638-00-6

Basic information

• Product Name: 2,4-DIMETHYLTHIOPHENE
• Synonyms: Thiophene, 2,4-dimethyl-;2,4-DIMETHYLTHIOPHENE
• CAS NO: 638-00-6
• Molecular Formula: C₆H₈S
• Molecular Weight: 112.19
• EINECS: 211-312-3
• Mol File: 638-00-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: -66.9°C (estimate)
• Boiling Point: 139-141°C
• Flash Point: 23 °C
• Appearance: /liquid (estimate)
• Density: 0,994 g/cm3
• Vapor Pressure: 0.035mmHg at 25°C
• Refractive Index: 1.5078
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2,4-DIMETHYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIMETHYLTHIOPHENE(638-00-6)
• EPA Substance Registry System: 2,4-DIMETHYLTHIOPHENE(638-00-6)

Safety Data

• Statements: 10-36/37/38
• Safety Statements: 16-36/37/39-26
• RIDADR: 1993
• HazardClass: IRRITANT
• Hazardous Substances Data: 638-00-6(Hazardous Substances Data)

Usage

Uses

2,4-Dimethylthiophene is a biochemical used for proteomics and food research.

InChI:InChI=1/C6H6Br2S/c1-3-5(7)4(2)9-6(3)8/h1-2H3

Synthetic route

4-bromo-2-methylthiophene (29421-92-9) + methylmagnesium chloride (676-58-4) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 22h;	79%
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; diethyl ether Kumada coupling; Heating;

thiophene-2,4-dicarbaldehyde (932-93-4) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol	76%

3-Methylthiophene (616-44-4) + methyl iodide (74-88-4) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; for 4h; Further stages.;	73%
Stage #1: 3-Methylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 0 - 20℃; for 3h; Stage #2: methyl iodide at 0 - 20℃; for 5h;	68%
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; pentane at -78 - 20℃; for 2h;

methyl magnesium iodide (917-64-6) + 4-bromo-2-methylthiophene (29421-92-9) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
nickel 1,3-bis(diphenylphosphino)propane In diethyl ether for 22h; Heating;	66%

4-methylthiophene-2-carbaldehyde (6030-36-0) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
Bildung ueber das Hydrazon;

2,5-Dimethyl-[1,4]dithiin (78334-38-0) → 2,4-dimethylthiophene (638-00-6)

4-methyl-pent-3-en-2-one (141-79-7) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With sulfur at 200℃;

2-methyl-4-oxopentanoic acid (6641-83-4) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With diphosphorus trisulfide
With phosphorous (V) sulfide

1,3-Dimethyl-1,3-butadien (1118-58-7) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With sulfur at 260℃;

methyloxirane (75-56-9, 16033-71-9) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With aluminum oxide; hydrogen sulfide at 400℃;

2-Methylthiophene (554-14-3) + Methyl fluoride (593-53-3) → 2,3-dimethylthiophene (632-16-6) + 2,4-dimethylthiophene (638-00-6) + 2,5-DIMETHYLTHIOPHENE (638-02-8)

Conditions	Yield
With oxygen; trimethylamine In gas at 37.5℃; Product distribution; Kinetics; Mechanism; radiolysis: 1.5*104 Gy at 5*105 Gy h-1; variable pressures;

2-Methylthiophene (554-14-3) → 2-ethylthiophene (872-55-9) + 2,4-dimethylthiophene (638-00-6) + 2,5-DIMETHYLTHIOPHENE (638-02-8) + 3-Methylthiophene (616-44-4)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 11.7 % Chromat. B 0.6 % Chromat. C 4.9 % Chromat. D 9.2 % Chromat.

2,3-dimethylthiophene (632-16-6) → 3,4-dimethylthiophene (632-15-5) + 2-ethylthiophene (872-55-9) + 2,4-dimethylthiophene (638-00-6) + 3-Methylthiophene (616-44-4)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 2.3 % Chromat. B 1.5 % Chromat. C 1.5 % Chromat. D 12.8 % Chromat.

3,4-dimethylthiophene (632-15-5) → thiophene (188290-36-0) + 2-Methylthiophene (554-14-3) + 2,4-dimethylthiophene (638-00-6) + toluene (108-88-3)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 1.9 % Chromat. B 1.4 % Chromat. C 6.2 % Chromat. D 2.4 % Chromat.

3,4-dimethylthiophene (632-15-5) → 2,3-dimethylthiophene (632-16-6) + 2,4-dimethylthiophene (638-00-6) + 2,5-DIMETHYLTHIOPHENE (638-02-8) + 3-Methylthiophene (616-44-4)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 5.1 % Chromat. B 6.2 % Chromat. C 1.1 % Chromat. D 12.2 % Chromat.

