110-66-7

Basic information

• Product Name: 1-Pentanethiol
• Synonyms: N-PENTYL MERCAPTAN;PENTYL MERCAPTAN;N-AMYL MERCAPTAN;1-Mercaptopentane;1-Pentanthiol;Amyl thioalcohol;amylmercaptan(non-specificname);amylmercaptannormal
• CAS NO: 110-66-7
• Molecular Formula: C₅H₁₂S
• Molecular Weight: 104.21
• EINECS: 203-789-1
• Mol File: 110-66-7.mol

Chemical Properties

• Melting Point: -76°C
• Boiling Point: 126 °C(lit.)
• Flash Point: 65 °F
• Appearance: /liquid
• Density: 0.84 g/mL at 25 °C(lit.)
• Vapor Density: 3.59
• Vapor Pressure: 27.4 mm Hg ( 37.7 °C)
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: Flammables area
• Solubility: 0.16g/l
• PKA: 10.51±0.10(Predicted)
• Water Solubility: practically insoluble
• Sensitive: Air Sensitive
• Merck: 14,611
• BRN: 1730979
• CAS DataBase Reference: 1-Pentanethiol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pentanethiol(110-66-7)
• EPA Substance Registry System: 1-Pentanethiol(110-66-7)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/22-36/37/38
• Safety Statements: 16-23-24/25-37/39-26
• RIDADR: UN 1111 3/PG 2
• WGK Germany: 3
• RTECS: SA3150000
• F: 9-13-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 110-66-7(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1-Pentanethiol is used as a raw material for the organic synthesis of sulfur compounds, playing a crucial role in the production of various chemical products.
2. Used in Hair Coloring Agents:
1-Pentanethiol is used as additives for hair coloring agents, contributing to the formulation and effectiveness of these cosmetic products.

Preparation

1-Pentanethiol is synthesized from n-pentyl alcohol and hydrogen sulfide catalyzed by thorium dioxide.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

1-Pentanethiol is incompatible with oxidizing agents, reducing agents, alkali metals, calcium hypochlorite, concentrated nitric acid .

Health Hazard

Inhalation may cause nausea because of offensive odor. Contact with eyes or skin causes slight irritation. Ingestion may cause vomiting.

Safety Profile

Moderately toxic by inhalation. A weak sensitizer and allergen. Local contact may cause contact dermatitis. A flammable liquid and dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidming materials. Hypergolic reaction with concentrated nitric acid. To fight fire, use foam, CO2, dry chemical. See also MERCAPTANS

Purification Methods

Dissolve the thiol in aqueous 20% NaOH, then extract with a small amount of diethyl ether. The aqueous solution is acidified slightly with 15% H2SO4, and the thiol is distilled out, dried with CaSO4 or CaCl2, and fractionally distilled under nitrogen. [Ellis & Reid J Am Chem Soc 54 1674 1932, Beilstein 1 IV 1453.]

InChI:InChI=1/C5H12S/c1-2-3-4-5-6/h6H,2-5H2,1H3

Synthetic route

1-thiocyanatopentane (32446-40-5) → n-pentanethiol (110-66-7)

Conditions	Yield
With tetraphosphorus decasulfide In toluene for 1.5h; Reflux;	87%

hexanethioic acid S-pentyl ester → n-pentanethiol (110-66-7)

Conditions	Yield
With titanium tetrachloride; zinc In dichloromethane at 25℃; for 0.166667h;	85%

C8H16O2S → n-pentanethiol (110-66-7)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;	70%

1-Chloropentane (543-59-9) → n-pentanethiol (110-66-7)

Conditions	Yield
With tetraethylammonium iodide; 1-(2-hydroxyethyl)-4,6-diphenylpyridin-2-thione In acetonitrile for 26h; Ambient temperature;	61%

pentan-1-ol (71-41-0) → n-pentanethiol (110-66-7)

Conditions	Yield
With phosphorous (V) sulfide; benzene Erhitzen des Reaktionsprodukts auf 190grad;

1-Bromopentane (110-53-2) → n-pentanethiol (110-66-7)

Conditions	Yield
With sodium hydrogensulfide; ethanol
With ethanol; potassium hydrosulfide
With potassium hydrosulfide

