22948-02-3

Basic information

• Product Name: 3-Aminothiophenol
• Synonyms: Benzenethiol, 3-amino-;m-aminothiophenol;3-AMINOBENZENETHIOL;3-AMINOTHIOPHENOL;3-MERCAPTOANILINE;Benzenethiol, 3-amino- (9CI);3-Aminothiophenol,98%;3-Aminothiophenol 97%
• CAS NO: 22948-02-3
• Molecular Formula: C₆H₇NS
• Molecular Weight: 125.19
• EINECS: 245-344-4
• Product Categories: THIOL;Phenol&Thiophenol&Mercaptan;Phenoles and thiophenoles;Miscellaneous
• Mol File: 22948-02-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 97 C
• Boiling Point: 80°C 16mm
• Flash Point: 175 °F
• Appearance: Pale yellow to brown/Liquid
• Density: 1.179 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00929mmHg at 25°C
• Refractive Index: n20/D 1.656(lit.)
• PKA: 6.75±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Stench
• CAS DataBase Reference: 3-Aminothiophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminothiophenol(22948-02-3)
• EPA Substance Registry System: 3-Aminothiophenol(22948-02-3)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34-37
• Safety Statements: 26-27-36/37/39-45-25
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 22948-02-3(Hazardous Substances Data)

Usage

Chemical Properties

Pale yellow to brown liquid

Uses

3-Aminothiophenol was used as analyte during the fabrication of top-to-bottom joined system consisting of a silver nanowire and nanospheres. It was used in formation of polyaniline-analog monolayer on gold surface by anchoring to the gold substrate through the thiol moiety.

InChI:InChI=1/C6H7NS/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2/p-1

Synthetic route

3-Iodoaniline (626-01-7) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
With copper(l) iodide; thiourea; L-proline; sodium t-butanolate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	82%

3-nitrophenyl thiocyanate (16671-77-5) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
With hydrogenchloride durch elektrolitische Reduktion an Bleikathode;

bis(3-nitrophenyl) disulfide (537-91-7) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
With sodium amalgam; ethanol
With sodium sulfide
With hydrogenchloride; iron In ethanol for 3h; Heating;

3-nitrobenzenesulphonyl chloride (121-51-7) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
With hydrogenchloride; tin

bis(3-aminophenyl)-disulfide (40897-41-4) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
With triphenylphosphine In 1,4-dioxane; water at 30℃; Rate constant;

hydrochloride of 3.3'-diamino-diphenyl dilsulfide → 3-aminothiophenol (22948-02-3)

Conditions	Yield
With sodium sulfide; sodium hydroxide

bis(3-nitrophenyl) disulfide (537-91-7) + sodium amalgam → 3-aminothiophenol (22948-02-3)

hydrogenchloride (7647-01-0) + 3-nitrophenyl thiocyanate (16671-77-5) → 3-aminothiophenol (22948-02-3) + bis-(3-thiocyanato-phenyl)-diazene-N-oxide

Conditions	Yield
bei der elektrolytischen Reduktion;

3-Nitrobenzenesulfonic acid (98-47-5) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl5 2: tin; hydrochloric acid View Scheme

3-nitrothiophenol (3814-18-4) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: alcohol; sodium amalgam View Scheme

3-nitro-aniline (99-09-2) → 3-aminothiophenol (22948-02-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: diluted hydrochloric acid / Diazotization.man laesst die Reaktionsloesung zu einer auf 70-75grad erwaermten Loesung von aethylxanthogensaurem Kalium zufliessen, verseift das sich abscheidende Oel mit alkoh. Kalilauge und saeuert mit Essigsaeure an 3: alcohol; sodium amalgam View Scheme

3-aminothiophenol (22948-02-3) + (2S,4S)-cis-2-(2-(4-chlorophenyl)ethyl)-2-(imidazol-1-yl)methyl-4-(p-toluene-sulfonyloxy)methyl-1,3-dioxolane (143327-62-2) → (+/-)-cis-2-(2-(4-chlorophenyl)ethyl)-2-(imidazol-1-yl)methyl-4-(3-aminophenylthio)methyl-1,3-dioxolane

