Product Name

  • Name

    2-Benzyl-2-thiopseudourea hydrochloride

  • EINECS 208-688-6
  • CAS No. 538-28-3
  • Article Data27
  • CAS DataBase
  • Density
  • Solubility 250 g/L (15 ºC)
  • Melting Point 177-179 °C
  • Formula C8H10N2S.HCl
  • Boiling Point 283.2 °C at 760 mmHg
  • Molecular Weight 202.708
  • Flash Point 125.1 °C
  • Transport Information UN 2811 6.1/PG 2
  • Appearance off-white to light beige crystalline powder
  • Safety 36/37/39-45-28A
  • Risk Codes 25
  • Molecular Structure Molecular Structure of 538-28-3 (2-Benzyl-2-thiopseudourea hydrochloride)
  • Hazard Symbols ToxicT
  • Synonyms Carbamimidothioicacid, phenylmethyl ester, monohydrochloride (9CI);Pseudourea, 2-benzyl-2-thio-,hydrochloride (7CI);Pseudourea, 2-benzyl-2-thio-, monohydrochloride (8CI);2-Benzyl-2-thiopseudourea hydrochloride;BTKh;Benzituron;Benzylisothioureahydrochloride;Benzylisothiouronium chloride;Benzylisothiuronium chloride;S-Benzylisothiourea hydrochloride;S-Benzylisothiouronium chloride;S-Benzylisothiouronium hydrochloride;S-Benzylisothiuronium chloride;S-Benzylthioformamidine hydrochloride;S-Benzylthiopseudourea hydrochloride;S-Benzylthiourea hydrochloride;S-Benzylthiouronium chloride;S-Benzylthiuronium chloride;U 19451A;
  • PSA 75.17000
  • LogP 3.41530

Synthetic route

benzyl chloride
100-44-7

benzyl chloride

thiourea
17356-08-0

thiourea

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

Conditions
ConditionsYield
for 24h; Heating;97%
In ethanol at 95℃; for 2h;86%
In ethanol for 4h; Heating;85%
benzyl bromide
100-39-0

benzyl bromide

thiourea
17356-08-0

thiourea

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

Conditions
ConditionsYield
Stage #1: thiourea With hydrogenchloride In ethanol; water for 0.5h;
Stage #2: benzyl bromide In methanol; ethanol; water
93%
thiourea
17356-08-0

thiourea

benzyl alcohol
100-51-6

benzyl alcohol

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

Conditions
ConditionsYield
With hydrogenchloride 2.) MeOH; Multistep reaction;
hydrogencarbonate of S-benzyl-isothiourea

hydrogencarbonate of S-benzyl-isothiourea

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

Conditions
ConditionsYield
With hydrogenchloride
benzyl alcohol
100-51-6

benzyl alcohol

(+-)-6-methyl-2-oxo-tetrahydro-pyran-3-carbaldehyde

(+-)-6-methyl-2-oxo-tetrahydro-pyran-3-carbaldehyde

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / pyridine / Ambient temperature
2: 85 percent / ethanol / 4 h / Heating
View Scheme
1-bromo-butane
109-65-9

1-bromo-butane

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

benzyl butyl sulfide
5184-47-4

benzyl butyl sulfide

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 0.666667h; Ambient temperature;98%
1-bromo-octane
111-83-1

1-bromo-octane

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

octyl benzyl sulfide
85293-39-6

octyl benzyl sulfide

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 0.666667h; Ambient temperature;96.7%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

benzenesulfonyl chloride
1939-99-7

benzenesulfonyl chloride

Conditions
ConditionsYield
With tert-butylhypochlorite In water; acetonitrile at 0 - 20℃;96%
With hydrogenchloride; sodium chlorite In acetonitrile at 10 - 20℃; for 0.5h; Solvent; Time; Green chemistry;82%
With hydrogenchloride; iodosylbenzene for 0.0833333h;65%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

α-bromoacetophenone
70-11-1

α-bromoacetophenone

2-benzylsulfanyl-1-phenylethanone
2408-88-0

2-benzylsulfanyl-1-phenylethanone

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 0.666667h; Ambient temperature;96%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

allyl(benzyl)sulfide
6937-97-9

allyl(benzyl)sulfide

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 0.666667h; Ambient temperature;96%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(benzylthio)-4-(2,4-dichlorophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
1362426-25-2

2-(benzylthio)-4-(2,4-dichlorophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;96%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(benzylthio)-4-(3,4,5-trimethoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
1362426-31-0

2-(benzylthio)-4-(3,4,5-trimethoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;95%
3,4-dimethylbenzaldehyde
5973-71-7

3,4-dimethylbenzaldehyde

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(benzylthio)-4-(3,4-dimethylphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
1362426-28-5