1-Bromopentane (110-53-2) + thiourea (17356-08-0) → n-pentanethiol (110-66-7)

Conditions	Yield
With water Zersetzen des Thiuroniumsalzes mit starker KOH auf dem Wasserbad;

cyano-dithiocarbonimidic acid dipentyl ester (56342-26-8) → n-pentanethiol (110-66-7)

Conditions	Yield
With hydrogenchloride

piperidine (110-89-4) → sulfure de pentamethylene (1613-51-0) + 2-methylthiolane (1795-09-1) + pyridine (110-86-1) + 1-pentylpiperidine (10324-58-0) + n-pentanethiol (110-66-7)

Conditions	Yield
With hydrogen sulfide; hydrogen; sulfidized Ni-W at 300℃; under 105008 Torr; for 5h; Product distribution;	A n/a B n/a C 0.59 % Chromat. D 3.59 % Chromat. E n/a

4-pentenyl-1-amine (22537-07-1) → sulfure de pentamethylene (1613-51-0) + 2-methylthiolane (1795-09-1) + diamyl sulfide (872-10-6) + n-pentanethiol (110-66-7) + pent-4-ene-1-thiol (17651-37-5)

Conditions	Yield
With hydrogen sulfide; hydrogen; sulfidized Ni-W at 300℃; for 5h; Product distribution;

1-pentanesulfonic acid (35452-30-3) → n-pentanethiol (110-66-7)

Conditions	Yield
With diphosphorus pentasulfide; water 1.) sulfolane, 90 deg C for 24 h; Yield given. Multistep reaction;

1-pentyl tosylate (4450-76-4) → n-pentanethiol (110-66-7)

Conditions	Yield
With diphosphorus pentasulfide; lithium aluminium tetrahydride 1.) sulfolane, 90 deg C for 24 h 2.) ether, room temperature for 30 min; Yield given. Multistep reaction;

1-pentanamine (110-58-7) → diamyl sulfide (872-10-6) + n-pentanethiol (110-66-7) + Di-n-amylamine (2050-92-2) + pentane (109-66-0)

Conditions	Yield
With hydrogen sulfide; hydrogen; sulfidized Ni-W at 300℃; for 5h; Product distribution;	A n/a B n/a C 2.3 % Chromat. D 3.2 % Chromat.

diamyl disulfide (112-51-6) + sodium hydrosulfide → n-pentanethiol (110-66-7)

hydrogenchloride (7647-01-0) + dithiooxalodiimidic acid dipentyl ester → n-pentanethiol (110-66-7) + S,S-dipentyl 1,2-ethanebisthioate (855395-51-6) + 1-thio-oxalamic acid S-pentyl ester + oxalic acid (144-62-7)

4-pentenyl-1-amine (22537-07-1) → sulfure de pentamethylene (1613-51-0) + 2-methylthiolane (1795-09-1) + methylbutane (78-78-4) + n-pentanethiol (110-66-7) + 2-Methyl-1-butene (563-46-2) + pentane (109-66-0) + 1-butyl-1-propyl sulphide, ethyl 1-pentyl sulphide,2,3-benzothiphene, C5H10S2, C8H16S, C9H14S, C9H18S

Conditions	Yield
With hydrogen sulfide; hydrogen Product distribution;

1-penten (109-67-1) → pentane-2-thiol (2084-19-7) + pentane-3-thiol (616-31-9) + n-pentanethiol (110-66-7)

Conditions	Yield
With hydrogen sulfide; TK-554 catalyst at 120 - 220℃; Product distribution / selectivity;

2-Methylthiophene (554-14-3) → 2-methylthiolane (1795-09-1) + n-pentanethiol (110-66-7) + 1-penten (109-67-1)

Conditions	Yield
With nonane; hydrogen

2-Methylthiophene (554-14-3) → 2-methylthiolane (1795-09-1) + n-pentanethiol (110-66-7) + 1-penten (109-67-1) + pentane (109-66-0)

Conditions	Yield
With nonane; hydrogen at 224.84℃;

2-Methylthiophene (554-14-3) → n-pentanethiol (110-66-7) + 1-penten (109-67-1)