Conditions	Yield
With potassium carbonate In acetone for 5h; Heating;	100%

3-aminothiophenol (22948-02-3) + 4-chlorpyridine hydrochloride (7379-35-3) → 4-(3-aminophenylthio)pyridine (92575-23-0)

Conditions	Yield
With potassium carbonate In hexane; ethyl acetate; N,N-dimethyl-formamide	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	66%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	66%

N-(3-bromo-phenyl)-4-chloro-3-nitro-benzamide (346723-27-1) + 3-aminothiophenol (22948-02-3) → 4-(3-amino-phenylsulfanyl)-N-(3-bromo-phenyl)-3-nitro-benzamide (943772-87-0)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 95℃; for 3h;	99%

3-aminothiophenol (22948-02-3) + orthoformic acid triethyl ester (122-51-0) → 3-tetrazol-1-yl-benzenethiol (578748-03-5)

Conditions	Yield
Stage #1: 3-aminothiophenol; orthoformic acid triethyl ester With sodium azide; acetic acid at 80℃; for 2h; Stage #2: With hydrogenchloride; sodium nitrite In water at 0℃;	99%

3-aminothiophenol (22948-02-3) + methyl chloroacetate (96-34-4) → methyl 2-((3-aminophenyl)thio)acetate

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 3.5h; Inert atmosphere;	99%

3-aminothiophenol (22948-02-3) → bis(3-aminophenyl)-disulfide (40897-41-4)

Conditions	Yield
With manganese(II)carbonate; 3,4,5-trihydroxybenzoic acid; oxygen; sodium carbonate In water at 80℃; under 2250.23 Torr; for 4h; pH=9; Schlenk technique; Green chemistry;	98%
With dimethyl sulfoxide at 80 - 90℃; for 4h;	92%
With pyridine; benzenesulfonyl chloride In dichloromethane Ambient temperature;	75%

3-aminothiophenol (22948-02-3) + 2-methylpropan-2-thiol (75-66-1) → 3-(tert-butyldisulfanyl)aniline

Conditions	Yield
With manganese(II)carbonate; 3,4,5-trihydroxybenzoic acid; oxygen; sodium carbonate In water at 80℃; under 2250.23 Torr; for 4h; pH=9; Schlenk technique; Green chemistry;	96%

tricarbonyl[(1-5-η)-pentadienyl]manganese + 3-aminothiophenol (22948-02-3) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → fac-Mn(CO)3(m-aminothiophenolato)(1,2-bis(diphenylphosphino)ethane-κ2-P,P') (1256627-58-3)

Conditions	Yield
In cyclohexane (N2); Mn complex and C2H4(P(C6H5)2)2 mixed in cyclohexane, H2NC6H4SH added, refluxed for 2 h; left to reach room temp., evapd. (vac.), washed (hexane), dissolved in CH2Cl2, filtered, evapd. (vac.), crystd. (CH2Cl2, -4°C); elem. anal.;	95%

N-(5-fluoro-2,4-dinitro-phenyl)-benzene-1,3-diamine (1229799-72-7) + 3-aminothiophenol (22948-02-3) → C18H15N5O4S (1333166-27-0)

Conditions	Yield
Stage #1: 3-aminothiophenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: N-(5-fluoro-2,4-dinitro-phenyl)-benzene-1,3-diamine In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	94%

3-aminothiophenol (22948-02-3) + calcium carbide (75-20-7) → 3-aminophenyl vinyl sulfide

Conditions	Yield
With water; potassium hydroxide In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere; Sealed tube; Green chemistry;	93%

3-aminothiophenol (22948-02-3) + methyl 3-(bromomethyl)thiophene-2-carboxylate (59961-15-8) → methyl 3-(3-aminophenylthiomethyl)thiophene-2-carboxylate

Conditions	Yield
With sodium bicarbonate; sodium chloride; triethylamine In dichloromethane	92%

