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104-06-3

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104-06-3 Usage

Chemical Properties

Solid

Uses

Thiacetazone (cas# 104-06-3) is used in combination chemotherapy, in preparation of nucleosides as inhibitors of adenylate-forming enzyme MenE.

Indications

Thiacetazone is active against many strains of M. tuberculosis. It is not marketed in the United States. However, because of its low cost, it is used as a first-line agent in East Africa, especially in combination with compounds such as isoniazid. The most common side effects of thiacetazone include GI intolerance and development of rashes. It causes significant ototoxicity, especially when coadministered with streptomycin. Lifethreatening hypersensitivity reactions, such as hepatitis, transient marrow aplastic syndromes, neutropenia, and thrombocytopenia, have been reported.

Pharmaceutical Applications

Thioacetazone (USAN amithiozone) is a synthetic compound discovered during initial work on the sulfonamides, to which it is structurally related. It is only slightly soluble in water. It is a weak bacteristatic drug, with frequent serious side effects, particularly in HIV-positive persons to whom it must never knowingly be given. On the advice of the WHO it no longer has a place in the treatment of tuberculosis, except as a last resort in cases of extreme drug resistance. In-vitro MICs vary considerably according to the medium used and bear little relation to in-vivo efficacy. Many strains of M. tuberculosis isolated in East Africa, India and Hong Kong are naturally more resistant than strains from Europe. Acquired resistance, as a result of monotherapy, is prevalent in the developing countries. Thioacetazone is well absorbed, achieving a plasma concentration of 1–4 mg/L 2–4 h after a 100 mg oral dose. The plasma half-life is 8–12 h. Little is known about the distribution of the drug. Several metabolites are described. About 20% is eliminated in the urine; the fate of the remainder is unknown. Rashes are common, occurring in 2–4% of patients in Africa but much more frequently in those of Chinese ethnic origin. More severe skin reactions, exfoliative dermatitis and Stevens–Johnson syndrome occur in less than 0.5% of HIV-negative patients, but there is a 10-fold increase of these reactions in HIV-positive patients, proving fatal in up to 3% of such patients. Other common side effects include gastrointestinal reactions, vertigo and conjunctivitis. Less common reactions include hepatitis, erythema multiforme, hemolytic anemia and, rarely, agranulocytosis. Prolonged therapy may rarely lead to hypertrichosis, gynecomastia and osteoporosis. It is very rarely used, but may occasionally be considered (with other antituberculosis drugs) in extremely drug resistant tuberculosis.

Check Digit Verification of cas no

The CAS Registry Mumber 104-06-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 104-06:
(5*1)+(4*0)+(3*4)+(2*0)+(1*6)=23
23 % 10 = 3
So 104-06-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H12N4OS/c1-7(15)13-9-4-2-8(3-5-9)6-12-14-10(11)16/h2-6H,1H3,(H,13,15)(H3,11,14,16)/b12-6+

104-06-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Acetylaminobenzaldehyde thiosemicarbazone

1.2 Other means of identification

Product number -
Other names N-[4-[(E)-(carbamothioylhydrazinylidene)methyl]phenyl]acetamide

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:104-06-3 SDS

104-06-3Synthetic route

4-acetylamino-benzaldehyde hydrazone

4-acetylamino-benzaldehyde hydrazone

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

(E)-2-(4-aminobenzylidene)hydrazinecarbothioamide
6957-91-1

(E)-2-(4-aminobenzylidene)hydrazinecarbothioamide

acetic anhydride
108-24-7

acetic anhydride

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

thiosemicarbazide
79-19-6

thiosemicarbazide

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N2H4
View Scheme
cis-anti-cis-Dicyclohexyl-18-crown-6
15128-66-2

cis-anti-cis-Dicyclohexyl-18-crown-6

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

C20H36O6*2C10H12N4OS

C20H36O6*2C10H12N4OS

Conditions
ConditionsYield
In methanol; ethyl acetate81%
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

acetic anhydride
108-24-7

acetic anhydride

4-Acetyl-2-acetylamino-5-p-acetylaminophenyl-4,5-dihydro-1,3,4-thiadiazol
107261-72-3