2-(benzylthio)-4-(3,4-dimethylphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;94%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

ethyl 4-methoxy-2-oxo-4-phenyl-but-3-enoate

ethyl 4-methoxy-2-oxo-4-phenyl-but-3-enoate

ethyl 2-(benzylthio)-6-phenylpyrimidine-4-carboxylate

ethyl 2-(benzylthio)-6-phenylpyrimidine-4-carboxylate

Conditions
ConditionsYield
Stage #1: S-benzylisothiourea hydrochloride With sodium carbonate In water at 20℃; for 0.5h;
Stage #2: ethyl 4-methoxy-2-oxo-4-phenyl-but-3-enoate In ethanol; water for 1h; Reflux;
94%
ethyl 4-methoxy-2-oxo-4-(4-nitrophenyl)-but-3-enoate

ethyl 4-methoxy-2-oxo-4-(4-nitrophenyl)-but-3-enoate

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

ethyl 2-(benzylthio)-6-(4-nitrophenyl)pyrimidine-4-carboxylate

ethyl 2-(benzylthio)-6-(4-nitrophenyl)pyrimidine-4-carboxylate

Conditions
ConditionsYield
Stage #1: S-benzylisothiourea hydrochloride With sodium carbonate In water at 20℃; for 0.5h;
Stage #2: ethyl 4-methoxy-2-oxo-4-(4-nitrophenyl)-but-3-enoate In ethanol; water for 1h; Reflux;
94%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

ethyl (benzylthio)acetate
2899-67-4

ethyl (benzylthio)acetate

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 0.666667h; Ambient temperature;93.7%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl 3-(benzylthio)propanoate
5331-36-2

methyl 3-(benzylthio)propanoate

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 0.25h; Michael addition;93%
morpholine
110-91-8

morpholine

5-(4-methoxybenzylidene)barbituric acid
49546-71-6

5-(4-methoxybenzylidene)barbituric acid

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

5-(4-methoxyphenyl)-7-morpholin-4-yl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione

5-(4-methoxyphenyl)-7-morpholin-4-yl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione

Conditions
ConditionsYield
58 Angstroem neutral alumina In tetrahydrofuran; ethanol for 0.0666667h; microwave irradiation;93%
p-methylbenzenesulfenyl chloride
933-00-6

p-methylbenzenesulfenyl chloride

di(4-methyl)phenylthiosulfonate
2943-42-2

di(4-methyl)phenylthiosulfonate

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

p-toluenesulphonic acid S-benzylisothiouronium salt
35469-22-8

p-toluenesulphonic acid S-benzylisothiouronium salt

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 115℃; 16 h.; 8 h.;A 92.6%
B 84.8%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(benzylthio)-4-(3,4-dimethoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
1362426-29-6

2-(benzylthio)-4-(3,4-dimethoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;92%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

Benzyl isothiocyanate
622-78-6

Benzyl isothiocyanate

benzyl N-(benzylcarbamothioyl)carbamimidothioate

benzyl N-(benzylcarbamothioyl)carbamimidothioate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 16h;92%
(E)-1-([1,1'-biphenyl]-4-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
36635-79-7

(E)-1-([1,1'-biphenyl]-4-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

1-([1,1'-biphenyl]-4-yl)-3-(benzylthio)-3-(3,4-dimethoxyphenyl)propan-1-one

1-([1,1'-biphenyl]-4-yl)-3-(benzylthio)-3-(3,4-dimethoxyphenyl)propan-1-one

Conditions
ConditionsYield
Stage #1: S-benzylisothiourea hydrochloride With sodium hydroxide In water Michael Addition;
Stage #2: (E)-1-([1,1'-biphenyl]-4-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one In ethanol; water for 5h; Michael Addition;
92%
4,4'-dichlorophenyl thiosulfonate
1146-44-7

4,4'-dichlorophenyl thiosulfonate

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

4-chloro-benzenesulfenyl chloride
933-01-7

4-chloro-benzenesulfenyl chloride

A

4,4'-dichlorodiphenyl disulfide
1142-19-4

4,4'-dichlorodiphenyl disulfide

B

S-benzylisothiuronium p-chlorobenzenesulfonate
29391-11-5

S-benzylisothiuronium p-chlorobenzenesulfonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 115℃; 16 h.; 8 h.;A 91.3%
B 83.2%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

methyl iodide
74-88-4

methyl iodide

[(methylthio)methyl]-benzene
766-92-7

[(methylthio)methyl]-benzene

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 0.666667h; Ambient temperature;91%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(benzylthio)-4-(4-bromophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
1220710-03-1

2-(benzylthio)-4-(4-bromophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;91%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

2-(benzylthio)-4-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile
1362426-26-3

2-(benzylthio)-4-(3,4-dichlorophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;91%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

chloroethylamine
689-98-5

chloroethylamine

2-benzylsulfanyl-ethylamine
1007-54-1

2-benzylsulfanyl-ethylamine

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 0.666667h; Ambient temperature;90%
morpholine
110-91-8

morpholine

5-benzylidenebarbituric acid
27402-47-7

5-benzylidenebarbituric acid

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

7-morpholin-4-yl-5-phenyl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione

7-morpholin-4-yl-5-phenyl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione

Conditions
ConditionsYield
58 Angstroem neutral alumina In tetrahydrofuran; ethanol for 0.05h; microwave irradiation;90%
piperidine
110-89-4

piperidine

5-<(3,4-methylenedioxyphenyl) methylene>-2,4,6 (1H,3H,5H)pyrimidinetrione
4551-03-5

5-<(3,4-methylenedioxyphenyl) methylene>-2,4,6 (1H,3H,5H)pyrimidinetrione

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

5-benzo[1,3]dioxol-5-yl-7-piperidin-1-yl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione

5-benzo[1,3]dioxol-5-yl-7-piperidin-1-yl-1H-pyrimido[4,5-d]pyrimidine-2,4-dione

Conditions
ConditionsYield
58 Angstroem neutral alumina In tetrahydrofuran; ethanol for 0.05h; microwave irradiation;90%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(benzylthio)-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidine-5-carbonitrile

2-(benzylthio)-6-oxo-4-(pyridin-4-yl)-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;90%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(benzylthio)-6-oxo-4-(4-methylphenyl)-1,6-dihydropyrimidine-5-carbonitrile
131890-33-0

2-(benzylthio)-6-oxo-4-(4-methylphenyl)-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;90%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

benzaldehyde
100-52-7

benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

1,6-dihydro-6-oxo-4-phenyl-2-[(phenylmethyl)thio]-5-pyrimidinecarbonitrile

1,6-dihydro-6-oxo-4-phenyl-2-[(phenylmethyl)thio]-5-pyrimidinecarbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;90%
S-benzylisothiourea hydrochloride
538-28-3

S-benzylisothiourea hydrochloride

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-(phenethylthio)-4-(3-chlorophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

2-(phenethylthio)-4-(3-chlorophenyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In methanol at 70℃; for 0.5h;90%

2-Benzyl-2-thiopseudourea hydrochloride Chemical Properties

Molecular Formula: C8H11ClN2S
Molar mass: 202.7 g/mol
EINECS: 208-688-6
Flash Point: 125.1 °C
Boiling Point: 283.2 °C at 760 mmHg
Vapour Pressure: 0.0032 mmHg at 25°C 
Melting point: 172-177 °C
Water solubility: 250 g/L (15 ºC)
Sensitive: Hygroscopic
Appearance: Off-white to light beige crystalline powder
Product categories:  Sulphur Derivatives
Structure of Benzylisothiourea hydrochloride (538-28-3):

H-Bond Donor: 3
H-Bond Acceptor: 2
Systematic Name:Benzylsulfanylformamidine hydrochloride 
SMILES: Cl.S(C(=[N@H])N)Cc1ccccc1 
InChI: InChI=1/C8H10N2S.ClH/c9-8(10)11-6-7-4-2-1-3-5-7;/h1-5H,6H2,(H3,9,10);1H 
InChIKey: WJAASTDRAAMYNK-UHFFFAOYAY 
Std. InChI: InChI=1S/C8H10N2S.ClH/c9-8(10)11-6-7-4-2-1-3-5-7;/h1-5H,6H2,(H3,9,10);1H 
Std. InChIKey: WJAASTDRAAMYNK-UHFFFAOYSA-N

2-Benzyl-2-thiopseudourea hydrochloride Toxicity Data With Reference

1.    

orl-rat LD50:150 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 90 (1947),260.
2.    

ipr-mus LD50:50 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
3.    

scu-mus LDLo:80 mg/kg

    NDRC**    National Defense Research Committee, Office of Scientific Research and Development, Progress Report No. 9-4-1-9,43 .
4.    

ivn-mus LD50:32 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00167 .

2-Benzyl-2-thiopseudourea hydrochloride Consensus Reports

Reported in EPA TSCA Inventory.

2-Benzyl-2-thiopseudourea hydrochloride Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits very toxic fumes of HCl, SOx, and NOx.
 

Hazard Codes: T
Risk Statements:
25:  Toxic if swallowed
Safety Statements:
28A     After contact with skin, wash immediately with plenty of water.
36:  Wear suitable protective clothing 
37:  Wear suitable gloves
39:  Wear eye/face protection
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

2-Benzyl-2-thiopseudourea hydrochloride Specification

 Benzylisothiourea hydrochloride (538-28-3) also can be called Pseudourea, 2-benzyl-2-thio-, hydrochloride ; Pseudourea, 2-benzyl-2-thio-, monohydrochloride ; Carbamimidothioic Acid Phenylmethyl Ester Monohydrochloride ; S-Benzylthiouronium chloride ; S-Benzylthiopseudourea hydrochloride ;Pseudourea, 2-thio-2-benzyl-, hydrochloride ; S-Benzylthiuronium chloride ;and 2-Benzyl-2-thiopseudourea hydrochloride .It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should  flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.
In addition, Benzylisothiourea hydrochloride (538-28-3) can be stable under normal temperature and pressure conditions.It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials.And also prevent it to broken down into hazardous decomposition products: hydrogen chloride, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.

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