3-aminothiophenol (22948-02-3) + 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one → 3-(((triisopropylsilyl)ethynyl)thio)aniline (1443746-58-4)

Conditions	Yield
Stage #1: 3-aminothiophenol With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one In tetrahydrofuran at 20℃; for 0.0833333h; chemoselective reaction;	92%

4-iodobenzonitrile (3058-39-7) + 3-aminothiophenol (22948-02-3) → C13H10N2S

Conditions	Yield
With pyridine; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide In N,N-dimethyl acetamide at 20℃; for 12h; Ullmann Condensation; Electrolysis; Inert atmosphere;	92%

3-aminothiophenol (22948-02-3) + NBD chloride (10199-89-0) → 3-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylthio)benzenamine (1458652-45-3)

Conditions	Yield
In ethanol for 0.416667h; Reflux; Alkaline conditions;	91%

3-aminothiophenol (22948-02-3) + (5S,6S,7Z)-methyl 5,6-oxido-9-(4-heptylphenyl)-7-nonenoate (104948-09-6) → (Z)-(5S,6R)-6-(3-Amino-phenylsulfanyl)-9-(4-heptyl-phenyl)-5-hydroxy-non-7-enoic acid methyl ester

Conditions	Yield
With triethylamine In methanol	90%

3-aminothiophenol (22948-02-3) + salicylaldehyde (90-02-8) → 2-{[(E)-3-Mercapto-phenylimino]-methyl}-phenol (109872-58-4)

Conditions	Yield
In ethanol for 0.5h;	90%
In ethanol for 0.5h;	55%

3-aminothiophenol (22948-02-3) + 5-bromosalicyclaldehyde (1761-61-1) → 5-Br-salATP (115695-35-7)

Conditions	Yield
In ethanol for 0.5h;	90%
In ethanol for 0.5h;	75%

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + 3-aminothiophenol (22948-02-3) → 2-{[(Z)-3-Mercapto-phenylimino]-methyl}-5-methoxy-phenol

Conditions	Yield
In ethanol for 0.5h;	90%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + 3-aminothiophenol (22948-02-3) → 2-{[(Z)-3-Mercapto-phenylimino]-methyl}-4-methoxy-phenol

Conditions	Yield
In ethanol for 0.5h;	90%

3-aminothiophenol (22948-02-3) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 2-{[(Z)-3-Mercapto-phenylimino]-methyl}-6-methoxy-phenol

Conditions	Yield
In ethanol for 0.5h;	90%

3-aminothiophenol (22948-02-3) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 1-{[(Z)-3-Mercapto-phenylimino]-methyl}-naphthalen-2-ol

Conditions	Yield
In ethanol for 0.5h;	90%

di-tert-butyl dicarbonate (24424-99-5) + 3-aminothiophenol (22948-02-3) → (3-mercaptophenyl)carbamic acid tert-butyl ester (195622-56-1)

Conditions	Yield
With zinc(II) perchlorate at 20℃; for 9h;	90%
With sodium hydrogencarbonate In acetone at 0 - 20℃; for 15.5h;	85.8%
With zinc(II) perchlorate at 25℃; for 12h;	69.4%
With sodium carbonate In water; acetone at 20℃; under 760.051 Torr; for 18h;	61%
With sodium carbonate In water; acetone at 20℃; for 18h;	61%

3-aminothiophenol (22948-02-3) + terephthalaldehyde, (623-27-8) → 4-[(3-mercaptophenylimino)methyl]benzaldehyde (936855-17-3)

Conditions	Yield
In ethanol at 20℃;	90%

3-aminothiophenol (22948-02-3) + 1-cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole → 3-thiocyanatoaniline (23905-49-9)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 23℃; for 0.0833333h; chemoselective reaction;	90%

7-chlorothieno[3,2-b]pyridine (69627-03-8) + 3-aminothiophenol (22948-02-3) → 3-(thieno[3,2-b]pyridin-7-ylthio)aniline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 2h;	90%