3,4-dimethylthiophene (632-15-5) → 2,4-dimethylthiophene (638-00-6) + 2,5-DIMETHYLTHIOPHENE (638-02-8) + 3-Methylthiophene (616-44-4) + benzene (71-43-2)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 6.2 % Chromat. B 1.1 % Chromat. C 12.2 % Chromat. D 17.6 % Chromat.

2,5-DIMETHYLTHIOPHENE (638-02-8) → 2-Methylthiophene (554-14-3) + 2,4-dimethylthiophene (638-00-6) + toluene (108-88-3) + benzene (71-43-2)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 15.4 % Chromat. B 3.3 % Chromat. C 2.6 % Chromat. D 36.9 % Chromat.

3-Methylthiophene (616-44-4) → thiophene (188290-36-0) + 2,3-dimethylthiophene (632-16-6) + 2,4-dimethylthiophene (638-00-6) + benzene (71-43-2)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 13.6 % Chromat. B 13.6 % Chromat. C 1.7 % Chromat. D 7.7 % Chromat.

3-Methylthiophene (616-44-4) → 2-Methylthiophene (554-14-3) + 2,3-dimethylthiophene (632-16-6) + 3,4-dimethylthiophene (632-15-5) + 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 14.4 % Chromat. B 13.6 % Chromat. C 1.7 % Chromat. D 1.7 % Chromat.

α-methyl-levulinic acid → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With diphosphorus trisulfide

hydrogen sulfide (7783-06-4) + methyloxirane (75-56-9, 16033-71-9) + aluminium oxide → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
at 400℃;

1,3-Dimethyl-1,3-butadien (1118-58-7) + sulfur → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
at 260℃;

3-Methylthiophene (616-44-4) + methyl iodide (74-88-4) → 2,3-dimethylthiophene (632-16-6) + 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
Stage #1: 3-Methylthiophene With methyllithium In tetrahydrofuran at 20℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; Further stages.;
Stage #1: 3-Methylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane Stage #2: methyl iodide In diethyl ether; hexane Further stages. Title compound not separated from byproducts.;

2-bromo-4-methylthiophene (53119-60-1) + methylmagnesium chloride (676-58-4) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; diethyl ether Kumada coupling; Heating;

2-bromo-5-methyl thiophene (765-58-2) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 80 percent / methanol / tetrahydrofuran; hexane 2.1: 79 percent / Ni(dppp)Cl2 / diethyl ether / 22 h View Scheme

3-Methylthiophene (616-44-4) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: butyl lithium; diethyl ether / Behandeln mit Dimethylformamid und Hydrolysieren 2: Bildung ueber das Hydrazon View Scheme

2,4-dimethyl-2,5-dihydrothiophene (78519-11-6) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With bunazosin In benzene

4-bromo-2-methylthiophene (29421-92-9) + methylmagnesium bromide (75-16-1) → 2,4-dimethylthiophene (638-00-6)

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride In diethyl ether for 24h; Inert atmosphere; Reflux;

thiophene (188290-36-0) + Dimethyldisulphide (624-92-0) → 2-Methylthiophene (554-14-3) + 3,4-dimethylthiophene (632-15-5) + 2,4-dimethylthiophene (638-00-6) + 2,3,4-trimethylthiophene (1795-04-6) + 2,5-DIMETHYLTHIOPHENE (638-02-8) + tetramethylthiophene (14503-51-6) + 3-Methylthiophene (616-44-4) + methylthiol (74-93-1) + dimethylsulfide (75-18-3) + hydrogen sulfide (7783-06-4)

Conditions	Yield
With Co/HZSM-5 at 300℃; under 760.051 Torr; Inert atmosphere; Flow reactor;

...Expand

2,4-dimethylthiophene (638-00-6) → 2,4-dibromo-3,5-dimethylthiophene (63862-00-0)

Conditions	Yield
With bromine for 0.05h; Ambient temperature;	96%
With bromine In acetic acid	65%
With carbon disulfide; bromine Erwaermen des Reaktionsprodukts mit methanol. Kalilauge;

2,4-dimethylthiophene (638-00-6) → 4-methylthiophene-2-carbaldehyde (6030-36-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Inert atmosphere;	95%

2,4-dimethylthiophene (638-00-6) + N,N-bis(4-methylphenyl)-N-(4-iodophenyl) amine (58047-43-1) → 2,4-dimethyl-5-(4-(N,N'-bis(4-methylphenyl)amino)phenyl)thiophene