Conditions	Yield
With nonane; platinum on alumina; hydrogen at 224.84℃;

n-pentanethiol (110-66-7) + mercury(II) nitrate → bis(1-pentanethiolato)mercury(II) (4080-30-2)

Conditions	Yield
In ethanol; water the thiol was added to soln. of Hg(NO3)2 in EtOH/H2O in a Schlenk tube; soln. was stirred for 12 h in the dark; ppt. was filtered off, washed with cold EtOH and dried in vacuo;	100%

n-pentanethiol (110-66-7) + benzenesufonyl hydrazide (80-17-1) → benzenethiosulfonic acid S-pentyl ester

Conditions	Yield
With tert.-butylhydroperoxide; sodium iodide In acetonitrile at 25℃;	100%
With tert.-butylhydroperoxide; sodium iodide In acetonitrile at 20℃; for 12h;	99%
With ammonium iodide In acetonitrile at 20℃; for 3h; Electrochemical reaction;	78%

n-pentanethiol (110-66-7) → diamyl disulfide (112-51-6)

Conditions	Yield
With water; dihydrogen peroxide In various solvent(s) at 20℃; for 0.166667h; Oxidation; Dimerization;	99%
With aluminum oxide In neat (no solvent) for 0.333333h; Milling; chemoselective reaction;	98%
With oxygen; SiO2-Cl In dichloromethane at 0℃; for 0.166667h;	97%

n-pentanethiol (110-66-7) + propargyl bromide (106-96-7) → pentyl propargyl thioether (77202-44-9)

Conditions	Yield
Stage #1: n-pentanethiol With sodium hydroxide In dichloromethane for 1h; Stage #2: propargyl bromide In dichloromethane; toluene for 2h;	99%
With potassium hydroxide

n-pentanethiol (110-66-7) + N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (115975-33-2) → 2,2,2-Trifluoro-1-[4-pentylsulfanyl-3-(2,2,2-trifluoro-acetyl)-naphthalen-1-yl]-ethanone (127053-12-7)

Conditions	Yield
In acetonitrile for 41h; Heating;	99%

5-Hexen-1-ol (821-41-0) + n-pentanethiol (110-66-7) → 6-(pentylsulfanyl)hexan-1-ol

Conditions	Yield
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 20℃; for 3h;	99%

n-pentanethiol (110-66-7) + (4S)-N-tert-butoxycarbonyl-4-[[(4'-methylbenzenesulfonyl)oxy]methyl]-2,2-dimethyl-1,3-oxazolidine (140645-28-9) → 4(S)-2,2-dimethyl-4-(pentylthiomethyl)oxazolidine-3-carboxylic acid tert-butyl ester (935547-63-0)

Conditions	Yield
Stage #1: n-pentanethiol With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: (4S)-N-tert-butoxycarbonyl-4-[[(4'-methylbenzenesulfonyl)oxy]methyl]-2,2-dimethyl-1,3-oxazolidine In N,N-dimethyl-formamide at 40℃; for 1h;	99%
With sodium hydride In N,N-dimethyl-formamide at 60 - 80℃;

n-pentanethiol (110-66-7) + methacrylic acid methyl ester (80-62-6) → methyl (2R)-2-methyl-3-(pentylsulfanyl)propanoate

Conditions	Yield
With C47H57N4O4PS In diethyl ether at 20℃; for 24h; Michael Addition; enantioselective reaction;	99%

n-pentanethiol (110-66-7) + tert-Butyl acrylate (1663-39-4) → tert-butyl 3-(pentylthio)propanoate

Conditions	Yield
Stage #1: n-pentanethiol In acetonitrile at 20℃; for 0.0833333h; Stage #2: tert-Butyl acrylate In acetonitrile at 50 - 60℃; for 0.25h;	99%
With potassium carbonate In dichloromethane at 20℃; for 20h; Michael Addition; Inert atmosphere;

tert-butyl diphenylmethylsilylglyoxylate + n-pentanethiol (110-66-7) → C24H34O3SSi