1,1,1-trifluoro-2-iodoethane (353-83-3) + 3-aminothiophenol (22948-02-3) → 3-[(2,2,2-trifluoroethyl)sulfanyl]aniline

Conditions	Yield
With potassium carbonate; sodium hydroxide In dimethyl sulfoxide; acetonitrile at 45℃; for 18h;	88.3%

3-aminothiophenol (22948-02-3) + 2,6-dinitrobenzonitrile (35213-00-4) → 2-[(3-Aminophenyl)thio]-6-nitrobenzonitrile (171102-60-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h;	88%

3-aminothiophenol (22948-02-3) + 5-Nitrosalicylaldehyde (97-51-8) → 5-NO2-salATP (109894-27-1)

Conditions	Yield
In ethanol for 0.5h;	87%

3-aminothiophenol (22948-02-3) + acetic anhydride (108-24-7) → N-(3-mercaptophenyl)acetamide (67937-79-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	87%
In ethyl acetate at 0 - 20℃; for 1h;	85%
In ethyl acetate at 0 - 20℃; for 2h;	83%

3-aminothiophenol (22948-02-3) → N-(3-mercaptophenyl)acetamide (67937-79-5)

Conditions	Yield
With acetic anhydride; triethylamine In dichloromethane	87%
Multi-step reaction with 2 steps 2: sodium hydroxide; ethanol; water / 0.33 h / 50 °C / Heating / reflux View Scheme

Upstream product

• 16671-77-5 3-nitrophenyl thiocyanate 
• 40897-41-4 bis(3-aminophenyl)-disulfide 
• 626-01-7 3-Iodoaniline 
• 99-09-2 3-nitro-aniline 
• 3814-18-4 3-nitrothiophenol 
• 98-47-5 3-Nitrobenzenesulfonic acid 
• 7647-01-0 hydrogenchloride 
• 537-91-7 bis(3-nitrophenyl) disulfide 
• 121-51-7 3-nitrobenzenesulphonyl chloride 

Downstream Products

• 109688-85-9 1,2-bis-(3-amino-phenylsulfanyl)-ethane 
• 40897-49-2 m-Aminophenyl-p-acetylphenyldisulfid 
• 224558-82-1 2-(3-amino-phenylsulfanylcarbonylamino)-pentanedioic acid di-tert-butyl ester 
• 247090-60-4 N₁-[4-cyano-3-(trifluoromethyl)phenyl]-(2R)-3-[(3-aminophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide 
• 27260-84-0 3-(benzylsulfanyl)aniline 
• 153242-32-1 ethyl 2-((3-aminophenyl)thio)acetate 
• 95901-60-3 N-(3-mercaptophenyl)formamide 
• 95901-53-4 3-((3-Ethoxy-2-methyl-1,3-dioxopropyl)amino)-phenylmercaptan 
• 95901-35-2 3-((3-Hydroxy-1-oxopropyl)amino)phenylmercaptan 
• 1783-82-0 3-(ethylthio)aniline 
• 73443-67-1 3-Ethoxycarbonylaminothiophenol 

Relevant articles and documents

Copper-catalyzed coupling of thiourea with aryl iodides: The direct synthesis of aryl thiols

A general, economical and efficient protocol for the direct copper-catalyzed coupling of thiourea with aryl iodides is developed and it will be potentially applied in large-scale industry as a preferred process.

Fiber reactive anthraquinone dyes

Fiber reactive dyes of the anthraquinone type which provide brilliant violet colors without metal complexing. These dyes may be represented by the formula: STR1 wherein W is selected from NR2 and oxygen; R is independently selected from hydrogen, C1 -C6 alkyl; C1 -C6 alkoxy, sulfo and carboxy; R1 is selected from hydrogen, C1 -C6 alkyl and phenyl; R2 is selected from hydrogen and C1 -C6 alkyl; R3 is selected from hydrogen, and C1 -C4 alkyl; n is an integer of 1 or 2; and Y is CH=CH2, or CH2 CH2 Z wherein Z is a group capable of being split off by the action of an alkali reagent.