4-Acetyl-2-acetylamino-5-p-acetylaminophenyl-4,5-dihydro-1,3,4-thiadiazol

Conditions
ConditionsYield
at 80 - 120℃;56%
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

4-acetylamino-benzaldehyde-semicarbazone
22592-41-2

4-acetylamino-benzaldehyde-semicarbazone

Conditions
ConditionsYield
With oxygen; methylene blue In acetone for 1.66667h; Irradiation;44%
With oxygen; methylene blue In methanol for 1.66667h; Product distribution; Mechanism; Irradiation; var. solvents; var. photosensitisers; var. singlet oxygen scavangers;28%
1,2-dichloroethyl acetate
10140-87-1

1,2-dichloroethyl acetate

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

acetic acid-[4-(thiazol-2-ylhydrazono-methyl)-anilide]
100517-73-5

acetic acid-[4-(thiazol-2-ylhydrazono-methyl)-anilide]

Conditions
ConditionsYield
With sodium acetate
β-Propiolactone
57-57-8

β-Propiolactone

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

3-[(4-acetylamino-benzylidenehydrazono)-amino-methylsulfanyl]-propionic acid

3-[(4-acetylamino-benzylidenehydrazono)-amino-methylsulfanyl]-propionic acid

4-(chloroacetyl)antipyrine
6630-73-5

4-(chloroacetyl)antipyrine

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

acetic acid-{4-[4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-thiazol-2-ylhydrazonomethyl]-anilide}
96267-62-8

acetic acid-{4-[4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-thiazol-2-ylhydrazonomethyl]-anilide}

Conditions
ConditionsYield
With ethanol
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

acetic acid-[4-(amino-[1,3,4]thiadiazol-2-yl)-anilide]
90916-70-4

acetic acid-[4-(amino-[1,3,4]thiadiazol-2-yl)-anilide]

Conditions
ConditionsYield
With water; iron(III) chloride
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

N,N'''-bis-(4-acetylamino-benzylidene)-μ-disulfido-dicarboxamidrazone
114164-09-9

N,N'''-bis-(4-acetylamino-benzylidene)-μ-disulfido-dicarboxamidrazone

Conditions
ConditionsYield
With dibenzoyl peroxide
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

1-(4-acetylamino-benzyl)-thiosemicarbazide
59643-83-3

1-(4-acetylamino-benzyl)-thiosemicarbazide

Conditions
ConditionsYield
With ammonia; sodium; ammonium chloride unter Einleiten von CO2;
With sodium amalgam; sodium hydrogencarbonate unter Einleiten von CO2;
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

acetic anhydride
108-24-7

acetic anhydride

4-diacetylamino-benzaldehyde-(4-acetyl thiosemicarbazone)
110175-75-2

4-diacetylamino-benzaldehyde-(4-acetyl thiosemicarbazone)

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

chloroacetic acid
79-11-8

chloroacetic acid

acetic acid-({4-[5-(2-chloro-benzyliden)-4-oxo-thiazolidin-2-ylidenehydrazono]-methyl}-anilide)
111531-25-0

acetic acid-({4-[5-(2-chloro-benzyliden)-4-oxo-thiazolidin-2-ylidenehydrazono]-methyl}-anilide)

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

para-acetamidobenzaldehyde
122-85-0

para-acetamidobenzaldehyde

chloroacetic acid
79-11-8

chloroacetic acid

5-(4-acetylamino-benzylidene)-thiazolidine-2,4-dion-2-(4-acetylamino-benzylidenehydrazone)
115272-07-6

5-(4-acetylamino-benzylidene)-thiazolidine-2,4-dion-2-(4-acetylamino-benzylidenehydrazone)

Conditions
ConditionsYield
With acetic acid
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