Conditions	Yield
Stage #1: 2,4-dimethylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 20℃; for 2h; Stage #2: With zinc(II) chloride In diethyl ether at 20℃; for 5h; Stage #3: N,N-bis(4-methylphenyl)-N-(4-iodophenyl) amine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20 - 50℃; for 7h;	92%

2,4-dimethylthiophene (638-00-6) + iodobenzene (591-50-4) → 2,4-dimethyl-5-phenylthiophene (57021-49-5)

Conditions	Yield
Stage #1: 2,4-dimethylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In diethyl ether; hexane at -30 - 20℃; for 6h; Metallation; Stage #2: iodobenzene; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether; hexane at 50℃; for 12h; Phenylation;	90%
Yield given. Multistep reaction;

2,4-dimethylthiophene (638-00-6) → 2,4-dimethyl-5-chloro-thiophene

Conditions	Yield
With sulfuryl dichloride In dichloromethane for 2h; Reflux;	85%
	28%
With sulfuryl dichloride In dichloromethane

2,4-dimethylthiophene (638-00-6) + (E)-4-bromostilbene (13041-70-8) → 3,5-dimethyl-2-(4-styrylphenyl)thiophene

Conditions	Yield
Stage #1: 2,4-dimethylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In diethyl ether; hexane at -30 - 20℃; for 6h; Metallation; Stage #2: (E)-4-bromostilbene; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether; hexane at 50℃; for 12h; Arylation;	80%

2,4-dimethylthiophene (638-00-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3,5-dimethyl-2-thiophenecarboxaldehyde (85895-83-6)

Conditions	Yield
With trichlorophosphate 1.) r.t., 1 h, 2.) heating, 30 min;	77%
With trichlorophosphate at 70 - 75℃; for 3h;	66%
With diethyl ether anschliessendes Hydrolysieren;

2,4-dimethylthiophene (638-00-6) + trifluoroacetic anhydride (407-25-0) → 1-(3,5-dimethylthiophen-2-yl)-2,2,2-trifluoroethanone (65613-26-5)

Conditions	Yield
With magnesium perchlorate dihydrate In 1,2-dichloro-ethane at 60℃; for 12h; Friedel-Crafts Acylation; regioselective reaction;	76%

3,5-dimethylthiophene-2-carbonyl chloride (679806-34-9) + 2,4-dimethylthiophene (638-00-6) → bis(3,5-dimethyl-2-thienyl) ketone (910479-27-5)

Conditions	Yield
With aluminium trichloride In dichloromethane for 4h;	72%

2,4-dimethylthiophene (638-00-6) + tert-Butyl acrylate (1663-39-4) → tert-butyl (E)-3-(3,5-dimethylthiophen-2-yl)acrylate

Conditions	Yield
With 4-(ethylthio)-N,N-dimethylaniline; palladium diacetate; acetic acid; hydroquinone at 60℃; for 3h;	65%

2,4-dimethylthiophene (638-00-6) → 3,3',5,5'-tetramethyl-2,2'-bithiophene

Conditions	Yield
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -78℃; for 3h; Inert atmosphere;	44%
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -78℃;	44 % Chromat.

2,4-dimethylthiophene (638-00-6) + oxalyl dichloride (79-37-8) → 1,2-bis(3,5-dimethyl-2-thienyl)ethane-1,2-dione (779332-89-7)

Conditions	Yield
With aluminium trichloride In n-heptane; 1,2-dichloro-ethane at -20℃; for 2.3h; Friedel-Crafts reaction;	44%

2,4-dimethylthiophene (638-00-6) + 2-bromoaniline (615-36-1) → 2-(2'-bromophenyl)-3,5-dimethylthiophene (106183-35-1)

Conditions	Yield
With isopentyl nitrite at 70℃; for 4h;	43%

2,4-dimethylthiophene (638-00-6) + 1-(2,3,3,4,4,5,5-Heptafluoro-1-cyclopenten-1-yl)-2-methylnaphthalene (1309657-46-2) → 3,5-dimethyl-2-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-1-naphthalenyl)-1-cyclopenten-1-yl]thiophene (1628556-77-3)

Conditions	Yield
Stage #1: 2,4-dimethylthiophene With N,N,N,N,-tetramethylethylenediamine In diethyl ether at 0℃; Inert atmosphere; Stage #2: With n-butyllithium In diethyl ether; hexane Inert atmosphere; Reflux; Stage #3: 1-(2,3,3,4,4,5,5-Heptafluoro-1-cyclopenten-1-yl)-2-methylnaphthalene In diethyl ether; hexane at -70 - 20℃; Inert atmosphere;	43%

