628-00-2

Basic information

• Product Name: 2-HEPTANETHIOL
• Synonyms: 2-HEPTANETHIOL
• CAS NO: 628-00-2
• Molecular Formula: C₇H₁₆S
• Molecular Weight: 132.26694
• Mol File: 628-00-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: -141°C
• Boiling Point: 174.25°C (estimate)
• Flash Point: 43 °C
• Appearance: /
• Density: 0.8311
• Vapor Pressure: 2.47mmHg at 25°C
• Refractive Index: 1.4454
• CAS DataBase Reference: 2-HEPTANETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HEPTANETHIOL(628-00-2)
• EPA Substance Registry System: 2-HEPTANETHIOL(628-00-2)

Safety Data

• Hazardous Substances Data: 628-00-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid; pungent, sulfurous odor.

InChI:InChI=1/C7H16S/c1-3-4-5-6-7(2)8/h7-8H,3-6H2,1-2H3

Synthetic route

2-(acetylthio)heptane (76790-71-1) → heptane-2-thiol (628-00-2)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at -10 - 20℃; for 2h;	82%
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 2h; Inert atmosphere;

2-(p-toluenesulfonyl)heptane (5011-57-4) → heptane-2-thiol (628-00-2)

Conditions	Yield
With sodium hydrogensulfide In N,N-dimethyl-formamide at 80℃; for 2h;	40%
Multi-step reaction with 2 steps 1: 84 percent / dimethylformamide / 2 h / 80 °C 2: 82 percent / LiAlH4 / diethyl ether / 2 h / -10 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 2: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere View Scheme

1-Heptene (592-76-7) + diethyltetrasulfane (13730-34-2) → Diethyl disulfide (110-81-6) + heptane-2-thiol (628-00-2)

Conditions	Yield
at 180℃; im Rohr;

1-Heptene (592-76-7) + diethyltetrasulfane (13730-34-2) → heptane-2-thiol (628-00-2)

Conditions	Yield
at 180℃; bei 10.-stdg.Erhitzen im Rohr;

2-iodoheptane (18589-29-2) → heptane-2-thiol (628-00-2)

Conditions	Yield
With ethanol; potassium hydrosulfide

2-bromoheptane (1974-04-5) → heptane-2-thiol (628-00-2)

Conditions	Yield
With ethanol; potassium hydrosulfide zuletz bei Siedetemperatur;

2-Heptanol (52390-72-4, 543-49-7) → heptane-2-thiol (628-00-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / pyridine / 0 - 20 °C 2: 40 percent / NaHS*H2O / dimethylformamide / 2 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1: 76 percent / pyridine / 0 - 20 °C 2: 84 percent / dimethylformamide / 2 h / 80 °C 3: 82 percent / LiAlH4 / diethyl ether / 2 h / -10 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: HBr / 60 °C 2: alcohol; KSH / zuletz bei Siedetemperatur View Scheme
Multi-step reaction with 2 steps 1: phosphorus; iodine 2: alcohol; potassium hydrosulfide View Scheme
Multi-step reaction with 3 steps 1: pyridine / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere View Scheme

n-pentylmagnesium bromide (693-25-4) → heptane-2-thiol (628-00-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether 2: phosphorus; iodine 3: alcohol; potassium hydrosulfide View Scheme

heptane-2-thiol (628-00-2) + carbon dioxide (124-38-9) + cyclohexylamine (108-91-8) → C14H27NOS (1018985-23-3)

Conditions	Yield
Stage #1: carbon dioxide; cyclohexylamine In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: heptane-2-thiol With triphenylphosphine; diethylazodicarboxylate In dimethyl sulfoxide at 20℃; for 4h; Further stages.;	90%

carbon disulfide (75-15-0) + heptane-2-thiol (628-00-2) + cyclohexylmethanethiol (2550-37-0) → C15H28S3 (1051887-04-7)

Conditions	Yield
Stage #1: carbon disulfide; heptane-2-thiol In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: cyclohexylmethanethiol With triphenylphosphine; diethylazodicarboxylate In dimethyl sulfoxide at 20℃; for 3h; Further stages.;	90%

heptane-2-thiol (628-00-2) → 2-chlorosulfonyl heptane (922-76-9)

Conditions	Yield
With chlorine; acetic acid
With chlorine; acetic acid

tetrachloromethane (56-23-5) + heptane-2-thiol (628-00-2) → bis-(1-methyl-hexyl)-sulfane (45162-42-3) + Na2S

Conditions	Yield
at 260℃; im Rohr;Geschwindigkeit der Reaktion;

heptane-2-thiol (628-00-2) + methyl iodide (74-88-4) → 2-(methylthio)heptane

Conditions	Yield
Stage #1: heptane-2-thiol With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0 - 20℃; for 0.333333h; Inert atmosphere;

Upstream product

• 1974-04-5 2-bromoheptane 
• 693-25-4 n-pentylmagnesium bromide 
• 52390-72-4 2-Heptanol 
• 76790-71-1 2-(acetylthio)heptane 
• 5011-57-4 2-heptyltoluene-p-sulphonate 
• 18589-29-2 2-iodoheptane 
• 592-76-7 1-Heptene 
• 13730-34-2 diethyltetrasulfane 

Downstream Products

• 54063-12-6 2-(methylthio)heptane 
• 1051887-04-7 C₁₅H₂₈S₃ 
• 1018985-23-3 C₁₄H₂₇NOS 

Relevant articles and documents

Structure-odor correlations in homologous series of alkanethiols and attempts to predict odor thresholds by 3d-qsar studies

Homologous series of alkane-1-thiols, alkane-2-thiols, alkane-3-thiols, 2-methylalkane-1-thiols, 2-methylalkane-3-thiols, 2-methylalkane-2-thiols, and alkane-1,??-dithiols were synthesized to study the influence of structural changes on odor qualities and odor thresholds. In particular, the odor thresholds were strongly influenced by steric effects: In all homologous series a minimum was observed for thiols with five to seven carbon atoms, whereas increasing the chain length led to an exponential increase in the odor threshold. Tertiary alkanethiols revealed clearly lower odor thresholds than found for primary or secondary thiols, whereas neither a second mercapto group in the molecule nor an additional methyl substitution lowered the threshold. To investigate the impact of the SH group, odor thresholds and odor qualities of thiols were compared to those of the corresponding alcohols and (methylthio)alkanes. Replacement of the SH group by an OH group as well as S-methylation of the thiols significantly increased the odor thresholds. By using comparative molecular field analysis, a 3D quantitative structure-activity relationship model was created, which was able to simulate the odor thresholds of alkanethiols in good agreement with the experimental results. NMR and mass spectrometric data for 46 sulfur-containing compounds are additionally supplied.