4-Nitrophenacyl bromide
99-81-0

4-Nitrophenacyl bromide

3-(4-acetylamino-benzylidenamino)-4-(4-nitro-phenyl)-3H-thiazol-2-one-imine

3-(4-acetylamino-benzylidenamino)-4-(4-nitro-phenyl)-3H-thiazol-2-one-imine

Conditions
ConditionsYield
With ethanol
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

benzaldehyde
100-52-7

benzaldehyde

chloroacetic acid
79-11-8

chloroacetic acid

5,5'-benzylidene-bis-thiazolidine-2,4-dione-2,2'-bis-(4-acetylamino-benzylidenehydrazone)
102901-19-9

5,5'-benzylidene-bis-thiazolidine-2,4-dione-2,2'-bis-(4-acetylamino-benzylidenehydrazone)

Conditions
ConditionsYield
With acetic acid
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

benzaldehyde
100-52-7

benzaldehyde

chloroacetic acid
79-11-8

chloroacetic acid

acetic acid-{[4-(5-benzyliden-4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}
109568-33-4

acetic acid-{[4-(5-benzyliden-4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

benzyl chloride
100-44-7

benzyl chloride

acetic acid-[4-(S-benzyl-isothiosemicarbazonomethyl)-anilide]

acetic acid-[4-(S-benzyl-isothiosemicarbazonomethyl)-anilide]

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

salicylaldehyde
90-02-8

salicylaldehyde

chloroacetic acid
79-11-8

chloroacetic acid

5,5'-salicylidene-bis-thiazolidine-2,4-dione-2,2'-bis-(4-acetylamino-benzylidenehydrazone)
125544-42-5

5,5'-salicylidene-bis-thiazolidine-2,4-dione-2,2'-bis-(4-acetylamino-benzylidenehydrazone)

Conditions
ConditionsYield
With acetic acid
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

acetic acid-{[4-(4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}
95708-02-4

acetic acid-{[4-(4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

chloroacetone
78-95-5

chloroacetone

4-acetylamino-benzaldehyde-(4-methyl-thiazol-2-ylhydrazone)

4-acetylamino-benzaldehyde-(4-methyl-thiazol-2-ylhydrazone)

(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

chloroacetic acid
79-11-8

chloroacetic acid

acetic acid-{4-[(5-trans-cinnamyliden-4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}
113223-43-1

acetic acid-{4-[(5-trans-cinnamyliden-4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

chloroacetic acid
79-11-8

chloroacetic acid

acetic acid-{[4-(4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}
95708-02-4

acetic acid-{[4-(4-oxo-thiazolidin-2-ylidenehydrazono)-methyl]-anilide}

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

chloroacetic acid
79-11-8

chloroacetic acid

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

2-[2-(4-acetylamino-benzylidenehydrazono)-4-oxo-thiazolidin-5-ylidenemethyl]-benzoic acid

2-[2-(4-acetylamino-benzylidenehydrazono)-4-oxo-thiazolidin-5-ylidenemethyl]-benzoic acid

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

chloroacetic acid
79-11-8

chloroacetic acid

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

2-{bis-[2-(4-acetylamino-benzylidenehydrazono)-4-oxo-thiazolidin-5-yl]-methyl}-benzoic acid

2-{bis-[2-(4-acetylamino-benzylidenehydrazono)-4-oxo-thiazolidin-5-yl]-methyl}-benzoic acid

Conditions
ConditionsYield
With acetic acid
N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

1-bromoacetone
598-31-2

1-bromoacetone

4-acetylamino-benzaldehyde-(4-methyl-thiazol-2-ylhydrazone)

4-acetylamino-benzaldehyde-(4-methyl-thiazol-2-ylhydrazone)

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

methyl iodide
74-88-4

methyl iodide

acetic acid-[4-(S-methyl-isothiosemicarbazonomethyl)-anilide]
94504-53-7

acetic acid-[4-(S-methyl-isothiosemicarbazonomethyl)-anilide]

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide
104-06-3

N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide

1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

4-acetylamino-benzaldehyde (4-chloromethyl-thiazol-2-yl)-hydrazone
24698-85-9

4-acetylamino-benzaldehyde (4-chloromethyl-thiazol-2-yl)-hydrazone

Conditions
ConditionsYield
In acetone for 1h; Heating;
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