13242-44-9

Basic information

• Product Name: 2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE
• Synonyms: 2-DIMETHYLAMINOETHYL MERCAPTAN HYDROCHLORIDE;2-DIMETHYLAMINOETHANETHIOL HCL;2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE;DIMETHYLAMINOETHYL MERCAPTAN HYDROCHLORIDE;DIMETHYLAMINOETHANETHIOL HCL;DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE;2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE , F. FLUORESC. 10GR*;Ethanethiol, 2-(dimethylamino)-, hydrochloride
• CAS NO: 13242-44-9
• Molecular Formula: C₄H₁₂NS*Cl
• Molecular Weight: 141.66
• EINECS: 236-221-6
• Product Categories: Derivatization agentsOrganic Building Blocks;Biochemicals and Reagents;Luminescent Compounds/Detection;Sulfur Compounds;Thiol/Mercaptan Salts
• Mol File: 13242-44-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 150-160 °C(lit.)
• Boiling Point: 121.9°Cat760mmHg
• Flash Point: 27.5°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 14.3mmHg at 25°C
• Storage Temp.: Refrigerator (+4°C)
• BRN: 3906670
• CAS DataBase Reference: 2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE(13242-44-9)
• EPA Substance Registry System: 2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE(13242-44-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3335
• WGK Germany: 3
• RTECS: KJ1051000
• F: 3-10-13-23
• Hazardous Substances Data: 13242-44-9(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

InChI:InChI=1/C4H11NS.ClH/c1-5(2)3-4-6;/h6H,3-4H2,1-2H3;1H

Synthetic route

(2-chloroethyl)dimethylamine hydrochloride (4584-46-7) → 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9)

Conditions	Yield
Stage #1: (2-chloroethyl)dimethylamine hydrochloride With sodium thiosulfate In water for 10h; Heating; Stage #2: With hydrogenchloride at 85℃; for 2h; Further stages.;

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + 1-(Chloromethyl-dimethyl-silanyl)-2-{tris-[2-(chloromethyl-dimethyl-silanyl)-ethyl]-silanyl}-ethane (199983-80-7) → [2-({Dimethyl-[2-(tris-{2-[(2-dimethylamino-ethylsulfanylmethyl)-dimethyl-silanyl]-ethyl}-silanyl)-ethyl]-silanyl}-methylsulfanyl)-ethyl]-dimethyl-amine

Conditions	Yield
With sodium hydroxide In ethanol; water at 80℃; for 9.5h;	99%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + suberoyl chloride (10027-07-3) → (2-thiosuberoyloxydiethyl)-bis(dimethylamine) dihydrochloride (143434-02-0)

Conditions	Yield
In dichloromethane for 24h; Heating;	98.6%

bismuth(III) chloride (7787-60-2) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → Bi(3+)*3Cl(1-)*SC2H4NH(CH3)2=BiCl3SC2H4NH(CH3)2

Conditions	Yield
In tetrahydrofuran; ethanol pptn.; recrystn. (water); elem. anal.;	97%

bismuth(III) chloride (7787-60-2) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → BiCl3(SCH2CH2N(CH3)2H) (200342-37-6)

Conditions	Yield
In tetrahydrofuran; ethanol (N2); elem. anal.;	97%

8-dioxane-3-cobalt bis(dicarbollide) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C10H28B9NO2S(1-)*Co*C2H9B9*Na(1+)

Conditions	Yield
With sodium hydride In tetrahydrofuran; toluene; mineral oil Heating;	95%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → 2-(dimethylamino)ethane-1-sulfonyl chloride hydrochloride (118646-39-2)

Conditions	Yield
With chlorine In methanol; water at -5 - 0℃; for 1.5h;	94%

(+)-brefeldin A (20350-15-6) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → (E)-(2S,3aR,4S,5R,9S,14aS)-5-(2-Dimethylamino-ethylsulfanyl)-2,4-dihydroxy-9-methyl-1,2,3,3a,4,5,6,9,10,11,12,14a-dodecahydro-8-oxa-cyclopentacyclotridecen-7-one

Conditions	Yield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In methanol; water for 2h; Ambient temperature;	94%

C27H52O2Si3 + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C43H96N4O2S4Si3*4ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 4h; Irradiation; regioselective reaction;	93%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + chloroacetic acid (79-11-8) → 2-((2-(dimethylamino)ethyl)thio)acetic acid hydrochloride (1415981-68-8)