Conditions	Yield
With C39H60N4O4; yttrium(III) trifluoromethanesulfonate In dichloromethane at -60℃; for 4h; enantioselective reaction;	99%

n-pentanethiol (110-66-7) + 2-(4-allyl-1-piperazinyl)-4-chloroquinazoline (122009-56-7) → 2-(4-Allyl-piperazin-1-yl)-4-pentylsulfanyl-quinazoline (134249-89-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃;	98%

n-pentanethiol (110-66-7) + 12-Chloro-8,9,10,11-tetrahydro-7H-benzo[4,5]imidazo[1,2-a]cyclohepta[d]pyridine-6-carbonitrile (163080-54-4) → 12-Pentylsulfanyl-8,9,10,11-tetrahydro-7H-benzo[4,5]imidazo[1,2-a]cyclohepta[d]pyridine-6-carbonitrile

Conditions	Yield
With 5-bromo-2'-deoxyuridine In benzene for 4h; Ambient temperature;	98%

n-pentanethiol (110-66-7) + prop-2-en-1-yl 2,3,4-tri-O-acetyl-α-L-fucopyranoside (191540-37-1) → Acetic acid (2S,3R,4R,5S,6R)-3,5-diacetoxy-2-methyl-6-(3-pentylsulfanyl-propoxy)-tetrahydro-pyran-4-yl ester

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In 1,4-dioxane at 75℃;	98%

n-pentanethiol (110-66-7) + bis-(dimethylamino)methane (51-80-9) → N,N-dimethyl-1-(pentylsulfanyl)methaneamine (1369272-96-7)

Conditions	Yield
With samarium(III) chloride hexahydrate at 60℃; for 1.5h; Inert atmosphere; chemoselective reaction;	98%

4-(morpholinomethyl)morpholine (5625-90-1) + n-pentanethiol (110-66-7) → N-(pentylsulfanylmethyl)morpholine (1394913-18-8)

Conditions	Yield
With zinc(II) chloride dihydrate at 60℃; for 6h; Temperature; Reagent/catalyst; Time;	98%

n-pentanethiol (110-66-7) + 4-methyl-benzaldehyde (104-87-0) → S-pentyl 4-methylbenzothioate (1034012-61-7)

Conditions	Yield
With Phenazin; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 90℃; for 12h; Temperature; Schlenk technique;	98%

n-pentanethiol (110-66-7) + tert-butyl (E)-crotonate (79218-15-8) → C13H26O2S

Conditions	Yield
With C49H53N4O4PS In diethyl ether at 0℃; enantioselective reaction;	98%

n-pentanethiol (110-66-7) + C19H21NO5 → C24H33NO5S

Conditions	Yield
Stage #1: n-pentanethiol; C19H21NO5 In dichloromethane for 0.5h; Stage #2: With Dimethyl(phenyl)phosphine In dichloromethane at 20℃; for 3h;	98%

thiophene (110-01-0) + n-pentanethiol (110-66-7) + dimethyl amine (124-40-3) → Thiram (137-26-8)

Conditions	Yield
Stage #1: thiophene; n-pentanethiol; dimethyl amine With sodium nitrate at 24℃; for 2.83333h; Stage #2: With lead(IV) tetraacetate; nickel dibromide at 18℃; for 4h; Temperature;	97.8%

furfural (98-01-1) + n-pentanethiol (110-66-7) → 2-(bis(pentylthio)methyl)furan

Conditions	Yield
With H-beta(19) zeolite In neat (no solvent) at 23℃; for 6h;	97%
With graphene oxide In neat (no solvent) at 20℃; for 3h; Green chemistry; chemoselective reaction;	92%

triethylsilane (617-86-7) + n-pentanethiol (110-66-7) → triethyl(pentylthio)silane (33577-01-4)

Conditions	Yield
With [RuCl(η5-(3-phenyl)indenyl)(PPh3)2] In toluene at 80℃; for 16h; Glovebox;	96%
(i) NiCl2, (ii) /BRN= 1730979/; Multistep reaction;

n-pentanethiol (110-66-7) + 4-Chloro-2-(4-methyl-1-piperazinyl)quinazoline (39213-06-4) → 2-(4-Methyl-piperazin-1-yl)-4-pentylsulfanyl-quinazoline (129663-85-0)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	96%

n-pentanethiol (110-66-7) → 1-pentanesulfinic acid (76008-87-2)