2,4-dimethylthiophene (638-00-6) + 1-[2,4-dimethyl-5-(2'',4'',5''-triphenylimidazolyl-4'-yl)-3-thienyl]perfluorocyclopentene (360561-22-4) → 1-(3,5-dimethyl-2-thienyl)-2-[2,4-dimethyl-5-(2'',4'',5''-triphenylimidazol-4'-yl)-3-thienyl]perfluorocyclopentene (360773-76-8)

Conditions	Yield
Stage #1: 2,4-dimethylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 1-[2,4-dimethyl-5-(2'',4'',5''-triphenylimidazolyl-4'-yl)-3-thienyl]perfluorocyclopentene In tetrahydrofuran at -78℃; for 1h; Further stages.;	42%

2,4-dimethylthiophene (638-00-6) + 3,3-dimethoxy-4-oxo-cyclohexa-1,5-dienecarbonitrile (246222-31-1) → 4-(3,5-dimethyl-thiophen-2-yloxy)-3-methoxy-benzonitrile + (1S,2S,6S,7S)-10,10-Dimethoxy-4,6-dimethyl-11-oxo-3-thia-tricyclo[5.2.2.02,6]undeca-4,8-diene-9-carbonitrile

Conditions	Yield
for 5h; Diels-Alder reaction; Heating;	A 3% B 40%

2,4-dimethylthiophene (638-00-6) + 4-acetyl-6,6-dimethoxy-cyclohexa-2,4-dienone (219755-75-6) → 1-[2-(3,5-dimethyl-thiophen-2-yl)-4-hydroxy-3-methoxy-phenyl]-ethanone + (1S,2S,6S,7S)-10-Acetyl-9,9-dimethoxy-4,6-dimethyl-3-thia-tricyclo[5.2.2.02,6]undeca-4,10-dien-8-one

Conditions	Yield
for 5h; Diels-Alder reaction; Heating;	A 33% B 21%

2,4-dimethylthiophene (638-00-6) + 3,3-dimethoxy-4-oxo-cyclohexa-1,5-dienecarboxylic acid methyl ester (124667-66-9) → 4-(3,5-dimethyl-thiophen-2-yloxy)-3-methoxy-benzoic acid methyl ester + 2-(3,5-dimethyl-thiophen-2-yl)-4-hydroxy-3-methoxy-benzoic acid methyl ester + (1S,2S,6S,7S)-10,10-Dimethoxy-4,6-dimethyl-11-oxo-3-thia-tricyclo[5.2.2.02,6]undeca-4,8-diene-9-carboxylic acid methyl ester

Conditions	Yield
for 5h; Diels-Alder reaction; Heating;	A 6% B 12% C 32%

2,4-dimethylthiophene (638-00-6) + chloromethyl methyl ether (107-30-2) → 2,4-bis(chloromethyl)-3,5-dimethylthiophene (133296-08-9)

Conditions	Yield
With titanium tetrachloride In carbon disulfide Ambient temperature;	22%

2,4-dimethylthiophene (638-00-6) + carbamic chloride (463-72-9) → 3,5-dimethyl-thiophene-2-carboxylic acid amide (98547-25-2)

Conditions	Yield
With carbon disulfide; aluminium trichloride

2,4-dimethylthiophene (638-00-6) + acetic anhydride (108-24-7) → 1-(3,5-dimethyl-[2]thienyl)-ethanone (50382-14-4)

Conditions	Yield
With phosphoric acid; benzene

2,4-dimethylthiophene (638-00-6) + acetyl chloride (75-36-5) → 3-Acetyl-2,5-dimethylthiophen (2530-10-1)

Conditions	Yield
With tin(IV) chloride; benzene

2,4-dimethylthiophene (638-00-6) → 2-iodo-3,5-dimethyl-thiophene

Conditions	Yield
With iodine; mercury(II) oxide; benzene

2,4-dimethylthiophene (638-00-6) → 3,5-dimethyl-2-thiophenecarboxaldehyde (85895-83-6)

Conditions	Yield
With n-butyllithium; diethyl ether

2,4-dimethylthiophene (638-00-6) → 3,5-dimethyl-thiophene-2,4-disulfonyl chloride

Conditions	Yield
With sulfuric acid; sulfur trioxide Erwaermen des Dinatrium-Salzes der erhaltenen Disulfonsaeure mit Phosphor(V)-chlorid;

