bromisoval

potassium thioacyanate
333-20-0

potassium thioacyanate

2-amino-5-isopropyl-thiazol-4-one
3805-17-2

2-amino-5-isopropyl-thiazol-4-one

Conditions
ConditionsYield
With butanone
bromisoval
496-67-3

bromisoval

2-amino-5-isopropyl-oxazol-4-one
15900-26-2

2-amino-5-isopropyl-oxazol-4-one

Conditions
ConditionsYield
With ammonium carbonate
bromisoval
496-67-3

bromisoval

sodium O,O-diethyl phosphorodithioate
3338-24-7

sodium O,O-diethyl phosphorodithioate

(α-diethoxythiophosphorylsulfanyl-isovaleryl)-urea

(α-diethoxythiophosphorylsulfanyl-isovaleryl)-urea

Conditions
ConditionsYield
With 4-methyl-2-pentanone
bromisoval
496-67-3

bromisoval

2,4-diisopropyl-3-thia-glutaric acid-diureide
26843-84-5

2,4-diisopropyl-3-thia-glutaric acid-diureide

Conditions
ConditionsYield
With potassium sulphide; ethanol
With sodium sulfide In ethanol
bromisoval
496-67-3

bromisoval

Antipyrinsaeurechlorid
61226-21-9

Antipyrinsaeurechlorid

N-(α-bromo-isovaleryl)-N'-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbonyl)-urea

N-(α-bromo-isovaleryl)-N'-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbonyl)-urea

bromisoval
496-67-3

bromisoval

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-N'-(2-bromo-isovaleryl)-urea

N-acetyl-N'-(2-bromo-isovaleryl)-urea

Conditions
ConditionsYield
With sulfuric acid at 60℃;
bromisoval
496-67-3

bromisoval

chloral
75-87-6

chloral

N-(α-bromo-isovaleryl)-N'-(2,2,2-trichloro-1-hydroxy-ethyl)-urea

N-(α-bromo-isovaleryl)-N'-(2,2,2-trichloro-1-hydroxy-ethyl)-urea

bromisoval
496-67-3

bromisoval

sulfanilamide
63-74-1

sulfanilamide

4-(5-isopropyl-2,4-dioxo-imidazolidin-1-yl)-benzenesulfonic acid amide

4-(5-isopropyl-2,4-dioxo-imidazolidin-1-yl)-benzenesulfonic acid amide

Conditions
ConditionsYield
at 155℃;
bromisoval
496-67-3

bromisoval

potassium ethyl xanthogenate
140-89-6

potassium ethyl xanthogenate

Dithiocarbonic acid O-ethyl ester S-(2-methyl-1-ureidocarbonyl-propyl) ester
26843-82-3

Dithiocarbonic acid O-ethyl ester S-(2-methyl-1-ureidocarbonyl-propyl) ester

Conditions
ConditionsYield
In ethanol
bromisoval
496-67-3

bromisoval

phenylmethanethiol
100-53-8

phenylmethanethiol

(2-Benzylsulfanyl-3-methyl-butyryl)-urea
26843-83-4

(2-Benzylsulfanyl-3-methyl-butyryl)-urea

Conditions
ConditionsYield
In ethanol
bromisoval
496-67-3

bromisoval

thioacetic acid
507-09-5

thioacetic acid

Thioacetic acid S-(2-methyl-1-ureidocarbonyl-propyl) ester
26843-85-6

Thioacetic acid S-(2-methyl-1-ureidocarbonyl-propyl) ester

Conditions
ConditionsYield
With sodium hydroxide In ethanol
bromisoval
496-67-3

bromisoval

alcoholic KOH

alcoholic KOH

4-oxo-2-imino-5-isopropyl-oxazolidine

4-oxo-2-imino-5-isopropyl-oxazolidine

bromisoval
496-67-3

bromisoval

alcoholic KOH-solution

alcoholic KOH-solution

dimethylacrylic acid ureide

dimethylacrylic acid ureide

ethanol
64-17-5

ethanol

bromisoval
496-67-3

bromisoval

ammonium sulfite

ammonium sulfite

A

ammonium salt of α-sulfoisovaleric acid-ureide

ammonium salt of α-sulfoisovaleric acid-ureide

B

isovalerylurea(?)

isovalerylurea(?)

496-67-3Relevant articles and documents

Gershanovskii et al.

, (1973)

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