Conditions	Yield
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride; chloroacetic acid With potassium methanolate In methanol at 40℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In isopropyl alcohol pH=2;	93%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + 1-{Bis-[2-(chloromethyl-dimethyl-silanyl)-ethyl]-methyl-silanyl}-2-[tris-(2-{bis-[2-(chloromethyl-dimethyl-silanyl)-ethyl]-methyl-silanyl}-ethyl)-silanyl]-ethane (199983-94-3) → C84H204N8S8Si13

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 85℃; for 11h;	92%

N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indole-3-yl)-pyrimidine-2-amine (1421372-94-2) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → N-(4-((2-(dimethylamino)ethyl)thio)-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine

Conditions	Yield
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.75h; Inert atmosphere; Stage #2: N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indole-3-yl)-pyrimidine-2-amine In N,N-dimethyl-formamide Inert atmosphere;	90.42%
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 4h;	71%
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With sodium hydride In hexane; N,N-dimethyl-formamide for 0.75h; Inert atmosphere; Stage #2: N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indole-3-yl)-pyrimidine-2-amine In hexane; N,N-dimethyl-formamide Inert atmosphere;	2.5 g

C15H28O2Si + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C23H50N2O2S2Si*2ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 4h; Irradiation; regioselective reaction;	90%

C51H100O2Si7 + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C83H188N8O2S8Si7*8ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 4h; Irradiation; regioselective reaction;	90%

C61H120O2Si7 + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C93H208N8O2S8Si7*8ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 4h; Irradiation; regioselective reaction;	89%

6,7-dibromo-2,3-naphthalenedicarbonitrile (74815-81-9) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → 2,3-dicyano-6,7-bis[(2-dimethylamino)ethylthio]naphthalene (1335029-25-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide at 20℃; for 1h;	88%

C25H48O2Si + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C33H70N2O2S2Si*2ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 4h; Irradiation; regioselective reaction;	88%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + nocathiacin I → C65H71N15O18S6

Conditions	Yield
With triethylamine In water at -20℃; for 24h; Michael addition;	87%

9-hydroxyxanthene (90-46-0) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → 9-<<2-(dimethylamino)ethyl>thio>-9H-xanthene hydrochloride (78264-38-7)

Conditions	Yield
In acetonitrile for 1.25h; Heating;	86%

C50H70Cl3NP2Si4 (1401456-65-2) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → (Ph2PCH2)2N(C6H4-4-Si(CH2CH2CH2SiMe2(CH2S(CH2)2NMe2))3) (1401456-67-4)

Conditions	Yield
With sodium hydroxide In ethanol; water at 80℃; Inert atmosphere;	86%

C9H17N3Si (1426827-47-5) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C17H39N5S2Si*2ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 3h; Inert atmosphere; Irradiation;	86%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + phenylacetyl chloride (103-80-0) → (2-phenylthioacetoxyethyl)dimethylammonium chloride (143434-00-8)

Conditions	Yield
In dichloromethane a.) RT, 45 min, b.) reflux, 24 h;	85.88%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + 2-chloro-4-(thien-2'-yl)pyrimidine (83726-75-4) → N,N-dimethyl-2-<<4'-(thien-2''yl)pyrimidin-2'-yl>thio>ethylamine (83726-78-7)

Conditions	Yield
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With sodium ethanolate at 20℃; for 0.25h; Stage #2: 2-chloro-4-(thien-2'-yl)pyrimidine at 70℃; for 12h; Further stages.;	85%
With sodium ethanolate In ethanol for 5h; Heating;	1.25 g

C29H45NO2Si3 (1426827-54-4) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C45H89N5O2S4Si3*4ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 3h; Inert atmosphere; Irradiation;	84%

C37H72O2Si3 + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → C53H116N4O2S4Si3*4ClH

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran; methanol for 4h; Irradiation; regioselective reaction;	84%

(NEt4)[Ni(2-(N-(dimethylaminoethyl)aminocarbonyl)benzenethiolate)Cl] + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → [Ni3(2-(N-(dimethylaminoethyl)aminocarbonyl)benzenethiolate)2(N,N-dimethylaminoethanethiolate)2]

Conditions	Yield
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With sodium hydroxide In methanol for 0.0833333h; Inert atmosphere; Stage #2: (NEt4)[Ni(2-(N-(dimethylaminoethyl)aminocarbonyl)benzenethiolate)Cl] In methanol for 24h; Inert atmosphere;	84%

6-chloro-7-fluoro-8-nitro-9H-β-carboline (783349-34-8) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → [2-(6-chloro-8-nitro-9H-β-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amine (783349-57-5)