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane at -40℃;	96%

n-pentanethiol (110-66-7) + allyl methyl carbonate (35466-83-2) → allyl pentyl sulfide (3393-13-3)

Conditions	Yield
With chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) In acetonitrile at 20℃; for 1h; Alkylation;	96%

n-pentanethiol (110-66-7) + 1,2,4,5-tetrabromomethylbenzene (15442-91-8) → 1,2,4,5-tetrakis(pentylsulfanylmethyl)benzene (261912-38-3)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Substitution;	96%

1-benzhydryl-3-azetidinyl methanesulfonate (33301-41-6) + n-pentanethiol (110-66-7) → 1-(diphenylmethyl)-3-(pentylthio)azetidine (1309207-50-8)

Conditions	Yield
Stage #1: n-pentanethiol With sodium hydride In dimethyl sulfoxide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-benzhydryl-3-azetidinyl methanesulfonate In dimethyl sulfoxide at 0 - 20℃;	96%

n-pentanethiol (110-66-7) + 2-methyl-but-3-yn-2-ol (115-19-5) → C10H20OS

Conditions	Yield
With (N,N′-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene)Pd(acac)Cl; 3-isopropyl-6-methylcyclohexa-1,4-diene; triethylamine In neat (no solvent) at 100℃; for 8h; Green chemistry; regioselective reaction;	96%

n-pentanethiol (110-66-7) + 5-hexynonitrile (14918-21-9) → C11H19NS

Conditions	Yield
With (N,N′-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene)Pd(acac)Cl; 3-isopropyl-6-methylcyclohexa-1,4-diene; triethylamine In neat (no solvent) at 100℃; for 8h; Green chemistry; regioselective reaction;	96%

n-pentanethiol (110-66-7) + epichlorohydrin (106-89-8) → 3-chloro-1-pentylsulfanyl-propan-2-ol (26404-98-8)

Conditions	Yield
With dimethylbromosulphonium bromide at 20℃; for 0.0666667h; regioselective reaction;	95%
With zinc(II) chloride

n-pentanethiol (110-66-7) + methyl (3-phenylprop-2-yn-1-yl) carbonate (420121-38-6) → pentyl 3-phenylprop-2-ynyl sulfide

Conditions	Yield
With N-methylcyclohexylamine; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 100℃; for 8h;	95%

Upstream product

• 71-41-0 pentan-1-ol 
• 110-53-2 1-Bromopentane 
• 17356-08-0 thiourea 
• 56342-26-8 cyano-dithiocarbonimidic acid dipentyl ester 
• 110-89-4 piperidine 
• 543-59-9 1-Chloropentane 
• 22537-07-1 4-pentenyl-1-amine 
• 35452-30-3 1-pentanesulfonic acid 
• 4450-76-4 1-pentyl tosylate 
• 110-58-7 n-Pentylamine 
• 112-51-6 diamyl disulfide 
• 7647-01-0 hydrogenchloride 
• 109-67-1 1-penten 
• 554-14-3 2-Methylthiophene 

Downstream Products

• 872-10-6 diamyl sulfide 
• 847040-08-8 6-pentylmercapto-nicotinic acid 
• 7133-20-2 Amyl-cyclohexyl-sulfid 
• 5409-98-3 1,2,4,5-tetrachloro-3,6-bis-pentylsulfanyl-benzene 
• 112-51-6 diamyl disulfide 
• 6303-18-0 n-pentanesulphonyl chloride 
• 66923-44-2 (2,4-dinitro-phenyl)-pentyl sulfide 
• 5443-89-0 6-pentylmercapto-7⁽⁹⁾H-purine 
• 56052-25-6 pentylsulfanyl-acetone 
• 102447-45-0 2-pentylsulfanyl-1,4-diphenyl-butane-1,4-dione 
• 91881-66-2 Pentyl-p-tolyl-trithiocarbonat 
• 1741-83-9 1-(methylthio)pentane 
• 30786-91-5 thiophosphoric acid O-(2-chloromethyl-4-nitro-phenyl) ester S-pentyl ester 
• 13923-26-7 (N-2,4-Dichlor-phenoxyacetyl)-S-n-amyl-thiocarbamat 

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