2,4-dimethylthiophene (638-00-6) → 3-hydroxy-3,5-dimethyl-2,3-dihydro-[2]thienylmercury (1+); mercury chloride-double salt of chloride

Conditions	Yield
With ethanol; sodium acetate; mercury dichloride

Upstream product

• 6641-83-4 2-methyl-4-oxopentanoic acid 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 
• 7783-06-4 hydrogen sulfide 
• 75-56-9 methyloxirane 
• 53119-60-1 2-bromo-4-methylthiophene 
• 676-58-4 methylmagnesium chloride 
• 78519-11-6 2,4-dimethyl-2,5-dihydrothiophene 
• 29421-92-9 4-bromo-2-methylthiophene 
• 75-16-1 methylmagnesium bromide 
• 188290-36-0 thiophene 
• 624-92-0 Dimethyldisulphide 
• 1118-58-7 1,3-Dimethyl-1,3-butadien 
• 932-93-4 thiophene-2,4-dicarbaldehyde 
• 616-44-4 3-Methylthiophene 

Downstream Products

• 921596-17-0 N-tert-butoxycarbonyl-4-[4-(3,5-dimethyl-4-bromothiophen-2-yl)phenoxymethyl]piperidine 
• 921596-21-6 N-tert-butoxycarbonyl-4-[4-[5-(3,5-dimethyl-4-bromothiophen-2-yl)thiophen-2-yl]phenoxy]piperidine 
• 921596-33-0 tert-butyl N-[2-[4-[4'-(hexafluorocyclopent-1-enyl)-3',5'-dimethyl[2,2']bithyophen-5-yl]phenoxy]ethyl]-N-methyl carbamate 
• 921596-22-7 N-tert-butoxycarbonyl-4-[4-[5-[3,5-dimethyl-4-(perfluorocyclopenten-1-yl)thiophen-2-yl]thiophen-2-yl]phenoxy]piperidine 
• 172872-73-0 4-bromo-3,5-dimethylthiophene-2-boronic acid 
• 85895-83-6 3,5-dimethyl-2-thiophenecarboxaldehyde 
• 2530-10-1 3-Acetyl-2,5-dimethylthiophen 
• 50382-14-4 1-(3,5-dimethyl-[2]thienyl)-ethanone 
• 98547-25-2 3,5-dimethyl-thiophene-2-carboxylic acid amide 
• 1421332-32-2 1,5-bis-3-(2-chloro-3,5-dimethylthienyl)-1,5-pentadione 
• 1421332-29-7 1,2-bis-(2,4-dimethyl-5-(4-methylphenyl)thien-3-yl)cyclopent-1-ene 
• 503308-96-1 2,4-dimethylthiophene-3-carboxylic acid 
• 87895-88-3 diethyl <2-(3,5-dimethyl-2-thenoyl)phenyl>phosphonate 
• 87895-69-0 2-(2-azidobenzoyl)-3,5-dimethylthiophene 

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Provided herein are thiophene compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

1,3-bicyclo[1.1.1]pentanediyl: The shortest rigid linear connector of phenylated photochromic units and a 1,5-dimethoxy-9,10-di(phenylethynyl) anthracene fluorophore

An excess of bis-1,3-(4-iodophenyl)bicyclo[1.1.1]pentane, prepared in 63% yield by iodination of 1.3-diphenylbicyclo[1.1.1]pentane, was selectively mono-coupled with 9-ethynyl-1,5-dimethoxy-10-phenylethynylanthracene (26), and subsequently with the zinc derivatives of 1-(2-methyl/methoxy-4-methyl-5- phenylthiophen-3-yl)-2-(2-methyl/methoxy-4-methylthiophen-3-yl) perfluorocyclopentenes (38-H-41-H). Regioselective synthesis of the 2-unsubslituted thiophenes 38-H-41-H required intermediate prepara tion of 2-trimethylsilyl-3,5-dimethyl-4-bromothiophene (37) or 2-trimethylsilyl-5- methoxy-3-methyl-4-bromothiophene (40). Protection of the α-position of the thiophene ring with a 2-trimethylsilyl group blocks the rearrangement of the 4-lithio derivatives into the corresponding 2-lithiated thiophenes. With the bicyclo[1.1.1]pentane frag ment linking the photochromic units 1-3 and 1,5-dimethoxy-9,10-di(phenylethynyl)anthracene as a fluorescent part, quantitative resonance energy transfer between the excited state of the fluorophore (donor) and the closed form of the photochromic units 1-3 (acceptors) was observed. The closed forms of the methoxy-substituted photochromic units 2 and 3 are less resistant to UV light (313 nm) than the closed form of 1.