Conditions	Yield
Stage #1: 6-chloro-7-fluoro-8-nitro-9H-β-carboline; 2-(N,N-dimethylamino)ethylthiol hydrochloride With n-butyllithium In DMF (N,N-dimethyl-formamide) at 20℃; for 0.583333h; Stage #2: With sodium hydrogencarbonate In water at 20℃;	83%
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With n-butyllithium In DMF (N,N-dimethyl-formamide); hexane at 20℃; for 0.0833333h; Stage #2: 6-chloro-7-fluoro-8-nitro-9H-β-carboline In DMF (N,N-dimethyl-formamide); hexane at 20℃; for 0.5h; Stage #3: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide); hexane; water at 20℃;	83%

{(platinum(II))(μ-chloro)(σ,π-8-methoxy-cycloocten-1-yl)}2 + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → [Pt(SCH2CH2NMe2)(8-methoxycyclooct-4-ene-1-yl)] (1338246-79-9)

Conditions	Yield
With NaOMe In methanol (N2); using Schlenk techniques; addn. of NaOMe in MeOH to methanolic soln. of Me2NCH2CH2SH*HCl, addn. of Pt2(μ-Cl)2(C8H12OMe)2, stirring for 15 min; evapn. to dryness, extn. with CH2Cl2; elem. anal.;	83%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → bis(N,N-dimethyl-2-aminoethyl)disulfide (1072-11-3)

Conditions	Yield
With sodium chlorite In methanol; water at 25℃; for 0.5h; Dimerization;	82%
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With iodine In methanol Stage #2: With sodium hydroxide In water pH=> 10;	80%
With sodium chlorite In methanol; water at 0℃; Dimerization;

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium (12092-47-6) + 2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) → [Rh2(S(CH2)2N(CH3)2)2(C8H12)2]

Conditions	Yield
With potassium tert-butylate In methanol stirring (30 min), evaporation; drying, extracting (CH2Cl2), filtration, concentration, addition (CH3CN), coo;ing (-20°C), filtration (with cool CH3CN), drying (vac.); elem. anal.;	82%

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + 2-chloro-4-(2'-furanyl)pyrimidine (124959-28-0) → N,N-dimethyl-2-<(4'-furan-2''-ylpyrimidin-2'-yl)thio>ethylamine (109628-19-5)

Conditions	Yield
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With sodium ethanolate at 20℃; for 0.25h; Stage #2: 2-chloro-4-(2'-furanyl)pyrimidine at 70℃; for 12h; Further stages.;	81%
Stage #1: 2-(N,N-dimethylamino)ethylthiol hydrochloride With sodium ethanolate In ethanol at 20℃; for 0.25h; Inert atmosphere; Stage #2: 2-chloro-4-(2'-furanyl)pyrimidine In ethanol at 70℃; Inert atmosphere;	81%

Upstream product

• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 

Downstream Products

• 13724-91-9 3-(2-Dimethylamino-aethylmercapto)-rifamycin SV 
• 85274-35-7 Dimethyl-[2-(7-methyl-3-phenyl-quinolin-2-ylsulfanyl)-ethyl]-amine 
• 110486-80-1 2-(2-Dimethylamino-ethylsulfanyl)-3-phenyl-quinoline-4-carboxylic acid amide 
• 85275-20-3 2-(2-dimethylaminoethylthio)-3-(p-hydroxyphenyl)quinoline hydrochloride 
• 85273-96-7 ICI 169369 
• 143434-00-8 (2-phenylthioacetoxyethyl)dimethylammonium chloride 
• 102941-56-0 2-<<2-(N,N-dimethylamino)ethyl>thio>-4'-chloroacetophenone 
• 110487-30-4 [2-(3-Cyclohexyl-quinolin-2-ylsulfanyl)-ethyl]-dimethyl-amine 
• 110486-79-8 [2-(2-Dimethylamino-ethylsulfanyl)-3-phenyl-quinolin-7-yl]-dimethyl-amine 
• 110486-96-9 Dimethyl-{2-[3-(1-phenyl-ethyl)-quinolin-2-ylsulfanyl]-ethyl}-amine 

Relevant articles and documents

Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: Versatile and switchable access to functionalized proteins

An efficient and robust oxidative elimination of cysteine to dehydroalanine has been discovered. The reaction is induced by O-mesitylenesulfonylhydroxylamine (MSH) and is compatible with methionine. The key elimination has been executed on protein surfaces and allows ready access to different post-translationally modified proteins through conjugate addition of sulfur nucleophiles to dehydroalanine. Treatment of the resulting thioether with MSH results in regeneration of dehydroalanine, allowing a "functional switch" by subsequent addition of a different thiol. Copyright